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.
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.
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.
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.