Assumptions are a dangerous thing.
They can lead you to a belief that everything is in good order, working perfectly, that strategies are intact, the future is assured - when the reality could actually be quite different. In this case, you aren't prepared to ask probing questions, because you are prepared to assume that all is fine, and sheepishly, you don't want to look like you don't know what is going on. So you hold back.on your curiosity with respect to what you are hearing, blindingly accepting the current situation as is. The status quo prevails. Until, of course, it doesn't.
What can hold you back from asking your 'dumb questions' - and remember, they might not actually be that dumb! - is peer pressure. Who wants to look like the only fool in the room? But if an organization develops a culture in which peer intimidation leads to a situation in which no one is prepared to ask anything at all, then communication suffers, and information sharing is stifled. The mere act of refusing to accept dumb questions leads to a reality in which important questions are never asked at all because no one dares to challenge the status quo or to single out information that doesn't make sense.
Peer pressure leads to peer thought - everyone begins to assume everyone else knows what is going on, and so they don't dare to challenge conventional wisdom. Yet at the very heart of it, the conventional wisdom might be the actual problem in the room because it's wrong!
You should never be intimidated into not seeking the knowledge that you are looking for. The most important thing to remember is this: if you ask a dumb question, you might look pretty stupid for a few minutes. But by not asking your question, you'll stay stupid forever.
Great leaders don't hold back from asking dumb questions, because one of their key character traits is challenging assumptions and running up against ingrained attitudes. They are the ones who are seeking out the elephant in the room or the obvious major problems that need to be addressed. They know there are no stupid questions - only additional clarity or further knowledge.
There is no such thing as a stupid question - there are only the wrong assumptions that are often held dear!