Questions to Ask a Leader- 25 Questions

Questions to Ask a Leader

A pandemic is sweeping our planet and it’s time to learn from those who are leading. In a world where leaders demonstrate their skills, we can educate ourselves by following their examples. Remind and encourage leaders, this is what they’re trained for, but by interacting with and learning from them too. By asking questions, we may be able to learn and grow more effectively. Get in touch with leaders who are already doing the work you wish to do and ask them about it. Speak with those who have gone down a completely different path and find out how it went. Let’s discuss some Questions to Ask a Leader.

Learning from others can only be achieved by actively participating. Listed below are 25 questions that other leaders should answer to help you further develop as a leader.

25 questions that other leaders should answer

1. Which mentors do you look up to and why?

Almost all of today’s greatest leaders can trace the people who guided them in their journey. Leaders are shaped by mentors. Generally, mentors are from a variety of backgrounds, so guidance looks different for each mentor. If you have a mentor who is an older relative, a professor from the school, or someone you met at a networking event, you can learn something about who the person is through their lessons and struggles. When an individual tells where and why their mentor came into being, it can provide insight into what a leadership journey can look like.

2. How did your mentors teach you a lesson you will never forget?

Following on from the first question, this question asks what leadership lessons a leader took away from the people who helped him or her along the way. These lessons can also be helpful to you as you navigate your path. As the leader is the evidence, the advice comes complete with proof that it worked. Mentoring can often impart knowledge that will stick with people forever, as opposed to courses and seminars.

3. Can you share some of the most valuable lessons learned from your mentors?

The purpose of this question is to understand the relationship between a mentor and their followers in addition to the lessons they have learned. It can be challenging to actively and regularly teach others, but a valuable attribute to a leader is a willingness to learn and share. Leaders who share their learnings will likely be respected and will be perceived as being more engaged with the organizational culture. Effective leaders understand that sharing knowledge is the key to success.

4. Was there anything you wished someone had told you when you were starting your career?

The point of this question is to provide a leader with the opportunity to reflect on a valuable lesson they may have learned on the spot. If they had known what to expect, would their response have been different? Here you have the opportunity to discover what a leader has to offer, specifically and personally. Despite the fact that a leader can never be prepared for every situation, what they learn from them gives them an edge they can use in other situations.

5. When selecting a potential employee, what are your key requirements and why?

Not only can you get insight into what you need to do to develop these qualities, but the answer to this question gives insights into what leadership qualities are important. Leaders must be able to recognize that others have valuable characteristics as well. Finding out what to look for can prove challenging, but if you know what to look for, it will be much easier. By developing these qualities within yourself, you can then start seeing these qualities in others and start to notice the difference it can make on a team.

6. Do you remember a time when you felt scared when developing your career?

When asked this question, a leader is more likely to respond emotionally instead of telling about a risk they took. Leaders in scary positions are often not equated with emotions like fear, even though they often face something frightening themselves. Instead of pretending no leader has ever been scared, ask them when they overcame fear and what they learned from that experience. 

While leaders can teach us how to take on fear head-on, it is okay to feel scared sometimes. You will find that you can better relate to leaders when you understand their career journey and the emotions that play into their decision-making. Some leaders also come from unconventional backgrounds, which can teach you unexpected things. 

7. How do you continue to improve your leadership skills?

Leadership does not stop at a point in one’s life, but continues to grow and learn throughout. People who are leaders are continuously discovering new things about themselves and working toward their ambitions. 

Observing great leaders, we often forget this. Knowing what a leader is doing, on the other hand, can give you the strength to keep going. The issue they are tackling might be something you are struggling with as well, and their answer might be helpful for you as you develop a specific skill.

8. What are some ways you make time for learning as you lead?

Following on from the previous question, the second question asks the leader to discuss how he or she prioritizes time to build these leadership qualities. In answering this question, you might want to know how you incorporate learning into your personal life. Time management is the focus of the question, but leadership also is emphasized. The more time you spend preparing to become a leader, the easier it is to get lost in the daily tasks and projects, but you and your teams benefit from creating a space where you can continue to grow.

9. When it comes to leadership and traits such as empathy, how do you feel they contribute?

Despite being highly specific, this question reveals leadership characteristics that are often overlooked. Leadership has increasingly become more and more important during the unprecedented times our world currently experiences. These difficult times have allowed many of the leaders who are admired today to gain their admiration through their kind deeds. In addition to these qualities being essential for any leader, understanding how they are involved in specific leadership roles can help develop these qualities.

10. In what ways, encourage creativity in others by leading brainstorming sessions?

It can be a challenge to lead brainstorming sessions and encourage creativity. Organizations vary in their approach to these tasks. You can add tools to your own leadership toolkit by learning from other leaders how they encourage innovation in their organizations. Having a way to bring people together that sparks creative dialogue may be one of their skills. To help our teams, we can learn these tips and tricks from other leaders.

11. Is it possible to inspire others while maintaining your passion for the organization’s mission?

As leaders, we expect them to keep us motivated and encourage others all the time, but it is easy to feel drained when trying to do so. To get an understanding of what others have discovered, you should ask other leaders this question. Being able to understand the tactics and tools used by a leader in order to accomplish the balancing act effectively will help you in your own leadership journey.

