116 Strategic Questions to Ask Senior Leaders - With Sample Answers (2024)

Strategic questions to ask senior leaders

Most executives agree that strategy is essential for any business, but what exactly is strategy? One definition comes from seasoned executive strategist Ellie Pidot, who explains that strategy is simply a long-term plan that is put into action. But, of course, there is more to it than that.

To develop an effective strategy, businesses must ask themselves essential questions and collect data to help answer them. This can be difficult, as it often requires tough choices between good alternatives. However, by developing a strategic plan, businesses can set themselves up for long-term success.

When it comes to your career, it pays to ask the right questions. If you have the opportunity to meet a senior leader, make the most of it by asking strategic questions that will help you learn more about your field and advance your career. Some questions to consider include:

• What are the biggest challenges facing our industry?
• How did you get to where you are today?
• What do you see as the next big trend in our field?
• What are the biggest obstacles to career growth in our industry?
• What are some tips for success in our field?

By asking thoughtful questions, you can gain valuable insights that will help you accelerate your career growth. So, next time you have the chance to meet a senior leader, make sure to ask the right questions.

There are many benefits to communicating with your leaders, including the development of new procedures and tactics. However, one of the most beneficial aspects is the ability to pose questions that might result in a breakthrough in your company or sector. By asking questions, you can better understand the goals and objectives of your leaders, as well as their vision for the future.

This knowledge can help you develop more effective strategies and procedures that can improve the overall performance of your company or sector. In addition, by communicating with your leaders, you can build relationships and trust, which can further improve the effectiveness of your communication. Ultimately, by communicating with your leaders regularly, you can significantly enhance the development and performance of your company or sector.

Even better, by asking these questions to senior leaders and comparing their responses to the sample ones provided, you will get a good feel for whether this leader knows their strategy concepts and practices or not. If asking good questions is critical, why don’t we spend more time and energy on discovering and framing them? One reason may be that much of our Western culture focuses on knowing the “right answer” rather than discovering the “right question.”

Our educational system focuses more on memorization and static answers than on the art of seeking new possibilities through dynamic questioning. We are rarely taught how to ask powerful questions. Nor are we often taught why we should ask compelling questions in the first place. Part of the reason may be that we live in a culture that values certainty and discourages doubt.

Asking questions is often seen as a sign of weakness or a lack of knowledge. But if we want to understand something or create something new, we need to be willing to ask questions and explore different possibilities. Only by doing so can we hope to find the answers we seek.

Aversion to creative questions might get in the way of solutions because we either can’t or don’t want to reflect and have conversations that explore multiple perspectives. Instead, we quickly look for a fix or gravitate towards black-and-white thinking. This might be due to the rapid pace of our lives and work, which prevents us from being reflective.

Additionally, organizations often incentivize leaders to find fixes instead of breakthrough thinking. As a result, we might not be open to new perspectives even when facing unprecedented challenges. By watering down our aversion to creative questions, we could improve problem-solving in our lives and work.

Why Asking Strategic Questions to Senior Leaders Matters

The only constant in today’s business environment is change. Organizations must adapt quickly to new market conditions and changes in customer demand to succeed. However, it can be difficult for leaders to know where to turn for guidance in a volatile and uncertain environment. One of the most credible stances leaders can take is to assist their organizations in discovering the right questions at the right time.

Key leadership responsibility is creating infrastructures for dialogue and engagement that encourage others at all levels to develop insightful questions and search for innovative paths.

Leaders must also consider reward systems that incentivize members to work across organizational boundaries to discover those challenging questions that create a common focus and shared forward movement. By taking these steps, leaders can create an environment where innovation thrives and organizational success is more likely.

Workable strategies begin to emerge in response to compelling questions and to the images of possibility that these questions evoke. Much like a jigsaw puzzle, as you piece the different elements together, a clearer picture starts to form of what the final product will look like. And, just as with a puzzle, a few pieces always don’t quite fit.

But with perseverance and looking at the problem from different angles, you can usually find a way to make it work. Of course, the cycle is never complete. Relevant business data, ongoing conversations with internal and external stakeholders, informal conversations among employees, and feedback from the environment enable you to assess the business landscape, revealing new questions continually.

By continually asking questions and seeking out new information, you can ensure that your strategies remain relevant and responsive to the ever-changing needs of your business.

Many organizations are stuck in a “problem-solving orientation” regarding strategy. They can’t seem to shake the focus on fixing short-term problems or seeking immediate (but ineffective) solutions. By shifting their attention to a deliberate focus on essential questions, they can develop an inquiry-oriented approach to evolving organizational strategy (see “How Can I Frame Better Questions?”).

In a knowledge economy, this approach provides an opportunity for developing the capability of strategic thinking in everyone and fostering sustainable business and social value.

By asking essential questions and encouraging others to do the same, organizations can create a culture of inquiry that is conducive to long-term planning and creative problem-solving. In addition, this approach can help leaders identify and cultivate strategic thinkers’ talents within their ranks. Ultimately, an inquiry-oriented approach to strategy can help organizations develop the adaptability and resilience needed to thrive in an ever-changing world.

Strategic Questions to ask leaders

1. How clear is your vision for what corporate responsibility should be like in your organization in the future? Is the direction that the organization wants to go in clear and understandable?

A company’s direction is only as good as its employees’ understanding. If your staff can’t explain what the company is working toward, they will likely not fully understand the vision themselves.

This can lead to confusion and frustration, both of which can hamper progress.

Clearly communicating the organization’s goals and objectives is essential to ensuring that your employees are on the same page. This way, everyone will work toward the same outcome and know their roles in helping to achieve it.

• How do you plan to communicate and reinforce the vision of corporate responsibility across all levels of the organization to ensure alignment and commitment? This question focuses on understanding the strategies for effectively conveying the corporate responsibility vision to employees and stakeholders.
• What specific initiatives or programs will be implemented to operationalize your vision of corporate responsibility within the organization? This question explores the concrete steps the organization will take to turn its corporate responsibility vision into reality.
• How will you measure and track the success of your corporate responsibility efforts and ensure continuous improvement over time? This question aims to understand the methods and metrics the organization will use to assess the impact of its corporate responsibility initiatives and maintain progress toward its vision.

When everyone is rowing in the same direction, it’s much easier to reach the finish line.

2. What time frame should our strategic plan cover?

The time frame for our strategic plan is an important consideration. We need to look into the future to be confident that our company’s environment will be stable, but not so far that the plan becomes unrealistic.

In most cases, a three- to five-year horizon is a good balance. This gives us the flexibility to review and update the plan regularly.

• What are the key short-term and long-term goals our strategic plan should address within the chosen time frame? This question focuses on identifying the organization’s main objectives and how they align with the proposed duration of the strategic plan.
• How will the strategic plan’s time frame align with our organization’s growth projections and market trends? This question seeks to ensure that the strategic plan’s duration is in sync with anticipated business developments and industry dynamics.
• How​​ do we plan to monitor progress and adapt our strategies within the chosen time frame to ensure continued success? This question aims to understand the organization’s approach to regularly reviewing and adjusting the strategic plan in response to evolving circ*mstances and performance.

3. Where are we now, and where do we want to be?

Having a clear idea of where your business is currently and where you want it to be in the future is essential.

Developing an effective plan for achieving your goals can be difficult without this focus. Your current situation should be detailed and quantifiable, so you can accurately compare it to your desired future state.

• What are our organization’s key strengths and weaknesses? How do they impact our ability to achieve our desired future state? This question focuses on understanding the organization’s current position and the factors that may influence its progress toward its goals.
• What are the most significant opportunities and threats in our market or industry? And, how can we leverage or address them to move closer to our desired future state? This question explores external factors that may impact the organization’s journey toward its goals and the strategies to capitalize on or mitigate them.
• What specific actions or initiatives must we undertake to bridge the gap between our current and desired future state? This question aims to identify the practical steps the organization must take to progress from its current position toward the envisioned future state.

This comparison will help you identify the gaps that need to be filled to reach your goal. Once you have a good sense of where you are and want to be, you can develop a roadmap for getting there. This roadmap should include specific steps and milestones to help you track your progress and stay on course.

With a clear destination in mind and a well-defined plan for how to get there, you can confidently move forward with growing your business.

4. Where have we come from? Where are we now? And, where do we want to be?

One of the most important things for a leader is asking the right questions. This is especially true regarding senior leaders, who are often responsible for making high-level decisions that can significantly impact an organization.

Asking strategic questions can help to ensure that these decisions are based on a clear understanding of an organization’s history, current situation, and desired future state.

Some essential questions that senior leaders should ask include:

• “Where have we come from?”
• “Where are we now?”
• Where do we want to be?”

By taking the time to reflect on these critical issues, senior leaders can make sure that they are making decisions that will help their organizations move in the right direction.

5. What do you feel is the biggest strength of our company right now?

Our company possesses many strengths, but if I had to choose one, it would be our ability to adapt and change. We live in a constantly evolving world, and the companies that can keep up with the times are the ones that succeed.

• How does our biggest strength differentiate us from our competitors? How can we leverage it to gain a competitive advantage in the market? This question focuses on understanding the unique value proposition of the company’s strength and its potential impact on its market position.
• How can we ensure that our biggest strength remains a sustainable advantage in the face of changing market conditions and industry trends? This question explores strategies for maintaining and enhancing the company’s strength in a dynamic business environment.
• Are there any potential risks or challenges associated with our biggest strength, and how can we proactively address them? This question aims to identify any potential downsides or vulnerabilities related to the company’s strengths and understand the plans to mitigate or manage these risks.

6. What goal do you have for the company?

The old saying goes, “A goal without a plan is just a wish.” Having a goal for your company—and, more importantly, a plan to achieve that goal—is essential for success.

But what should that goal be?

Certainly, profits are substantial, but they shouldn’t be the only thing you’re striving for. Instead, focus on creating value for your customers and positively impacting your community.

• How does the goal align with our company’s mission, vision, and overall strategic direction, and how will achieving it contribute to our long-term success? This question focuses on understanding the connection between the goal and the company’s broader objectives and aspirations.
• What specific resources, capabilities, and actions will we need to achieve the goal, and how do we intend to mobilize them? This question delves into the practical steps and resources required for accomplishing the goal, addressing any potential challenges or barriers.
• How will we measure progress toward the goal and evaluate its impact on our organization once it is achieved? This question aims to understand the metrics and milestones that will be used to track progress and assess the goal’s overall success and impact on the company’s performance.

Doing so will make your company more successful in the long run and make it a better workplace. And isn’t that what we all want?

7. Who is our target customer?

Let’s first consider our company’s purpose in determining who our target customer is. Our company exists to provide window installation and repair services for those who need them. With that in mind, we can see that our target customers are those people who have recently damaged or broken their windows and need immediate help.

This may include clients whose windows have been unintentionally broken or have suffered damage from severe weather.

• What are our target customers’ key characteristics, preferences, and pain points, and how do our products or services address their specific needs? This question focuses on understanding the target customer’s profile and the company’s value proposition to meet their requirements.
• How do our marketing, sales, and customer support strategies effectively reach, engage, and serve our target customers? This question explores the tactics and channels used to connect with the target customer and deliver a positive customer experience.
• How do we plan to continuously adapt and innovate to meet the evolving needs and expectations of our target customers? This question aims to understand the organization’s approach to staying relevant and competitive in the face of changing customer preferences and market conditions.

By better understanding the needs of our target customers, we can more effectively provide the services they need and exceed their expectations. As a result, we can improve customer satisfaction and increase revenue for the company.

8. What are the biggest challenges the company is facing?

The company is currently facing several challenges, both internally and externally. One of the biggest internal challenges is the development of employee skills and knowledge. Rapid technological changes make it difficult for employees to keep up with the latest advancements in their field.

As a result, they may become less productive and effective. Another internal challenge is poor communication between departments. This can lead to confusion and frustration, as well as decreased productivity.

One of the biggest challenges the company faces is competition from other businesses. With more and more businesses entering the market, staying ahead of the competition can be difficult.

The company is also facing a challenge from a lack of product demand. In some cases, people may not need or want the product. In other cases, they may not be aware of the product or its benefits. Either way, this can lead to decreased sales and revenue.

Questions:

• What strategies and initiatives are in place to address and overcome these challenges? How do they align with our overall business goals? This question focuses on understanding the organization’s plan of action for tackling the identified challenges and ensuring that the efforts contribute to its long-term success.
• How are we leveraging our company’s strengths and resources to mitigate these challenges’ impact on our operations and performance? This question seeks to explore how the company uses its competitive advantages and available resources to counter the effects of its challenges.
• What indicators or warning signs should we monitor to stay proactive and responsive to these challenges as they evolve? This question aims to understand the key metrics and signals that the organization will track to detect any changes in the challenges’ scope or severity and adjust its strategies accordingly.

To overcome these challenges, the company needs to find practical solutions. For example, it could invest in employee training and development programs to help them stay up-to-date with the latest advancements in their field. Additionally, it could improve communication between departments by implementing regular meetings or using specific software platforms. Finally

9. How can you improve the company’s current product?

As any business owner knows, the key to success is continually improving your product. Whether developing a new feature, redesigning an existing one, or even just listening to customer feedback, making your product the best it can be is essential to staying ahead of the competition and keeping up with market demand.

And while it’s essential to always look for ways to improve, sometimes the most obvious place to start is with the product or service you already have.

Investigating customer feedback is a great way to get ideas for improving your current product. Read through customer surveys, social media activity, and any other feedback you can find to see what people say about your product.

• Are there any common complaints?
• Is there something people keep asking for that you haven’t provided?
• Identifying areas where your product falls short can help you prioritize which changes need to be made.

Of course, you can’t please everyone all the time. But by constantly striving to improve your product, you can ensure that your business is always moving in the right direction.

10. How did the company get to where it is?

Asking leaders the strategic question, “How did the company get to where it is?” is important for several reasons:

• Understanding historical context: By analyzing the company’s journey, leaders can gain valuable insights into the decisions, strategies, and external factors contributing to the organization’s current position. This historical perspective can help inform future decision-making and avoid repeating past mistakes.
• Identifying key success factors: Examining the company’s past performance enables leaders to identify the factors that have driven success, such as unique competencies, strong market positioning, or effective leadership. Recognizing these factors helps leaders to prioritize and reinforce the elements that will continue to support the company’s growth and competitiveness.
• Learning from challenges and failures: Reflecting on the company’s history also reveals its challenges and setbacks. Understanding how these obstacles were managed or overcome can provide valuable lessons for future problem-solving and risk mitigation.
• Building and maintaining organizational culture: A clear understanding of the company’s history and evolution can help leaders foster a strong organizational culture that reflects the company’s values, mission, and vision. Recognizing the company’s roots and development can also contribute to employee engagement and a sense of belonging.
• Enhancing stakeholder communication: Having a comprehensive understanding of the company’s journey allows leaders to communicate its story effectively to stakeholders, such as investors, customers, and employees. This transparent communication can help build trust, credibility, and a strong brand reputation.

