Ask questions. Ask lots of questions. Ask stupid questions. Keep asking until you find and understand the answer.
This is how we learn.
If you want to ask a question, it’s because you don’t know the answer. And since you don’t know what the answer is, there’s only one way to find out if it will help you.
Not asking silly, inane, or stupid questions always deprives you of knowledge. It is also a great way to squash your inherent inquisitiveness and thus inhibit innovation.
It’s not quite true that there are no stupid questions, but I’ve not yet been able to come up with a concise definition that works.
The one caution you must heed is that the case when someone behaves like you are asking a stupid or inane question and that you’re annoying them. There are several possibilities, and you just have to guestimate and feel around for which one is closest:
They don’t know the answer, and are annoyed and ashamed when confronted with such questions.
Go ask someone else, because they won’t be of any further help. But the fact that another person doesn’t know the answer may mean that it’s a question worth asking.
They don’t know the answer, and don’t care about it.
Ask someone else—but find someone whom you believe has reason to care about the topic, question, or answer.
They know the answer, but say or act like it’s a stupid question, and either don’t answer or do while putting you down.
They’re arrogant, and think anyone who can’t work at their level is stupid. As long as they don’t think you can help them in any way, they’ll behave just the same. You can either go ask someone else, or up-level the conversation and change their mind. But you have to be careful—because there’s a small chance you are asking a stupid question. If you keep doing this, you won’t be able to recover easily. What is this stupid question? Anything that shows a lack of fundamental knowledge on the topic. You shouldn’t be asking advanced questions if you don’t understand the basics (well, you should, just not with this type of expert). But you have to figure this out before they turn off.
So, when you get to the second or third question (or variation of the original) and are still getting the same treatment, stop. Show the others around that you grok the intelligence imbalance and are as strong as he with a subtle dig—call him Sheldon. (If they watch TBBT, they’ll get it, and this might help turn them to your side, which is extremely important.) Then do what Leonard would do, and appeal to his sense of logic and his ego. Tell him that you sought out his advice because you heard he was the most knowledgeable one around, and that what you’re trying to learn from him will help the company/organization/school/whatever, and could he please steer you to some primers that you can learn the fundamentals from.
Go research those fundamentals. When you grok them, you’ll then have a better idea about what questions to ask, and when you’ve learned enough to ask questions of Sheldon again, and learn something the books can’t teach you.
If you are a principal and you run across any of these behaviors, please don’t hire the person (or promote them, give them tenure, a recommendation, or even keep paying them). These behaviors are fundamentally incompatible with teaching and encouraging young minds to learn.
And oh, yeah—one more caveat. If they’re an engineer or programmer by trade or training, only ask one question at a time. This is the lesson that all good tech writers have learned the hard way.