You hired an engineer 3 months ago, he's clearly not a good fit, but he's a father of 4 and was unemployed for a year. What do you do? (I asked this question on LinkedIn, got some great comments)
Did you squirm inside a bit?
Here’s my version of it:
A few years ago, I had a remote developer from Ukraine who was clearly underperforming. Not answering Slack messages, barely making progress on tasks. I gave him clear feedback and expectations. He improved for a couple of weeks, then went right back.
I planned to let him go (really!). Then the war with Russia broke out.
In the first month, we didn't expect any work from him and gave him full pay. He escaped to Prague, found a place, and slowly got back to work. And then the same behavior repeated itself.
I gave him some leeway - this guy was a refugee in a different country, of course he couldn't work the same. But after a few months, it was really dragging the team down.
I still couldn't do it. My manager ended up forcing the decision.
Afterward, I felt pure relief. Thank god someone made the call for me.
Don’t they see?
Every engineering manager has a version of this thought running in their head:
Someone requests a vacation at the worst possible time, and you think: "Don't they see it's bad timing? Why make me decide?"
Someone asks for a promotion they're not ready for, and you think, "Can't they see how far they still have to go?"
Someone's doing the bare minimum, and you think, "Don't they know I can see it? Why not just leave?"
Someone asks to work from home when the company is strict about office days. You think, "Don't they see I can't allow it? Why put me in this spot?"
In all of these cases, you're hoping reality will do your job for you, that the situation will somehow resolve itself. That people will magically improve (or magically quit), that they will just make the right choices themselves.
With my developer in Ukraine, I was hoping the same. That he'd improve, or that he'd just leave - anything but me being the one to make that decision.
Me dragging my feet had a price.
The team always knows
My team carried the frustration for months. They depended on this guy and he wasn't delivering, and they saw I was delaying. I've seen this pattern play out dozens of times across my career: when a manager finally lets someone go, the team is almost never surprised. I don't remember a single case where the team was angry at the manager for the decision, or didn't understand where it came from.
What the manager feels, the team almost always feels stronger.
The Radical Candor lie
Kim Scott’s Radical Candor is one of the most famous leadership books. The TLDR is simple: a 2x2 matrix. The X axis is how direct you are. Do you give tough feedback, do you let people go when needed, do you say no to requests. The Y axis is how much you care.
On the bottom left you have the manipulators, who never tell you anything to your face and don't care about you. On the bottom right you have direct and cold managers who will tell you exactly what you do wrong, but won't give a shit about your feelings. On the top left you have the most common trap: Ruinous Empathy. Managers who really care about their people and don't want to hurt them, but end up hurting their careers because they don't provide any tough feedback.
And on the top right, the goal: care personally and challenge directly. Sounds amazing, right? I can be kind AND do the right thing!
The problem is that the framework describes YOUR intent, not the other person's experience.
You can be in the Radical Candor quadrant and the engineer sitting across from you still experiences it as Obnoxious Aggression. You think you're being caring and direct, and they think you're being an asshole.
And there is no way to completely eliminate that gap.
Most of us became managers because we care about people, we genuinely want them to succeed. But human beings are social creatures. When you care about someone, feeling disliked or hated feels almost physically uncomfortable.
We have that strong need for the other person to recognize our good intentions in real time, to think: “wow, he's being so candid but I can tell he really cares!” (yeah, that never happens).
I don't want anyone to be angry with me, to dislike me, to hate me. I don't want to ruin someone’s day (or year).
I want to be un-hateable.
Being OK with ruining people’s days
I sometimes ask managers in interviews: 'Tell me about a time you ruined someone's day.' The actual question is: are you willing to put the team's needs above the need to be loved?
After 7+ years of managing, I still haven't completely figured it out.
I still catch myself wishing someone would "just understand" instead of me having to say it.
But I'm now willing to step into what might feel like Obnoxious Aggression to the other side, as long as I feel deep inside that I'm doing the right thing (which doesn’t mean always laying people off).
I'm more ok with people being angry at me, not liking me, or even thinking I'm unfair. Hopefully it won't get to hate, but that might happen too. I still squirm inside a bit every time - which I think is a good sign. When I stop squirming, it’ll mean I stopped caring.
Discover Weekly
What every dev should know about AI sandboxes. If you don’t build agents yourself, I feel it’s truly a must-read for every EM in 2026.
Irreducibility - Mental Model: Find the Floor. On simplifying a process until the ‘floor’. With LLMs, it’s common to think a process is easier than it actually is (thus creating a shitty automation).
Too many meetings? Try this. A great short overview of why meetings multiply and how to combat that.