Overall, asking leaders about the company’s past enables them to reflect on its trajectory and use those insights to guide strategic planning, decision-making, and future growth.

• What key decisions or turning points in the company’s history have significantly contributed to its current position and success? This question focuses on understanding the critical choices and events that have shaped the organization’s trajectory.
• What challenges and setbacks has the company faced in the past, and how were they managed or overcome? This question explores the lessons learned from past obstacles and how they can inform future problem-solving and risk-mitigation strategies.
• How has the company’s mission, vision, and values evolved over time, and how has this evolution impacted its growth and development? This question aims to understand the role of the company’s guiding principles in shaping its direction and progress.

11. Where does the company want to go?

• What does the company want to achieve?
• How does it want to develop?

Every business should answer these two crucial questions to create a clear and focused plan for the future. The company can stay on track and avoid deviating from its main objectives by setting a small number of important goals over a long period of time.

• What are the specific short-term and long-term objectives that the company aims to achieve to reach its desired future state? This question focuses on understanding the milestones and goals guiding the organization’s journey.
• How does the company’s vision for the future align with current industry trends, market opportunities, and potential challenges? This question focuses on understanding the organization’s preparedness and adaptability in the face of evolving market conditions and industry dynamics.
• How does the company plan to differentiate itself from competitors and create a unique value proposition to succeed in its target market? This question explores the strategies and initiatives to help the company stand out and capture market opportunities.

Developing an effective action plan to achieve these goals is essential. Still, it is also important to have some flexibility built into the plan if the company needs to pivot or make changes along the way. Answering these questions can help any business create a roadmap for success.

12. What should the company do more of?

A company’s success depends on its ability to adapt to changing market conditions and seize growth opportunities. As such, leaders must regularly assess the company’s strengths and weaknesses. Here are a few strategic questions that can help senior leaders steer the company in the right direction:

• What are we doing well?
• What could we be doing better?
• What are our most extensive opportunities for growth?
• What are our biggest threats?
• What do our customers think of us?
• What do our employees think of us?

By asking these questions regularly, senior leaders can better understand the company’s current situation and make informed decisions about where to focus their efforts.

13. Do you currently have any strategic uncertainties?

Strategic uncertainty is any goal or objective the company might have trouble achieving. You need to identify any strategic uncertainties the company has because it can help you avoid potential challenges and ensure the success of your company strategy.

After you find any strategic uncertainties, it’s beneficial to reevaluate the company’s current trajectory by examining competitors, tracking sales numbers, and conducting market research to see if the company needs to adjust or fix anything.

As a leader, it’s crucial to identify and assess your company’s strategic uncertainties. These objectives can’t be accurately predicted given the available data and information. To properly assess these uncertainties, it’s crucial to consider the company’s goals and the data needed to achieve those objectives.

For example, if the company wants to increase customer satisfaction but doesn’t have enough surveys to determine the current level of satisfaction, customer satisfaction would be deemed a strategic uncertainty. By taking the time to identify and assess these uncertainties, you can develop a plan of action to address them and help your company achieve its goals.

In addition to the question about strategic uncertainties, here are a few other essential questions to ask senior leaders:

• What are our goals? It’s important to know what the company is trying to achieve so that you can align your objectives with the company’s and contribute to its success. Furthermore, if company goals change, you must know them to adjust your plans accordingly.
• What are our action plans? Knowing the company’s plans of attack for achieving its goals is essential for all employees, but especially those in leadership positions. This information can help you determine where to focus your efforts and how you can best contribute to the company’s success.
• What are our priorities? Understanding the company’s priorities helps you focus on the most critical tasks and ensures you’re not wasting time on less pressing issues. It also lets you see how your work fits into the bigger picture and where you can have the most impact.

Asking these questions allows you to better understand the company’s strategy and direction so that you can make more informed decisions and contribute more effectively to its success.

14. How often can your organization assess its strengths, weaknesses, opportunities, and threats to understand its current business climate?

Many organizations think that their current strategy is working well enough, so they don’t spend the time and resources necessary to assess their strengths, weaknesses, opportunities, and threats regularly.

However, this can lead to complacency and an inability to adapt to changing business conditions. Measuring these aspects of the strategy will help to analyze the company’s current approach to strategic evaluation and reveal if it is necessary to analyze it more often.

• What mechanisms or processes does the organization have in place to continuously monitor internal and external factors that impact its business climate? This question focuses on understanding the organization’s approach to staying informed and responsive to changes in its operating environment.
• How does the organization incorporate the insights from regular SWOT assessments into its strategic planning, decision-making, and resource allocation processes? This question seeks to explore how the company leverages its understanding of its strengths, weaknesses, opportunities, and threats to inform its overall strategy and direction.
• How does the organization ensure cross-functional collaboration and effective communication of SWOT assessment findings throughout the company? This question aims to understand the processes in place for sharing insights and fostering alignment among various departments and teams in response to the organization’s evolving business climate.

Asking senior leaders how often they assess these factors will give you insight into whether the company can adapt its strategy as needed. It can also reveal if the leadership team is appropriately evaluating the current business climate and making decisions based on accurate information.

Asking these questions can help you ensure that your organization makes strategic decisions based on a complete understanding of the current landscape.

15. How often does your organization analyze the competition to understand competitive advantages and disadvantages and identify areas for investment or needs for improvement?

Regular assessment of the competitive landscape is a crucial determinant of corporate strategy, and fine-tuning the frequency of this evaluation will help reveal how your company’s doing in competitor analysis. Many organizations fail to assess the competitive landscape regularly, which can have profound implications for corporate strategy.

By not keeping a close eye on the competition, companies may miss opportunities to invest in areas of advantage or improve upon areas of disadvantage. They may also be unaware of new threats hindering their success path.

Asking senior leaders how often they analyze the competition can help to uncover any blind spots in this vital area. Generally, the more frequently an organization assesses the competitive landscape, the better equipped it will be to form a productive corporate strategy.

• What tools or methods does the organization use to systematically track and evaluate competitors’ activities, strategies, and performance? This question focuses on understanding the organization’s approach to maintaining up-to-date and comprehensive knowledge of the competitive landscape.
• How does the organization incorporate competitive analysis findings into its strategic planning, decision-making, and resource allocation processes? This question explores how the company leverages its understanding of its competitive advantages and disadvantages to inform its overall strategy and direction.
• How does the organization foster cross-functional collaboration and effective communication of competitive analysis insights throughout the company? This question aims to understand the processes in place for sharing competitive intelligence and promoting alignment among various departments and teams to respond to emerging competitive threats and opportunities.

Of course, there is no “perfect” frequency for assessment, and it will vary from one company to the next depending on factors such as industry dynamics and resources. However, organizations can stay one step ahead of the competition by ensuring that this evaluation is conducted regularly.

16. How well does your organization strategically differentiate from the competition in terms of the capabilities of its product? How clear is your organization’s strategy for this?

Any organization needs to know how it differentiates itself from the competition. This question helps to analyze and assess competition in a clear, specific way that will yield insight into the differentiation strategy. A well-differentiated product is essential for success in today’s marketplace, and a clear understanding of the strategy behind that product is critical for senior leaders.

• What specific product features or attributes contribute to its unique value proposition, and how do they address the target customers’ needs more effectively than competitors’ offerings? This question focuses on understanding the factors that set the organization’s product apart from the competition.
• How does the organization communicate its product differentiation strategy to customers, employees, and other stakeholders to ensure a clear and consistent message? This question explores the tactics used to convey the organization’s strategic positioning and value proposition to its target audience.
• How does the organization plan to continuously innovate and evolve its product capabilities to maintain its competitive edge and adapt to changing customer preferences and market conditions? This question aims to understand the company’s approach to sustaining its product differentiation strategy in the face of dynamic industry trends and competitive pressures.

This question allows leaders to assess the capabilities of their product and compare it to the competition, giving them a better understanding of where they stand and what needs to be done to improve their position.

Asking this question also helps to create a dialogue about differentiation within the organization, raising awareness of the importance of this topic and fostering a culture of strategic thinking. Ultimately, this question can help senior leaders make better decisions about positioning their product in the market and ensuring it remains competitive.

17. Is our long-term view reflected in our short-term priorities? Are we pouring effort into initiatives today that connect with where we expect ourselves and the market to be in the future?

Any good strategy must be based on clearly understanding the current situation and where the company wants to be. With that in mind, here are three critical questions that every senior leader should ask themselves when crafting a long-term strategy:

• What is our current market position?
• Where do we want to be in the future?
• How do we get there?

Answering these questions is not always easy, but doing so is essential to developing a robust and sustainable strategy.

Without a clear understanding of where you are today and where you want to be tomorrow, developing a plan to get there will be impossible. So take the time to answer these questions thoughtfully, and you’ll be well on crafting a winning strategy.

18. How do the potential negative consequences of implementing a new strategy compare to the potential positive outcomes?

Any time a company looks to implement a new strategy, it is vital to consider the potential positive and negative consequences. On the positive side, a new strategy could increase profits, market share, or efficiency.

However, risks are also involved any time a company changes. A new strategy could alienate customers or employees, cause disruptions in the supply chain, or lead to other unforeseen problems. As a result, it is crucial to carefully weigh any new strategy’s potential risks and rewards before moving forward.

• What are the key risks and challenges associated with implementing the new strategy, and how could they impact the organization’s performance, reputation, or financial stability? This question focuses on understanding the potential downsides of the proposed strategic change.
• What mitigation measures and contingency plans do the organization have to address the identified risks and challenges associated with the new strategy? This question seeks to explore the company’s preparedness to manage potential negative consequences and maintain resilience during the transition.
• How do the anticipated benefits and opportunities of the new strategy align with the organization’s overall goals and objectives, and what is the estimated return on investment (ROI) or value creation? This question aims to understand the positive outcomes that the company expects to achieve through the strategic change and how they contribute to its long-term success.

Only by fully understanding the implications of a change can a company make an informed decision about whether or not to proceed.

19. When developing and implementing strategy, does our organization balance short- and long-term priorities effectively?

Every company has a culture, whether it is intentional or not. This culture arises from the people’s shared values, experiences, and beliefs within the organization. Therefore, when developing and implementing a strategy, it is crucial to consider the impact that the strategy will have on the company culture. Will the strategy reinforce the existing culture or require a culture shift?

For example, a long-term growth strategy may require a culture shift if the company focuses on short-term results.

• How does the organization’s strategic planning process ensure that both short-term objectives and long-term goals are considered and integrated into the overall strategy? This question focuses on balancing immediate needs with future aspirations in the strategic planning process.
• What mechanisms are in place to monitor and evaluate the progress and impact of both short-term initiatives and long-term investments and how does the organization adapt its strategy based on the outcomes? This question explores how the company tracks and learns from its strategic efforts to ensure continued alignment between short- and long-term priorities.
• How does the organization foster a culture of balancing short-term performance and long-term sustainability among employees, leaders, and stakeholders? This question aims to understand the steps taken to promote a mindset that values both immediate results and future growth, ensuring that the organization remains agile, resilient, and forward-thinking.

However, a culture change might be necessary if the company’s current goal is long-term growth rather than a short-term outcome. In either scenario, it is critical to think about how the strategy will affect the corporate culture and whether the organization is equipped to implement the required changes.

20. To what degree are your offerings differentiated in their market?

To assess how well your company’s offerings are differentiated in their market, it is vital to ask senior leaders strategic questions. This will allow you to analyze how your company distinguishes its products from competitors, thus working to permeate the market as much as possible.

• What are the key product or service features that set your offerings apart from competitors, and how do they address the unique needs and preferences of your target customers? This question focuses on understanding the specific factors contributing to the differentiation of the organization’s offerings.
• How do the organization’s marketing, branding, and communication strategies effectively convey its differentiated value proposition to the target audience? This question explores the tactics used to ensure that customers and other stakeholders know and appreciate the unique benefits of the organization’s offerings.
• How does the organization plan to maintain or enhance its differentiation in the face of evolving market conditions, industry trends, and competitive pressures? This question aims to understand the company’s approach to sustaining its competitive edge and adapting its offerings to address emerging customer needs and preferences.

This question is essential when assessing your competition and analyzing your product itself. By asking these questions, you can better understand how your company’s products are positioned in the market and what needs to be done to improve market share.

21. How much ease and expense is required for your customer to switch to a competitor’s offering?

As a senior leader, it is crucial to always ask yourself strategic questions to stay ahead of the competition.

One key question is: how much ease and expense is required for your customer to switch to a competitor’s offering?

This will give you valuable insight into how customers value your product and whether they will likely switch to a competitor.

If customers require little effort or expense to switch, this may indicate that they do not view your product as unique or valuable. On the other hand, if customers willingly go through significant effort or expense to switch, this indicates that they see real value in your product.

• What are the key barriers or switching costs that customers may face when considering a move to a competitor’s offering, and how does the organization leverage these factors to retain and build customer loyalty? This question focuses on understanding the challenges customers might experience when switching and how the company capitalizes on these barriers to enhance customer retention.
• How does the organization continuously monitor and assess customer satisfaction, needs, and preferences to ensure that its offerings remain competitive and aligned with customer expectations? This question explores the company’s efforts to stay informed of customer requirements and proactively address potential issues that could prompt customers to switch to a competitor.
• How does the organization plan to enhance its offerings and customer experience to minimize the risk of customers switching to competitors, and what investments or initiatives are in place to support this goal? This question aims to understand the company’s approach to maintaining its competitive edge and customer loyalty by continuously improving its products, services, and overall customer experience.

Understanding customer switching costs is essential for making strategic decisions about how to position your product in the marketplace.

22. How well do the organization’s products solve the customers’ problems and meet their expectations?

As a business leader, it’s important to regularly evaluate how well your products or services solve your customers’ problems and meet their expectations. This can help you ensure that you deliver value and do not fall behind the competition. There are a few key questions you can ask to get started:

• How well do our products or services solve the customer’s problem?
• How easily can customers find and use our products or services?
• Are there any areas where our products or services fall short of customer expectations?
• How does our product or service compare to similar offerings from other companies?

