Something I've found is that there are two types of people when it comes to planning / forecasting:
SALES -- Wants to hear only positive things. Likes to ignore predictable issues, pretend unlikely risks will never happen, just go-go-go. Often sounds unreasonably optimistic to other people, which can be off-putting.
ENGINEERING -- Wants to hear all the bad things before committing. Likes to mull over all predictable issues to determine if they're show-stoppers and/or if workarounds are available. Often sounds unreasonably pessimistic to other people, which can be off-putting.
Both types can be in agreement that a project is a "good idea" while one type is listing only the upsides and the other type is listing only the downsides.
This can result in rather poor communication and missed opportunities.