30 Engaging Questions to Ask Your Senior Leaders

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Guest Post by Benjamin Wann

Originally Posted @ BenjaminWann.com

In the entire stretch of your professional career, there is a slight chance that you will get to talk to another influential person– even possibly your senior leaders in the industry– that you look up to.

So if the chance to ask an influential person or a leader presents itself, it is better to be prepared with questions that can pave the way for a breakthrough in your company or industry.

Talking to those who hold leadership positions in your organization is essential to your career’s progress and one of the most effective ways to enhance your procedures and methods.

As the world strives to thrive under a global pandemic, now is the moment to learn from the leaders. It is amid challenging circumstances that true leaders are revealed; we should use this opportunity to further our education.

Encourage leaders and remind them that this is what they were trained for, but also use this opportunity to engage with them and learn from them.

Learning takes place when one is actively engaged with the activities of others.

Asking questions is one of the most effective intellectual and personal development methods. Inquire with the senior leaders who are already accomplishing what you want to accomplish and what it takes to get there. Also, take time to learn about experiences with those in leadership positions who took completely different routes.

What You Should Know About Your Leaders

Understanding how to maintain humility is one of the most essential skills for aspiring leaders to acquire. Leaders need to be conscious that their leadership does not come from anything; they need to nourish themselves with the traits of the figures who inspire them.

They need to be aware that their leadership only emerges from something which requires a certain amount of effort to prove that they are indeed efficient. Therefore, openness to other people’s experiences is indispensable to investigate the factors contributing to great leaders’ success.

Having a brief conversation with a leader and talking about how your separate paths have led you to where you are now can be highly formative and inspirational in a sense. A professional will increase the likelihood of success in achieving their set objective if they proceed in this manner.

Preparing engaging questions to ask leaders can assist one in identifying the most relevant topics for both sides. Below is a list of 20 questions to ask senior leaders that will get them talking.

1. What Would You Say Is The Primary Motivating Factor Behind Your Leadership?

First, knowing what drives and motivates leaders to embark on the leadership path is wise. It is especially true when determining how to lead others best.

If you listen to what people who have achieved success in your industry have to say, you will be able to recognize yourself in their way of thinking, which is encouraging.

In addition, it may cause you to reconsider your goals and objectives in life. It is good to align your principles with a senior leader’s experience; think of it as having a map that could help you get to your career’s success.

However, it is crucial to remember that various people have different goals, and there is no “right” or “wrong” response to this question. However, almost all leaders will emphasize working together as a team.

A leader’s success is entirely contingent on the efforts of his people. His group can evaluate the quality of his output. As a result, the desire to succeed in life as a whole serves as a component of the leading motivation of each individual.

2. Who Are Your Role Models, And Why Did You Choose Them?

The majority of today’s most successful leaders can reflect on their lives and identify the individuals who served as mentors to them along the way. Mentors help mold their mentees into future leaders.

Because people from diverse walks of life can serve as mentors, the characteristics of mentoring can take on a variety of forms and could share different values and principles.

Whether the mentor is an older family member, a professor from an earlier school, or someone met through a networking event, the people who impart knowledge and lessons to today’s leaders can reveal a great deal about a person’s background and character.

A glimpse of what a successful leadership path can be gained by listening to a leader discuss who their mentor is and why they admire them.

3. What Life-Changing Lessons Did You Pick Up From The People Who Helped Guide You?

This particular question is a follow-up to the preceding one. It asks for additional information about what insights a leader got from those who mentored or supported the leader throughout the leadership journey.

Lessons learned through mentors can frequently be the wisdom that people keep with them forever, longer than what is known in a class or seminar.

These lessons may be beneficial to you as well and may transfer to other aspects of your journey. Guidance is accompanied by evidence demonstrating its efficacy, with the leader serving as the evidence.

Asking this specific question can help give you a clear understanding of the emphasis of a mentor’s impact on a leader’s life and leadership progress. Gaining valuable advice can be a catalyst for your professional journey.

