7 Questions You Should Ask Your Mentor
Thirty years. That’s how long I have been on this journey of studying leadership — reading the books, attending the conferences, sitting across from mentors, making the mistakes, learning the lessons, and then getting up and doing it all over again. When I started, I thought leadership was mostly about having the right answers. Three decades later, I’ve come to understand that the best leaders are actually defined by something else entirely: the quality of their questions.
Leadership development is not a destination. It’s a pursuit — and it is one of the most rewarding pursuits you will ever commit yourself to. Along the way, I have had the privilege of learning from some remarkable people. But few have shaped my thinking more than one of the greatest leadership teachers of our time, John Maxwell. His books, his wisdom, and his example have challenged me to grow in ways I didn’t know I needed — and I am a better leader because of it.
One of the most practical and powerful things I picked up from John Maxwell is a simple set of seven questions. These aren’t questions to ask yourself. They are questions to ask the mentors in your life — the people who are further down the road, who have seen things you haven’t seen yet, and who carry wisdom you can’t afford to leave untapped. The next time you sit down with a mentor, try asking these seven questions. I promise you, the answers will be worth far more than the courage it takes to ask them.
1. What’s the Greatest Lesson You’ve Ever Learned in Your Life?
This question cuts straight through the small talk and gets to the gold. Every person who has lived and led long enough has at least one defining lesson — a moment, a failure, a season, or a conversation that changed the way they see everything. When you ask this question, you are essentially asking someone to hand you the most valuable thing experience taught them, without you having to go through everything they went through to learn it.
Don’t rush past the answer. Sit with it. Ask follow-up questions. The greatest lesson of someone’s life didn’t come easily — and understanding the story behind it will help you carry it forward in a way that actually shapes how you lead.
2. What Are You Learning Right Now?
This question does two things at once. First, it tells you something important about the mentor themselves — because a great mentor is always still growing. If someone has stopped learning, they may be a wonderful person, but their best mentoring days are likely behind them. Second, it opens a window into what is currently shaping their thinking, and that real-time insight is often more immediately applicable than anything they learned ten years ago.
The best mentors are lifelong students. When you find one who lights up answering this question, you’ve found someone worth investing significant time in. Their current growth has a way of becoming your current growth — and that kind of momentum is contagious.
3. How Has Failure Affected Your Life?
Here is where the conversation gets real. Anyone can tell you about their wins. It takes a certain kind of trust — and a certain kind of leader — to walk you through their failures honestly. But those stories are where the richest lessons live. Failure has a way of teaching things that success simply cannot, and a mentor who is willing to open up about their lowest moments is giving you an extraordinary gift.
Don’t be afraid to ask this question, and don’t be surprised if it takes a moment for your mentor to answer it. What they share will likely humanize them in a way that makes their success more believable — and their guidance more trustworthy. It will also give you permission to fail forward in your own journey, knowing that the people you admire most have been there too.
4. Who Do You Know That I Should Know?
This is one of the most strategically important questions on this list — and the one most people never think to ask. Your mentor has spent years, maybe decades, building a network of relationships with other high-caliber leaders, thinkers, and influencers. When you ask this question, you are potentially unlocking access to an entirely new circle of people who could change the direction of your life and leadership.
A warm introduction from someone your mentor respects carries weight that a cold outreach never will. One conversation with the right person — a person your mentor connects you to — can open doors that would have otherwise remained closed for years. Don’t leave a mentoring relationship without asking this question. The answer could be the most valuable thing that comes out of the meeting.
5. What Have You Read That I Should Read?
Leaders are readers — and the people ahead of you on the leadership journey have usually gotten there, in part, because of the books that shaped them. This question gives you a curated, personalized reading list from someone who has already done the filtering for you. Instead of wandering through endless book recommendations online, you get the titles that actually moved the needle for a person whose results you respect.
But here’s the key: don’t just collect the titles. Ask your mentor why a particular book mattered to them. What did they take from it? How did it change their thinking? That context will make the book infinitely more impactful when you sit down to read it — because you’ll know what to look for before you even open the cover.
6. What Have You Done That I Should Do?
This question is an invitation for your mentor to transfer their experience directly into your development. It might be a specific training they completed, a risk they took, a habit they built, a conversation they initiated, or an opportunity they said yes to that changed everything. Whatever the answer, it comes from lived experience — not theory — and that makes it uniquely valuable.
The best mentors will give you more than a suggestion here. They’ll give you a roadmap. Pay close attention, take notes, and then actually follow through. There is nothing more flattering to a mentor than watching someone take their advice and run with it — and nothing that will strengthen the mentoring relationship faster than showing that you not only listened, but that you acted.
7. How Can I Serve You?
Save this one for last — and mean it with everything you have. This question is what separates someone who extracts value from a mentor and someone who genuinely honors them. Mentorship is a gift. The people who invest in your growth are giving you something that money cannot fully repay: their time, their experience, and their attention. Asking how you can serve them communicates that you understand that — and that you value the relationship, not just the information.
The answers will vary. Sometimes a mentor needs an introduction you can make. Sometimes they need a task completed, a message shared, or simply someone to pray for them or encourage them. Whatever it is, show up and do it. A mentoring relationship that flows in only one direction eventually runs dry. When you bring a spirit of generosity to the table, you create the kind of relationship that lasts — and the kind that a mentor is glad to keep investing in.
The leaders I admire most — the ones who have sustained growth over the long haul — didn’t get there by accident. They were intentional. They sought out people who were further along, asked the right questions, and had the wisdom to apply what they learned. John Maxwell taught me that your growth is largely determined by who you spend time with and what questions you bring to the table.
You have everything you need to start today. Find your mentor. Schedule the meeting. And bring these seven questions with you.
The answers just might change everything.
