Very Strategic Questions to Ask Senior Leaders

Strategic questions to ask senior leaders about career growth. Within your career, you may have a once-in-a-lifetime opportunity to meet another leader you like. Both of you may be seated next to one another on a long-haul trip or at the same conference table for refreshments.

This is an excellent opportunity to pose questions to this leader that might result in a breakthrough in your company or sector. Communicating with your leaders is critical for your development and one of the most effective methods to enhance your procedures and tactics.

strategic questions to ask senior leaders

Questions to ask leaders to advance your career

Having a list of questions prepared ahead of time will assist ensure a successful meeting with your executives. Whether you save these questions to your phone or memorize them, have them on hand so you can capitalize on the moment you meet face to face with one of your leaders. It not only helps you appear prepared, but it distinguishes you as someone who is committed to their work and strives to improve. To get you started, here are 15 key questions to ask respected leaders:

  • Who inspires or mentors you?
  • What is one choice you wish you had avoided?
  • How do you encourage your team in the face of disagreement and adversity?
  • What are the most critical characteristics of today's effective leaders?
  • Which characteristics are lacking in today's leaders?
  • What are your immediate objectives?
  • Which one of your accomplishments makes you the proudest?
  • What is the greatest significant risk you have taken and why?
  • How do you maintain your leadership development and growth?
  • How do you ensure that your company is operating in accordance with your vision and mission?
  • How does your company develop outstanding ideas?
  • What are the most critical characteristics to look for in a new employee?
  • Which three leadership books would you recommend?
  • What factors do you examine while making a promotion?
  • What is the most perilous attribute a leader may possess?

Who inspires or mentors you?

It is critical for a leader to maintain relationships with role models and mentors. Regardless of a leader's success, these are the people they turn to for counsel.

Perhaps this question will inspire you to seek out mentors in your field who have overcome similar obstacles to those you are presently facing. By gaining knowledge from their mistakes, you can avoid common traps along the path.

The leader's response may even be unexpected. You may choose to emulate the same role models. This can serve as a point of connection for the establishment of a rewarding, long-term relationship.

What is one choice you wish you had avoided?

A necessary component of progress is the ability to learn from the errors of others. Even after conducting a SWOT analysis, there is always more to discover about your own capabilities. You may save time and money by engaging with leaders who have made errors in similar situations to yours. Additionally, it may be beneficial to enquire about the mental processes and activities that resulted in those errors. This enables you to benefit from the experience of others who have failed.

strategic questions to ask senior leaders

How do you encourage your team in the face of disagreement and adversity?

This is one of the most revealing inquiries to ask senior executives since it entails their vision and their role in assisting their business in accomplishing its objectives. Effective leaders understand that people require more than cash rewards to commit to long-term goals.

Regardless of your business, this inquiry might provide effective tactics for motivating employees or coworkers to work together toward a common goal. This requires more than savvy leadership; it also requires offering a source of incentive, which your leaders are almost certainly adept at. Discussing the appropriate motivation for teams might assist you in determining how to approach this with regard to your team's unique demands.

What are the most critical characteristics of today's effective leaders?

Certain individuals are born leaders. They have the ability to unite others behind their ideas and manage them toward a shared objective. If you lack this inherent quality, you may still develop into an extraordinary leader by studying the practices of successful leaders in your field.

This question demonstrates the value of communication abilities, empathy, vision, strategic thinking, and other desired leadership characteristics. Additionally, it can identify the optimal mix of attributes for enhancing your leadership style and providing superior counsel to your team or business.

What characteristics do today's leaders lack?

Again, this is a strong question that may shed light on your own leadership flaws. Being in a position of leadership may instill a sense of invincibility, but it's beneficial to check in with others to improve on areas you're unaware of. Almost certainly, asking this question will result in an answer that assists you in identifying your own strengths and limitations.

What are your immediate objectives?

Leaders who excel frequently have objectives in mind, even if they are already successful or enjoy a position of prominence.

When you ask this question, take note of the number of objectives, their breadth, and the method by which they intend to fulfill them. Compare your methods and techniques to determine how you may enhance your goal setting for maximum career progress. Additionally, understanding how to prioritize goals effectively will help you focus on the most critical aspects of your firm.

What makes you the proudest of yourself?

This reaction may disclose an aspect of the person you were unaware of. While many individuals admire leaders for their professional successes, many do not view these achievements as the pinnacle of self-actualization. Their family, their spouse, their ability to speak a foreign language, or their artistic aptitude may be their greatest accomplishments.

These kinds of questions frequently assist in putting life into perspective by revealing the things that are truly essential away from the business. If nothing else, they can help you maintain a healthy balance between your time at and away from the office.

What is the greatest significant risk you have taken, and why?