Asking these questions regularly can help you identify areas where your business needs to improve to serve your customers better.

23. How often does our organization analyze the competition to understand competitive advantages and disadvantages and identify areas for investment or needs for improvement?

If you’re looking to get insights from your senior leaders about your organization’s competitive posture, here are a few strategic questions you can ask:

• How often does our organization analyze the competition to understand competitive advantages and disadvantages and identify areas for investment or needs for improvement?
• What are our organization’s core strengths and weaknesses? How do they compare to our competitors?
• What do we believe are our competitors’ key strategies, and how are we preparing to counter them?
• What industry trends affect our business, and how will we respond?
• What are our customers saying about us relative to our competitors? What do they value most?

Asking probing questions like these can help you uncover whether or not your company understands the competitive landscape and what it takes to compete effectively. If not, it may be time to make some changes.

24. Based on your knowledge of current efforts to promote our services, what are the significant internal barriers to selling your services to clients?

One internal barrier to selling services is a lack of understanding of the client’s needs. If your company does not take the time to understand the specific problem the client is facing, it won’t be easy to sell them a solution. Another internal barrier is a lack of passion for the product or service.

If your sales team isn’t enthusiastic about what they’re selling, it won’t be easy to transfer that excitement to the client.

Finally, another internal barrier is a lack of focus on the client’s journey. If your company is more focused on its own goals and objectives, it will be challenging to sell the client the value of your services.

• How do the organization’s internal processes, systems, and structures support or hinder the effective marketing and sales of its services to clients? This question focuses on understanding any operational challenges or inefficiencies that may impact the organization’s ability to sell its services successfully.
• What are the key skills, knowledge, or capabilities that may be lacking within the sales and marketing teams, and how do these gaps impact the organization’s ability to promote and sell its services? This question explores the human resource-related challenges that may hinder the company’s sales efforts and client acquisition.
• How does the organization’s culture, communication, and collaboration between different departments influence the effectiveness of its sales and marketing initiatives? This question aims to understand any internal barriers related to organizational culture, cross-functional alignment, or communication that may affect the company’s ability to sell its services to clients.

By determining these internal barriers, your company can find ways to avoid them and strategize better.

25. Does our product offering encourage innovation for the customer through versatility, usability, and efficiency?

What are our customers’ unmet needs? This is always the starting point for any company seeking to create valuable products:

• What need does the customer have that is not currently being met?

Once this need is identified, the company can begin designing a product that meets this demand. However, it is not enough to create a new product; the offering must also be versatile and easy to use, or else customers will quickly become frustrated and look elsewhere.

• How does the organization’s product development process incorporate customer feedback, industry trends, and emerging technologies to continuously improve versatility, usability, and efficiency? This question focuses on understanding the approach to innovation and how it aligns with customer needs.
• What mechanisms are in place to measure and assess the effectiveness of the product’s versatility, usability, and efficiency regarding customer satisfaction, market adoption, and competitive advantage? This question explores the methods used to evaluate the product’s innovative features and their impact on the customer experience and market success.
• How does the organization foster a culture of innovation and collaboration among employees and teams to continuously enhance the product’s versatility, usability, and efficiency? This question aims to understand the steps taken to promote an innovative mindset within the organization, enabling continuous improvement and customer-focused innovation.

Efficiency is also vital, as customers do not want to waste time using a complicated or inefficient product. By asking these strategic questions, companies can ensure that they are on the right track to developing valuable, innovative offerings that appeal to their target market.

26. What is the direction and state of our innovations? Is the direction suitable for now, 5 years from now, and 10 years in the future?

Knowing whether or not your company is on the right track can be challenging. After all, getting caught up in the day-to-day and losing sight of the bigger picture is easy.

That’s why it’s essential to assess your company’s direction periodically. One way to do this is to ask senior leaders some tough questions.

For example, you might ask them about the state of your company’s innovations.

• Are you truly pushing the envelope, or are you playing it safe? It’s also important to consider the future when evaluating your strategy.
• Is your product roadmap still relevant 5 or 10 years down the road?

By asking these questions, you can better understand whether your company is on track and make adjustments as needed.

27. Does our organization have several strategies for differentiation, innovation, customer alignment, and a detailed forecasted strategy plan?

Differentiation, innovation, and customer alignment are essential to any business strategy.

• Does your organization have a clear plan for differentiating itself from the competition?
• What innovative new products or services can you offer that appeal to your target market?
• And how will you ensure that your offerings are aligned with the needs and want of your customers?

These are all critical questions for senior leaders to understand the organization’s future direction.

Without a clear plan for differentiation, innovation, and customer alignment, it will be challenging to maintain a competitive edge in the marketplace. Therefore, these questions should be at the forefront of any discussion about company strategy.

28. Does your organization’s pricing strategy match the availability of your current resources?

Many organizations clearly understand their need to optimize their pricing strategy. They know that they need to align their prices with the availability of their current resources, but they often struggle to do so. The problem is that they often don’t clearly understand how much their resources are worth.

As a result, they end up overpricing their work and forfeiting profit. To avoid this, it’s essential to closely examine your organization’s resources and determine their actual value.

• How does the organization’s pricing strategy consider the cost of production, operations, and other resource-related expenses? Ensure profitability and sustainability? This question focuses on understanding the alignment between the pricing strategy and the costs associated with the company’s resources.
• How does the organization monitor and adapt its pricing strategy in response to changes in resource availability, cost fluctuations, or other external factors impacting resource management? This question explores the company’s approach to maintaining a pricing strategy that remains responsive to resource-related challenges and opportunities.
• How does the organization effectively communicate the value of its offerings in relation to its pricing strategy, ensuring that customers perceive the pricing as fair and competitive given the resources involved in delivering the products or services? This question aims to understand the tactics used to convey the price-value relationship to customers and maintain their trust and loyalty.

Once you have a good understanding of what your resources are worth, you can then price your work accordingly. Optimizing your pricing strategy ensures you’re making the most of your resources and maximizing your profits.

29. Can we clearly define our target customer or market where we will concentrate our attention and resources?

When planning for business growth, it is essential to have a clear understanding of your target market.

• Who are your potential customers?
• What needs or problems do they have that your product or service can address?
• What are their buying habits?

Once you have a good sense of your target market, you can develop strategies for reaching them.

It is also essential to ask whether your current offerings are well-suited to the needs of your target market. If not, what modifications need to be made? Are there new products or services that you could introduce that would better meet the needs of your target market? These questions can help you develop a growth strategy tailored to your business’s specific needs.

Finally, it would help to consider what resources you will need to implement your growth strategy. Do you have the necessary financial resources? Is staff in place with the skills and knowledge required? Is the necessary infrastructure in place? Such as manufacturing facilities or distribution channels?

Once you have identified any gaps, you can develop plans for addressing them. By asking these strategic questions, you can ensure that your business is well-positioned for growth.

30. What do our customers value or need? How do we know that? Do we provide that value? How do we know that?

Asking the right questions is essential for any business leader who wants to ensure that their company provides value to its customers.

Two critical questions are:

• “What do our customers value or need?”
• “Do we provide that value?”

Knowing what your customers need and want is the first step to being able to provide it for them.

There are several ways to research this, such as surveys, customer interviews, and focus groups. Once you understand what your customers want, you can ask whether your company supplies that.

This second question is just as important as the first because even if you think you know what your customers want, it’s all for nothing if you’re not providing it. The best way to assess this is usually through feedback mechanisms, such as customer surveys or web analytics.

Regularly asking these two strategic questions can help ensure that your company is always on the right track when it comes to providing value to its customers.

31. Are we clear about who isn’t our target customer so that we avoid trying to be all things to everyone?

Any good business leader knows that focus is key to success. Trying to be all things to all people is a recipe for disaster, as it inevitably leads to diluted resources and a lack of clear direction.

That’s why it’s so important to have a well-defined target customer and ensure that everyone in the organization knows that customer.

One way to ensure this is to regularly ask senior leaders strategic questions about the target customer, such as

• Who are we trying to reach with our products and services?
• Who are we not trying to reach? What needs does our target customer have that we can address?
• What are our target customers’ pain points?

By asking these questions, you can help keep everyone focused on the task at hand: serving the needs of your target customer.

32. What makes our product or service distinct or different from competitors? How do we know that?

If you’re preparing to interview a senior leader at a company, it’s crucial to ask strategic questions that will give you insights into the business.

To get started, you can ask about what distinguishes the company’s product or service from competitors. This question can help you understand the company’s unique selling proposition and how it differentiates itself.

• How has the organization conducted market research and competitive analysis to identify the unique features, benefits, or value propositions that set its product or service apart from competitors? This question focuses on understanding the evidence and insights that inform the company’s understanding of its differentiation.
• What feedback have you received from customers, industry experts, or other stakeholders that validate or challenge the distinct aspects of your product or service compared to competitors? This question explores real-world perspectives and experiences that support or question the organization’s differentiation claims.
• How does the organization track and respond to changes in the competitive landscape, evolving customer preferences, or emerging trends that could impact the distinctiveness of its product or service? This question aims to understand the company’s approach to maintaining its competitive edge and ensuring its offerings stand out.

Additionally, you can ask the senior leader how they know the product or service is distinct. This question can help you understand the research and development process behind the product or service and how the company assesses its market position.

You can gain invaluable insights into a company’s business model and operations by asking these strategic questions.

33. What makes our product or service distinct or different from competitors?

When trying to gain a competitive edge, it’s essential to understand what makes your product or service distinct from your competitors. This question can help uncover areas where you have a unique selling proposition. It’s also important to understand what your competitors are doing well and where they may fall short.

This question can give you insights into how you can improve your offerings. Asking tough questions can help you better understand the market and position yourself to succeed.

34. How big is our market? How is it defined (slices or segments)?

Asking senior leaders strategic questions is essential for the development of any business. By understanding the market’s size and scope, businesses can make informed decisions about allocating resources.

• What methods or data sources has the organization used to estimate the size and value of its target market(s), and how accurate and up-to-date is this information? This question focuses on understanding the approach to measuring the market potential and its reliability.
• How does the organization segment its target market(s) based on customer demographics, behaviors, needs, or other relevant criteria, and how do these segments inform its marketing, sales, and product development strategies? This question explores the company’s market segmentation approach and alignment with business objectives.
• How does the organization monitor and respond to changes in the size, dynamics, or structure of its target market(s), such as shifts in customer preferences, emerging trends, or competitive forces? This question aims to understand the company’s approach to staying informed and agile in the face of evolving market conditions and ensuring its offerings continue to meet the needs of its target customers.

Furthermore, businesses can target their products and services by segmenting the market. As such, asking senior leaders questions about the market is a crucial step in ensuring the success of any business.

As anyone in business knows, market share is essential for long-term success. Companies that fail to maintain a strong market position will eventually be forced to scale back or even close their doors.

That’s why it’s so important for senior leaders to regularly ask themselves tough questions about their company’s market share.

• What is our share for each market in which we compete?
• Are we losing, gaining, or holding shares?
• How does our share compare to our competitors?
• Where do we need to focus our efforts to improve our position?

By regularly asking these types of questions, senior leaders can help ensure that their company remains competitive and prosperous for years.

36. Where are the opportunities for growth (in our core business or adjacencies)?

One of the most critical questions that any senior leader should ask is where the growth opportunities are. In today’s rapidly changing business environment, it is essential to identify new markets and products that can drive growth.

• How does the organization evaluate and prioritize growth opportunities within its core business, such as expanding into new markets, launching new products or services, or improving existing offerings? This question focuses on understanding the approach to identifying and pursuing growth opportunities within the company’s existing business model.
• How does the organization assess and pursue opportunities in adjacent markets or industries that could complement or enhance its existing offerings or capabilities? This question explores the company’s approach to expanding its business beyond its core operations and leveraging its strengths to capitalize on new opportunities.
• What mechanisms or criteria does the organization use to measure and evaluate the success of its growth initiatives, and how does it adapt its strategies and tactics based on the outcomes? This question aims to understand the company’s approach to managing and optimizing its growth efforts, ensuring that they align with business objectives and contribute to long-term success.

For many companies, this means looking beyond their core business and exploring adjacencies. However, is is essential to ensure that any growth strategy is aligned with the company’s core values and competencies.

Only by asking the right questions can senior leaders ensure that their companies are positioned for long-term success.

37. Can we clearly articulate the unique benefits we seek to provide to our target customers, the price we expect them to bear, and how this entire value proposition is unique (our competitive advantage)?

As a young professional, it can be daunting to approach a senior leader with tough questions. However, asking the right questions is essential to ensuring that your company is on the right track. When it comes to strategic planning, there are a few key questions that every senior leader should be able to answer.

• First, can we clearly articulate the unique benefits we seek to provide our target customers?
• Second, what price or cost are they willing to bear for these benefits?
• And finally, how is our entire value proposition unique?

Answering these questions honestly and thoughtfully will help ensure your company remains competitive and thrives in the long run.

38. Do we “stay the course” when necessary and shift strategies appropriately, avoiding day-to-day reactions and programs of the month?

Many senior leaders find themselves bogged down in the day-to-day aspects of running a company, and as a result, they can lose sight of the big picture. This is why it’s crucial to have strategic questions that will help keep them focused on the organization’s long-term goals.

Some examples of such questions include:

• “What are our core values?”,“What is our long-term vision for the company?” a“What are the biggest threats to our success?”

Additionally:

• What mechanisms or processes does the organization have in place to monitor and evaluate the effectiveness of its strategies and initiatives? How does it use this information to determine when a shift in strategy is needed? This question focuses on understanding the approach to strategy evaluation and adaptation.
• How does the organization balance the need for flexibility and agility in responding to changing market conditions and customer needs with the importance of maintaining a clear and consistent strategic direction? This question explores the company’s approach to balancing short-term responsiveness with long-term vision and planning.
• What steps does the organization take to ensure that its employees and stakeholders are aligned with the company’s strategic direction and understand their roles in executing the strategy effectively? This question aims to understand the tactics used to promote a culture of strategic focus and ensure that day-to-day decisions and actions support the company’s long-term objectives.

By asking these questions regularly, senior leaders can ensure they make decisions aligned with the company’s overall strategy.

Any good business leader knows that it’s essential to understand the competitive landscape in which their company operates clearly. After all, how can you devise a winning strategy if you don’t know who your opponents are?

That’s why, when entering a new market or planning a major business initiative, it’s essential to ask senior leaders critical questions about the competitive landscape.

