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.