There's a particular kind of frustration that comes with managing someone who is clearly capable but consistently unreliable. Missed meetings. Late deliverables. And then, a day or so later, an apologetic email explaining that they were struggling.
I had a developer like this. Good at his job. Genuinely good. But the pattern was there and I couldn't ignore it.
Here's the thing nobody tells you about being a leader: caring about someone and needing to let them go can exist in the same moment. And sitting with both of those things without letting one cancel out the other is one of the harder parts of the job.
I knew he was being vulnerable with me every time he sent one of those emails. I also knew that vulnerability didn't change what I needed from the role. I needed someone reliable. I needed someone I could count on. And he was struggling to be that person right now.
So I made a decision. I set clear expectations — not as punishment, but as structure. If you're going to miss a meeting, tell me beforehand. If you're struggling to complete something, let me know so I can step in or redirect. Not because I'm watching you, but because I need to be able to do my job, and that means knowing what's actually happening.
He agreed. And then he took some time off.
When he came back, he was a different person. Responsive, productive, communicative. For a while it seemed like we'd turned a corner.
We hadn't.
When the pattern returned, I reached out to our outsourcing partner to start the transition process. And in that email, I wrote something I almost deleted before hitting send.
I wish I could say I am a stranger to mental health struggles — and I know that in certain times in my life, having a manager or a job that would be willing to be patient and work with me would have meant everything.
It was a risk. It was personal. It was true.
What came back wasn't a transactional response about process and timelines. It was a partnership. They paired him with another developer to ensure continuity, protected my business while protecting him, and handled the eventual offboarding with more care than I've seen in a lot of fully domestic teams.
And then, after his exit interview, their Chief Experience Officer reached out to me.
He told me that my developer had been extraordinarily clear about how kind and gracious I had been. He said that not all clients lead from a place of empathy. He thanked me for being thoughtful and genuine with someone half a world away.
I didn't do anything extraordinary. I just tried to remember that behind every missed deadline is a person, and that person is probably already aware they're falling short. Piling on doesn't fix the work. It just makes everything harder.
My response was simple:
I've been a developer for a long time and I've always approached it from the place of — how can I make someone's life easier? As much as I am able, I will never work to make someone's life harder.
Life is hard enough.
That's not a management philosophy I read in a book. It's something I know from the other side of it. And it's the thing I keep coming back to when I'm standing at that crossroads between what the work needs and what the person needs.
You don't always get to save the situation. Sometimes people aren't able to meet the bar regardless of how much grace you extend, and the right call is still to move on. Empathy doesn't mean accepting dysfunction indefinitely. It means making sure that when someone lands, they land as softly as possible.
The work still has to get done. And people still deserve to be treated like people while it does.
June 4, 2026