7 questions to ask great leaders

August 2014

Last year, a friend of CARE for AIDS, Sarah Kamienski, was training our counselors in Kenya, and she told them that in order to be a great counselor they must be both curious and humble. I’ve found that the leaders I most respect embody this same principle. They are curious enough to ask questions that go beneath the surface, and they are humble enough to listen intently to and learn from the response.

Whether they are trying to solve a problem or just seize an opportunity to learn from another leader, these leaders always seem to have the right question(s) for the occasion. Therefore, a few years ago, I began collecting great questions to add to my leadership arsenal. Last year, someone shared with me an article by John Maxwell in which he shares the seven questions that he tries to ask when he has the chance to sit down and learn from another leader. I want to share these with you below because these questions have allowed me to glean insights from leaders of all ages and experiences.


1. What is the greatest lesson you have ever learned? Andy Andrews wrote in his book The Noticer, “Experience is not the best teacher. Other people’s experience is the best teacher.” We can gain years worth of wisdom by asking others this simple question.

2. What are you learning now? This question unlocks what that person is most passionate about today and may reveal challenges that they are currently facing. It may open up a door for you to serve them by sharing a connection or resource.

3. How has failure shaped your life? This question will tell you a lot about a person’s attitude by their willingness to admit and learn from failures. And, once again, you get the benefit of learning from others mistakes.

4. Who do know that I should know? This may sound very transactional, but I ask it a slightly different way. I ask, “Who do you know that would want to learn about what CARE for AIDS is doing in Kenya?” Before asking this question, the person is not proactively thinking of introductions to make, and this activates their thinking. This question has led to countless new relationships.

5. What have you read that I should read? There are just too many books to read them all, and I hate wasting my time on a bad book. I mitigate that risk by only reading those that have been recommended to me. Unfortunately, that list is already too long to ever finish!

6. What have you done that I should do? I love expanding my world with new experiences. Whether it is a trip, a restaurant, or a local activity, I always want to try new things that will add adventure and awareness to my life.

7. How can I add value to you? This is by far the most important question because it reveals your true objective, to add value to them, not extract it.

These are just a sampling of great questions to ask leaders in your life. What are some of your favorite questions to ask of leaders you meet?