Every leader I respect, whether they run a hundred person shop or a firm managing tens of billions, has a version of the same story. Somebody took a chance on them when they did not yet look like a safe bet. What confuses me, thirty years into this industry, is how few of those same leaders turn around and do it for somebody else.
I have been doing this long enough to know quite a few of these stories. One sticks out about a candidate that I knew almost thirty years ago, back when we were both starting out around the same age. At the time, he had bounced around a couple of different firms in a couple of different roles, and honestly did not seem to have much direction. Nothing dramatic, just a guy still figuring out where he actually fit. Then he landed at a firm where his boss decided to actually invest in him, and that was the turn. He is COO of a decent sized alternative investment manager today, the kind of seat people spend a career trying to reach. He has told me more than once that it was not really the firm that changed things for him. It was that one boss who saw something worth developing and decided to actually develop it.
Look across the people this industry actually respects, and a surprising number of them did not walk in with the golden pedigree everyone assumes matters most. Not the white shoe firm on the resume, not the connections, not the degree from the school that opens every door on its own. Plenty of them came up through smaller shops, unglamorous roles, or a path that looked unremarkable for years before it did not. What they had instead was somebody along the way who was willing to look past what did not yet show up on paper, and they delivered on that trust when it counted. That pattern shows up often enough that it stops looking like luck and starts looking like the actual mechanism behind a lot of real careers in this business.
What that actually looked like
It was not a formal mentorship program. Nobody assigned it. His boss just made a habit of explaining the why behind decisions, not only the what. Pulled him into meetings a year or two above his actual level, not because he had earned it on paper yet, but because the only way to grow into that level is to spend time in the room before you feel ready for it. Corrected him directly when he was wrong, without making him feel small about it, and made a point of saying so when he got something right that nobody else had noticed. None of this took extraordinary effort. It took a boss who decided that building people was part of the job, not a distraction from it.
Why this seems to be getting rarer, not more common
I hear plenty of leaders talk about developing talent. I see far fewer actually doing the harder version of it, the version that means taking on someone who is not already polished, already confident, already an easy bet. This has nothing to do with the size of the firm. A founder running a fifteen person shop has exactly the same opportunity to build someone up as the head of a division at a global platform managing billions, and plenty of both do it well. It is much safer to hire the finished product, at any size firm. It takes real effort, and real patience, to take a talented but rough around the edges employee and actually invest in making them better. Somewhere along the way, a lot of leadership seems to have quietly decided that development is somebody else’s job, HR’s job, a training program’s job, anybody’s job but the boss sitting across from that person every day.
The trouble with only wanting the finished product
Every leader currently running a firm, sitting in a corner office, respected across the industry, was once the unfinished version of themselves too, whether that firm employs fifteen people or fifteen hundred. Somebody carried the risk of believing in them before the results caught up. If everyone who reached the top only ever hires people who already look exactly like the finished product, the whole industry quietly stops replenishing itself with anyone who did not already have every advantage walking in the door. The next generation of strong COOs, CFOs, portfolio managers, and heads of compliance is sitting in junior seats right now, at boutique shops and behemoth platforms alike, a little rough, a little unproven, waiting for somebody to do for them what somebody once did for the leaders currently deciding whether they are worth the effort.
What mentorship actually costs, and what it actually returns
It costs time that feels, in the moment, like it would be better spent elsewhere. It costs the discomfort of correcting someone directly instead of just doing the task yourself because it is faster. It costs a real willingness to be wrong about someone occasionally, because not every bet pays off the way his did. What it returns, when it works, is not just one strong hire. It is a person who remembers exactly who did this for them, and who is far more likely to do it for somebody else one day because they know firsthand what it is worth.
As the year winds down
December tends to be a natural moment for this kind of reflection, before the calendar resets and everyone moves on to next year’s goals. If you are a leader who had somebody do this for you, that is worth remembering honestly, not as a nice story, but as a debt that is still technically unpaid until you have done it for someone else. If you are already doing this for someone on your team right now, that matters more than almost anything else on your plate this year, even if it will never show up on a performance review.
That is exactly the kind of leadership we see up close in this business every day, and it is always worth pointing out at Ramax Search and Staffing.
