What Should I Prepare Before Each Mentoring Session?

Here's a hard little truth I've watched play out for years: most mentoring sessions don't fail because the mentor was bad. They fizzle because the mentee showed up empty-handed. No agenda, no real question, no notes from last time — just "so, uh, what've you got for me?" And a mentor can only do so much with that. Preparing for a mentoring session isn't about being fancy or writing a term paper. It's about respecting the hour, your mentor's and your own. Do fifteen minutes of prep and an ordinary meeting turns into a real one. Skip it, and you'll wonder why nothing's moving. So let's talk about exactly what to bring.

Let me be honest about where I learned this. I started working at 17, and for a long stretch I thought "showing up" was the same as "being ready." It isn't. It took me years — and more than a few wasted meetings with people far wiser than me — to figure out that the folks who grew fastest weren't the smartest ones in the room. They were the ones who came prepared. They walked in knowing what they wanted, and they walked out with it. I've spent a career now, from the factory floor up through leadership at some very big companies, watching that pattern hold. Preparation is the cheapest advantage there is, and almost nobody uses it.

Why Prep Is the Whole Game

Think about what a mentoring session actually is. Someone who's further down the road than you has agreed to stop, turn around, and hand you a piece of what they know. That's a generous thing. Whether they're doing it for free or you're paying for it, their time is the real currency here — and you get a fixed, small amount of it. An hour. Maybe less. When that hour starts with you fumbling to remember what you even wanted to talk about, you've just burned ten minutes of a gift you can't get back.

Prep flips the whole thing. When you walk in ready, three good things happen at once. First, you respect your mentor — and believe me, they notice. Nothing makes a mentor want to keep showing up like a mentee who clearly did their homework. Second, you get better answers, because a sharp question pulls a sharp answer out of someone. And third, you actually make progress, because the session becomes about moving forward instead of catching up. Preparation is the difference between a nice conversation and a real one. I dug into that gap in what makes a mentoring conversation actually effective — and it starts long before you sit down.

Here's the mindset shift that changes everything: stop treating the session as the mentor's meeting and start treating it as yours. You called it. You set the table. You're the host. A host doesn't wait to see what happens — a host has a plan.

The Simple Pre-Session Checklist

You don't need a binder. You need about fifteen minutes and a short, honest look at where you are. Here's the whole thing, and it fits on an index card.

That's it. Notice this isn't about impressing anybody. It's about arriving with your side of the work done so the mentor can do theirs. The biggest mistake I see is people bringing problems they haven't even wrestled with yet. If you haven't tried anything, all your mentor can do is guess along with you. But if you show up and say, "I tried A and B, here's exactly where they broke down," now they can give you something you couldn't have found on your own. You've handed them a real starting point instead of a blank page.

And write things down — actually write them, on paper or a note on your phone, before you get there. The question that feels crystal clear in your head has a funny way of turning to fog the second you're sitting across from someone. A written question stays sharp.

Bring One Real Question, Not Ten Vague Ones

This one's counterintuitive, so stay with me. When people finally get prep-minded, they overcorrect and show up with a laundry list — twelve questions, rapid-fire, trying to squeeze every drop out of the hour. It backfires. You end up skating across the surface of a dozen things and going deep on none of them. The mentor never gets enough context to give you their best, and you leave with a pocketful of shallow answers.

One good question beats ten weak ones. Pick the single thing that, if you got real clarity on it, would unlock the most. Then give it room. Let your mentor ask you questions back. Let the conversation actually go somewhere. The best sessions I've ever been part of, on either side of the table, orbited one meaty question for most of the hour — and everybody left smarter. If you're not sure which questions carry that kind of weight, I put together a starter set in what questions to ask your mentor in your first meeting, and the same instinct applies to every meeting after it.

There's a bonus here, too. Choosing your one question forces you to figure out what actually matters to you right now. That little act of prioritizing is half the growth by itself. A lot of the time, people don't need a new answer — they need to get honest about the real question. Picking the one that counts is how you get there. It also keeps you from scattering your energy across a dozen skills at once; I unpacked that in how to know which skills to focus on with your mentor.