• First, is the market concentrated or fragmented? This will give you a sense of how many competitors you’re up against and how tough the competition will likely be.
• Second, who are our competitors? Knowing their names is insufficient; you must understand their strengths, weaknesses, core customer base, and market share.

Only then will you be able to develop a comprehensive strategy for success.

Asking the right questions is critical to making sound strategic decisions. When it comes to senior leaders, a few key questions can help guide the way.

• First, what must the organization maximize to create superior value for customers? This question helps to ensure that the focus remains on the customer and that any decisions made will be in their best interest.
• Second, what needs to be done to generate returns for shareholders? This question keeps the bottom line in mind and ensures that any actions taken will be financially responsible.
• Finally, what sort of opportunities can be created for employees? This question ensures that employees are considered in any decision-making process and that their needs are considered.

By asking these strategic questions, senior leaders can make informed decisions that will benefit all stakeholders.

41. What are the emerging trends that have the potential to change the way we do business? Do we fully understand the key opportunities and potential threats influencing our customers? Competitors? Technology? Regulatory environment? Suppliers?

With the ever-changing business landscape, it’s more important than ever for senior leaders to stay strategic and ahead of the curve. Asking the right questions is a vital part of this process. Some essential questions that every leader should ask are:

• What are the emerging trends that can potentially change the way we do business?
• Do we fully understand key opportunities and potential threats influencing our customers? Competitors? Technology? Regulatory environment? Suppliers?

By taking the time to consider these questions, leaders can better understand the forces at play and make informed decisions about the best way to move forward. In today’s business world, being strategic is the key to success.

42. Have we clearly defined who we are as an organization (mission, vision, values)? What are the implications for our strategies and structure?

Any leader worth their salt knows that one of the most critical parts of their job is to ask questions. The right questions can help to clarify goals, identify problems, and create solutions. When it comes to strategic planning, there are a few key questions that every senior leader should ask.

• First, have we clearly defined who we are as an organization? What are our mission, vision, and values? What are the implications for our strategies and structure?
  Without a clear sense of identity, it will be challenging to develop a cohesive plan.
• Second, what are our core competencies? What do we do better than anyone else? This question can help to focus your team’s energies on the areas where you have the most significant potential for success.
• Third, what are the trends affecting our industry? How might these trends impact our business in the future?
  You can position your company for long-term success by staying ahead of the curve. Asking these tough questions is essential for any senior leader who wants to create a winning strategy.

43. What external opportunities and threats can help or hinder achieving these ambitions? What internal strengths and weaknesses can help or hinder achieving these ambitions?

Before setting any goals, it’s essential to understand the landscape in which they will be achieved.

For this reason, senior leaders must ask themselves two key questions:

• What external opportunities and threats can help or hinder achieving these ambitions?
• And what internal strengths and weaknesses can help or hinder achieving these ambitions?

By carefully considering both sets of factors, leaders can develop a more informed and effective strategy for achieving their goals.

44. How are you defining the boundaries of the business?

Senior leaders need to be able to define the boundaries of their business. After all, significant risks and opportunities can often sit ‘upstream’ or ‘downstream’ from the business itself.

For example, the chemicals and water used to grow cotton for an apparel brand or how food brands can deliver nutritional benefits while avoiding ’empty calories.’ That’s why leaders need to consider the whole value chain, from the consumer’s use to the disposal of the product or service.

• What factors or criteria does the organization use to define the boundaries of its business, such as the products or services it offers, the markets it serves, or the geographic regions it operates in? This question focuses on understanding the approach to defining the scope and scale of the company’s operations.
• How does the organization assess and evaluate potential opportunities to expand or redefine its business boundaries, such as through mergers and acquisitions, partnerships, or new product development? This question explores the company’s growth and expansion approach and alignment with the existing business strategy.
• What mechanisms or strategies does the organization use to manage and optimize its portfolio of business activities and ensure that each component contributes to the company’s overall success? This question aims to understand the tactics used to maintain a clear and consistent focus on the core business while managing the risks and opportunities associated with business expansion and diversification.

The boundaries of the value chain should reflect the business’ categories and geographies. By asking senior leaders how they’re defining the boundaries of their business, you can get a better sense of their strategic thinking and where they see the most significant risks and opportunities.

45. How will you identify current and future risks, disruptions, impacts, and opportunities?

As the world becomes increasingly complex, leaders must learn to think strategically to identify risks, disruptions, and opportunities.

• What methods or frameworks does the organization use to identify and assess potential risks, disruptions, and impacts to its business operations, such as SWOT analysis, risk management frameworks, or scenario planning? This question focuses on understanding the approach to risk management and mitigation.
• How does the organization stay informed and anticipate future trends and disruptions that could impact its business, such as technological changes, regulations, or customer preferences? This question explores the company’s approach to horizon scanning and its alignment with the business strategy.
• What mechanisms or strategies does the organization use to capitalize on new opportunities that emerge due to changing market conditions, customer needs, or other external factors? This question aims to understand the company’s approach to identifying and pursuing opportunities for growth and innovation in a rapidly changing business environment.

Leaders can better understand their business model’s potential impacts and constraints by taking an outside-in approach and working with external experts. Scenario planning can also be used to ‘wind tunnel’ the business model and highlight vulnerabilities and opportunities.

By thinking strategically and taking advantage of available resources, leaders can make informed decisions to help their businesses thrive in an ever-changing world.

46. Are the company’s purpose and business model compatible with the rapidly changing context?

As the world around us continues to change rapidly, it is more important than ever for companies to take a strategic view of their business. One of the critical questions that senior leaders need to ask is whether the company’s purpose and business model are compatible with the changing context. The analysis stage will likely highlight significant changes to the business’s core processes, products, structure, and even its fundamental business model.

This may require a revision of the business’ values and purpose to adapt to business disruptions as usual and seize new opportunities to create commercial value by meeting society’s needs. Before moving on to strategic priorities, aligning critical stakeholders on the fundamental purpose and future business model is essential.

Taking this holistic view of how the business can create long-term value by meeting society’s needs presents an opportunity to sharpen or revise the company’s purpose. It also provides a framework for setting strategic priorities to enable the company to thrive in a changing world.

47. What are the strategic priority areas?

Leaders are responsible for setting the direction of an organization and ensuring that it remains aligned with its goals.

As such, they need to be able to answer strategic questions about the organization’s priorities.

• What are the most critical areas for the organization to focus on?
• What are the most significant transition points that need to be addressed?
• How can the organization best access opportunities and remove negative impacts?

Leaders must clearly understand these issues to make informed decisions about the organization’s future.

By asking senior leaders strategic questions, we can better understand their priorities and how they plan to address the organization’s challenges.

48. Describe trends you see in the industry. How will we evaluate those trends, and which do we need to be in front of?

Asking the right questions is critical for any leader, but working with senior leaders can be incredibly challenging.

With so much experience and knowledge, it can be challenging to know where to start. However, there are a few strategic questions that can help to get the conversation flowing.

For example, you might ask about trends that senior leaders have observed in their industry.

What are they seeing, and how will they know if the company is on the right track? This can help to open up a discussion about strategic planning and goal setting.

Additionally, you might ask about the senior leader’s experience with a particular issue or challenge. What did they learn from it, and how would they handle it differently now?

These questions can help build trust and rapport while also providing valuable insights.

49. Who will be a part of this planning process? What will be their role for the people who are a part of this process?

In strategic planning, involving the right people in the process is vital. This includes senior leaders with a wealth of experience and knowledge to share. But what questions should you ask these senior leaders to get the most out of their input? Here are a few suggestions:

• Who will be a part of this planning process? Ensuring that all key stakeholders are involved in the planning process is vital. This way, everyone will be on the same page, and there will be no surprises down the road.
• What will their role be once you have identified who will be involved in the process, it is essential to clarify their role. This will help ensure everyone understands their responsibilities and that the process runs smoothly.
• What are your goals for this planning process? Senior leaders should be able to articulate the goals of the planning process. These goals should be realistic and achievable so the planning process can succeed.

What are the potential risks and challenges associated with this plan? No plan is perfect, and it is essential to identify any potential risks or challenges associated with your strategy. This way, you can develop contingency plans or take steps to mitigate these risks.

50. How much creative dissonance vs. resonance are we seeking?

You might want to ask your senior leaders how much creative dissonance vs. resonance they seek.

• How does the organization balance the need for creative dissonance and diverse perspectives with the importance of maintaining a shared vision and strategic direction? This question focuses on understanding the approach to fostering innovation and creativity while maintaining a cohesive and aligned team.
• What mechanisms or strategies does the organization use to encourage creative dissonance and avoid groupthink, such as diverse hiring practices, open communication channels, or cross-functional collaboration? This question explores the company’s approach to building a culture of creativity and innovation.
• How does the organization evaluate and measure the effectiveness of its efforts to promote creative dissonance and ensure that diverse perspectives are being leveraged to drive innovation and growth? This question aims to understand the tactics used to track and optimize the impact of creative dissonance on business outcomes.

This question seeks to uncover how open the organization is to hearing dissenting opinions and new ideas and whether there is a preference for consensus, stimulating through argument, or creative disagreement.

If the answer is that the organization values creative disagreement, then you can be more comfortable presenting your own dissenting opinions. However, if the organization prefers creative resonance, you will need to be more careful about how you present your ideas so as not to cause undue disruptions.

By asking this question, you can better understand the organization’s culture and what role you can play in it.

51. What uncomfortable changes must the organization make in the next 5 years?

Asking difficult questions is never easy, but it’s essential if you want to get to the heart of the matter. If you’re looking for honest feedback from senior leaders, try asking them about the uncomfortable changes the organization will have to make in the next five years.

This question can help surface some hidden agendas and reveal tension within the company. It also shows that you’re interested in making tough decisions and are willing to have difficult conversations.

• How does the organization identify and prioritize the necessary changes to achieve its strategic objectives, and what criteria or metrics does it use to evaluate the urgency and impact of these changes? This question focuses on understanding the approach to change management and its alignment with the business strategy.
• What potential barriers or resistance does the organization anticipate in implementing these changes, and what strategies or tactics does it use to address or mitigate these challenges? This question explores the company’s approach to managing change and ensuring buy-in from stakeholders.
• How does the organization measure and communicate the progress and impact of these changes to employees, customers, and other stakeholders, and what mechanisms or strategies does it use to ensure that the organization stays on track with its objectives? This question aims to understand the company’s approach to change measurement and reporting and its commitment to accountability and transparency.

Asking this question can help build trust and open up lines of communication between you and senior leaders.

Planning Questions to ask leaders

52. Do you have an achievable, clear, defined, documented strategy and plan? How are you going to manage the transition?

A senior leader must have a clear and attainable strategy and plan. You must also be able to manage the transition to ensure success.

The following are strategic questions you can ask senior leaders to help them develop a successful strategy:

• What are our organization’s core values?
• What are our long-term goals?
• What is our competitive advantage?
• How will we know if we are successful?
• What are the risks and potential challenges we face?
• How do we plan to overcome these challenges?

By asking these questions, you can gain valuable insights into the senior leaders’ thought processes and help them develop a sound strategy for success.

53. Who should be part of the strategic planning process

The strategic planning process is typically led by the strategic planner, usually the top or several executives. They will need the help of a cross-functional team that should include representatives from finance, human resources, operations, sales, and other critical functions.

The process should not be limited to just senior management. If you want the plan to work, it must engage everyone to some degree.

So, while the leadership team may be more involved in final decisions, those decisions should be based on input from managers and their teams.

• What are their thoughts on the future of the business?
• What do they think your company is doing well, and where must it improve?

These are all critical questions that can help shape the company’s direction.

54. What obstacles lie in our path, and how do we remove them?

Every strategic plan will face risks and potential derailments. Some of these risks can be foreseen (for example, the internal weaknesses you discover as part of a SWOT analysis), while others cannot. This is one of the most challenging steps in developing a strategic plan, but the company’s long-term success is worth the temporary discomfort of having candid conversations.

Management teams should outline the known risks and financial impacts and articulate the mitigation plans to prevent or curtail them. Sometimes, identifying and removing one critical obstacle can make your company more profitable.

To overcome potential obstacles, it is crucial first to identify what they are. Once you have done this, you can develop a plan to remove them. You can interview employees, customers, and other stakeholders to identify obstacles. You can also review company records and data to look for trends or patterns indicating an obstacle.

Once you have identified an obstacle, you can develop a plan to remove it. This may involve changes to company policy, processes, or procedures. It may also require employee training or changes to how work is performed. Whatever the solution, it is crucial to implement it in a practical and feasible way.

55. When should we change or update our strategic plan?

A strategic plan is a roadmap for your business, so it’s essential to periodically review and update it to ensure it’s still relevant. You should always review your plan at least once a year to see if any changes in the marketplace or your industry require you to adjust your high-level goals and objectives.

• What mechanisms or processes does the organization use to monitor and evaluate the effectiveness of its current strategic plan, and how does it determine when changes or updates are necessary? This question focuses on understanding the approach to strategy evaluation and adaptation.
• How does the organization balance the need for flexibility and agility in responding to changing market conditions and customer needs with the importance of maintaining a clear and consistent strategic direction? This question explores the company’s approach to balancing short-term responsiveness with long-term vision and planning.
• What factors or events might trigger a need to revise or update the strategic plan, such as changes in market conditions, new competitive threats, or shifts in customer preferences? This question aims to understand the company’s approach to scenario planning and its commitment to remaining responsive and adaptive in a rapidly changing business environment.

You may also need to add new projects, change or update how you track KPIs or change your KPI targets. Periodic strategy refreshes allow you to keep the elements of your plan valid while making necessary changes to the parts that are not. This will help ensure that your strategic plan is always up-to-date and aligned with your business goals.

56. How often should we review progress on our strategic plan?

At the beginning of each year, organizations must review their progress on strategic plans and set up regular meetings to ensure they are on track. The frequency of these meetings depends on the goals of the review:

57. Is your organization pursuing growth and business development with as much passion as it does operational efficiency?

This question still addresses the importance of planning for the future and focuses on the sense of urgency for growth. Finding the balance between day-to-day operations and new developments is critical for your company’s future success.

Many CEOs and top executives are so focused on operational efficiency that they lose sight of the need for growth. But without growth, companies will eventually stagnate and die. The key is to find the right balance between operational efficiency and growth.