12. What are the ways you manage your team to ensure they stay committed to the organization’s vision and mission?

It is not complicated, but it is useful. Leadership does not just consist of barking orders at their followers. A mission-driven and vision-happy organization creates an environment where every member can use their specific skills to achieve the organization’s mission and vision. It is impossible to lose sight of the mission and vision in the mundane, daily tasks, but how do you inspire your team to embrace this vision? Leaders come into play here, and that is why asking other leaders this question is valuable.

13. What are some ways you promote a positive working environment?

Empathic leaders are often overlooked. It might not be the trophy that you are hoping for, but a positive and healthy work environment is highly beneficial to any company. Learning some methods other leaders use to create positive work environments can help you become a leader who is more concerned with your organization’s success than your own.

14. Ask your employees a thought-provoking question now and then.

Despite the fact that you’re asking a leader questions, he or she probably has questions they ask employees as well. To enhance critical thinking and problem-solving skills in their employees, leaders are simultaneously expected to be challengers and encouragers.

15. Where do you strike the right balance between planning for the future and paying attention to your employees?

Among the aspects of being a leader are to be of service in the present as well as to consider the future. A leader has to balance two conflicting mentalities often, as this can feel like a balancing act. It can help you to manage your priorities as a leader to explore how leaders may compartmentalize the present and future. Naturally, there will be overlap since everything is intertwined. Nevertheless, the leader must keep an eye on the future while supporting their daily work.

16. When it comes to leadership, what is your greatest challenge?

You might describe it as something huge and a challenge all the time, or maybe it is something deeply personal. Identifying what obstacles you might encounter and preparing for them can give you an advantage.

17. Are there any best practices leaders can use to support other leaders, both within and outside their organization?

It need not be lonely once you reach a leadership position. People in similar positions will always look for ways to support each other. However, what is the best ways to do so in each of your situations? Having the right support can change lives for leaders, but the best way to provide that support varies with each individual.  

18. In your spare time, do you do any activities that help you be a leader in your career?

Whatever you do in your personal life, whether it’s meditating, exercising, or something else, building healthy habits fuels your leadership abilities and outlook on life.

19. When you think of work-life balance, what does it mean to you?

The answer to this question is always intriguing to hear, and it can provide a lot of insight into a company and how it treats its employees during an interview. An organization’s work-life balance perspective is also likely to play a crucial role in how it is designed to develop its leaders. They could also have evolved in their understanding of work-life balance over time. Taking a look at how others are progressing in their careers can provide insights into how you can continue that path.

20. How do successful leaders today distinguish themselves from others?

Some people are born leaders. Rather than bringing people apart to achieve a common goal, they can unite them behind their ideas. Studying the habits of successful leaders in your industry can help you become an exceptional leader for those without this natural talent.

A leader’s ability to communicate effectively, empathize, be visionary, show strategy, and demonstrate other positive traits can be proven with this question. Furthermore, it can help you decide which traits to combine to realize your leadership style and provide top-quality leadership to your team or organization.

21. What is your proudest achievement?

You may discover a side of the person you didn’t know existed. Leaders may be respected for their professional accomplishments, but these achievements are not always seen as a sign of self-actualization. They may be most proud of their family, spouses, their ability to speak a foreign language, or their artistic talent.

It is often through questions like these that we gain perspective on life, as they reveal what is truly important outside of business. Rather than causing you to lose track of time, they can help you balance your time at work and home.

22. What are the most important traits to look for when hiring a new employee?

Any organization relies on its employees. It is crucial to carry out thorough screenings before hiring, as these candidates can either benefit or hinder your business. Although some candidates may have a compelling resume and cover letter, they may lack the skills or techniques they need to excel on your team.

Describe the hiring process this leader uses and what they look for in hiring. As a result, you might be able to identify new hiring strategies to employ and employee traits to look for.

23. In your opinion, what is the most dangerous characteristic of a leader?

You may possess personality traits that prevent you from reaching your professional potential. Although these characteristics can often be difficult to identify objectively in ourselves, they are very real. It is possible to get further insight into these traits by discussing them with another person, and this is likely to aid your professional development in the longer term.

The challenge of asking questions you find useful when meeting another leader is that the answers may have a far-reaching effect on your career. Having a list of questions to ask such a person before meeting them eliminates anxiety, even if you are nervous. The knowledge you will gain during your brief collaboration is invaluable to your career advancement.

24. How do you decide to partner with someone?

Leadership decisions often depend on a variety of factors, including the type of clients and colleagues the leader works with. Ask yourself the following question whenever you need to make decisions of this nature. If you ask this leader about their preferences, you may realize they tend to favor people with good communication skills. Additionally, their responses can provide insights into which skills and qualities you should emphasize in your performance.

25. If you were a new leader, what resources would you suggest?

The perfect way to conclude with a great question! Though we can gain so much from other leaders and their experiences, they may have gained their knowledge from books, podcasts, or other great thinkers. Take advantage of those resources, too.


These questions emphasize the importance of remembering that leaders are also human. Asking specific personal questions, rather than just “How did you do it”?  You should consider the humanistic qualities that make a leader, and you should ask questions based on this understanding. It is important to have care and intention behind our questions so that we can gain insight from other leaders. This isn’t an exhaustive list of all the answers, but rather a collection of tools that you can add to your leadership repertoire. Leaders each have unique stories and different advice they can offer, so the more curiosity and eagerness with which you approach them the more you will learn.

Questions to Ask a Leader- 25 Questions

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