What to Ask Mentors

Awesome! You’ve finally landed that half-hour conversation with “the guy”. 

You know “the guy”- he’s the person that you admired from afar. He’s the guy who is where you want to be in 10-20 years. He’s the mentor. The one who is leading the ground-breaking team, influences the multitudes, or is at the top of their field. He (or she) is the one whos success you would love nothing more than to emulate. And he has carved out 30 minutes of his time over lunch/coffee to sit with you and share the wisdom of how he got there. What an amazing opportunity!

And here you are. You have the date on the calendar, but looking at it with a mixture of both excitement and… well… trepidation. You know you won’t be able to meet with this person regularly, so how do you make the most of this opportunity? 

“What do I ask…?”

Engaging with mentors is one of the most fruitful ways for leaders to grow and make a greater impact in their desired fields. But how do you make the most of the time together, not squandering the potential opportunity of a lifetime? 

Here’s what we don’t want to do (and I’m speaking from experience here): talk about yourself. Here’s the truth- if you’re talking, you’re not learning. The best way to waste an opportunity with a mentor is to center the meeting around you: your life story, your problems, and ways your mentor can give you what you want. The worst way to value your mentor’s time (and make sure you’re never invited for another coffee) is to unload your sales pitch hoping your mentor will fix all your problems. He won’t.

But if you understand that the success of a leader is not so much what they do but rather who they are, you can come prepared to learn what makes them tick and how to implement their insight into your own personal context.

So if you want to learn, you need to come into a meeting prepared. But how do you ask the right questions? Here are five key principles for making the most of our time with successful people:

1. Prepare with Intentionality.

Before you meet, take a few minutes to reflect on what you hope to gain from the conversation. Are you looking for career advice, personal development insights, or perspective on a specific challenge that your mentor was able to overcome? You should be able to finish this statement: “This time will be successful if I learn ______.”

A clear focus ensures you don’t waste time on surface-level conversation. Begin with a warm greeting and express appreciation for their time. Then, briefly share why you admire them and what you hope to learn, setting a purposeful tone for the discussion. Realize that your mentor has likely sacrificed valuable time/resources to allow this conversation to happen, and value that sacrifice by being tactfully concise.

2. Focus on “Why” and “How”.

You don’t want to just know what they do, you want to know how and why they do it. Ask questions that help you discover principles instead of just practices.

For example, instead of asking, “What do you do in your role?” or “How did you grow your (church/business/platform) to X number of followers” try instead, “How did you develop the skills needed for your role?” or “What was your strategy for growth?” Open-ended questions like these encourage your mentor to share meaningful insights, personal experiences, and lessons learned along the way. 

Remember, you can’t copy exactly what someone does, but you can learn how they think. You will never be able to copy and paste the details of your mentor’s life experiences and skills or the context in which they were successful. However, you may find key principles that are universal and will be effective in your own setting. 

3. Ask about their Influences

Great leaders and mentors are often shaped by the people and ideas they surround themselves with. You want to learn what interests them. What books are they reading? What podcasts are they listening to? What sources are they pouring from as they pour into others? Not only does this provide you with valuable resources to explore, but it also gives you insight into their thought processes and values.

4. Try to find the Real Story

This is a more advanced strategy. You want to ask questions that help you discover what’s in a leader’s heart, not just their head. Dig deeper into their story by asking, “What experiences have shaped you the most?” or “Can you share a time when you faced a major challenge and how you overcame it?” These questions open the door to personal stories that reveal resilience, adaptability, and wisdom—lessons you can apply to your own life.

Most people never get to this level of a conversation. In fact, there are many leaders who have never been asked questions about what separated them from their peers.  Ask your mentor something similar to, “Hey, there’s something special about you. Can you tell me the part of your story most people don’t know or wouldn’t understand?” You might be surprised to learn what they consider the key towards their success vs. the popular opinion.

5. Take Notes and Apply

And here’s what really counts- taking the conversation from potential to reality. Taking notes directly after your coffee chat shows that you value their time and advice. Jot down key takeaways, action steps, and any recommended books, tools, or contacts they mention. If writing feels distracting, make a quick voice memo afterward to capture fresh insights. Do it while the conversation is fresh, so you won’t forget the key piece of information months from now after the opportunity has passed.

But notes alone won’t help you grow—application is key. Implement what you’ve learned, whether it’s refining your approach, tackling a challenge differently, or reaching out to a suggested connection. 

Afterwards, don’t forget to follow up with your mentor. A simple message sharing how their advice helped you not only strengthens the relationship but also shows that you’re serious about learning. A small gift or other token of your appreciation will also show your appreciation, and even potentially give additional opportunities to learn from your mentor in the future!

So, the next time you sit across from “the guy” with a cup of coffee in hand, make sure to make every question count!