Hey Reader,

I’ve noticed there’s one person who’s come up in the last few newsletters that I haven’t named yet:

My mentor, Mike.

Over the past 15 years, we’ve worked together on countless projects, navigated some tricky situations, and had a lot of honest conversations with each other.

Reflecting on my years of working with Mike, I wanted to spend this week exploring what it means to be a good mentor. A lot of us might have been the mentee over the course of our careers, but might not have a solid idea of what it looks like to be on the other side of that relationship.

Most employers will pair you up with someone, and the results can be a mixed bag. Sometimes it works incredibly well. Sometimes you end up with someone operating at a high level who just isn’t that well-suited to the role. Those formal arrangements can be valuable, but they’re not the only way a mentor and mentee find each other.

Mike and I didn’t start with any kind of formal arrangement. He was the leader on my first M&A engagement, and because I wanted to do a good job, I gave it everything I had. That working dynamic mattered more than I realized. He noticed that I’d ask for guidance and act upon it to help the overall project. Over time, our working relationship grew from project to more than that. To one of mentorship.

He and I did great work together for the next couple of years. Whenever he had a new client, he’d bring me in to help on the project. Whenever I found an opportunity I thought he’d fit, I gave him a heads up. As we both grew in our careers, there was this symbiotic relationship because we genuinely wanted to help each other.

He had strengths I didn’t, especially when it came to understanding how decisions actually get made inside large companies. I’m great at connecting with people on a personal level, but the systemic side of the company just isn’t my strong suit. Having someone who could point out what I was missing in certain situations was genuinely helpful, and to give back, I kept doing my best work on every project we shared.

That back-and-forth is why we’ve enjoyed working together for so long. It’s made it possible for us to be open with each other whenever one of us needed support. I’d be comfortable enough to share struggles I was facing, and he’d be comfortable enough to candidly share the lessons he’s learned that could help.

That candor is what separates a supportive colleague from a truly great mentor. A lot of leaders assume that being a good mentor means being highly involved and stepping in to help a team member navigate every obstacle they come across. Of course, that’s part of the role. But there’s a fine line between offering guidance and literally spelling out every step of what you’d do to solve a problem. One helps someone grow. The other just makes them dependent on you.

One of the most valuable things Mike has done for me was to stay candid during moments where it would have been easier to let things slide. He’s not one to shy away from uncomfortable conversations, and that’s helped me develop without ever feeling like a burden or incapable of figuring things out.

Which brings me to something worth sitting with before you take on a mentoring role.

If you’ve got this far and thought, “I want to be like Mike,” that’s great. Watching someone reach a new level of confidence and knowing you had a part to play in that is fantastic.

And it also brings up an important question:

Do you actually want to do this? And if so, why?

Being a mentor isn’t a light-touch role where you check in occasionally and offer a bit of advice here and there. A mentee is trusting you with their career and growth, and they’ll feel it if your heart isn’t really in it.

If that relationship is already forming, and you’re already helping each other out, set some time aside to have a real chat with them. Learn more about them as a person: how they think, what they’re worried about, and how they want their career to progress. Don’t be afraid to make it a two-way street, either. Be honest about where you’re headed, the wins and lessons you’ve learned over the years, and everything in between. Mike and I have worked so well together because we’ve been honest about where we’re strong and where we’re still figuring things out. That honesty kept the relationship real rather than performative.

A great mentor-mentee relationship tends to make both people better.

Is there someone in your life or career who's played that role for you? Or someone you've been showing up for recently? Hit reply and let me know. I read every message.