The Wrong Way to Find a Mentor (And What Works Instead)

Nobody actually teaches you how to find a mentor. You just hear that you need them.

And so you try. You identify someone impressive, draft a carefully worded message, ask them for coffee, show up with a list of thoughtful questions, send the thank-you note afterward. You do everything right. And most of the time, it’s a lovely conversation, but typically, the relationship ends at the coffee date, fizzling out before it ever starts. I know this because it’s happened to me countless times.

You’re left wondering what you did wrong.

I’ve had mentors who genuinely changed the direction of my career. Not one of these started the way we’ve assumed mentor/mentee pairings begin.

Earlier in my career, I worked under a CFO who was one of the sharpest operators and most incisive thinkers I’d ever seen up close. He had this way of immediately understanding a new topic, clearly seeing what others were missing. Two different skills, more often than you’d think.

He let me tag along. Project meetings. Leadership meetings. Budget reviews. Partnership meetings. I’d sit off to the side, mostly quiet, and just watch how he graciously handled a question framed in a way he didn’t care for. How he pushed back on a number that didn’t add up without making the person who made the calculation feel stupid. How he knew when to speak and, maybe more importantly, when not to. How he always debriefed with me on what happened in the meeting (now I’m a heavy debriefer 😀).

The interesting part: neither one of us called our working relationship a mentorship. We never had a formal mentor/mentee check-in. I’m not even sure he knew how much I learned just by being in those rooms. But I exited that period of my career differently than I entered, with a clearer sense of how decisions actually get made, how leaders actually behave under pressure, and what it looks like to operate with real integrity when the stakes are high.

That was mentorship. It just didn’t look like it. Call it an “incidental mentorship.”

The formal mentor model puts too much pressure on both parties. It asks us to build a meaningful, trust-based relationship starting from zero with someone who doesn’t know you, who is almost certainly super busy, and who has no real reason yet to invest in you. The cold ask to a near-stranger essentially says: I admire your career. Will you devote time and energy to mine? It’s a big request to make with no established foundation.

Most people on the receiving end of that ask don’t respond. I don’t believe it’s because they’re unkind, but because the math doesn’t work yet. They don’t know you. They don’t know what you need. They can’t imagine what they’d actually say to you at that coffee. So they move on.

And even when a formal relationship does get off the ground, it often feels a little forced. You show up every month with your list of topics. They answer them. You both feel like you’ve checked the box. But there’s no real interpersonal depth.

The best mentorships I’ve experienced began organically, because two people are already in proximity, already working together or around each other, already building mutual respect in the day-to-day. The mentorship begins because the conditions support it.

So what do you do instead? Here’s what I’ve learned from experience on both sides of the mentorship.

The best mentor candidate is almost always someone you already have access to. Maybe that’s a manager, or maybe it’s a senior colleague whose judgment you’ve come to trust. You don’t need to look far and wide for a mentor. Instead, notice who’s already influencing how you think and work and invest more intentionally in that relationship.

Think about the person in your orbit right now whose way of working you find yourself studying. Start with that person.

“Will you be my mentor?” is a big ask. It implies an ongoing commitment that is too big too early. Most busy people will deflect this request even if they like you, because it sounds like a lot.

A better ask is specific and low-lift: “I’m working through a situation with X. Could I get 20 minutes of your perspective?” One conversation and super clear value. No big long-term obligation. Do that a few times with the same person over time, and the relationship builds itself, gradually, with real content underneath it. By the time you’ve had four or five of these conversations, you have a mentor. You just didn’t have to make it weird by labeling it.

As I described above, some of my most valuable mentors were never formally my “mentors.” They were simply people I admired and trusted, people with whom I cultivated relationships gradually over time. Informal relationships are often more durable than formal ones, because they’re not held together by obligation. They’re held together by mutual respect and are rewarding for both parties. When you need to lean on a mentor, the foundation is already there because you’ve been building it all along, not just when you needed something.

The biggest mistake people make with mentors is only showing up when they need something. This is the worst thing you can do. The relationship goes cold between crises, and then it feels awkward to revive when you actually need help. The ask lands like a burden for both sides when it’s been months since you’ve been in touch.

It doesn’t take much to keep a relationship warm. A quick note when you come across something relevant to their work. A one-liner update on how that advice they gave you actually played out. A genuine “thinking of you” when they hit a milestone. These gestures take two minutes, and they signal something important: that the relationship matters to you beyond what you can get from it.

That’s the kind of mentee people actually want to show up for.

Here’s what I want you to actually take away from this: you probably already have mentors. You might have simply overlooked them or haven’t invested as intentionally as these relationships deserve.

There’s someone in your life right now who has changed how you think, whose judgment you trust in a particular domain, who has made you better at something. Maybe it’s a former boss you still grab lunch with. A colleague who’s always straight with you. Someone a level or two ahead of you who seems to genuinely want to see you figure it out.

That’s a mentor. Maybe not the formal, LinkedIn-announcement kind. But the real kind.

The CFO who let me into his meetings never signed up to change how I work. But he did because he was generous with access, and I was paying attention. The mentorship was happening whether either of us named it or not.

Stop waiting to find the perfect mentor through the perfect process. Look around at who’s already in your orbit. Figure out whose way of working you want to learn from. Find a small, sincere reason to get in the room with them. And then just pay attention.

The rest tends to take care of itself.

As always, would love to hear your thoughts. Have a great week.

Dave