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

You are invited to click HERE to find out how you can join over 750 other leaders who have become Book Ambassador’s for the 3rd Edition of “LEADING WITH QUESTIONS” by Michael Marquardt and Bob Tiede.  This is Your Opportunity to increase the Leadership Effectiveness of Everyone in the Shadow of Your Influence and in Appreciation You will Receive a Complimentary, Signed 3rd Edition!

Guest Post by Benjamin Wann

Originally Posted @ BenjaminWann.com

Today’s Post is Part Two – sharing Benjamin’s Questions 63-116.   

Click HERE to view Part One – where Benjamin shared his first 62 of 116 Questions.  

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.

Ownership & Accountability Questions to Ask Leaders:

63. Describe the role + accountability you expect from me?

As a senior leader, it is essential to be clear about the role you expect someone to play on your team. This will help them to 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?

One of the most important things you can do when developing a strategy is to create a stakeholder map. 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 takes into account the needs of all of your key constituents.

65. Does everyone in our organization understand what we’re trying to accomplish– an aggressive, worthwhile stretch goal or vision significant enough to generate a shared passion and broad alignment across the entire organization? 

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 the organization’s 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/role contributes to accomplishing this vision? 

In any organization, everyone must understand how their job contributes to the company’s overall 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 need to consider changing the structure to align it with the company’s goals better. 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 success level. This is why it’s so important for senior leaders to regularly ask themselves strategic questions that will help them stay on track and continue making progress.

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 and 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. 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 appropriately accountable for delivering targeted results?

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 to 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 fulfill the role of Business Change Manager(s) responsible for realizing the benefits delivered by the strategy [ typically drawn from the areas of the organization affected by the changes and 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, it’s essential to ask the right questions to ensure 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? 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 this strategy, plan, 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 to 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 do you see as the key challenges and opportunities facing the program in the coming months?’ and ‘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?

It is essential when crafting a company’s purpose and strategy that senior leaders are 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. 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 a crucial part of 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 is an effective way to build 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 make its employees their best proponents.

Encouraging employees to promote the company actively can be done in several ways, such as 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. By taking advantage of this valuable resource, companies can ensure that their message is promoted by those most passionate about it.

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 the 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. Only by taking active steps to address cultural dissonance can senior leaders hope to create a more cohesive and productive workplace.

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 measure 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. 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 leads to increased 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 when it comes to strategy is who will be responsible for overseeing and executing the plan. Too often, there is no clear leader with ultimate accountability, leading 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 in 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?

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 it’s important to offer various training options. 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 to 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:

    1. What are our top priorities?
    1. What are our biggest challenges?
    1. 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 to prevent them from becoming more significant problems down the road. 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 to 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 to 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 to prevent unintended consequences. Asking strategic questions like this can help to ensure that meaningful conversations are productive and focused on moving forward.

86. What must supporting tactics 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/processes to get from where we are now to where we want to be?

Asking the right questions is essential for any leader who wants to bring their team to the next level. When it comes to senior leaders, there are a few key questions that can help to 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 need to ask what resources are available and what constraints need to 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?

Before any strategy can be successfully implemented, several questions need to be answered by senior leaders. 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, it is necessary to think about what could go wrong and how to mitigate any potential risks. 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 a question we should be asking 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?

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:

    1. What are the most critical issues facing our organization?
    1. How will this decision impact our stakeholders?
    1. 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?

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/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:

1) What customer needs does our proposed value proposition address?

2) What problem are we solving for our customers?

3) What is our unique selling proposition?

4) Who are our target customers?

5) What are our core competencies?

6) Do we have the necessary capabilities in-house, or do we need to outsource/partner with someone who has them?

7) How will we reach our target market?

8) How will we generate demand for our products/services?

9) What is our pricing strategy?

10) How will we measure success?

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

How efficient and organized is your organization’s plan to improve and evolve the 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 get a sense of 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?

Asking your senior leaders how efficient your organization is from an operational standpoint 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 need to 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 a lack of effective 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 a lack of effective strategy? By examining these factors, you can develop a plan to optimize your company’s resources, including its people’s most valuable asset. 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 are these capabilities developed in our organization?

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 needs to be done to achieve success. 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/competitive advantages compared to ours?

As a young leader, it can be challenging to engage with senior 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. 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 circumstances. 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 are areas of the company distinct/unique/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 circumstances. 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.

Strategic KPI (Key Performance Indicators) Questions to Ask Leaders:

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

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. 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? We recommend 20-30 measures at each level, from the enterprise level to the division level to the department level. 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 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?

What are our core values? What do we stand for? What is our purpose? How can we articulate our unique selling proposition? These are all critical questions to ask when crafting a strategy, but they’re significant when communicating that strategy 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, if 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%, the company knows that unless it makes adjustments, it won’t meet the objective.

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, monthly checking in 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?

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 answering these questions upfront, senior leaders can put their team on the path to success.

106. Do we set evidence-based targets?

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: are we setting evidence-based targets? What is our strategy for achieving these targets? Are we committed to continual improvement? What are the risks and opportunities associated with our current course of action? 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 to spark meaningful conversations about sustainability within the company.

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?

When working with senior leaders, it is vital to ask strategic questions to help ensure that the organization’s goals are met. For example, does the leader have a plan to achieve the desired benefits? What processes will be put in place to ensure these benefits are achieved? What resources will be necessary to achieve the goals? 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 benefits realization, good communication is critical. Senior leaders need to be kept in the loop about the improvements due to the benefits 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 see the value in benefits realization and buy into the process. Senior leaders should ask these two crucial questions to ensure successful benefits realization.

Strategic Fit Questions to Ask Leaders:

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

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 to 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 well does our organization maximize existing resources to deliver the product offering? This question 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 is maximizing its resources and where improvements can be made. Additionally, this question can help leaders understand how efficient their delivery process is 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 is offering products that fit the market’s needs and align with the company’s strengths.

This information will help you better understand how well the company is positioned and what steps need to 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. One of the most critical questions is, “Do we have a clear idea about where our organization can be distinctively competent?”

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, there are a few key questions that 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 can help clarify senior leaders’ thinking and ensure that the organization is focused on the right priorities.

115. What areas are you willing to 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 getting a read on 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. Asking senior leaders about what is ‘untouchable’ and why is critical in gaining a deep understanding of an organization. It also shows a commitment to respecting those boundaries. By asking these strategic questions, team members can better appreciate staying within the lines.

Benjamin Wann

ABOUT THE AUTHOR

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 

MORE RECENT POSTS

If You Ask Me

Note From Bob:   How many times have you connected with someone who has lost their spouse and not quite...

Do you know how to lead with questions?

Originally posted @ SmartBrief.com Many leaders find themselves working with teams from diverse backgrounds....

A Simple Recipe for When Conversation Feels Stuck

Guest Post by Amber Johnson A few years ago, I heard a cookbook author on a radio program. She mentioned that...

Everyone Can Ask Powerful Questions

Excerpted with permission from the 20th Chapter of “When Everyone Leads” by Ed O’Malley and...

Engaging God through Character-Centric Questions

Guest Post by Tom Steffen and Ray Neu Why didn’t Jesus play the role of the Bible Answer Man during his...

Study Reveals A Conversation Trick That Motivates People To Change Their Behavior

Guest Post by Amy Morin Originally posted @ Forbes.com Whether you want your New Year’s resolution to...

 Leaders Ask Questions

Excerpted with permission from Chapter 5 of “Thrown In: Ready or Not, You Are the Leader” by Mark...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.