116 Strategic Questions to Ask Senior Leaders – With Sample Answers – Part One

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Guest Post by Benjamin Wann

Originally Posted @ BenjaminWann.com

Today’s Post is Part One – sharing the first 62 of Benjamin’s 116 Questions. 

Click HERE to read Part Two – sharing Questions 63-116.

Any leader will tell you that asking the right questions is key to success. But what happens when you’re the one being asked the questions? Asking strategic questions of senior leaders can be a powerful way to gain insights, build relationships, and advance your career.

Here are a few tips for asking strategic questions of senior leaders:

1. Do your homework. Before you ask a question, ensure you have a firm understanding of the issue. This will help you ask more insightful questions.

2. Be respectful. Remember, these are busy people with a lot on their plate. Don’t waste their time with frivolous questions.

3. Be prepared to follow up. If you get an answer that isn’t what you were hoping for, be prepared to follow up with additional questions or research.

Senior leaders need to be dual accountable, strategic, and thorough. Asking the right questions is crucial to ensuring both. By asking these questions, organizations can ensure that their strategies are aligned with their values, vision, and objectives. Additionally, they can identify any gaps or areas of improvement.

Asking these questions is not always easy, but it is necessary to create a successful strategy. Senior leaders must be willing to be both accountable and thorough in creating a strategy that will help the organization achieve its goals.

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 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 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 to 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.

Why Don’t We Ask Better Questions?

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 is focused on knowing the “right answer” rather than discovering the “right question.”

Our educational system focuses more on memorization and static answers rather 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 esteems certainty and discourages doubt. Asking questions can be seen as a sign of weakness or 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 are looking for.

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 rapid pacing in our lives and work, which prevent us from taking the time to be 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. Watering down our aversion to creative questions, we could improve problem-solving in our lives and work.

In today’s business environment, change is the only constant. 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 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 to search for innovative paths forward. Leaders also need to consider reward systems that provide incentives for members to work across organizational boundaries to discover those challenging questions that create 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, there are always a few pieces that 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. Moving 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 to develop the adaptability and resilience needed to thrive in an ever-changing world.

Strategy 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.

To ensure that your employees are on the same page, clearly communicating the organization’s goals and objectives is essential. This way, everyone will work toward the same outcome and know their roles in helping to achieve it. 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 the five-year horizon is a good balance. This gives us the flexibility to review and update the plan regularly.

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

It is essential to have a clear idea of where your business is currently and where you want it to be in the future. Without this focus, developing an effective plan for achieving your goals can be difficult. Your current situation should be detailed and quantifiable, so you can accurately compare it to your desired 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? Where do we want to be?

One of the most important things for a leader is asking the right questions. This is especially true when it comes to 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?” and “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.

Our company has shown time and time again that we are willing to make changes when necessary, whether it’s adopting new technologies or changing our processes. This adaptability has been our key strength and has helped us stay ahead of the competition. I believe this is more important than ever in today’s rapidly changing business landscape.

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

7. Who is our target customer?

Let’s first consider our company’s purpose of 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 might include customers who have accidentally broken their windows and those whose windows were damaged by severe weather. 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.

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 upon your current 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 always to 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?

Today, the company is a powerhouse in the industry. It’s well-known for its quality products and exemplary customer service. But how did it get to where it is?

The company’s journey to the top began with intelligent decisions. First, the company invested in high-quality materials and hired experienced craftspeople. This ensured that its products were of the utmost quality. Second, the company focuses on providing excellent customer service. It hired friendly and helpful employees and trained them to resolve customer issues quickly and efficiently.

Finally, the company created a strong marketing strategy. It developed catchy advertising campaigns and ensured its products were visible in critical locations.

Thanks to these decisions, the company quickly rose to prominence. Its products were well-made, and its customer service became renowned for being speedy and effective. As word spread, more and more people began seeking out the company’s products. Soon, it was one of the most popular brands in the industry.

Today, the company continues to build on its successes. It remains focused on quality, customer service, and marketing. And it continues to make intelligent decisions that help it maintain its position as a leader in the industry.

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. Having a handful of essential goals over several years can help the company stay on track and avoid getting sidetracked by smaller goals or objectives.

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?

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 its 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 need to be aware of 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.

Asking senior leaders how often they assess these factors will give you insights into whether or not the company is prepared to 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 that could hinder 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. 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, by ensuring that this evaluation is conducted regularly, organizations can stay one step ahead of the competition.

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.

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 a clear understanding of 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:

1. What is our current market position?

2. Where do we want to be in the future?

3. 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, it will be impossible to develop a plan to get there. 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?

Anytime 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 lead to increased 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. 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 effectively balance short- and long-term priorities?

Every company has a culture, whether it is intentional or not. This culture arises out of the shared values, experiences, and beliefs of the people 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 will it require a culture shift?