• How does the organization prioritize and allocate resources between growth and new business/market development initiatives and operational efficiency initiatives, and what metrics or criteria does it use to measure the success of each area of focus? This question focuses on understanding the approach to resource allocation and performance management.
• How does the organization promote a culture of innovation and risk-taking in pursuit of growth and new business/market development? What mechanisms or strategies does it use to ensure that employees have the necessary skills and support to drive these initiatives forward? This question explores the company’s approach to building a culture of growth and innovation.
• What mechanisms or processes does the organization use to evaluate the impact of growth and new business/market development initiatives on the company’s overall success, and how does it adjust its strategies and tactics based on these outcomes? This question aims to understand the company’s approach to managing and optimizing its growth efforts, ensuring that they align with business objectives and contribute to long-term success.

That’s why asking your senior leaders whether they are pursuing growth with as much passion as operational efficiency is essential. If not, then you need to rethink your priorities. Growth should be a top priority for any organization if it wants to survive and thrive in the long term.

Operational efficiency is essential, of course. But it’s not enough on its own. You also need to be constantly looking for new growth opportunities. Otherwise, you’re just treading water, and eventually, you’ll start to drown.

Focus questions to ask leaders

58. Will it be actively used in a structured manner to maintain focus throughout your Change Program?

Asking questions is vital to effective communication, especially regarding Change Programs. Here are some strategic questions to ask senior leaders to maintain focus and ensure successful change:

• What are the specific goals of the Change Program?
• Who is responsible for each aspect of the Program?
• What are the timeline and budget for the Program?
• What are the risks and potential roadblocks?
• How will progress be monitored and reported?
• What is the communications plan for communicating progress and changes to stakeholders?

Asking these questions from the start will help ensure everyone is on the same page and that the Change Program stays on track. By asking these questions, you can help ensure your Change Program is successful.

59. What must be done to align and commit key stakeholders to this strategy?

Getting buy-in from all key stakeholders is essential when developing a new strategy. Without alignment and commitment from everyone involved, the strategy will likely fail. So, what questions should you ask senior leaders to ensure they are on board with the plan?

• First, you need to understand what their goals and priorities are. What are they trying to achieve, and what are their biggest challenges? Once you know this, you can start crafting a strategy to help them meet their objectives.
• Next, you need to get a clear understanding of their budget. How much money do they have to invest in this new strategy, and how much leeway do they have to increase spending if necessary? This will help you to tailor your proposals accordingly.
• Finally, it would help if you determined their timeframe for implementing the new strategy. Are they looking for immediate results, or are they willing to give it some time to bed in? This will affect the type of strategy you recommend.

By asking these questions, you can ensure that you have the senior leaders’ total commitment before moving forward with your plans.

Decentralization questions to ask leaders

60. How do we make our strategic plan flexible to allow for changes?

Leaders are constantly asking themselves how they can improve their organization.

One way to do this is to develop a strategic plan. This document provides a road map for where the organization wants to go and how it intends to get there. However, even the best-laid plans can go off course. That’s why ensuring that your strategic plan is flexible enough to accommodate changes is essential. A strategic plan’s three elements should be regularly updated: goals, measures, and projects.

Goals should be reviewed every one to five years to ensure they are still relevant and realistic. Measures should be updated every six to 24 months to ensure they are aligned with the goals. Projects should be reviewed quarterly to ensure they are still on track. If any changes need to be made to a project, such as an adjustment to the budget or end date, this can be done at the quarterly review. Regularly reviewing and updating your strategic plan ensures it remains relevant and responsive to changes. This will help you continue progressing towards your goals, even when things don’t go exactly as planned.

61. Do we have the proper governance in place?

The current ways of setting goals for each person and each department must be in line with the overall goal and strategy, making sure that the right metrics, indicators, and decision-making tools are used.

• How does the organization define and evaluate the effectiveness of its current governance structure, such as its board of directors, executive leadership team, or internal committees? This question focuses on understanding the approach to governance and its alignment with the company’s strategic objectives.
• What mechanisms or strategies does the organization use to ensure that its governance practices are transparent, accountable, and aligned with best practices in the industry? This question explores the company’s commitment to responsible and ethical governance.
• How does the organization adapt its governance structure and practices in response to changing market conditions, regulatory requirements, or other external factors that may impact the company’s operations or reputation? This question aims to understand the company’s approach to risk management and mitigation and its commitment to continuous improvement and adaptation.

Boards are ultimately accountable for the business’s performance, impact, risks, and disclosure. Many boards need to be equipped to lead and scrutinize the business’ ambitions and plans.

Many leaders have established an advisory board with external expertise to provide expertise, scrutiny, and guidance.

62. What is the difference between strategic and operational work plans?

A strategic plan is built on a long-term vision for your company’s future. It typically looks out three to five years, involves your key goals, and is broad-reaching across your organization.

An operational work plan tends to be an annual plan for a division or department. It is built with a budget and lists the key activities you commit to executing in a particular year.

• How does the organization define and differentiate between strategic work plans designed to achieve long-term goals and objectives and operational work plans focused on day-to-day operations and processes? This question focuses on understanding the organization’s planning approach and alignment with business strategy.
• What mechanisms or processes does the organization use to ensure that strategic and operational work plans are integrated and aligned with one another, and how does it balance short-term operational needs with long-term strategic goals? This question explores the company’s approach to balancing tactical and strategic planning.
• How does the organization measure and evaluate the success of its strategic and operational work plans? What mechanisms or strategies does it use to adjust these plans as necessary to ensure continued progress toward its goals? This question aims to understand the company’s approach to performance management and continuous improvement and its commitment to agility and adaptation.

Many companies mistakenly treat their strategic and operational plans as two separate entities. However, the most successful businesses are holistic, linking their long-term vision with annual targets. By aligning your operational work plan with your strategic plan, you can ensure that everyone in your organization is working towards the same goals. This can help increase efficiency and avoid duplication of effort.

It can also help keep your team focused and on track, leading to better results in the long run. So, if you want your business to thrive, link your strategic and operational plans.

Ownership and Accountability Questions to Ask Leaders

63. Could you describe the role and accountability you expect from me?

As a senior leader, being clear about the role you expect someone to play on your team is essential. This will help them know what is expected of them and hold them accountable for meeting those expectations. When discussing the role with a potential team member, ask strategic questions to help clarify the expectations.

For example, you might ask how they see themselves contributing to the team’s success or what kind of experience they have in similar roles.

By asking the right questions, you can ensure that everyone on your team is aligned and working towards the same goal.

64. Do you have a stakeholder map?

Creating a stakeholder map is one of the most important things you can do when developing a strategy. This will help you identify all the individuals and groups with a stake in your plan and their particular interests.

Once you know your stakeholders, you can develop relationships with them and address their concerns. Additionally, you can use your stakeholder map to identify potential allies and opponents and develop strategies for dealing with them.

By creating a stakeholder map, you can ensure that your strategy considers the needs of all of your key constituents.

If you’re a senior leader in an organization, it’s essential to ensure everyone is on the same page regarding what the organization is trying to achieve. This means having a clear and attainable goal that everyone can rally behind. Without this, it’s easy for people to get frustrated and disengaged with their work.

Asking everyone in the organization whether they understand its goals and how they fit into them is an essential first step in ensuring everyone is aligned and working towards the same thing. Additionally, leaders must be open to employee feedback and suggestions about how the organization can improve.

By soliciting employee input, leaders show that they value their opinions and are willing to listen to new ideas. This creates a more collaborative environment where people feel invested in their work and are more likely to be productive. Ultimately, asking these strategic questions can help create a more efficient and effective organization.

66. Does everyone in the organization know how their job or role contributes to accomplishing this vision?

Everyone in any organization must understand how their job contributes to the company’s vision. Without this knowledge, it can be challenging to maintain a cohesive and motivated workforce. As a result, one of the most critical questions that senior leaders can ask is whether everyone in the organization knows how their job fits into the larger picture.

This question can help ensure everyone is on the same page and working towards the same goal.

Additionally, it can be helpful to ask whether the current organizational structure effectively achieves the vision. If not, senior leaders must consider changing the structure to better align it with the company’s goals.

By asking these strategic questions, senior leaders can ensure that they take proactive steps to achieve success.

67. What more can I do in my role to help achieve this goal?

Good leaders know that the key to success is setting and achieving goals. But what happens when you reach the top and have nowhere else to go?

For many people, this can be a challenge. After all, staying motivated and avoiding stagnation can be difficult once you’ve achieved a certain level of success. This is why it’s so important for senior leaders to regularly ask themselves strategic questions to help them stay on track and continue progressing.

One such question is, “What more can I do in my role to help achieve this goal?” Asking this is about getting your CEO’s feedback, presenting information about yourself, and underlining your commitment to the company.

By showing that you’re willing to go above and beyond what’s expected of you, you’ll motivate yourself and inspire others to do the same. So if you’re looking for a way to stay ahead of the competition, asking yourself this question is an excellent place to start.

68. Are your employees committed to helping each other?

A company leader must ensure that employees work together effectively. After all, teamwork is essential for achieving company goals, improving the workplace, and boosting productivity. Consider conducting anonymous surveys to understand whether your employees are helping each other.

This will help you identify potential communication issues or challenges within your team. If you want to improve employee collaboration, consider hosting team-building exercises. These can help boost morale and develop trust and teamwork skills among team members.

• How does the organization promote and incentivize employee collaboration and teamwork, and what mechanisms or strategies does it use to foster a sense of shared purpose and commitment to common goals? This question focuses on understanding the company’s approach to building a culture of collaboration.
• What metrics or criteria does the organization use to measure the effectiveness of its employee collaboration initiatives, and how does it adjust its strategies and tactics based on these outcomes? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its commitment to employee collaboration and teamwork is aligned with its broader business objectives, and what mechanisms or processes does it use to ensure that collaboration efforts contribute to the company’s overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that employee collaboration efforts are aligned with business strategy.

By taking these steps, you can encourage your employees to work together more effectively and achieve success as a company.

69. Does the organization hold its leaders accountable for delivering targeted results appropriately?

If an organization is not seeing the results it wants, it may be time to start asking some tough questions of the senior leaders.

• Does the current leadership team have the skills and experience necessary to deliver the desired results?
• Are they held accountable for their performance? If not, why not?
• What processes are in place to ensure that leaders make decisions that align with the organization’s goals?

Asking these types of questions can help you get to the root of any problems and develop a plan for moving forward.

By taking a strategic approach to senior leadership, organizations can ensure they are on track to achieve their goals.

Communication questions to ask leaders

70. Who will play the part of the Business Change Manager(s) who are in charge of achieving the benefits of the strategy [typically chosen from the organization’s change-affected areas and most likely to be senior departmental management]?

Coming up with the right strategy for your business can be difficult. But once you’ve got a plan in place, asking the right questions is essential to ensuring it’s executed effectively.

• For example, who will be responsible for driving the changes laid out in the strategy?
• What will departmental managers need to be involved in?
• What resources will be required?

By asking these questions, you can help ensure that your strategy is implemented smoothly and that the desired results are achieved.

71. Have these roles [and the names of those undertaking them] been communicated to staff?

Senior leaders must be on the same page regarding roles and responsibilities. Have these roles been communicated to staff? If not, why not?

Without clear communication from the top, it can be difficult for employees to know who to approach with questions or concerns. Furthermore, it can lead to confusion and frustration if staff members are unsure who is responsible for what.

By asking this question, you can help ensure that everyone is on the same page and knows who to go to with various issues.

72. Are these strategies, plans, and objectives fully communicated to all staff?

As a senior leader, you must ensure that your strategy, plan, and objectives are fully communicated to all staff. Otherwise, you risk losing the buy-in and support of your team. To help make sure that everyone is on the same page, consider asking the following questions:

• What is our strategic vision?
• What are our long-term goals?
• What are our shorter-term objectives?
• Who is responsible for each element of the strategy?
• How will we know if we’re successful?
• When do we need to review and adjust our strategy?

By asking these questions, you can help to ensure that your team is aligned and focused on achieving your organization’s goals.

73. Do you have a two-way communications plan?

As a leader, it is vital to communicate effectively with your team to ensure everyone is on the same page and working towards the same goal.

• One way to do this is to develop a two-way communication plan. This communication plan allows for a back-and-forth exchange of information and feedback between you and your team. This way, you can ensure that everyone understands the project’s goals and their role in achieving them.
• Additionally, a two-way communication plan can help build trust and rapport within your team.

By listening to your team’s concerns and suggestions, you can show that you value their input and are committed to working together towards a common goal.

74. What are the feedback mechanisms and processes that are going to make this a two-way communication process? What are the processes that will ensure they are informed about the use of their feedback to influence the program?

It is essential to ensure that you maintain open communication with your senior leaders. This can be achieved by asking them strategic questions that will help gauge their engagement and commitment to the program.

Some examples of such questions include:

• ‘What are your thoughts on the progress of the program so far?’
• ‘What are the key challenges and opportunities facing the program in the coming months?’
• ‘What are your expectations for the program’s outcome?’

By asking these questions, you will gain valuable insights into how senior leaders view the program, and you can use this information to make adjustments where necessary.

In addition, these questions will help to build a foundation for future collaboration and cooperation between you and your senior leaders.

Are key internal stakeholders, strategy, and business planning teams engaged early on?

When crafting a company’s purpose and strategy, senior leaders must be engaged early on in the process. This will help to ensure that the business owns the strategy and that key stakeholders are committed to it.

• How does the organization identify and engage key internal stakeholders, such as department heads, team leaders, and subject matter experts, in the business planning process, and what mechanisms or strategies does it use to ensure that their input is integrated into the planning process? This question focuses on understanding the organization’s stakeholder engagement and collaboration approach.
• What mechanisms or processes does the organization use to ensure that its strategic planning and business planning teams have access to the information and resources necessary to make informed decisions and develop effective strategies? This question explores the company’s approach to data management and knowledge sharing.
• How does the organization ensure that its business planning process is aligned with its broader strategic objectives, and what mechanisms or strategies does it use to ensure that its planning efforts contribute to the company’s overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that business planning efforts are aligned with business strategy.

The best way to engage senior leaders is through workshops, one-to-one, and virtual meetings. Online platforms can also be used to consult with and engage a broader range of colleagues.

By engaging senior leaders early on, businesses can craft a purpose and strategy that everyone is committed to.

75. How well are we communicating our value proposition to the market?

Leaders of successful organizations are always looking for ways to improve. Asking questions is crucial to this process, allowing leaders to gather feedback and identify improvement areas. Senior leaders can ask a few strategic questions when communicating the value proposition.

