Saying goodbye professionally is a very normal and natural thing. When done right, it can even be a beautiful thing.
General note: you don't have to do this alone, so please ask for advice and help!
Someone is underperforming. Give actionable feedback and try to provide concrete points to work on concerning their personal goals. Don't wait for the feedback cycle, the time is always now.
Someone stopped growing or learning. This isn't necessarily an immediate problem, but it could be because most people like working at Lifely for the chance to learn and grow as much as they can. If someone isn't progressing in the past year, this is a red flag.
Someone's role is no longer a match. Roles, jobs, and their demands change. They aren't static. Pay attention to changing roles and put effort into telling your people what changed instead of implicitly expecting people to understand what changed. A changing role can be a reason for someone to no longer be the perfect match. Tell someone what we expect from them, make it clear. Work together to match those new demands but be honest if it doesn't work.
This also works the other way around: some roles don't change, but people do.
Someone wants to grow in a different direction. Lifely is still a small company so we can't just offer every possible career path. Use 1-on-1s to talk about someone's ambition and career path. Be honest and realistic about the possibilities at Lifely. Think about whether you think someone would be a good fit for that role and tell them what would be needed to get to that point (in terms of skills, expertise, personality, experience). The next question is whether Lifely has a role like that vacant. Be realistic and open about this.
Someone believes in a different direction for the company or the team. Everybody is really invested on an abstract level. We get out of bed every morning because we believe in what we're doing. That belief might shift and that's okay, as long as we talk about it. If you notice someone is losing belief and probably disagreeing with most things that happen at Lifely, that's a red flag.
The time's up. Sometimes it's this simple. People grow, evolve, change, Lifely does the same. People have the tendency to go for what they know. We believe it's very healthy to move on after a while, before the milk turns sour.