For example, a long-term growth strategy may require a culture shift if the company focuses on short-term results. On the other hand, if the company is currently focused on long-term growth, the strategy for a short-term result may require a culture shift. In either case, it is essential to consider how the strategy will impact the company culture and whether or not the company is prepared to make the necessary 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.

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 always to 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 or not they are likely to 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. 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 easy is it for customers to 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. 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.

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 plan of forecasted strategies?

Differentiation, innovation, and customer alignment are essential aspects of 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 to ask 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 with 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. 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? Do you have the staff in place with the skills and knowledge required? Do you have the necessary infrastructure, 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 customer’s value/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/need?” and “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 start asking yourself whether or not your company is supplying that. This second question is just as important as the first because even if you think you know what your customers want if you’re not providing it, it’s all for nothing. 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 in providing value to its customers.

31. Are we clear about who our target customer is not so that we avoid trying to be all things to all people?

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 to ensure that everyone in the organization knows who that customer is.

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/ service distinct/ 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.

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. By asking these strategic questions, you can gain invaluable insights into a company’s business model and operations.

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(s)? How is it defined (slices/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. 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.

35. What is our share for each market in which we compete? Are we losing, gaining, or holding shares?

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 share? 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.

For many companies, this means looking beyond their core business and exploring adjacencies. However, ensuring that any growth strategy is aligned with the company’s core values and competencies is also essential. 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/cost 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 ensure 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 that we seek to provide to 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 thriving 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?” and “What are the biggest threats to our success?” By asking these questions regularly, senior leaders can ensure that they are constantly making decisions that align with the company’s overall strategy.

39. What is the competitive landscape? Is it concentrated or fragmented? Who are our competitors? What is their share of the market?

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 not enough; you need to understand their strengths, weaknesses, core customer base, and market share. Only then will you be able to develop a comprehensive strategy for success.

40. What must the organization maximize to create superior value for customers, shareholder returns, and employment opportunities?

Asking the right questions is critical to making sound strategic decisions. When it comes to senior leaders, there are a few key questions that can help to 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 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 have the potential to 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 the achievement of these ambitions? What internal strengths and weaknesses can help or hinder the achievement of 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 the achievement of 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 use and disposal of the product or service.

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, disruption, impacts, and opportunities?

As the world becomes increasingly complex, leaders must learn to think strategically to identify risks, disruptions, and opportunities. Leaders can better understand the potential impacts and constraints on their business model 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 some significant changes required to the business’ core processes, products, structure, and even its fundamental business model.

This may require a revision of the business’ values and purpose to adapt to the disruptions to business as usual and to 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 that will 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?

When it comes to strategic planning, it is vital to involve the right people in the process. 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? It is vital to ensure that all key stakeholders are involved in the planning process. This way, everyone will be on the same page, and there will be no surprises down the road.

What will be their role? Once you have identified who will be involved in the process, it is essential to clarify their role. This will help to ensure that everyone is clear on 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 that the planning process can be successful.

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. 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 or Stimulating Creativity 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 does the organization have to 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 to surface some hidden agendas and reveal areas of tension within the company. It also shows that you’re interested in making tough decisions and are willing to have difficult conversations. Asking this question can help to 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?

As a senior leader, it is crucial to 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 does it need to 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 turn your company into a more profitable one.

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 that may indicate 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.

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 to your high-level goals and objectives.

Additionally, you may need to add new projects, change or update how you’re tracking KPIs, or change your KPI targets. Periodic strategy refreshes allow you to keep the elements of your plan still 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 need to 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: setting up monthly meetings might include a director from each department, quarterly meetings require a smaller set of leaders, and annual strategic retreats are usually reserved for the highest levels of leadership.

Getting these meetings on the calendar early reserves the times and sets an expectation for preparedness. By preparing in advance and ensuring that the appropriate participants are invited, organizations can make the most of their strategic planning sessions and ensure that their plans remain on track.

57. Is your organization pursuing growth and new business/market 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.

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 achieve alignment and commitment of key stakeholders to this strategy?

When developing a new strategy, getting buy-in from all the key stakeholders is essential. 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. And 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 to plan.

61. Do we have the proper governance in place?

Existing methods of cascading departmental and individual objectives must be aligned to the purpose and strategy, ensuring appropriate metrics, indicators, and decision-making tools.

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

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

62. What is the difference between a strategic plan and an operational work plan?

A strategic plan is built off 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.

Many companies mistake treating their strategic and operational plans as two separate entities. However, the most successful businesses take a holistic approach, 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 to increase efficiency and avoid duplicated effort. Additionally, it can help to 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.


Benjamin Wann


Benjamin Wann drives business results by building relationships, empowering others, unleashing analytics, and removing complexity.  Benjamin is the author of 13 books including, “Strategic Questions to Ask Senior Leaders.”   You can connect with Benjamin at BenjaminWann.com 


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