I often encourage not just my people but everyone to ask questions. Asking good questions is a must for a healthy environment (personal & professional) and growth.
A few years back my manager told me to ask him some questions related to our day to day work but I was reluctant to ask any.
I was reserved and afraid of asking questions will make me look like a fool in front of others.
Anyways my manager was supportive, he pinched this to me almost every day and I then started to ask questions, at the very beginning the questions were not that good, however, my manager honestly encouraged me to keep on asking because it was a necessity for the growth of everyone including the company.
Then just after a few months, that day came; I asked a very basic yet good question and my manager smiled at me and said he has no answers at the moment but he will get back to me in a few days with the answer.
I learned how important it is to ask questions not just to others but to yourself too.
As an investor and a founder, now it is in my habit that I ask questions and these questions are worth to scrutinize.