[esharef]

I think these questions are awesome. As someone who lost one co-founder early on (there were three of us and one person quit right after YC), I wish we'd talked about some of this stuff more.

Having said that, I actually think in reality this conversation is very difficult to have.

If you've never started a start-up before you just don't know what to expect so some of these questions don't make sense. I would have WANTED to answer these honestly, but when I started HireArt I really had no clue whether I'd want to raise outside money (let's just get started was my motto) or which attributes we'd en up clashing on.

I think this makes more sense if you've started a company before and can anticipate the feelings and issues that will arise (but in that case you probably already know which questions to ask and don't need a guide).

Overall I guess I think it's really important to talk and to talk a lot. However, don't estimate how much there is that you just don't know about yourself until you're doing the start-up.

[smirksirlot]

I agree that this is a super hard conversation to have. BUT, if you're working with the right people, I think they'll understand that a lot of these questions are "must-have" conversations. Might not get to all of them, but even some will be super helpful to at least orient the ship and crew in the same direction.

[jmalter]

agree with both of you - not always easiest conversations, but they are important questions. As I say in the post, it's ideal to try to have a more natural conversation - not just go down the list. But sometimes you just have to ask tough questions - it's more awkward/painful to "break-up" down the road.