14 Great Questions To Ask Leaders for Career Growth

Guest Post By Indeed Editorial Team

Previously posted at Ca.Indeed.Com.

Leaders are exceptional individuals who have the skills, values, and knowledge to direct the affairs of an organization or group. A leader’s vast experience and expertise often mean they have valuable insights into a variety of topics. You need to prepare yourself to ask the right question to maximize your relationship with a leader. In this article, we discuss the importance of asking leaders questions and highlight some important questions to ask leaders around you.

Importance of Asking Leaders Questions

It is always useful to ask leaders insightful questions when you have the opportunity. Having a few minutes with them can make you better prepared for success. Here are some reasons why asking leaders questions is a good idea:

It teaches you valuable lessons

Leaders usually have years of experience and knowledge to reach their status. Their positions mean they’re exposed to more complex issues and responsibilities. For these reasons, leaders usually have a unique way of thinking and a wealth of knowledge. Asking leaders questions can expose you to valuable lessons about their lives and careers. It can also expose you to a fresh approach for solving a problem or understanding an issue.

It can help you build your network

Asking questions is a great way to get to know a person and establish connections. Asking leaders questions can help them warm up to you. A question you ask may lead to a meaningful conversation that begins a positive relationship. You may also discover things you have in common with the leader. This can help expand your professional network and can even secure you a mentor.

It allows you to demonstrate your intelligence

Asking insightful questions can show that you’re thoughtful and intelligent. It is unlikely leaders meet many people that have a mental list of interesting questions for them. This shows that you’re intellectually curious and you take the time to prepare. An added benefit is that asking questions also improves your thinking.

It can help you solve current problems

Solving problems creatively and efficiently is a foundation of leadership. If you ask a leader a question, they may share a similar problem they’ve faced in the past. You may also get advice on how they solved their challenge, which can help you solve your own.

It can aid your career

Engaging with leaders exposes you to new knowledge that can be a significant boost to your career. For instance, asking the right question can expose you to quality mentorship and give you the opportunity to impress the leader. As a result, you have someone to provide you with advice and speak on your behalf, which can be essential for your career.

14 Examples of Questions to Ask Leaders

When you meet a leader, you have limited time to make an impression, so you need to ask the right questions. Here are some strategic questions to ask leaders:

1. What’s something you wish you knew earlier in your career?

As people advance in their careers, they develop more efficient ways of navigating the industry. They also discover valuable insights about personal systems, values, people, and life. When you ask this question, the leader considers the knowledge they have gained that has shaped their careers. This can be an invaluable source of self-optimization tips and other ways to advance quickly. This question is especially great if the leader is in your industry, so you can apply their advice to your own professional life.

2. Who are the mentors that have had the greatest impact on you?

Leaders typically have multiple mentors in their professional life. This question makes them think about their most beneficial mentorship relationship and why it was important. In their answer, they may provide essential tips about picking a mentor for yourself and maximizing mentor relationships. Engaging with a mentor may challenge you, but insight might improve your experience. It is also possible that you and the leader admire the same people. They may introduce you to that person and speak highly of you. This can be a way to bond and create a stronger relationship.

3. What is your biggest regret in your career?

Everyone makes mistakes, even the most qualified leaders. Asking leaders about their past errors and how they learned from them can help you avoid similar errors. The leader can also expose you to certain problematic values or thinking patterns that lead them to the error. Using their insights can help you save time and avoid mistakes.

4. What do you do to encourage creativity in your organization?

Encouraging creativity among others can be a tasking ordeal, even for competent leaders. It requires creativity, communication skills, and people management skills to inspire creativity among employees. Asking this question can expose you to uncommon tips for managing people and improving your creativity. This can also help you better understand how creativity serves an organization.

5. What qualities do you think leaders today lack most?

As a leader or aspiring leader yourself, this question can be an immense benefit to you. There are limits to which we can assess ourselves and there may be mistakes you make that the leader can point out. Hearing from someone who has progressed in your field can help enrich your perspective and help you become a better leader.