• First, how well are we conveying our message to the market?
• Are we using clear and concise language that accurately reflects our brand?
• Second, what kind of reaction are we getting from the market?
• Are potential customers engaging with our message or tuning us out?
• Finally, what can we do to improve our communication strategy?
• Can we make any changes to better connect with our target audience?

By asking these questions, leaders can better understand how effective their communication strategies are and make the necessary adjustments to drive results.

Culture questions to ask leaders

76. Are you adapting your culture and capacity?

Leaders of organizations face many challenges in light of the COVID-19 pandemic. As such, they need to be strategic in their thinking and decision-making. The following are three critical questions that senior leaders should ask themselves to ensure that their organization is best positioned to respond to the crisis:

• First, are we adapting our culture and capacity? Current working practices, such as new product development, may need to be prioritized and adapted to reflect the purpose and strategy. Doing so reduces friction, optimizes decision-making, and realizes opportunities.
• Secondly, do we have the right skills and capabilities in place? The purpose and strategy will likely require new skills and capabilities from colleagues. Staff groups must be identified and prioritized, and plans will be implemented to build their capacity, such as best-practice sharing forums. Finally, are our communications effective?

Internal and external communications will need to reflect the purpose and strategy. A transparent, two-way, honest, and humble tone effectively builds credibility and rapport with stakeholders.

By asking these questions, senior leaders can ensure that their organization is well-positioned to respond effectively to the challenges posed by COVID-19.

77. Does our organization promote itself through its people? Do the people actively promote our organization?

As a result, companies need to ask themselves whether their organization promotes itself through its people.

• Do the employees actively promote the company?
• Are they given opportunities to do so?
• Do they feel proud to work for the organization and feel that their work is meaningful? If the answer to these questions is “no,” the company has some work to do to make its employees their best proponents.

Encouraging employees to promote the company actively can be done in several ways, such as by providing opportunities for them to share their experiences with others, offering referral incentives, or simply making sure they feel proud to work for the organization.

Companies can guarantee that those who are most passionate about their message will promote it by making use of this useful resource.

78. Have we identified the areas of cultural dissonance?

In any organization, there will always be some degree of cultural dissonance. Differences in values, beliefs, and attitudes will always exist between different groups. Senior leaders must be aware of these differences and take steps to address them. Otherwise, they risk causing strife and division within the company.

One way to identify areas of cultural dissonance is to ask strategic questions. For example, leaders can ask employees what they think the company could do better. They can also ask employees about their experiences with discrimination or harassment. By asking these types of questions, leaders can better understand the areas of tension and how to address them.

Of course, it’s not enough to ask these questions; leaders must also be willing to listen to the answers and take action. Senior leaders hope to create a more cohesive and productive workplace by addressing cultural dissonance.

Strategic Questions to Ask Leadership

79. How will you engage and motivate your team?

Engaging and motivating your employees is crucial because it can help increase the company’s productivity. When answering this question, it can be helpful to understand what best motivates your employees, including incentive programs, bonuses for exceptional work, or a supportive work environment.

If you’re unsure what best motivates your employees, try using multiple techniques and periodically measuring their effectiveness. If you notice that employees are more receptive to one of them, that might be the best technique to use for the foreseeable future.

• How does the organization promote a culture of employee engagement and motivation, and what mechanisms or strategies does it use to ensure that employees feel valued, supported, and motivated to contribute to the company’s success? This question focuses on understanding the company’s approach to building a positive work environment.
• What mechanisms or processes does the organization use to measure and evaluate employee engagement and motivation, and how does it adjust its strategies and tactics based on these outcomes? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to employee engagement and motivation is aligned with its broader business objectives? Which mechanisms or strategies does it use to ensure employee engagement efforts contribute to its overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that employee engagement efforts are aligned with business strategy.

It’s also possible that some employees may prefer an incentive program, while others prefer bonuses for exceptional work. If that’s the case, it might be helpful to implement both programs to ensure that all employees feel motivated.

Ultimately, engaging and motivating your team can create a positive work environment that increases productivity.

80. Who will be the strategy director with overall strategic leadership and ultimate accountability for the strategy [reporting to the board]?

A key question for any board regarding strategy is who will oversee and execute the plan. Too often, a lack of a clear leader with ultimate accountability leads to a lack of focus and direction. For the strategy to be successful, it is essential to have a Strategy Director who reports directly to the board.

This individual should have a strong vision for the future of the organization and the ability to rally others around a common goal. Additionally, the Strategy Director should have experience leading complex initiatives and be able to navigate organizational politics. With the right person in place, the organization can confidently move forward.

Asking the right questions is crucial to developing an effective organizational strategy. When crafting questions for senior leaders, it is crucial to focus on critical areas such as accountability, responsibility, and measurable goals.

• Who will be accountable for executing the strategy?
• Who will be responsible for leading and overseeing the strategy process?
• What specific goals does the organization hope to achieve with this strategy?

By answering these and other vital questions, organizations can ensure that their strategy is well-defined and actionable. Only then can they hope to achieve their desired results.

Strategic Skills to ask leaders

81. How will you train and develop our teams?

How will you train and develop our teams?

Senior leaders must think about how they will train and develop their teams. How employees are trained can significantly impact how well they learn and perform their job duties. Employees might prefer different learning methods, so offering various training options is important.

For example, some team members might prefer a trainer to walk them through the company’s process step-by-step, while others might prefer a hands-on approach, learning and developing as they work.

When answering this question, it’s helpful to talk with your employees and determine their preferred learning method. If possible, consider using multiple training methods to ensure each one of your employees can grow and develop efficiently.

However, it’s also important to consider training costs and how they will fit into the budget. Training can be expensive, so leaders need to ensure they get the most bang for their buck.

By carefully considering these factors, leaders can develop a training plan that meets the needs of their employees without breaking the bank.

82. Do we have the in-house skills to do this properly?

Leaders are often so focused on the day-to-day tasks of running a company that they can lose sight of the big picture. Asking strategic questions can help leaders make better decisions, set priorities, and allocate resources efficiently.

However, not all questions are equally valuable. When posing a question to a senior leader, it is essential to ensure that it is relevant, clear, and concise. Otherwise, you risk overwhelming them with information or wasting their time. With that in mind, here are three strategic questions to ask senior leaders:

• What are our top priorities?
• What are our biggest challenges?
• What are our strengths and weaknesses?

Asking these questions can help to focus a leader’s attention on the most critical issues facing their company. By understanding where their priorities lie, they can make more informed decisions about allocating their time and resources.

Additionally, identifying challenges early on can help prevent them from becoming more significant problems. Finally, understanding their company’s strengths and weaknesses can help leaders decide where to invest their resources. Ultimately, asking strategic questions is essential to being an effective leader.

Strategy Execution questions to ask leaders

83. What strategic objectives need to be achieved to realize these ambitions?

Any organization, whether for-profit or nonprofit, needs to have a clear understanding of its strategic objectives. These objectives are the long-term goals that the organization wants to achieve.

They should be specific, measurable, achievable, relevant, and time-bound. Without a clear understanding of these objectives, it will be difficult for the organization to make decisions and allocate resources in a way that will lead to success.

Asking strategic questions is one of the most important things senior leaders can do when setting objectives. By taking a critical and analytical approach to setting goals, senior leaders can ensure that the organization is on track to achieve its ambitions.

Questions such as:

• What strategic objectives need to be achieved to realize these ambitions?” and
• “To what extent are these objectives realistic?” can help senior leaders identify potential risks and roadblocks associated with achieving their goals.

By asking these questions, senior leaders can develop a clear and actionable plan for success.

84. Where are the gaps between now and where do we want to be?

Any leader worth their salt is always looking for ways to improve and grow personally and professionally. However, it can be challenging to identify areas of improvement without some guidance. Asking senior leaders strategic questions is a great way to gain insights into areas of opportunity.

• For example, asking a senior leader, “Where are the gaps between now and where we want to be?” can help identify areas where the company may fall short.
• Similarly, asking, “What are our biggest challenges?” can help surface pressing issues that must be addressed.

By asking thoughtful questions, you can gain valuable insights that can help move your company forward.

85. What steps are needed to close the gaps? What are the implications of this?

Asking questions is a fundamental part of any leader’s toolkit. However, not all questions are created equal. When talking to senior leaders, it’s vital to ask strategic questions that will help move the conversation forward.

One question that can be helpful is, “What steps are needed to close the gaps?”

This question forces leaders to identify the specific actions that need to be taken to achieve their goals. It also forces them to consider the implications of those actions, which can help prevent unintended consequences.

Asking strategic questions like this can help ensure meaningful conversations are productive and focused on moving forward.

86. What supporting tactics must be implemented to achieve these objectives?

There is no substitute for sound strategic planning for setting and achieving business objectives.

However, all too often, organizations focus exclusively on the big-picture goals while neglecting the details of how those goals will be achieved. As a result, senior leaders may find themselves scrambling to put together a last-minute plan when it becomes clear that the initial strategy is not working.

To avoid this situation, asking a few key questions upfront is essential.

• What specific steps need to be taken to achieve the desired outcome?
• What resources will be required?
• What potential obstacles could get in the way?

By answering these questions, senior leaders can develop a more comprehensive and effective strategy that sets their organization up for success.

87. Do you know the tasks, steps, and processes to get from where we are now to where we want to be?

Asking the right questions is essential for leaders who want to bring their team to the next level. When it comes to senior leaders, a few key questions can help create a strategic plan for success.

First, it is essential to ask what the desired outcome is. What is the company trying to achieve, and how will it know if it has been successful?

Once the goal has been established, leaders must ask what resources are available and what constraints must be considered. With a clear understanding of the situation, leaders can develop a plan considering all of these factors.

Senior leaders can set their teams up for success by asking the right questions.

88. Have you identified, for each step, the implications, issues, and exposures that have to be addressed to progress to the next step?

Senior leaders must provide answers to a number of questions prior to successfully implementing any strategy. First, it is essential to identify the goals the strategy is trying to achieve. Without a clear understanding of what is trying to be accomplished, it will be challenging to develop an effective plan.

Once the goals have been identified, the next step is determining who will be responsible for each aspect of the strategy. It is also essential to consider what resources will be required and whether or not they are available. Additionally, thinking about what could go wrong and how to mitigate any potential risks is necessary.

By asking these types of questions, senior leaders can ensure that they have considered all of the factors that could impact the success of their strategy.

89. How will you know how you’re doing?

How will you know how you’re doing? It’s a question we often ask ourselves, but it’s also one we should ask our senior leaders. In today’s business world, staying ahead of the competition is more important than ever, which means constantly looking for ways to improve.

Asking your senior leaders how they plan to measure success is a great way to start.

• What metrics will they be using?
• How often will they be reviewed?
• What targets do they need to hit?

Answering these questions can help ensure that your team is focused on the right things and making progress toward your company’s goals.

Asking tough questions shows that you’re invested in your company’s success and want to be part of a winning team. So don’t be afraid to ask the tough questions; it could be the key to taking your career to the next level.

90. Have you analyzed, categorized, and prioritized the issues arising across all functional areas impacted by the transition? – Strategic Questions to Ask Senior Leaders

Leaders at all levels need to be able to think strategically to make the best decisions for their organizations.

However, senior leaders face unique challenges in identifying and addressing these issues. They need to see the big picture and understand how all the pieces fit together. In addition, they must be able to ask the right questions to get the information they need to make informed decisions. Here are three strategic questions that senior leaders can use to get started:

• What are the most critical issues facing our organization?
• How will this decision impact our stakeholders?
• What are the risks and opportunities associated with this decision?

Asking these questions can help senior leaders better understand their organizations’ issues and make more informed decisions.

91. Have you documented what differences should be noticeable between now and the close of the change program? – Strategic Questions to Ask Senior Leaders

Asking the right questions is crucial to the success of any change program. When working with senior leaders, it is crucial to ask strategic questions that will help to ensure that the program is on track and achieving its desired outcomes. Here are some examples of questions that can be helpful to ask:

• What are the goals of the change program?
• What are the key milestones that need to be achieved for the program to be considered a success?
• What are the biggest challenges that must be overcome to achieve these goals?
• Who is responsible for each aspect of the change program?
• What resources are needed to make the program a success?
• What risks are associated with the change program, and how can they be mitigated?
• What communications plans are in place to keep stakeholders informed about the program’s progress?

Asking these questions will help you better understand the change program and its chances for success. Doing so can ensure that you do everything possible to support the program and its success.

Core Competency questions to ask leaders

92. What capabilities and competencies do we need to deliver this distinct customer value proposition?

Organizations must have the right capabilities and competencies to deliver a distinct customer value proposition. Here are some strategic questions senior leaders can ask to ensure their organization has what it takes:

• What customer needs does our proposed value proposition address?
• What problems are we solving for our customers?
• What is our unique selling proposition?
• Who are our target customers?
• What are our core competencies?
• Do we have the necessary capabilities in-house, or do we need to outsource or partner with someone who has them?
• How will we reach our target market?
• How will we generate demand for our products and services?
• What is our pricing strategy?
• How will we measure success?

93. How efficient and organized is your organization’s plan to improve and evolve its strategic objectives over time?

How efficient and organized is your organization’s plan to improve and evolve its strategic objectives over time?

This is an important question to ask senior leaders in your company to gauge the company’s future success. Having a plan for the future is not enough; it must be structured, logical, and well-communicated to help direct your company.

A company’s strategic objectives should be reviewed and updated regularly to ensure they are still relevant and achievable. Furthermore, all employees must know the objectives and how their work fits into the bigger picture.

By asking this question, you can understand how well your company is prepared for the future and whether or not you need to make any changes.

94. How efficient is our organization from an operational standpoint? – Strategic Questions to Ask Senior Leaders

From an operational standpoint, asking your senior leaders how efficient your organization is is a great way to determine the reasons behind your current strategy’s success or lack thereof.

Your company can identify key process improvements by discovering the operational inefficiencies inhibiting success. This will help you determine if your current strategy is effective and what changes must be made to make it more successful.

By constantly evaluating and improving your organization’s efficiency, you can ensure that your company is continually operating at its best.

95. How well does our organization utilize its people as an asset to help it improve, stay competitive, and strategically meet goals? Are people used efficiently, or is talent wasted due to an ineffective strategy?

To develop an effective strategy, asking the right questions is essential. Regarding senior leaders, some key questions are: how well does our organization utilize its people as an asset? Are people used efficiently, or is talent wasted due to ineffective strategy?

