There are two kind of people when it comes to asking questions: First of all there are the people who don’t want to ask ‘stupid’ questions. These people are afraid that others would laugh at them, or that others would consider them stupid. The more people are involved in the conversation, the harder it is for these guys to ask for help – even when they know they should. These guys end up paying high conference fees, smiling, nodding and telling how everything was wonderful – although they don’t have a clue what was talked about.
I personally believe there is no such thing as a ‘stupid question’. It’s not matter of stupidity – it’s matter of knowing something or not knowing something. If in the middle of a conversation, a company stakeholder asks “What’s Java?” – the programmers might smile or think “How crazy is this? Guy owns a tech company making applications primarily in Java, and he don’t even know what the term means”. Well, if the programmer then need to ask “What’s ROI?” – the stakeholder might smile. Both are extremely basic information, but you just have to know what they mean if you want to talk about them. It’s not matter of stupidity, it’s matter of knowing terms.
Then there are those people who ask questions. If they don’t know a meaning of something, they might simply others to give more information. They might ask “could you clarify, what you mean by ‘company strategy’ in this context?”. Or they might say “You mentioned bump mapping, I’m not quite sure what it means or how it would enhance the user experience. Could you give me bit more information about how it works?”. The higher levels the talk goes, the more important it is to know exactly what people are talking.
Being afraid does not help anything, and if others smile at you… well, then that’s basically their problem – not yours. You cannot change the way other people think about you, and it’s up to you to whether you understand or not what others are talking about.