One of the trickiest leadership moments?
When you like the person, but they’re not delivering.
It’s common in startups. You spend intense time together. You grow close.
But over time, performance starts slipping. And suddenly, you’re stuck.
Do I risk the relationship by bringing it up?
Or do I risk the company by staying silent?
Here’s how great founders handle it:
1. Separate the person from the performance
Don’t make it personal.
This isn’t about who they are, it’s about what’s not getting done.
Say:
“I care about you. But this isn’t meeting expectations. Here’s how we change it.”
2. Remember: You’re colleagues first
Not enemies.
Not best friends.
Colleagues.
You’re here to build something together. That’s the mission.
If you become friends along the way? Amazing.
But the mission still comes first.
3. Build a culture that prioritizes outcomes
Be clear that results matter.
Be fair. Be kind.
But don’t avoid the hard conversations, especially with people you like.
Because avoiding them doesn’t preserve the relationship.
It erodes the trust underneath it.
Leading with clarity is hard.
But it’s also the kindest thing you can do, for them, and for the company.
Keep building,
Peter
