One of my biggest hurdles was trying to figure out if microservices were right for us (a small distributed team) and then communicating/selling the benefit of them to my team and bosses.

This involved creating a mutually agreed upon definition of what we actually meant by "microservices". I literally repurposed paragraphs out of Sam Newman's book to do this.

As a small team, I also didn't have examples to support my argument that microservices would benefit us.