Few things that would help: - Find the next best person/team members who could shadow some of what you do, if not all. Work closely with them to pick up your s

Few things that would help: - Find the next best person/team members who could shadow some of what you do, if not all. Work closely with them to pick up your stuff even before you leave - Document all the complex stuff you do as much as possible. Never underestimate the power of documentation, even if not perfect. We maintain an internal Wiki and I am always pushing everyone to document whatever they can especially repeating processes. No matter how small. - Start delegating already and do trial runs. For example, you run that monthly meeting ? Let the other person run it while you are still around and on the meetings. - Set expectations early on that you will not be available and the rest of the team has to work accordingly. Unfortunately, in lean teams, there is no easy way. But it is also true that nothing stops just because 1 person is not available even though it can be a bit difficult. Human beings are very good at adapting especially when they have no choice. So do your best and enjoy your time off.