20 Great Questions to Ask Other Leaders

Originally posted @ Caffeine Marketing

 As our world grapples with a global pandemic, now is the time to learn from the leaders. Leaders are shining in an powerful situation and this is our chance to educate ourselves. Encourage leaders and remind them this was what they have been trained for (check out more on that in this blog), but take this time to engage and learn from them as well. Maybe one of the best ways to grow and learn is to ask questions. Ask the leaders who are doing what you want to do what it takes. Ask the leaders who are on very different paths what their journey was like. Learning happens through active engagement with others. Below are 20 questions to ask other leaders in order for you to continue growing as a leader as well.

 1.     Who are your mentors and why?

Most great leaders today can look back and pinpoint the people that guided them along the way. Mentors shape people into leaders. Mentors come from all walks of life, so the guidance can look different for everyone. Whether the mentor is an older family member, a professor from 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 what a leadership path can look like.

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

A follow-up to the first question, this question asks for further information about what takeaways a leader gained from the people that supported him or her through his or her journey. These lessons can be valuable to you and transfer to your journey as well. It’s advice that comes with proof it worked, as the leader is evidence. Lessons learned through mentors can often be the advice that sticks with people forever, longer than what is learned in a class or a seminar.

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

Continuing with the mentor theme, this question seeks to understand how a leader continues to take the lessons and share them with others. An important attribute to a leader is a willingness to teach and share, but it can be difficult to actively and regularly teach others. Leaders who share what they have learned may be more respected and may be viewed as more engaging with others. A good leader understands success lies within sharing knowledge with others.

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

This question 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 a chance to find the specific and personal lessons a leader can offer. It is impossible to be prepared for every situation, but what a leader learns from that gives them more advice to share with others.

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

Not only does this give you information on what type of qualities to cultivate in yourself, but the answer to this question gives insight into what qualities are important to leaders. Part of being a good leader is seeing important qualities in others. This can be a challenge, but knowing what to look for is half the battle. As you work on these qualities in yourself, you can then begin to notice them in others and watch the difference it can make for a team.

 6.     Can you describe a time 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. Often, emotions like fear are not equated with leadership, when in fact, leaders are often in positions with scary situations. Rather than pretending that leaders are never scared, ask them a time they overcame that fear and what they learned from that. It is okay to be scared sometimes, but leaders can show how to tackle that head-on. When asking leaders questions, it is very helpful to you to understand the emotions that play a role in a career journey. They may also have an unconventional life path that can teach you surprising lessons.

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

Leaders do not just get to a point in their lives and stop growing and learning. 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 not to give up either. Maybe what they are working on is something you are struggling with too, 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 personally orient their time to incorporate learning. It is a question that picks at time management, but at a leadership level. As you work hard to become a leader, it is easy to get swept away by the daily projects and tasks, but creating space for you to continue to grow is important to you and to your employees or teams.

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

This question is very specific, but it shines a light at the traits that can often be overlooked in leadership. During the unprecedented times our world is currently in, these qualities have increasingly shown to be vital to leadership. Many of the leaders who are respected today have earned admiration through their kindness during these difficult times. Qualities such as empathy and vulnerability are important 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 among their organization can add tools to your own leadership toolkit. They may have prompting questions or a unique way of bringing people together that drives the creative conversation. These are the tips and tricks we can learn from other leaders to help our own 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 do this all the time, and we expect it from them. It is a difficult task, so this is a great question to ask other leaders in order to find out what they have discovered on their own journey. Learning what tactics and tools a leader uses to achieve the balancing act successfully will be advantageous to your own journey as a leader.

 12.  What are the daily ways 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. 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 be expecting, but a positive and healthy work environment is invaluable for an organization. Studying the ways other leaders instill a positive work environment helps you become a leader that is 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 over time, leaders formulate questions to prompt critical thinking and problem-solving among their employees.

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

Part of being a leader is being to serve others in the present while also looking into the future. This is another balancing act for leaders, as it can feel like two conflicting mentalities sometimes. Walking through how a leader may compartmentalize the present and future can help you manage priorities as a leader as well. 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.

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

Maybe it is something really broad and a constant challenge, or maybe it is deeply personal. This question can give a warning to what challenges you might occur and how to prepare for anything that could come up.

 17.  What are the best ways that leaders can support other leaders, whether within the same organization 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 positions, but what are the best ways to support each other in your respective situations? Leaders should not have to go it alone, but knowing the best way to support each other can change lives.

18.  Is there anything you do in your personal 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, starts in your personal life.

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 the 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 own career path.

 20.  What are resources you would 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 key, because these leaders are people with stories just like us. Remember that humanistic qualities are a part of being a leader, and questions should reflect this understanding. To truly gain insight from other leaders, our questions should have the care and intention behind them. Do not go into this expecting all the answers, but more tools to add to your leader toolkit. Every leader has a different story with different advice, so the more curiosity and eagerness you bring to them, the more you can learn.

Evan Knox


Throughout his life, Evan Knox, has been on a mission to help other people. This desire let him to found his marketing agency and co-founded a private equity group so that founders could be successful. Starting Caffeine Marketing and Tactos has enabled him to help hundreds of make marketing profitable and get the value they deserve out of their business.  Evan has been featured on more than 100 podcasts teaching about leadership, marketing, and business growth.


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