20 Great Questions to Ask Leaders

Leaders shine in a powerful situation; this is our chance to educate ourselves. Encourage leaders and remind them this was what they had been trained for, but take this time to engage and learn from them. Learning happens through active engagement with others. One of the best ways to grow and learn is to ask questions to successful entrepreneurs and leaders. Ask your senior leader or vice president about a position you strive to be in and what it takes to excel in this person’s career. It’s an excellent time to learn what soft skills are essential and work on professional development that promotes career growth. Ask the leaders on very different paths what their journey was like. Below are 20 effective leadership questions to ask other leaders for you to continue growing in your professional life as a leader.

1. Who are your mentors, and why?

Finding mentors is an important step toward personal growth and business success. Great leaders today can look back and pinpoint the people who guided them. Mentors shape people into leaders. Mentors come from all walks of life, so guidance can look different for everyone. Whether the mentor is an older family member, a professor from a previous school, or met through a networking event, the people that provide lessons to today’s leaders can share a lot about a person. Hearing from a leader about who their mentor is and why offers a glimpse into a leadership path.

2. What memorable lessons did you learn from your mentors?

In a follow-up to the first question, this question asks for further information about what takeaways a leader gained from the people who supported him or her through his or her journey. Having a mentor can be a game-changer as a business owner or aspiring successful entrepreneur. Lessons learned through mentors can often be the advice that sticks with people forever, longer than what is known in a class or a seminar. By learning from their successes and failures, you can develop the skills and knowledge needed to succeed in your own career or business. These lessons can also be valuable to you and transfer to your journey. It’s advice that comes with proof it worked, as the leader is evidence.

3. How do you pass on the impactful lessons you learned from mentors?

Continuing with the mentoring theme, this question seeks to understand how a leader continues to take the lessons and share them with others. A good, successful leader understands success lies in sharing knowledge with others. An essential attribute of a leader is a willingness to teach and share, but it can be challenging to talk actively and regularly teach others. Leaders who share what they have learned may be more respected and viewed as more engaging with others. These are nice career development questions to keep in mind.

4. What do you wish someone had told you during your career journey?

This is a great career growth question! It flips the mentor questions and challenges a leader to reflect on a valuable lesson they may have had to learn on the spot. What advice would have prepared them for that? This is a chance to find the specific and personal lessons a leader can offer. It is impossible to be ready for every situation, but what a leader learns from that gives them more advice to share with others.

5. What qualities do you look for in a future employee and why?

This is one of the best questions to ask managers! Not only does this give you information on what qualities to cultivate in yourself and your leadership skills, but the answer to this question gives insight into what qualities are essential to leaders. This type of question could also be beneficial in a job interview! Part of being a good leader is seeing important qualities in others. As you work on these qualities in yourself, you can notice them in others and watch the difference they can make for a team. This can be challenging, but knowing what to look for is half the battle.

6. Can you describe when you were scared during your career journey?

Instead of asking about a risk they took, this question invokes a more emotional response from a leader. These are a type of thought-provoking strategy questions, and often emotions like fear are not equated with leadership when leaders are often in positions with scary situations. These can be looked at as strategic questions to ask senior management. Rather than pretending leaders are never scared, ask them about when they overcame that fear and what they learned. It is okay to be scared sometimes, but leaders can show how to tackle that head-on. When asking leaders questions, it is beneficial to understand the emotions that play a role in a career journey. They may also have an unconventional life path that can teach surprising lessons.

7. What are the leadership qualities you are continuing to work on?

This is a great question to ask an executive you look up to! Leaders do not just get to a point in their lives and stop growing and learning. This question directly reports what they value as important qualities for continued growth. A leader is someone who continuously works on themselves and their passions. Often, this is forgotten when observing a great leader. However, knowing what a leader is working on can empower you as a business leader not to give up. Maybe they are working on something you are struggling with, and their answer can assist you as you develop a specific quality.

8. How do you make room for continuing to learn while leading?

A follow-up to the previous question, this question asks the leader to share how they have time to work on those leadership qualities while doing the daily work. This question prompts them to share how they orient their time to incorporate learning. Maybe they would like to improve on a technical skill that is also something that interests you! It is a question that picks at time management but at a leadership level. These are great career development questions as you work hard to become a leader. It is easy to get swept away by the daily projects and tasks, but creating space to continue growing is essential to you and your employees or teams. Keep up with industry trends, as those can be great starting points for questions!

9. How do you feel traits like empathy and vulnerability play a role in your leadership?

This question is particular but highlights the traits often overlooked in leadership. These qualities have become vital to leadership during our world's unprecedented times. Many respected leaders today have earned admiration through their kindness during these difficult times. Qualities such as empathy and vulnerability are essential to any leader, but understanding how the qualities are involved in a specific leadership role can make it helpful in learning how to cultivate these qualities.

