> But we don't do a great job on explaining that estimates are probabilistic by nature, there are risks involved

Ironically, I've recently been catching flak for "not being confident enough" when I give confidence intervals around my estimates indicating uncertainty.

In some sense, literally can't win. I then realized it was more about my lack of doing this: https://www.csun.edu/~to18470/articles/Managing_your_boss.pd...