TL;DR
Founders often delay hard people decisions because they feel responsible for their team’s success and don’t want to hurt anyone, especially during the holidays. The real issue is usually uncertainty about whether the problem is the person or the system around them. You can either fix the system, find them a better seat, or help them exit with dignity. You don’t have to make that call alone.
Your spouse sees you stressed but doesn’t understand why you can’t “just fire them.” Your friends think you’re the boss, so it should be easy. Your investors just want to see numbers improve.
None of them gets it.
None of them sees how this person has kids. How did they just buy a house? How they try so hard but just can’t seem to get there. How letting someone go during the holidays feels like playing Scrooge in your own story.
Maybe you’re telling yourself you want to create a workplace that feels like a family. Perhaps they were your first hire, or someone you brought over from your last company. Someone you believed in.
The Weight Nobody Talks About
Here’s what I’ve learned after 20 years of sitting across from founders as they make these decisions. The weight isn’t really about them. It’s about you.
It’s about feeling like you somehow failed them. Like maybe with different training, different systems, different leadership, they could have succeeded. It’s about wondering if you’re becoming the kind of boss you swore you’d never be.
You might be delaying because you want to believe they’re not that bad. That maybe after the holidays, with a fresh start, things will click.
But deep down, you know. You’ve known for weeks, maybe months.
What Compassion Really Looks Like
I had a founder tell me recently: “I kept someone six months too long because I didn’t want to be heartless. Then I realized I was being cruel to them, to my team, and to myself.”
Keeping someone in a role where they can’t succeed isn’t compassionate. It’s enabling failure while penalizing everyone else.
They know they’re struggling. They feel it every day. Your team knows too, and they’re watching to see what you’ll do.
Sometimes the kindest thing is honesty. Sometimes it’s helping them find where they can actually thrive.
You Don’t Have to Carry This Alone
The hardest part about these decisions isn’t making them. It’s making them alone. Every founder I know has sat in their car after a family dinner, checking Slack, carrying decisions nobody else can help them make.
But here’s what I know. The problem might not be the person. It might be the system they’re operating in.
Maybe your sales rep can’t close because your messaging is unclear. Maybe your marketing lead seems ineffective because there’s no real go-to-market strategy. Maybe that underperformer is a good person in the wrong seat, or in a broken system.
Three Paths Forward
Fix the system around them. Sometimes people fail because we’ve set them up to fail. If you don’t have transparent processes, training, and support, that’s on us, not them.
Find their correct seat. I’ve seen failed salespeople become excellent customer success managers. Wrong role doesn’t mean wrong person.
Help them transition with dignity. If it’s genuinely not working, help them leave well. Generous severance, good references for what they did well, and support in finding their next role.
The Decision After the Holidays
Monday is coming. Then December. Then January. The decision you’re avoiding won’t get easier with time.
But you don’t have to figure it out alone. That’s why we exist. To help founders determine if it’s a people problem or a systems problem. To build the go-to-market infrastructure that allows good people to succeed. To be the outside perspective when you’re too close to see clearly.
The loneliest part of being a founder isn’t making hard decisions. It’s thinking you have to make them alone.
You don’t.
