When I was a child, my father encouraged our learning and curiosity by often saying, "There's no such thing as a stupid question." I took him up on that with many questions, to my siblings' chagrin!
But that approach has served me well. Thoughout my career, I've worked in situations where I must get up to speed on a new industry, process, culture, or group of people quickly. People are generally receptive to answering my questions when the intention is good. They appreciate my interest in a subject they are passionate about or appreciate my wanting to learn about them. Far too often I see others miss opportunities to learn or to connect or to broach the elephant in the room because they are afraid their question will sound stupid or be judged.
But like Bill, with time and experience I have amended my thinking. I acknowledge there is wisdom in discerning when and how and to whom to ask questions. And when that discernment is missing, there can indeed be non-productive questions (although still not "stupid")! These concepts apply whether I'm tackling the tricky interpersonal dynamics of family business, mastering a new topic, or negotiating.
When: I can learn a lot by listening first. If it's a new technical topic or negotiation, before I advertise my lack of knowledge, I listen to see what I can infer to research later and be able to ask more nuanced follow-up questions. If it's a tricky family topic, I try to be intentional about finding a time when others will be receptive to discuss and have the opportunity to be prepared also.
How: In family business situations, I try to resist the temptation to ask a question with an assumed answer or an implied accusation. Do a gut check. Are you asking in a way that is truly seeking to understand, or seeking to prove your point? And physically how: for a difficult topic, discuss in a person or on the phone. For a content question taht may need documentation, email may be more appropriate.
To whom: Some people are passionate teachers, some are not. Some can be trusted with the touchy topics, some cannot.
So like my dad, I share the same coaching with my children, trying to teach the nuance along the way.