The short break was supposed to fix it.
He came to us saying he was dealing with health issues (screen fatigue), the kind that builds up quietly when you’re behind a screen for hours every day with no real separation between work and rest. We talked, we agreed on a short break, and I thought we’d handled it. He’d rest, he’d come back, we’d move on.
He didn’t come back. Not then.
When he reached out again, it wasn’t to confirm a return date. It was to say he needed much more time, an open-ended leave that, in practical terms, meant he was off the team indefinitely. As close to a resignation as you can get without using the word.
I called him the same day.
The Call
He was direct. I appreciated that. He didn’t make me read between lines or ask careful questions to get to the real answer. He said what was happening, the fatigue hadn’t lifted, the health issues were still there, he needed time he couldn’t put a number on yet.
I didn’t try to negotiate him back. I didn’t pitch the team or remind him what he’d be leaving. I just listened, and then asked one question: what do you actually need right now?
He told me. I said I’d take it to the founder.
What We Did
The conversation with the founder was simple. We kept the door open completely, no conditions, no timeline. He could come back whenever he was ready. No pressure, no expiration date on the offer.
That felt like the right call. Not because it was generous, but because it was honest. Pushing someone to commit to a return date when they’re dealing with a health issue doesn’t get you a reliable team member back. It gets you someone who either says what you want to hear, or cuts contact entirely to avoid the conversation.
We chose not to do that.
What I Got Wrong
Here’s the part I think about more than the outcome.
When I look back at the weeks before he asked for that first short break, the signs were there. Quieter in standups than usual. Slower responses. A kind of low-level flatness I noticed but didn’t act on. I told myself he was having a rough stretch. I checked in on the work. I didn’t check in on him.
That’s what I’d do differently. Not the way we handled the leave, I think we got that right. The period before it. The moment I noticed something was off and filed it away instead of picking up the phone.
A short check-in isn’t an intrusion. It’s not making assumptions about someone’s personal life. It’s just saying, “Hey, you seem quiet lately, everything alright?” Most of the time people say they’re fine and mean it. But sometimes that question is exactly what someone needed someone to ask.
We didn’t ask it soon enough.
Where Things Stand
He’s still on leave. The door is still open.
I don’t know if he’ll come back. I try not to sit with that question too much, there’s no productive version of it right now. What I can do is make sure that when he’s ready, the answer is still yes.
That’s the whole job sometimes. Not resolving things cleanly. Just keeping the door open and meaning it.
I tell this story not because it ended well, it hasn’t ended yet. I tell it because the lesson isn’t in the outcome. It’s in the gap before everything happened, when someone on my team was struggling and I was looking at his tickets instead of looking at him.
People management doesn’t start when something goes wrong. It starts in the quiet weeks when everything seems fine, and probably is, except when it isn’t.
I’m trying to catch it earlier now. That’s all I’ve got.
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