[mattferderer]

Risks, risks & risks.. That's my #1 priority on communicating estimates.

Overall this is a nice short summary on the topic. The one thing I would add that I found very helpful on larger projects is communicating the risks & unknowns. I suggest listing them out at the start of the project & update their status as you work on it.

I've worked on teams where it's done with a simple color (red, yellow or green) on how confident we are on the task estimate based on risks/unknowns. This is the simplest way in my opinion.

I also like Basecamp's Hill Charts - https://3.basecamp-help.com/article/412-hill-charts