4. How Do You Ensure That Others Benefit From The Life-Changing Knowledge You Gained From Your Mentors?

In line with mentoring, this question tries to gain an even deeper understanding of how a leader takes information and passes it to others. A good and successful leader recognizes that passing their knowledge to others is the key to their success.

It might be tough to teach others consistently, an essential quality that a leader should possess actively. However, the willingness to teach and share knowledge is an essential factor.

Leaders willing to enlighten others and educate them with what they have discovered may garner more respect from people they interact with and be seen as more engaging with their audience.

5. If Members Of Your Team Have Differing Views, How Do You Resolve The Conflict?

When the methods implemented are different from one another, there is a greater possibility that the response you get will highlight the communication skills of your counterpart.

It is of the utmost importance to maintain one’s composure when circumstances so demand is of the utmost importance. It is also vital for a leader to mediate disagreements to preserve a peaceful and healthy environment conducive to debate and decision-making.

The ability to manage this kind of issue so that each party can clarify their reasons, which will assist in finding a standard solution, does not require the leader to be partial.

A competent leader will be able to do this. Always remember that a leader’s role within his team includes that of a mediator.

6. What Is The Most Difficult Choice You Have Ever Been Required To Make?

Only a few leaders can navigate their way to the top without encountering obstacles along the way. You can better grasp the thought process and prepare yourself for the challenges you will face at some point in your career if you are aware of the difficulties others have faced along their path and how they overcame them.

A professional’s level of success is directly proportional to two factors: first, the ability to recover from setbacks, and second, the capacity to avoid allowing oneself to be debilitated by exceptionally trying circumstances.

Because regardless of the magnitude of the challenge, there is no such thing as an insurmountable barrier; nonetheless, there are situations in which one must make compromises or even sacrifices.

7. What Advice Do You Wish Someone Had Given You Earlier In Your Career?

This question flips away from the mentor-related questions. It pushes a leader to reflect on a valuable lesson they may have had to learn on the spot when they were in a position of authority over others.

What kind of guidance could have better prepared them for that situation?

It presents an opportunity to discover the specific and individual lessons a leader has to offer while reflecting on past experiences. A leader can’t be prepared for every imaginable scenario.

Still, the lessons they take away from such scenarios provide them additional insight to pass on to their people.

8. Do You Believe Personal Qualities Such As Empathy And Vulnerability Play A Part In Your Ability To Lead?

Although this question may sound specific, it draws attention to frequently ignored qualities in leadership roles. These characteristics have progressively been proven crucial to leadership in light of the unique conditions in which our world currently finds itself.

During these trying times, many of the world’s most revered leaders gained acclamation for their selflessness, which is why they are respected today.

To be an effective leader, you need to possess qualities such as empathy and vulnerability, to name a few. However, knowing how these qualities are involved in a particular leadership role is helpful in learning how to develop them.

9. How Can You Inspire Others While Also Maintaining That You Continue To Be Inspired By The Organization’s Overall Mission?

It is easy to feel like you are spreading yourself too thin when you are trying to motivate yourself while also trying to motivate others, yet leaders must always do this, and people often demand it from them.

Given the difficulty of the assignment, it is an excellent question to ask senior leaders to learn what they have learned through their own experiences in the role.

One’s development as a leader can benefit from understanding the strategies and resources that great leaders employ to attain balance successfully.

10. What Are Some Aspects Of Leadership You Are Still Striving To Improve?

There is no predetermined period in a leader’s life at which they stop maturing and expanding their knowledge. Someone who consistently works on improving himself and their passions can be highly considered a leader.

When studying a great leader, it is something that is frequently overlooked. On the other hand, as a corporate leader, you will be better equipped to persevere if you are aware of the projects other leaders are working on.

They may be working on something you are also struggling with, and their response may help you develop a particular characteristic. It offers an opportunity to gain more knowledge that you can apply later. Learning is always a continuous process, even for leaders.

11. How Do You Create Time To Continue Learning While Simultaneously Leading Others?

As a supporting question to the previous one, this question intends to inquire how the leader finds the time to improve their leadership abilities while also completing their regular responsibilities. The following question prompts leaders to discuss organizing their time to incorporate learning.