By examining these factors, you can develop a plan to optimize your company’s resources, including its people’s most valuable assets. And, by maximizing the talents and skills of your employees, you can set your company up for success now and in the future.

96. To what extent have these capabilities been developed in our organization? – Strategic Questions to Ask Senior Leaders

Senior leaders must ask the right questions when developing a strategy to make informed decisions.

Some essential questions include:

• What are our organization’s core values?
• What are our strengths and weaknesses?
• What is our competitive landscape?
• What are our customers’ needs and wants?

By answering these questions, leaders can clearly understand their organization’s unique position and what must be done to succeed.

Additionally, these questions can help surface any potential risks that could threaten the organization’s success. Senior leaders can set their organization up for success by asking these strategic questions.

97. What are their distinctive or competitive advantages compared to ours?

It can be challenging to engage with senior leaders as young leaders. Fortunately, there are a few strategic questions that can help to break the ice and get a meaningful conversation started. One question is their distinctive or competitive advantages compared to your organization.

This can help you to understand their perspective and what they see as their key strengths. Another question to ask is what their biggest challenges are. Additionally, this can help you to identify areas where you may be able to offer assistance or collaboration.

By asking these questions, you can build relationships with senior leaders and foster a spirit of cooperation within your organization.

98. What is working well within the organization – that can be left alone?

Many organizations operate under the philosophy that if it isn’t broken, don’t fix it. This can be a good thing, as it can prevent change for the sake of change and unnecessary disruptions to staff and operations.

However, it can also lead to stagnation and a failure to adapt to new circ*mstances. As a result, it is vital for senior leaders to periodically ask themselves what is currently working well within the organization and what might need to be changed.

This can help to ensure that the organization remains agile and responsive to the ever-changing needs of its staff, customers, and other stakeholders. It can also help identify potential improvement areas, which can be addressed through targeted action plans.

By regularly asking these types of strategic questions, senior leaders can help keep their organizations moving forward positively.

99. What areas of the company are distinct, unique, or particular?

Many organizations operate under the philosophy that if it isn’t broken, don’t fix it.

This can be a good thing, as it can prevent change for the sake of change and unnecessary disruptions to staff and operations. However, it can also lead to stagnation and a failure to adapt to new circ*mstances.

As a result, it is vital for senior leaders to periodically ask themselves what is currently working well within the organization and what might need to be changed.

This can help to ensure that the organization remains agile and responsive to the ever-changing needs of its staff, customers, and other stakeholders. It can also help identify potential improvement areas, which can be addressed through targeted action plans.

Questions For Senior Leaders to Ask Themselves

• How does the organization define and measure its areas of distinctiveness or uniqueness, and what mechanisms or strategies does it use to ensure that these areas remain competitive and relevant in the marketplace? This question focuses on understanding the company’s approach to identifying and promoting its areas of strength.
• What mechanisms or processes does the organization use to ensure that its areas of distinctiveness or uniqueness are aligned with its broader business objectives, and what role do these areas play in the company’s overall strategic plan? This question explores the company’s approach to strategic alignment and its commitment to ensuring that areas of distinctiveness or uniqueness are leveraged to support business strategy.
• How does the organization communicate its areas of distinctiveness or uniqueness to key stakeholders, such as customers, investors, and employees, and what mechanisms or strategies does it use to ensure that these stakeholders understand the value proposition of the company’s offerings? This question aims to understand the company’s marketing and brand management approach and its commitment to effective stakeholder communication.

By regularly asking these types of strategic questions, senior leaders can help keep their organizations moving forward positively.

Strategic KPI questions to ask leaders

100. How can we organize and track strategic planning information and data?

In the fast-paced and constantly evolving world of business, strategic planning is critical to the success of any organization. However, gathering and organizing the information and data needed for strategic planning can often be challenging. This is why it is crucial to ask business leaders the question, “How can we organize and track strategic planning information and data?”

By doing so, we can gain insights and ideas from those who understand the business’s complexities and have strategic planning expertise. With their input, we can develop effective strategies that are based on reliable information and ensure that our plans are organized and monitored in a way that allows for adjustments and alterations as needed.

Ask them these three strategic questions to get more from your senior leaders.

• How can we better organize and track our strategic planning information and data?
• What processes do we need to ensure that our strategy is executed effectively?
• And finally, how can we continuously improve our strategy to remain relevant and responsive to our ever-changing environment?

By asking these questions, you’ll get insights into how your leaders think about strategy and uncover areas where there may be room for improvement.

Ultimately, asking this question can help us stay agile and responsive in an ever-changing business landscape. So go ahead and ask away; your company’s future success may depend on it.

101. How many measures should our strategic plan include?

No matter what level you’re at in your organization, it’s crucial to have a strategic plan in place. But how many measures should that plan include?

I recommend 5–10 measures at each level, from the enterprise to the division and department levels. This ensures that everyone stays focused on what’s essential and can review critical data in meetings without distraction or fatigue.

Of course, this could leave your company with hundreds of measures, but you don’t need to review them every quarter. Just focus on the information critical to your strategy in your department or division.

And use common sense—if a measure isn’t relevant to you, there’s no need to review it. By following these guidelines, you can ensure that your strategic plan is comprehensive and manageable.

102. Do we, or should we, use a balanced scorecard?

The Balanced Scorecard has proven to be a powerful and time-honored way to plan and execute strategy.

Regardless of whether you stick to the Norton-Kaplan methodology or use a variation, understanding the basic principles of a BSC—having clear goals, linking your projects to those goals, and setting up leading and lagging indicators—could help your strategy immensely.

And for any strategic planning model to work, you must have the right goals and a way to measure and achieve them.

103. How do we measure success? What key metrics should the leadership team regularly monitor to ensure that the organization is on track and progressing toward achieving its goals?

Asking business leaders how they measure success is crucial for any organization to ensure that it stays on track toward its goals. Identifying key metrics that the leadership team can regularly monitor to gauge the organization’s progress is important.

Without clear metrics, it is difficult to tell if the organization is progressing toward its objectives or struggling to keep up. With these metrics in place, leaders can fine-tune their approach and take proactive measures to keep the organization moving forward.

Ultimately, asking these questions keeps organizations accountable and focused on achieving their goals:

• How does the organization define success and determine which metrics to measure progress toward achieving its goals, and what mechanisms or strategies does it use to ensure that these metrics align with its broader business objectives? This question focuses on understanding the company’s performance management and measurement approach.
• What mechanisms or processes does the organization use to track and report on key metrics, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to measuring success is aligned with its broader business objectives, and what mechanisms or strategies does it use to ensure that its performance management efforts contribute to its overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that performance management efforts are aligned with business strategy.

These are all critical questions to ask when crafting a strategy, but they’re significant when communicating it to senior leaders. Your answers to these questions will help senior leaders understand what you’re trying to achieve and why it’s crucial.

But more than that, they’ll also help to build buy-in and support for your strategy. After all, no one will want to invest time and resources in a strategy that doesn’t align with their values or doesn’t make sense for the business. By clearly articulating the goals of your strategy and how they fit into the larger picture, you can increase the chances of getting buy-in from senior leaders.

104. What is the best way to measure our progress?

As you develop and implement a company strategy, measuring its progress is essential because it can help you determine if the strategy is working or if you need to make adjustments.

For example, suppose a company aims to increase its sales by 30% over one year, but its current monthly sales average predicts that sales will only increase by 20%. In that case, the company knows that it won’t meet the objective unless it makes adjustments.

Many great ways to measure progress include monthly check-ins and status reports from company departments. However, determining the best way to measure a company’s progress can often depend on the company itself.

For example, checking in monthly with each department might be the best way to measure progress if a company only has a few departments. On the other hand, tracking key performance indicators (KPIs) might be a better option if a company is large and has many moving parts.

No matter what method you choose, tracking progress is essential to ensuring that your company’s strategy is on track.

105. What metrics must we monitor to measure the progress and success of this strategy? Are these metrics purely financial, or has the leadership team determined the root causes and contributing factors leading to solid financial results?

Asking business leaders the question of what metrics they must monitor to measure the success of a strategy may seem like just another box to tick off in meetings. Still, in reality, it is a crucial step toward understanding the very foundation of the strategy.

Leaders must examine financial metrics and consider the root causes and contributing factors leading to solid financial results. Addressing these underlying issues is key to sustained success, rather than just achieving short-term gains.

When developing and implementing a successful strategy, there are a few key questions that senior leaders need to ask themselves.

• First, what metrics will be used to measure progress and success? Are these metrics purely financial, or have the root causes and contributing factors been considered?
• Second, how will the team know if the strategy is working?
• What are the benchmarks and thresholds that need to be met?
• Finally, what are the risks and potential roadblocks associated with this strategy?

By asking this question, leaders can gain a deeper understanding of the strategy and ensure that it aligns with the company’s values and goals for the long term. Ultimately, monitoring the right metrics and addressing the root causes of success will lead to sustainable growth and a thriving business.

106. Do we set evidence-based targets?

In the world of business, setting targets is an essential part of achieving success. However, setting targets without robust evidence can be a recipe for disaster. That’s why it’s vital to ask business leaders whether they set evidence-based targets.

This question can help eliminate guesswork and ensure businesses pursue their objectives based on reliable data. By setting evidence-based targets, businesses can improve decision-making, establish clear benchmarks for success, and ultimately achieve their goals. Additionally, businesses can better understand their operations and identify areas of improvement by analyzing evidence-based data.

It can be helpful to think of questions you can ask senior leaders to gauge how well they are doing in terms of sustainability.

A few examples of such questions are:

• How does the organization determine which targets to set and how to measure progress toward achieving them, and what mechanisms or strategies does it use to ensure that these targets are evidence-based and aligned with its broader business objectives? This question focuses on understanding the company’s goal-setting and performance management approach.
• What mechanisms or processes does the organization use to collect and analyze data, and how does it use this information to set and adjust targets over time? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to setting targets is aligned with its broader business objectives, and what mechanisms or strategies does it use to ensure that its performance management efforts contribute to the company’s overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that target-setting efforts are aligned with business strategy.

By asking these questions, you can better understand whether the company is on track to achieve its sustainability goals. If not, it may be necessary to make some changes to get back on track. Either way, these questions can help spark meaningful conversations about sustainability within the company.

Ultimately, asking business leaders if they set evidence-based targets can help ensure that businesses are heading in the right direction, making informed decisions, and maximizing their potential.

Strategic Benefits: The Why: Questions to ask leaders

107. Do you have planned processes to put in place to ensure that these benefits are achieved?

Asking business leaders if they have planned processes to ensure the achievement of benefits is crucial for the success of any enterprise.

Even the most promising business ideas can fail to deliver the desired results without proper planning. Leaders with a roadmap to achieve the benefits they seek are more likely to realize their goals promptly and efficiently. Knowing the steps that will be taken to tackle potential roadblocks, monitor progress, and adjust strategies accordingly is key to maintaining momentum and achieving objectives.

So, whether it’s increasing revenue or improving customer satisfaction, it’s important to ask business leaders if they have thought through their processes to achieve these benefits.

Questions to ask:

• How does the organization plan and implement processes to achieve its desired outcomes, and what mechanisms or strategies does it use to ensure that these processes are effective and aligned with its broader business objectives? This question focuses on understanding the company’s process improvement and change management approach.
• What mechanisms or processes does the organization use to monitor and evaluate the effectiveness of its processes, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to process improvement is aligned with its broader business objectives, and what mechanisms or strategies does it use to ensure that process improvement efforts contribute to the company’s overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that process improvement efforts are aligned with business strategy.

By asking these questions, you can help ensure that the leader understands what needs to be done to meet the organization’s objectives.

108. Do you have a mechanism for measuring the improvements arising from the realization of each benefit? Are these benefits communicated to staff?

When it comes to benefit realization, good communication is critical. Senior leaders need to be kept in the loop about the improvements due to the benefit realization process.

Furthermore, they need to be able to measure these improvements to determine whether the process is truly effective. Without these two elements, it will be difficult for senior leaders to realize the value of the benefits and buy into the process.

• How does the organization define and measure the improvements resulting from the realization of each benefit, and what mechanisms or strategies does it use to ensure that these improvements are aligned with its broader business objectives? This question focuses on understanding the company’s performance management and measurement approach.
• What mechanisms or processes does the organization use to track and report on improvements resulting from realizing each benefit? How does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that the benefits resulting from the realization of each benefit are communicated to staff, and what mechanisms or strategies does it use to ensure that staff understands the value proposition of the company’s offerings? This question aims to understand the company’s internal communication and employee engagement approach.

Strategic Fit questions to ask leaders

109. Does our organization’s strategy match the availability of your current resources?

Asking business leaders whether their organization’s strategy aligns with the availability of their current resources is a critical question that decision-makers should ask. In rapidly changing markets, ensuring that the organization’s strategy is flexible and adaptable is essential. The way to do this is by taking stock of the resources at hand before designing a strategy for the upcoming year.

With constant changes in customer needs, unpredictable market competition, and emerging technologies, businesses must be aligned with their resources to ensure smooth operations. To stay successful, it is essential to make strategic changes in response to fluctuating markets. Therefore, asking this question will ensure that organizations remain agile and focused on achieving their desired goals.

What are the questions you should be asking your organization’s senior leaders?

According to Forbes, you should keep four critical questions in mind.

• The first is whether or not the organization’s strategy matches the availability of current resources. This question addresses the strategy’s feasibility by determining if there is enough funding, time, people, and information to make it work.
• The second question is whether the strategy aligns with the company’s core values. This question helps to ensure that the proposed strategy is in line with what the company stands for and that employees will support it.
• The third question is whether or not the strategy is realistic. This question assesses whether or not the proposed plan is achievable and if it has been adequately thought out.
• The fourth and final question is whether or not implementing the strategy will create shareholder value. This question ensures that the proposed strategy will benefit those who have invested in the company.

Asking these four key questions can help ensure that a proposed strategy is well-thought-out and viable.

110. How well does our organization maximize existing resources to deliver the product offering?

• How does the organization define and measure the efficiency and effectiveness of its resource utilization, and what mechanisms or strategies does it use to ensure these efforts align with its broader business objectives? This question focuses on understanding the company’s resource management and optimization approaches.
• What mechanisms or processes does the organization use to track and report on resource utilization, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to resource utilization is aligned with its broader business objectives, and what mechanisms or strategies does it use to ensure that resource optimization efforts contribute to the company’s overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that resource utilization efforts are aligned with business strategy.

