It's a huge mental barrier for a lot of people... but can it overcome by talking to something you know is a bot?

Where does it say this is a bot? To me it looks like it's human coaches who use AI to quickly find answers. Maybe they're doing Facebook's approach of slowly replacing humans with bots, but for right now they seem to be human.

Edit: saw another comment by from Boost, they're doing Facebook's approach.

People are willing to accept talking to a rubber duck can be helpful, why not a bot?

Boost is _not_ a bot -- it's a team of AI-enhanced, real-life career coaches. Think Facebook's M.