Cultural differences matter and I’ve worked with one-too-many people from a culture in which asking a question is viewed negatively, since, in definition, it reveals your ignorance as to the subject matter at hand.
Deeply ingrained cultural attitudes are very hard to fight and clearly one won’t go from “never asking a question” to “asking too many questions” overnight, but here are some reasons why, on the tightrope of “how many questions to ask,” it’s better to err on the side of too many.
First, asking questions reveals that you’re engaging with the issues at hand. Clients and bosses, above all, want to see you engaging with their issues because it shows you’re focused on the problem at hand and trying to find a solution for it. If you hired someone who wasn’t sitting next to you (so you couldn’t see them working), wouldn’t you want clues that they’re working or not?
Secondly, asking questions reveals that you’re not just engaging with the issues, they reveal how good your thought and problem-solving process is. If your questions are good questions, that will reveal that you’re doing a good job trying to solve the problems. If your questions are bad, that will give your client the opportunity to help solve the problem better and for you to improve!
Thirdly, asking questions gives the rest of the team the ability to help improve the answers. Which answer will be better to a question, one you come up with on your own, or one in which your client or boss (who knows more about the product, market, or company than you do) helps you figure out? So, the overall quality of the work will improve.
These arguments lead to an interesting question: what’s the argument against asking more questions? In short, it may make you appear, to be blunt, a bit stupid.
But let’s think about that for a moment. To put it in stark terms: either you’re competent or you’re not (even if you’re in that large greyscale area in between, you always edge towards one side or the other.) If you’re competent, then your questions will only make you look better. And if you’re incompetent, your clients will discover it sooner or later—so isn’t it much better that they discover it on your own terms, with you voluntarily and pro-actively revealing what you don’t know (in the context of wanting to solve the business problems for company you’re working on, while you learn and improve) rather than hide it, and have the company discover later your true incompetence and thus be angry at you?