6. What drives you currently?

Regardless of how successful they are, leaders still have goals that are important to them. Asking a leader this question can help inspire you to challenge yourself. As the leader discusses their goals and strategy, it can offer you essential tips for goal-setting and strategic thinking. This can help you prioritize your goals and manage your resources more efficiently.

7. What is your greatest achievement?

This question can help you learn more about the leader and connect on a more personal level. The achievement might be a relationship, skill, or adventure that’s unrelated to their professional life. Even when the achievement is professional, they can tell you about the personal context that makes the achievement stand out. This can expose you to a personal side of the leader and help you gain valuable life lessons from their answer.

8. What do you do to improve yourself as a leader?

Effective leaders commit to continually bettering themselves and have systems to improve their skills. Asking this question can expose you to effective methods for self-development and improved leadership. Reading, mentorship, teaching, and meditation are common ways people sharpen their minds. You can improve your existing strategy with tips from the leader’s answer.

9. What things do you consider before a new hire?

It is challenging to navigate the hiring process of employees. Many times, candidates have great resumes and cover letters without being able to meet the company’s needs. Companies often choose employees based on their values, work ethic, and determination. Asking this question can expose you to insightful tips for more effective recruitment.

10. What are your favourite books?

Leaders are usually voracious readers since books are one of the greatest tools for gaining wisdom. It is likely the leader you’re speaking with has books that affected them, which can contain insights from other industry leaders that they look up to. You can add these books to your reading list and go through them to enhance your knowledge.

11. What behaviors should good leaders avoid?

Outstanding leaders have learned many of their skills, and they likely have had to adjust undesirable traits as they advanced in their careers and learn lessons about which traits hinder their advancement. Asking this question can help you identify if you have any of those problematic traits. This allows you to work on managing your weaknesses before they negatively affect your career.

12. Which leadership qualities are you still trying to improve?

Leaders are constantly on a journey of self-development and self-rediscovery. It is likely the leader you’re speaking to has a certain quality they still struggle with. This can encourage you to be humble and always willing to learn and grow. They may also be working on something you are currently struggling with. Their insight can inspire you to continue to pursue your goals and help you figure out how to overcome the challenge.

13. How do you keep your organization committed to your vision and mission?

What sets outstanding leaders apart is their ability to use their resources efficiently. Inspiring people and directing them to do productive work is one of the core responsibilities of a leader. Learning how a leader has navigated that responsibility can teach you important lessons. It can help inform and improve your personal strategy for managing people.

14. How do you promote a positive work environment?

The work culture at an organization affects staff morale and overall productivity. Responsibility falls on the leader to promote a warm and conducive work environment. They can have useful tips for boosting employee morale or ensuring standard customer service. Learning how a leader has handled this responsibility can help you improve your own strategy and become a better leader.



Indeed is the #1 job site in the world* with over 250M unique visitors every month. Indeed strives to put job seekers first, giving them free access to search for jobs, post resumes, and research companies. Every day, Indeed connects millions of people to new opportunities.


75 Best Sales Questions to Close More Deals

Guest Post by Paul Cherry Have you ever faced a situation where the sale seemed to be just about sealed,...

10 Questions to Ask Your Mom or Grandma on Mother’s Day

My Mom, Clara Tiede, was the best Mom I could have ever had.  With one year of Junior College she became a...

5 Questions for Helping Others with their Struggles

Guest Post by Dr. K. Shelette Stewart A few years ago, when I resigned from my leadership role at Harvard...

4 Best Icebreakers For Team Meetings

Guest Post by Dr. David Burkus Originally posted @ DavidBurkus.com Icebreakers are not just games or...

Do You Have a Hard Time Saying “No”?

Excerpted from Chapter 24 of “Now That’s a Great Question.” Click HERE to listen to Chapter...

Four Words

Excerpted with the permission of the authors from Chapter Three of Power Questions: “Four Words. ...

You need Questions…. Not Answers….Start here

Guest Post by Diana Kawarsky You’re a new hire in financial services, maybe an Analyst or Associate who...

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.