A fellow Heretic asked me on our little “Ideas for future posts” Google Doc: How do you know it’s time to fire an employee?
To be honest — once you start thinking about this question I would argue that you crossed that point already. Especially in the context of a startup where every single person and their contribution is paramount to the success of the company.
When founders come to me with that question, I ask them to explain exactly why they feel the person should not be part of the team anymore. I urge you to get clarity about your motivation; your co-worker deserves this.
As hard as it is to let someone go — I strongly believe that people are either a fit or not. Circumstances change, people change, situations change — and someone who was once a great fit, isn’t anymore.
What you want to do though is to bend over backwards to make the process as easy and positive for your co-worker as possible. The whole experience is always pretty traumatic (for both sides) — being empathetic goes a long way to make it easier.