You want to hire that VP you saw at an event, that was a VP at that hot company, that did it all there
But first, they probably didn't do it all
And second, if they did, they probably don't want to do it >all< again
It's probably a mirage
— Jason ✨BeKind✨ Lemkin 2️⃣0️⃣2️⃣2️⃣ (@jasonlk) September 15, 2020
Q: Have you ever regretted firing an employee?
I’ve regretted, and still regret almost daily:
- Waiting too long to make a critical hire. You overload the existing team, and progress stalls out.
- Not closing my A+++ top choice for a role, no matter what it took. This haunts me to this day. When there is a true game-changer, do whatever it possible takes to close them. And then even when they say No, remember, you still have another chance next week, next month, and next year.
- Underhiring. Not hiring someone experienced enough for a role.
- Hiring for the logo. Just because they worked at Zoom or Twilio does not mean they can do it at your little startup.
- Not topping a hire that has truly reached their limits. It’s tough to time this right, but if you leave someone in a senior role too long, once the business has gotten too big, you slow down.
- Settling for a top hire. At some point, sometimes, enough time goes by that you have to settle. But it’s never a great thing.
- Not working things out. With a key employee that left. Don’t let emotions cloud your decisions here too much. Find a way to keep the great ones, even if the role and position have to change.
For most of us, by the time that comes — we realize we should have done it months ago. Not only has the damage been done, but it continues to compound. And so much time was lost, without progress.
That, you never look back on. You just wish you’d done it much, much earlier.
(note: an updated SaaStr Classic answer)