These questions can help leaders identify areas of improvement regarding resource utilization. Organizations often have vast resources but are not using them to their full potential. By asking this question, leaders can better understand how well their organization maximizes its resources and where improvements can be made.

Additionally, this question can help leaders understand their delivery process’s efficiency and whether any bottlenecks need to be addressed. Ultimately, by asking this question, leaders can gain valuable insights into how their organization can improve its operations and better serve its customers.

111. How aligned are our organization’s offerings to meet market demand?

It’s essential to be strategic when questioning senior leaders to gain the most beneficial insights for your company.

A great question to ask is related to market demand and organizational alignment. You want to know if the company offers products that fit the market’s needs and align with the company’s strengths.

Questions to ask:

• How does the organization define and measure market demand, and what mechanisms or strategies does it use to ensure its offerings align with this demand? This question focuses on understanding the company’s market analysis and demand forecasting approach.
• What mechanisms or processes does the organization use to track and report on the alignment of its offerings with market demand, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its offerings are aligned with market demand, and what mechanisms or strategies does it use to respond effectively to changing market conditions? This question aims to understand the company’s approach to market responsiveness and its commitment to ensuring that its offerings meet its target customers’ needs.

This information will help you better understand how well the company is positioned and what steps must be taken to improve things. Additionally, it can provide helpful context when evaluating other aspects of the business. Asking tough yet thoughtful questions is essential for making progress in any organization.

Taking a strategic approach ensures you get the most out of your conversations with senior leaders.

112. Do we know where our organization can be distinctively competent?

Senior leaders must ask themselves some hard questions regarding strategic planning to ensure that the organization is headed in the right direction.

• How does the organization define and measure its distinctive competencies, and what mechanisms or strategies does it use to ensure these competencies align with its broader business objectives? This question focuses on understanding the company’s competency mapping and identification approach.
• What mechanisms or processes does the organization use to track and report on its distinctive competencies, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its approach to competency mapping aligns with its broader business objectives, and what mechanisms or strategies does it use to ensure that its distinctive competencies contribute to its overall success? This question aims to understand the company’s approach to strategic alignment and its commitment to ensuring that its distinctive competencies are aligned with business strategy.

This question forces leaders to consider what makes their organization unique and how to capitalize on those strengths. Without a clear answer to this question, organizations can quickly become lost in a sea of sameness, struggling to compete against more focused and efficient rivals. Asking this question early on can help leaders steer the organization in the right direction and ensure it can achieve its full potential.

113. What is the short list of critical initiatives the organization must successfully pursue to deliver its target value proposition and accomplish its overall vision?

Asking the right questions is critical to any organization’s success. When it comes to senior leaders, a few key questions can help them make strategic decisions and ensure that the organization is on track to meet its goals.

• First, what are the organization’s most critical initiatives? These are the projects or initiatives that, if successful, will make the most significant difference to the organization’s bottom line.
• Second, what is the overall vision for the organization? This helps to provide context for decision-making and ensures that everyone is working towards the same goal.
• Finally, what are the risks and opportunities associated with each initiative? Understanding each project’s potential upside and downside allows senior leaders to make more informed decisions about which initiatives to pursue.

Senior leaders can set their organizations up for success by asking these essential questions.

114. Is the organization effective in distinguishing strategy issues from execution issues?

Many organizations struggle to distinguish strategy issues from execution issues. A strategy issue is something that will have a significant impact on the direction of the organization.

In contrast, an execution issue is an operational matter that generally does not require a significant strategic decision.

Asking senior leaders whether they believe the organization is effective in this distinction can provide valuable insights into their thinking. If they are not confident in the organization’s ability to make this distinction, it may indicate that they are not confident in the overall direction of the organization.

Additionally, suppose senior leaders cannot point to specific examples of where the organization has effectively made this distinction. In that case, it may suggest they are unclear on the organization’s strategic priorities.

Asking these questions helps clarify senior leaders’ thinking and ensures that the organization is focusing on the right priorities.

115. What areas will you let go of, shed, or eliminate? What makes you sure those are the areas?

As a leader, being strategic about the questions you ask is important. This is especially true when it comes to questioning senior leaders. After all, they’re the ones who hold power and information. Asking the right questions can help you understand their thought process and decision-making. It can also help you build a case for your ideas or initiatives.

Asking the right questions is critical to any successful endeavor, but it can be incredibly challenging when attempting to gain insights from senior leaders. After all, these individuals are accustomed to being in control and may be reluctant to share vulnerable information.

However, by asking strategic questions, it is possible to get them to open up and share valuable insights into their thought processes. For example, one question that can elicit valuable responses is, “What areas are you willing to let go of, shed, or eliminate?”

By asking this question, you’re allowing the leader to share what they’re thinking about in terms of priorities and goals. Additionally, it’s a way of showing that you’re interested in their decision-making process and that you’re open to hearing about areas where they may be struggling. Asking this question can help create a more open and honest relationship with senior leaders, ultimately leading to better organizational decision-making.

With that in mind, here are some strategic questions to ask senior leaders:

• What are your thoughts on X?
  • This is an excellent question for insight into their thinking process on a particular issue. It also allows you to gauge their openness to new or different ideas.
• What are your priorities regarding Y?
  • This question can help you understand what they see as essential factors in a particular situation. It can also give you a sense of where their priorities lie.
• How do you feel about Z?
  • This is a good question for reading their emotional reaction to an issue or situation. It can also help you gauge how they might react in similar situations in the future.

Asking these types of questions can help you better understand senior leaders.

116. What is ‘untouchable’? Where are those boundaries?

No organization or individual can be successful without well-defined boundaries. Understanding where those boundaries lie is critical to organizational success.

Leaders must articulate why certain things are ‘untouchable’ and off-limits. This guides team members and helps them understand the importance of staying within those bounds. Furthermore, it sets the tone for an organization and creates a culture of respect for boundaries.

• How does the organization define its boundaries and identify what is considered ‘untouchable,’ and what mechanisms or strategies does it use to ensure these boundaries align with its broader business objectives? This question focuses on understanding the company’s approach to boundary setting and alignment.
• What mechanisms or processes does the organization use to track and report on its boundaries, and how does it use this information to make informed decisions and adjust its strategies and tactics as necessary? This question explores the company’s commitment to data-driven decision-making and continuous improvement.
• How does the organization ensure that its boundaries are aligned with its broader business objectives, and what mechanisms or strategies does it use to ensure that these boundaries do not impede progress or innovation within the organization? This question aims to understand the company’s approach to balancing risk management with the need for agility and innovation.

Asking senior leaders about what is ‘untouchable’ and why is critical in understanding an organization deeply. It also shows a commitment to respecting those boundaries. By asking these strategic questions, team members can better appreciate staying within the lines.

Recommended Reading- 116 Strategic Questions to Ask Senior Leaders- With Sample Answers

• What is the difference between strategy implementation and evaluation?
• 67 Ways to Tell if Your Organization Lacks the Ability to Execute Your Strategy
• 41 Leadership Interview Questions- Explained, Answered (with samples)
• 130 Powerful Questions To Ask The CEO
• 72 Strategic Questions to Ask Leaders of Manufacturing Organizations

Strategic Questions We Must Ask Leaders

There are a few key questions that every employee should ask their leaders to gauge the health of their organization. Here are four strategic questions employees must ask leaders:

1. What is our organization’s mission?
2. What are our core competencies?
3. What is our strategic plan?
4. How are we measuring success?
5. Who has to do what and by when to achieve our strategy?

These five questions will give you a good idea of where your organization is going and how it plans to get there. If you don’t understand the answers to these questions, it’s time to talk with your leaders about what they mean.

Why employees must ask leaders strategic questions

To be successful, employees must ask their leaders strategic questions. Doing so can ensure that they are on the same page and working together towards common goals. Additionally, asking questions allows employees to understand the leader’s thought process and decision-making criteria, which can benefit personal and professional development.

While it may seem intimidating at first, remember that leaders are typically open to answering questions from their team members. They often appreciate the engagement and dialogue that result from these exchanges. So don’t be afraid to speak up and ask away!

• Do you have any questions for me about this project?
• What are your thoughts on my proposed approach?
• Can you provide examples of similar projects that you’ve seen successful?
• What do you think is the most crucial aspect of this project?
• What are the potential risks and challenges associated with this project?
• How do you think we can best overcome those challenges?

When employees ask leaders strategic questions, engagement increases.

When employees ask leaders strategic questions, engagement increases. Asking questions helps ensure that employees are on the same page as their leaders and allows for two-way communication. This type of communication is essential for maintaining a high level of engagement in the workplace.

Leaders who encourage their employees to ask questions are more likely to be approachable and open to feedback. This creates a workplace environment where employees feel comfortable voicing their opinions and sharing ideas. In turn, this can lead to increased creativity and innovation.

Questions also allow leaders to understand their employees’ needs and concerns better. By listening to what employees have to say, leaders can make changes that improve the work environment and make it more enjoyable for everyone.

When employees feel their voices are being heard, they are more likely to be engaged in their work. Asking questions is one of the most effective ways to ensure that employees are engaged in their work and feel like their opinions matter. Leaders encouraging employee input by asking questions will create a more positive and productive workplace.

When employees ask leaders strategic questions, leadership accountability strengthens.

When employees ask leaders strategic questions, it strengthens leadership accountability. This is because when leaders are questioned about their decisions and strategies, they are more likely to be held accountable for their actions.

Additionally, questioning allows for a two-way conversation, which can help improve the leader-employee relationship. Asking questions also shows that employees are engaged and interested in the company’s success. Lastly, when leaders are held accountable, it can help improve decision-making and overall company performance.

When employees ask leaders strategic questions, alignment improves.

Organizations are always looking for ways to improve alignment between leaders and employees. One way to do this is by encouraging employees to ask their leaders strategic questions.

When employees feel comfortable asking their leaders tough questions, they trust them and believe they have the organization’s best interests at heart. Asking strategic questions helps employees better understand the leader’s vision and how their day-to-day work fits into it.

This leads to improved alignment between leaders and employees, which can help organizations achieve their goals more effectively. So if you’re looking for ways to improve alignment in your organization, encourage your employees to ask their leaders some tough questions.

When employees ask leaders strategic questions, communication improves.

When employees ask leaders strategic questions, communication improves. This is because when employees feel comfortable asking questions, they are more likely to feel comfortable communicating in general.

Furthermore, when leaders answer these questions thoughtfully and thoroughly, it shows that they are interested in their employees’ input and value their opinions. As a result, this creates a positive feedback loop of communication that can help improve overall morale and productivity in the workplace.

So, if you want to improve communication in your workplace, encourage your employees to ask you strategic questions. And when they do, make sure to take the time to answer them thoughtfully and thoroughly. Doing so will create a more positive and productive work environment for everyone involved.

When employees ask leaders strategic questions, ambiguity decreases.

When employees ask leaders strategic questions, ambiguity decreases. Leaders can provide employees with clarity by sharing their vision for the future and setting specific goals. Employees who understand the company’s direction are more likely to be engaged and motivated to succeed.

Asking strategic questions also allows leaders to gain insights into employee thinking and identify potential areas for improvement. By encouraging employees to ask questions, leaders can create a more open and transparent culture that promotes innovation and creativity.

When employees ask leaders strategic questions, it shows that they are engaged and interested in the company’s direction. This allows leaders to gain valuable insights into employee thinking and identify potential areas for improvement.

Asking questions also decreases ambiguity and creates a more open, transparent culture, promoting innovation and creativity. Leaders who encourage employees to ask questions are more likely to have a motivated and engaged workforce. Strategic questions help employees understand the vision for the future and what specific goals need to be achieved.

Employees who clearly understand the company’s goals are more likely to be engaged and motivated to succeed. When leaders provide employees with clarity, it decreases ambiguity and creates a more productive work environment.

Asking strategic questions is a valuable way for leaders to gain insights into employee thinking and identify potential areas for improvement. It also decreases ambiguity and creates a more open, transparent culture, promoting innovation and creativity. Leaders who encourage employees to ask questions are more likely to have a motivated and engaged workforce. When employees ask leaders strategic questions, it shows that they are interested in the company’s direction and are committed to achieving success.

When employees ask leaders strategic questions, strategy-execution probabilities improve.

Strategy-execution probabilities are improved when employees ask leaders strategic questions. This is because questioning allows for a two-way flow of communication, which can help ensure that everyone is on the same page regarding the company’s goals.

Additionally, questioning can surface new ideas and perspectives that may have gone unnoticed. Asking strategic questions thus helps create a more robust and execution-ready strategy.

Of course, not all questions are created equal. To be truly effective, strategic questions should be open-ended, specific, and relevant to the current situation. They should also be aimed at uncovering hidden assumptions or uncovering new information. By following these guidelines, employees can ensure that their questions are truly helpful in moving the company forward.

So, the next time you feel lost in a sea of strategic planning, don’t be afraid to ask your leaders some tough questions. It just might be the key to unlocking better execution and greater success.

When employees ask leaders strategic questions, strategy-execution gaps are identified

When employees ask leaders strategic questions, they help to identify strategy-execution gaps. Doing so provides valuable input that can help improve the execution of the company’s strategy. To encourage employees to ask such questions, leaders should create an environment conducive to open communication and collaboration.

Furthermore, leaders should make it a point to listen to employee suggestions and act on them when appropriate. By taking these steps, leaders can ensure that their company’s strategy is executed effectively and efficiently.

When employees ask leaders strategic questions, organizational core competencies are identified

When employees ask strategic questions, they identify the organization’s core competencies effectively. Doing so can help the organization focus on its strengths and improve overall performance. Additionally, this process can also help identify potential areas for improvement. Ultimately, asking strategic questions is integral to being an effective leader.

Employees must ask leaders strategic questions to ensure plans are achieved.

Employees must ask their leaders strategic questions to ensure that plans are achieved. Leaders must understand the organization’s goals and objectives, and employees are crucial in ensuring this understanding.

By asking questions, employees can help leaders clarify what needs to be done to succeed. Furthermore, questioning allows employees to hold leaders accountable for their actions and decisions. Ultimately, by asking strategic questions, employees can help ensure that organizational plans are achieved.

Employees play a vital role in ensuring that leaders clearly understand the organization’s goals and objectives. Leaders must articulate the company’s vision and strategy; employees can help by asking questions.

Asking questions allows employees to probe for clarification on what needs to be done to succeed. Furthermore, it allows employees to hold leaders accountable for their actions and decisions. Ultimately, by asking strategic questions, employees can help ensure that organizational plans are achieved.

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