One of your best team members walks into your office — or sends a message, or asks for a quiet word — and you can tell from the first sentence what’s coming. They’re moving on. And even as you listen, even as you nod and ask the right questions and wish them well, some quieter part of you is already calculating what their absence will cost you.
The Gardener's Dilemma
Managing people is, in many ways, like tending a garden.
You prepare the soil carefully, plant, water, check the conditions, and intervene when something threatens to go wrong. You invest time that doesn’t always yield immediate returns. And then, slowly, the plant grows.
It strengthens, it begins to fruit, and just as the fruit ripens, you discover it was not meant for you.
What Actually Enters Your Mind
When someone you've deeply invested in tells you they're leaving, the first thought is: "Now what?" Followed quickly by a mental inventory of everything they handle, everything you'll need to rebuild. This is not selfishness; it's a reasonable, human response to disruption.
The questions come fast.
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Who covers this?
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How long before a replacement is up to speed?
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What do we stand to lose in the transition?
The Rule I've Followed
In my over two decades of leading teams, I’ve had roughly a dozen direct reports leave.
Many were good. Some were excellent. A few were the kind of people you quietly hope you’ll work with again someday.
Each time, I’ve applied the same standard: find out why they’re going. Listen properly, not just for the official reason but for the real one. And then ask yourself whether you’d have done the same in their position. If the answer is yes, that’s your signal to let go cleanly and focus entirely on the transition.
This sounds straightforward, but it's harder than it appears. And the first few times, it doesn't feel natural at all. Because accepting that someone else's good decision is inconvenient for you requires a kind of maturity that doesn't come automatically. It has to be practised.
The Question That Managers Grapple With
At some point, almost every manager who has been through this starts to wonder whether investing in mentoring people is even worth it. If they’re going to leave once they’ve learned the ropes — once the training has taken hold and they’ve become genuinely useful — what’s the point of putting in the effort?
It’s a fair question. And it was answered with a management anecdote passed down over the years.
When asked what happens if you train people and they leave, this quote serves as a rebuttal to managers who are hesitant to invest in training their team: “What if you don’t, and they stay?”
Consider this for a moment.
The alternative to investing in your people isn’t a stable, loyal team; it’s an undertrained one. People who stay not because they’re fulfilled or growing, but because they don’t have the skills to go anywhere else. That is not retention, that is stagnation, and it costs you far more, in ways far harder to measure, than the departure of someone you developed well.
The Context Behind This Piece
The latest to leave my team is Mohit Sain. And I want to name him here, because he deserves more than an anonymous mention.
Two years ago, he moved into my team, relatively new to this part of the business.
He hit the ground running, picking up new skills along the way, polishing old ones that needed improvement, and seeking direction where he didn’t know enough till he became someone I could hand a task to and know it would be done well.
When he told me he was leaving, my first thought was “oh no”. But his reason was solid. And when I put myself in his position and asked whether I’d do the same, I got my answer.
What Gets You Through It
There’s a line I return to when these moments arrive: Que Sera Sera. What will be, will be.
You do what you ought to do. You train, you mentor, you invest, you build the best team you can with the people in front of you. And then you hold it all loosely enough that when something changes — as it always will — you’re not destroyed by it.
The transition plan matters, finding a replacement matters, and beginning the process again, however wearying that feels, matters, but none of that can happen properly if you're still grieving the person who left. Let them go cleanly, celebrate what they achieved while they were with you, and start again, because it turns out that starting again is most of what management actually is.
The Thought to Take With You
If you lead people — at any level, in any field — here is the thing I’d most want you to hold: Your job is not to keep your best people. Your job is to develop them so thoroughly that they have the confidence to go wherever they’re called — and to do it in a way that means they’ll always speak well of the time they spent with you. That’s the legacy, not the tenure, not the retention rate.
The reputation you earn as someone who made people better — better at the work, better in themselves — and who let them take that with them when it was time.
Mohit’s going to be fine. More than fine.
And we’ll rebuild. We always do.
This post is part of an ongoing series sharing life lessons from lived experience — honest accounts of what happens in the gaps between the leadership frameworks, where the real learning takes place.
About Me
I am a thinker at all times. I see, I think. I hear, I think. I read, I think. Every weekend I write. I would love to know what you think.