This particular question addresses the topic of time management but does it from a leadership perspective. While you are working hard to become a leader, it is easy to get swept away by the day-to-day initiatives and responsibilities.

However, making room for you to continue growing is crucial for you and the people working for you or your teams. It can benefit the audience receiving this shared knowledge as they can learn how to become more efficient and productive with their time.

12. What Are Some Of The Day-To-Day Strategies In Which You Ensure Your Staff Remains Focused On The Organization’s Mission And Vision?

Asking a straightforward question like this can sound intimidating, but it’s a practical one. Leaders need to do more than stand around and yell orders at the people in their vicinity. They make it possible for everyone in the organization to pursue the mission and vision by utilizing the particular set of skills that they already possess.

The routine, day-to-day work must be clear of the purpose and vision, but the question is how to instill that mission and vision in the members of your teams. This is where a leader comes in, so it is essential to ask this question to others in leadership positions.

Knowing how a leader manages the people in the organization shows how effective and efficient their leadership skills are.

13. Do You Have Any Questions That Encourage Deep Thought That You Frequently Ask Your Employees?

Even when you ask a leader, the leader most likely has questions of their own that they ask their people.

As a result of the dual role that leaders are expected to play—that of encouragers and challengers—they frequently ask their employees questions designed to stimulate analytical thinking and creative problem-solving with time.

These types of inquiries are fun questions to ask senior leaders. It allows them to peek at the qualities they could find valuable in their staff and possible future leaders.

14. As A Leader, What Do You Consider To Be One Of The Most Difficult Obstacles You’ve Faced?

As cliché as this question may be, it is one of the essential questions to ask a leader. It can be a question that warns about potential difficulties and offers guidance on preparing for anything that might arise.

Either it is an all-encompassing and ongoing difficulty or very personal to you. When you ask leaders open-ended questions, you are extending an invitation to them to share additional information about themselves and the experiences they’ve had.

15. What Are Some Of Your Biggest Strengths And Weaknesses As A Leader?

As aforementioned at the beginning of this article, vulnerability is one of the essential characteristics of an effective leader. Therefore, any competent team leader can take a step back from their actions and openly convey what they feel to be their shortcomings.

The work done can be understood better due to this. Realizing that you still have the potential to develop into an effective leader even when you are aware of the inadequacies in your character that keep you from acting is another helpful realization.

The flaws that another person has been able to change into strengths are the source of the assets they describe.

16. What Things You Do in Your Spare Time Enable You to Be a More Effective Leader in Your Professional Life?

For a leader, creating good habits that fuel leadership and a positive work outlook begin in their personal life. These habits could be things like exercising or meditating, or they could be something else entirely.

These are some entertaining questions to ask the CEO of your company. Asking inquiries and striking up conversations helps cultivate healthy relationships, whether maintained in a social or professional setting.

17. How Clear Is Your Vision For What The Future Of Corporate Responsibility Should Look Like In Your Organization?

When it comes to a company’s future, the employees’ level of comprehension is the most critical factor. If the staff members cannot articulate the organization’s goals, they will likely not fully get the vision. This might result in confusion and frustration, impeding the organization’s forward movement.

It is crucial to effectively communicate the goals and objectives of the firm to guarantee that a leader and all staff members are on the same page.

Everyone will work toward the same goal in this manner and be aware of their roles in accomplishing that goal. Crossing the finish line when everyone is rowing in the same direction is more straightforward.

18. In What Direction Does The Company See Itself Going?

What are the goals that the company hopes to accomplish? How does it want to develop its strategies and approaches toward its goals?

These are the two most important questions that every company should address to build a future strategy that is crystal clear and well-focused.

It is helpful for the organization to have several vital goals they want to achieve in multiple years to keep the business on course and prevent it from becoming distracted by less significant goals or objectives,

It is critical to devise an efficient action plan to accomplish these objectives. However, it is essential to incorporate some degree of adaptability into the strategy if the organization needs to shift its focus or make other adjustments along the road.

Finding the answers to these questions can assist any company in developing a strategy for future success.