Leaders make several sacrifices to attain their position. When individuals respond to this question, certain risks may evoke pleasant memories, while others may generate severe emotions associated with missed chances. Take away lessons on how to pick risks wisely in order to prevent making poor professional choices. Allow yourself a minute to reevaluate your priorities and the manner in which you are pursuing them.

strategic questions to ask senior leaders

How do you maintain your leadership development and growth?

The most admired executives understand how to maintain a competitive edge in their industry. They continue to develop their abilities, establish new connections, strengthen existing relationships, and seize worthwhile possibilities. Some leaders maintain these abilities by reading books; others instruct their employees and develop new approaches to old challenges.

Even if you already have a system in place for updating your abilities, you may expose yourself to new approaches to your job by asking others about their own leadership techniques.

How do you ensure that your company is operating in accordance with your vision and mission?

Successful leaders do not possess superhuman abilities. These folks excel because they understand how to best utilize people and resources to attain their common goals. Some organizations do this by mobilizing their team members to boost output. Others may leverage their position of leadership to get the support of critical stakeholders.

You may utilize the information gleaned from this question to enhance your business's plans for things like initiating new initiatives or altering the way your organization processes information.

How does your company develop amazing ideas?

Different companies employ a variety of different strategies for idea creation. Certain businesses have an organizational culture that values communication, information exchange, and feedback. Others have a process for encouraging and recording novel approaches to issue resolution, as well as reward systems to foster innovation.

By posing this question, you may identify new ways to help your employees or team members become more effective idea generators. An excellent idea might originate with the lowest-ranking employee or the highest-ranking executive. Assuring that everyone has access to tools that aid in the optimization of various ideas paves the road for your firm to flourish. Additionally, this inquiry might highlight flaws in your employee feedback policy and suggest ways to improve its effectiveness.

What are the most critical characteristics to look for in a new employee?

Employees are the bedrock of every business. It is critical to do extensive background checks on prospective workers, as these individuals may either assist or hinder your firm. Even with an excellent résumé and cover letter, some candidates may lack the abilities or practices essential to succeed on your team.

Can you recommend three books on leadership?

Books are excellent sources of wisdom and expertise from previous leaders since they help guide the development of effective new procedures and approaches. Having said that, each leader frequently has their own recommendations, so get them from the one you're interviewing.

What factors do you examine while making a promotion?

While you may not be able to promote anyone at the moment, it helps to understand the elements to consider when deciding between two or more similarly qualified personnel. The response to this question may disclose an efficient guideline to follow when a team member needs to be promoted. Additionally, it might educate you how to develop into a team player deserving of advancement within your firm.

What is the most perilous attribute a leader may possess?

There may be personality qualities that you possess that unintentionally impede your career development. However, it is sometimes difficult to objectively detect these characteristics in oneself. Speaking with another person about these characteristics may be enlightening and is likely to aid your professional development in the long run.

When you meet another leader who interests you, it might be challenging to formulate questions that will have a lasting influence on your career. Even if you are afraid, you may prevent anxiety by preparing a list of questions to ask such a person when you meet. The brief time you spend together might yield profound insights that will aid in your career advancement.

Additional questions to ask leaders

If these questions aren't enough, try one of these:

  • What qualities do you look for in a senior executive?
  • What are the ways that you keep your team motivated?
  • What do you think makes a successful leader?
  • What are successful leaders today missing?
  • How do you best align with other leaders in the organization?
  • When it comes to leadership skills, which ones are the most important?
  • How did you arrive in a leadership position yourself?
  • What's the best way to earn the trust of your direct reports?
  • What are the day-to-day challenges of being in a leadership position?
  • Which leadership qualities do you feel are the least important?
  • What's the organization's mission in 5-years/10-years?
  • How can we increase employee engagement?
  • How can we be a more client-centric culture?
  • What are some ways we can increase employee retention?
  • How did you end up on this professional path?
  • What do you value more, innovative ideas or bringing new ideas to life?
  • Aside from time-management, what other skills are important for a senior manager/business leader?
author: patrick algrim
About the author

Patrick Algrim is a Certified Professional Resume Writer (CPRW), NCDA Certified Career Counselor (CCC), and general career expert. Patrick has completed the NACE Coaching Certification Program (CCP). And has been published as a career expert on Forbes, Glassdoor, American Express, Reader's Digest, LiveCareer, Zety, Yahoo,, SparkHire,,, FairyGodBoss,, St. Edwards University, NC State University,, Thrive Global,, Work It Daily, Workology, Career Guide, MyPerfectResume, College Career Life, The HR Digest, WorkWise, Career Cast, Elite Staffing, Women in HR, All About Careers, Upstart HR, The Street, Monster, The Ladders, Introvert Whisperer, and many more. Find him on LinkedIn.

Fact checked: Our small and dedicated team rigorously evaluates every article, guide, and reference to ensure the information is accurate and factual. Learn more.


Help us by spreading the word