Close the Loop From Last Time

If there's one prep habit that separates the people who grow from the people who just keep meeting, it's this: they close the loop. Every session ends with some version of "I'll go try this." The prepared mentee opens the next session by reporting back on exactly that. "You told me to try X. I did. Here's what happened." Good, bad, or ugly — they bring it back.

This matters more than almost anything else you'll prepare, and here's why. A mentor is pouring wisdom into you, and they have no idea if it's landing unless you tell them. When you close the loop, you're not just being polite. You're giving them the feedback they need to mentor you better — to double down on what's working and change course on what isn't. You turn a one-way lecture into an actual working relationship. Advice is worthless until it becomes action, and closing the loop is proof you're doing the real work. I made that whole case in how to take action on your mentor's advice, because it's where most mentorships quietly live or die.

And yes — you have to report the flops too, not just the wins. The temptation is to only bring back the things that went well, so you look good. Resist it. The stuff that broke is where the gold is. A mentor can't help you fix what you hide. Showing up and saying "I tried it and fell flat" isn't failure — it's exactly the raw material a good session is built on.

None of this depends on how often you meet, either. Whether you sit down weekly or once a quarter, the loop is the same — you leave with an action, you come back with a report. If you're still sorting out the right rhythm, I worked through it in how often you should meet with your mentor.

Why This Is Really the Law of Intentionality

One of John C. Maxwell's 15 Laws of Growth is the Law of Intentionality, and it says something so simple it's easy to walk right past: growth doesn't just happen. You don't drift into becoming better. Nobody accidentally gets wiser, stronger, or more skilled. Growth is a choice you make on purpose, again and again, in a hundred small moments most people don't even notice.

Preparing for a mentoring session is that law shrunk down to something you can hold in your hand. The unprepared mentee is hoping growth will happen to them — that just being in the room with a wise person will somehow rub off. The prepared mentee has decided to make it happen. Same hour, same mentor, completely different result, and the only variable is intention. One person showed up to see what the session would give them. The other showed up having already decided what they'd take from it.

That's the whole thing. Fifteen minutes of prep isn't a productivity trick — it's you casting a vote for the kind of person you're becoming. Every time you review your notes, pick your one real question, and close the loop, you're telling yourself that your growth is worth being deliberate about. Do that enough times and it stops being a chore and starts being who you are. The people I've watched grow the most were never the most gifted. They were the most intentional — and it showed up in something as small and unglamorous as walking into a meeting ready.

That's the honest reason I ended up writing Leadership Between the Lines and building the LBL-10 workshop. Not because I had some rare talent, but because somewhere along the way I got intentional about my own growth and it changed the whole trajectory. Heroes aren't the folks with capes and superpowers. They're ordinary people who show up — and the ones who grow are the ordinary people who show up ready.

Reflection Questions

Run through a couple of these before your next session — that's prep, too:

1. Think back to my last mentoring session. Did I show up prepared, or did I wing it? What did that cost me?
2. What's the one problem I'm actually stuck on right now — and have I really wrestled with it, or am I hoping my mentor will do the wrestling for me?
3. What did I say I'd do last time? Did I do it? Am I willing to report back honestly, even if it flopped?
4. If I could only ask my mentor one question this session, what would it be? Why that one?
5. Am I treating this as my mentor's meeting or as mine? What would change if I acted like the host?

The Bottom Line

So what should you prepare before each mentoring session? Less than you think, and it matters more than you'd guess. Fifteen minutes: review your notes, pick one real question, jot down what you already tried, and come ready to close the loop from last time. That's it. You don't need a slide deck. You need to respect the hour and show up with your side of the work done.

Here's what I'd do before your very next session — tonight, or the night before. Grab a scrap of paper and write three things: what I promised to do last time and whether I did it, the one problem I'm truly stuck on, and the single question I most want answered. Bring that scrap with you. That's the whole prep. It's almost embarrassingly simple, and it will change the quality of every mentoring conversation you ever have. Because growth doesn't just happen. It shows up when an ordinary person decides to walk in ready — no cape required.

This ties back to The Law of Intentionality — one of John C. Maxwell's 15 Laws of Growth.