Not a founder here, so I'm just giving a general leadership perspective. I think you should completely disregard the vesting in your decision-making. I'm guess

Not a founder here, so I'm just giving a general leadership perspective. I think you should completely disregard the vesting in your decision-making. I'm guessing you've not developed a performance management process in your business yet. You've highlighted that you gave feedback, however I'm not sure if you've set out a process by which they stay or go. This isn't the end of the world, you can do this process now: 1. Give feedback on the behaviour (you've already done this) 2. Escalate the feedback to a written warning, highlight what you want to see change and when by 3. Once that date passes, if the change hasn't occurred, let them go This process doesn't need to take very long: it should depend on expected timeline to make these kinds of changes. If these are behavioural issues, then 2-4 weeks should be sufficient. Assuming the person doesn't change, you'll let them go. This will be a shock to your other employees, so call a meeting with everyone afterwards. Make it clear (without going deep into the details) that this was a performance-related sacking. Highlight the fact you gave feedback, with clear and actionable steps to improve, but the situation didn't work out. If this seems onerous consider it this way: you're not doing this for the team member you're letting go. You're doing it for the rest of the team. You want to reassure them that you're not just looking to screw the team out of vested shares and that, if you haven't discussed performance issues with them, there's nothing for them to worry about.