Kiersten Grover has worked with me for twelve years and reported to me for seven of them. They took a new role, on their own initiative, and it is the right move. I told them so, and I meant it, and I have spent most of the week since sitting with how much I am going to miss having them down the hall.
Earlier this week they sent me a letter. I am not going to reproduce it here, because it was written to me and not to an audience. What I will say is that it is the single most valuable piece of professional feedback I have ever received, and that reading it produced a reaction I did not expect.
It was not pride, at least not first. It was relief.
Every manager who takes the developmental part of the job seriously operates without instrumentation. You make a call about how much room to give somebody, and then you wait, and the results arrive on a timescale that makes it nearly impossible to connect any outcome back to any decision. Five years. Ten. Sometimes never, because the person leaves and takes the answer with them.
So you are running an experiment with no readout. You hand someone a project that is slightly beyond them, and they either grow into it or they drown, and if they drown you will never be certain whether the assignment was wrong or the support was thin or the timing was bad or none of those things. You let someone struggle with a problem you could solve in ten minutes, and you have no way of knowing in the moment whether you just gave them the experience that makes them or wasted three days of their life for nothing.
That is the actual texture of it. Not vision, not strategy, not any of the vocabulary that gets attached to leadership. A long series of small judgment calls about when to step in, made with insufficient information, whose consequences land years downstream on someone else's life.
Most managers never find out whether they got it right. I found out this week, for one person, and the answer was yes, and I did not realize how much I had been carrying the uncertainty until it lifted.
What struck me about the letter is that almost everything Kiersten thanked me for is something I did not do.
I did not let the chaos become theirs to carry. I did not hover over their decisions. When they came to me out of their depth, I did not take the problem off their plate. I did not let them settle in comfortably at a level they had already outgrown.
That is a strange list to be thanked for, and it points at something about this work that I have never seen stated plainly. The developmental part of leading people is mostly restraint. The growth happens in the space you leave, which means your primary job is leaving the right amount of it, which means most of what you are doing is a continuous exercise in not acting on impulses that feel like help.
Every one of those impulses is genuinely well-intentioned. When someone on your team is struggling with something you understand cold, the urge to fix it comes from care, plus efficiency, plus the entirely reasonable desire to stop watching somebody suffer. Acting on it is faster, it is kinder in the short run, and it ends the discomfort in the room.
It also takes the rep away from them. Every time you solve it, you have made a trade: today's problem is resolved and tomorrow's version of that person is slightly smaller. The trade is almost always worth making in an emergency and almost never worth making the rest of the time, and telling those two situations apart in the moment is the whole skill.
I got it wrong plenty. There were absolutely times I stepped in when I should have waited, and times I waited when somebody needed me. The letter did not mention those, which is generous, and I remember them anyway.
Here is what the march of time actually looks like from where I am sitting.
In 2019 Kiersten started reporting to me. In February of 2022 they finished a master's degree and announced, to me and to anyone else in earshot, that they were finished with school permanently. About eighteen months later they started an MBA. Somewhere in there came the Security+, then the renewal, then the ISC2 CC, then a set of responsibilities that would have been implausible to hand the version of them who walked in eleven years ago.
I encouraged some of that. My actual contribution deserves precision, though, because there is a way of telling this story that gives me more credit than I earned. I suggested the MBA. Kiersten did the MBA, at night, while doing a demanding job, for two years. The encouragement took me a conversation. The degree took them their evenings and weekends for a very long stretch of their life.
What I did was see it before they saw it. That is a real thing and I am not dismissing it, and it is also the smaller half of the transaction by an enormous margin. The person who grew is the person who did the growing.
The thing that gets me is the compounding. Day to day, it is invisible. You work alongside somebody for years and they seem like the same person, because change on a human timescale is too slow to perceive at close range. Then they take a new job and you sit down to write something about it, and you put the person who is leaving next to the person who arrived, and the distance is startling. They are not a more experienced version of who they were. They are somebody else, someone that person built over a decade.
I am staying, and they are going, and the asymmetry of that is its own thing to sit with.
Bay Path will be fine. The work Kiersten did will keep working, and somebody will take it over, and eventually the fact that they built it will be institutional trivia that nobody knows. That is the ordinary fate of all of it, and I have written before about how infrastructure disappears into the walls.
What does not transfer is the other thing. There is a specific kind of shorthand that develops between two people who have been through enough difficult weeks together, where you can say four words in a meeting and the other person knows the entire argument behind them. I have that with a small number of people in my career.
So there is a version of Monday morning coming where I turn to say something and the desk is empty, and I am aware that is going to happen for a while before it stops happening.
Kiersten: you did this. I gave you room and you filled it, repeatedly, faster than I expected every time. The letter you sent me is going in a folder I will keep for the rest of my career, and on some future day when I am sure I am bad at this job, I will take it out and read it again.
Go be excellent somewhere else. You are ready. You have been ready for a while, which is exactly why you are going.
— Chris