10. How do you lead brainstorming and foster creativity among others?

Leading brainstorming activities and spurring creativity can be so daunting. Moreover, this task can look different for every organization. Hearing from other leaders about how they encourage new ideas in their organization can add tools to your leadership toolkit. They may have prompting questions or a unique way of bringing people together that drives the creative conversation. We can learn these tips and tricks from other leaders to help our teams.

11. How do you inspire others while keeping yourself inspired about the organization’s mission?

It is easy to feel spread thin when trying to encourage others and keep yourself motivated, but leaders always do this, and we expect it from them. It is a difficult task, so asking other leaders to discover what they have found on their journey is a great question. Researching inspirational questions to ask and learning what tactics and tools leaders use to achieve the balancing act successfully will be advantageous to your journey as a leader.

12. How do you keep your team on track with the mission and vision of the organization?

This is a simple one but a useful one. Leaders do not simply bark orders at the people around them or various sales teams. They create an environment where everyone can chase after the mission and vision of the organization using their specific skill set. The mission and vision cannot be lost in the mundane, daily tasks, but how do you inspire that mission and vision in your teams? This is where a leader comes in and why this is a valuable question to ask other leaders.

13. How do you foster a positive work environment?

This may be one of the most underrated aspects of leadership. It is not the trophy you may expect, but a positive and healthy work environment is invaluable for an organization. Studying how other leaders instill a positive work environment helps you become a leader serving your organization, not just a leader greedy for individual success.

14. Are there any thought-provoking questions you often ask your employees?

Although you are asking a leader questions, he or she probably has questions he or she asks employees. Leaders are simultaneously meant to be encouragers and challengers, so often, they formulate questions to prompt critical thinking and problem-solving among their employees over time. These types of questions are fun questions to ask senior leaders. It allows a glimpse into what they might find helpful in future leaders. Thought-provoking questions require strategic thinking and can open the door to conversation.

15. How do you balance planning for the future while being present for your employees?

Part of being a leader is serving others in the present while looking into the future. This is another balancing act for leaders, as it can sometimes feel like two conflicting mentalities. Of course, there is a natural overlap, and everything intertwines. But in the end, the leader must represent future goals while daily supporting the employees. Walking through how a leader may compartmentalize the present and future can also help you manage priorities as a leader.

16. What has been one of your biggest challenges as a leader?

This question can warn as to what challenges might occur and how to prepare for anything that could come up. Maybe it is a comprehensive and constant challenge or deeply personal. By asking open-ended questions to leaders, you’re inviting them to share more information about themselves and their experiences.

17. What are the best ways leaders can support other leaders within the same or different organizations?

Once you arrive in a leadership position, it does not have to be lonely. There are always communities of people in similar jobs, but what are the best ways to support each other in your respective situations? Check out this blog that discusses what a great boss may need to hear! Leaders should not have to go it alone; knowing the best way to help each other can change lives.

Did you know that women account for almost half of the global workforce, yet only 27% of women hold leadership positions? Questions centered around women supporting women are excellent questions for female leaders.

18. Is there anything you do in your time that helps you be a leader in your career?

Maybe it is meditating or exercising or something more specific, but either way, developing healthy habits that fuel leadership and a healthy career outlook start in your personal life. These are fun questions to ask your CEO. Whether socially or professionally, asking questions and starting conversations fosters healthy relationships.

19. What does work-life balance mean for you?

This question is always interesting, and it is sometimes a good question to ask when interviewing for a job because it can be very telling about an organization and how it treats its employees. Likewise, a leader’s perspective on work-life balance is probably critical to how he or she got to where she is today. Alternatively, their understanding of work-life balance may have changed over the years. This can provide impactful insight into how to continue in your career path.

20. What resources would you suggest for new leaders?

Always a great question to conclude with! While we can learn so much from other leaders and their personal experiences, they may have been formed by books, podcasts, or other great thinkers. Those resources can be just as valuable to you!

A big theme among these questions is to remember leaders are human too. Asking specific and personal questions and not just asking a simple “how did you do it?” is critical because these leaders are people with stories just like us. You might even have a few funny questions to ask them! Remember that humanistic qualities are a part of being a leader, and questions should reflect this understanding.

Every leader has a different story with different advice, so the more curiosity and eagerness you bring to them, the more you can learn. To truly gain insight from other leaders, your questions should have care and intention behind them. Do not go into this expecting all the answers, but more tools to add to your leader toolkit and list of practical leadership questions.