19. Do You Currently Have Any Strategic Uncertainties?

Any goal or objective the organization may have difficulty accomplishing is considered a strategic risk. A leader must identify any strategic concerns the firm may have. Doing so can assist the organization in avoiding any obstacles and ensuring the success of the strategy a leader has devised for the company.

As a leader, it is essential to identify and evaluate your firm’s strategic issues. Given the facts and information that is currently available, it is not possible to make an accurate prediction regarding these goals.

It is essential to take into account the firm’s goals and the data required to attain those goals to assess these uncertainties accurately.

20. What Do You Believe to Be the Most Important Piece of Advice for a Learning Leader to Follow?

Providing an answer is typically more challenging because there is so much room for interpretation in this issue. As a result, some leaders will respond to it more effectively than others.

Consequently, conducting interviews with various successful leaders and consolidating the many pieces of advice you obtain is beneficial. In either case, those who have succeeded look back on their journey with gratitude and are happy to share the wisdom they have gained with future generations of influential people.

This may be the question that will be the most helpful to someone’s professional career. The senior leader you’re interviewing may know you well enough to recommend a modification that you should make to your behavior.

Be willing to put effort into bettering yourself, and embrace change enthusiastically.

10 Final Engaging Questions to Ask Your Senior Leaders:

What inspired you to pursue a career in your field, and how did you get started?

This question is a great way to get senior leaders to share their personal stories and provide insight into their career journeys. Their answers can inspire junior professionals and provide valuable lessons on career development.

  1. What are the most important qualities you look for when building a high-performing team?

    This question can offer insight into a leader’s management philosophy and highlight what they believe is most important for creating successful teams. The answer can also provide junior professionals with ideas on how to build their own teams.

  2. How do you stay current with industry trends and innovations and encourage your team to do the same?

    This question can offer insight into how senior leaders prioritize ongoing learning and development. It can also provide junior professionals with ideas on how to stay current in their field.

  3. What is your approach to dealing with conflict within your team or organization?

    This question can provide insight into a leader’s conflict management style and offer junior professionals guidance on navigating difficult situations in the workplace.

  4. What has been the most significant challenge you’ve faced in your career, and how did you overcome it?

    This question can provide valuable lessons in perseverance and problem-solving and can offer inspiration to junior professionals who may be facing similar challenges.

  5. What are the most important lessons you’ve learned in your career, and how have they influenced your leadership style?

    This question can offer insight into a leader’s management philosophy and guide junior professionals in developing their leadership style.

  6. How do you foster a culture of innovation and creativity within your team or organization?

    This question can provide insight into how senior leaders encourage creative thinking and foster an environment of innovation. It can also offer junior professionals ideas on how to do the same.

  7. What do you think sets successful leaders apart, and how do you strive to embody those qualities?

    This question can provide insight into a leader’s personal values and beliefs about leadership. It can also guide junior professionals in developing their leadership styles.

  8. What do you think are the biggest challenges facing our industry today, and how do you see us overcoming them?

    This question can offer insight into a leader’s perspective on industry trends and challenges. It can also provide junior professionals with ideas for preparing for the future.

  9. How do you prioritize work-life balance, and what advice do you have for junior professionals who are struggling to find balance?

    This question can offer insight into a leader’s perspective on work-life balance and provide junior professionals with guidance on managing their work-life balance.

30 Engaging Questions to Ask Your Senior Leaders – Conclusion

One of the essential takeaways from the following questions is to remember that leaders, like everyone else, are only human.

Because these influential people are humans with lives much like ours, it is essential to ask them in a detailed and personal way rather than merely inquiring, “How did you do it?”. Remember that having humanistic qualities is essential to being a leader, and ensure that your questions show this comprehension.

We need to put thought and purpose into the questions we ask other leaders to get the most out of the conversations we have with them.

Please do not go into this hoping to find all the answers; instead, use it as an opportunity to add more tools to your collection of leadership resources.

Because each leader’s journey is unique and their counsel is distinct, the more excitement and interest you bring to your interactions, the more you will take away from them.


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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