No One is Coming to Develop You
Productive Lunches, Mediocre Leaders
He had a mentor. Lunches twice a year, a LinkedIn endorsement, a standing offer to "make a call" if he ever needed it.
His team was falling apart and he had no idea what to do with it.
The mentor never helped with that, because the mentor wasn't in the room.
We have this story we tell ourselves about development — that somewhere out there is a more experienced person who will see our potential, invest their time, and hand us the map. We call it mentorship. We seek it out. We list it on development plans. We feel productive when we schedule the coffee.
What we're actually doing, most of the time, is networking with extra steps.
Real mentorship, the kind that actually changes how you operate, is rare. It requires someone with specific experience relevant to your specific problem, available at the exact moment you're in it, who also happens to be honest enough to tell you the uncomfortable version. That combination exists. It just doesn't look like what we've organized our professional development culture around.
What actually develops a leader isn't who they meet over lunch.
It's the decision they had to make before they were ready. The reorganization they had to explain to a room full of people who didn't want to hear it. The hire they fought for who didn't work out — and then the audit they did quietly, afterward, on exactly where their judgment broke down.
Pressure is the teacher. Not because suffering is good, but because the gap between what you know and what the situation demands is where real learning lives. You don't close that gap by talking to someone who's already closed it. You close it by operating in it, failing in it, thinking hard about what happened, and then operating in it again.
What a good mentor can do is compress that cycle. Put a name what you're experiencing faster than you'd name it yourself. Tell you that what feels like a unique disaster is actually a pattern with a shape. Give you the version of the lesson they paid for so you don't have to buy it at full price.
But that's a very specific transaction. It requires the mentor to have made the exact mistake in a context close enough to yours to matter. It requires trust. It requires them to be honest when the honest answer is that you were wrong.
Most mentorship relationships aren't built for that. They're built for good feeling, and not much else.
I've watched talented people spend years in mentorship relationships that made them feel supported without making them better. The mentor was credible. They liked each other. The conversations felt substantive. But when the hard moment came: when they had to call someone out, cut the underperformer, defend an unpopular position to someone with more power, none of those lunches mattered. They were alone in it. In reality, they'd always been alone in it.
The thing that actually moved them wasn't a mentor. It was a peer who'd been through something similar and would tell them the true version without protecting their feelings. Or a manager who gave them a problem that was two sizes too big and then got out of the way. Or their own post-mortem on a failure they'd been too busy to actually sit with.
The development conversation inside most organizations is still organized around the wrong thing.
"Do you have a mentor?" is a real question in real performance reviews. It signals investment. It signals intentionality. It produces a name.
What it doesn't produce is better leaders.
If you actually want to develop someone, give them a hard decision with real stakes and stay close enough to debrief it afterward. Put them in the room where they're not the most experienced person and ask them to lead something. Find them a peer cohort of people who will be honest with them, not just supportive. And if you're going to connect them with a senior person, be specific about what you're trying to accelerate — not a relationship, a problem.
The lunch is fine. The lunch is nice. But the lunch is not the work.
The most meaningful developmental leap of my career didn't come from anyone who knew they were developing me.
It came from being handed situations I wasn't sure I could handle. Submitting my very first scouting report, knowing that, right or wrong, my name was forever etched on that evaluation. It was being the sole executive on a road trip and having to tell a 10-year Major League veteran he was being released.
And from a handful of conversations where someone cared enough to say the thing I didn't want to hear.
None of that required a formal mentorship relationship. All of it required being honest about what actually makes people better, instead of what makes us feel like we're investing in them.
Your team doesn't need more mentors on their development plans. They need harder problems and someone willing to sit with them in the aftermath.
Those are different things. Most organizations are only delivering one of them.