The courage of knowing when to ask a question is partly about biting your tongue in the sense that good questions require good listening.
Just as listening is not a one-way process, questioning is not a one-way process. Questions beg for responses — answers if you will. Questions should leave room for growth.
Author and consultant Peter Block in his book Community: The Structure of Belonging, says questions should be ambiguous. Questions should be personal. Questions should create a bit of anxiety and accountability.
A good “how” question should call the recipient of the question to really do some serious introspection, e.g., “How could have handled that differently,” A good “how” question can make some connections to other things going on within the organization. That goes back to the idea of, “How is this in keeping with our values?”
One example I love to bring up is when somebody comes to you and complains about somebody else — for example, John comes to you and complains about Jeff. Jeff oversold something and John wants it delivered tomorrow.
Instead of reacting, for instance, to John’s problem about Jeff and then just going over there to yell at Jeff or telling him that he upset John or whatever else, why don’t you go back to John and say, “What’s your contribution to the very thing you’re complaining about?” It takes two to tango. See? There’s a question that’s ambiguous. It’s personal and it’s a little painful and it puts the resolution back to John and Jeff.
Using that example, you see it’s about the confidence of knowing how to ask the question (the art of asking questions) and the courage of knowing when to do it.
To use a silly example with a building that’s on fire, you don’t ask questions then like, “Well, what do you think we should do?” Get the hell out of the building! That’s what you should do. Save your questions for a time when there is learning or growth needed. That’s the courage of knowing when.