[throwaway2016a]

5. Managing people

Personally, I find the toughest part to be actually managing the people. You really need to trust your team to be self-motivating which can be tough for a manager to do, especially new ones, because you need to give up some control.

But even though you trust them you need to have a way to measure results. That means being more disciplined and mature in your project planning than you might be if everyone is co-located.

For a startup that is key. Startups often skimp on disciplined project management.

I also find it tougher to do things like say, identify when someone is having a rough time (personal or professional) and take steps to correct or accommodate for that. If a co-located employee starts underperforming but I can see they are clearly checked out (like their head is somewhere else) I might suspect there is something going on at home and adjust my management style with that person. If they are remote it is harder to tell those things. Communication becomes extremely important when body language / behavioral clues are lacking.

So to pile on a lot of the other answers here... communication, communication, communication.

[laughfactory]

Yes, this is why it's critical to adopt an output/outcome mentality. When you can't see if or when we're working the only signal of status is whether shit is getting done. This should be the only thing you care about, and it should be super obvious of you're project managing correctly.