Assigned mentors vs. aligned mentors: there’s a difference

Many organizations have formal mentorship programs, especially for employees showing potential for leadership roles. And I’m not knocking that. I’ve seen some great mentor-mentee relationships come from structured pairings. But I’ve also seen some forced matches that feel more like a corporate version of speed dating: awkward, ineffective, and destined to fizzle out by Q2.

So let’s talk about the mentor side of that equation.

According to the dictionary, a mentor is “an experienced and trusted adviser.” Not just someone who knows the ropes, but someone the mentee trusts to help them navigate the climb. That second part, the trust, can’t be assigned. It has to be earned. And that’s where some programs miss the mark.

Let me share a story.

While serving as a superintendent at the Air Force leadership school in Florida, I also taught martial arts a couple nights a week. One of my students worked in Security Forces; the Air Force’s military police, and also my old stomping grounds.

This young airman had mentioned a few times how disconnected he felt from leadership. He didn’t feel like anyone really had his back. Then one night, around 10 or 11pm, he called me. He was going through some personal challenges and just needed someone to talk to. So I said, “Come on over.”

We sat and talked for hours, about his professional frustrations, his personal life, and how all of it was starting to  bleed into his performance. I  knew exactly what he meant when he said Security Forces could be unforgiving. We had a reputation of “eating our own” when someone was struggling. I’d seen it. I’d lived it. And I wasn’t going to let him go through it alone.

I gave him some guidance. Not “fix it all” advice, but real talk; how to approach leadership, how to advocate for himself, and how to handle the personal side so it didn’t derail his career. We stayed in touch long after I retired. We still talk today.

He didn’t stay in the military like I did, but he’s doing big things now; he started a tech company that helps transitioning service members. In other words: he’s mentoring people who need it, just like he once did.

Now, here’s the thing: I was never officially his mentor. Nobody assigned me. We didn’t fill out any forms or schedule quarterly check-ins.  He found someone he connected with, someone who understood his goals, his struggles, and the context he was operating in.  That made all the difference.

That’s why I believe mentorship works best when it’s mutually chosen. When the mentee finds someone who aligns with their values, goals, and personality, and when the mentor genuinely wants to help that person succeed on their terms, not just turn them into a carbon copy of themselves, that’s when growth happens.

Sure, structured programs have their place. But, if you’re serious about developing real leaders, make room for the kind of mentorship thats built on connection…not convenience.

The right mentor doesn’t just show up on a roster…they show up when it matters most.

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