Getting clarification without looking incompetent

Do you have any advice on how to handle questions like “do you understand the situation here”? Particularly in cases where you think you understand the situation but aren’t sure what the other person means by that, and where asking for clarification would make you look incompetent and you need to not look incompetent?
It depends on the context. I’m assuming a professional context. In a professional context, I think the implied question is usually “are you going to do the work that needs to be done?”
Sometimes this is best:
  • Say yes, you understand (implying that you take the situation seriously and will do the work)
  • If you’re not sure you actually do understand, ask someone else (who won’t think you’re incompetent in ways that cause problems) for clarification once the person asking if you understood is out of earshot.
For instance:
Boss-person: Do you understand the situation?
You: Yes, I’m on it.
You to co-worker: Hey, are we supposed to be putting out the new legos now, or were we supposed to do something else first?
Sometimes this is best:
  • Saying something like this “Yes, I think so”
  • Then asking a *specific* clarifying question
For instance:
Boss-person: Do you understand the situation?
You: Yes, I think so. We’re putting out the new legos?
Sometimes questions like this are confusing because people ask them about things that seem not to be especially complicated, even things that you routinely handle all the time. When that happens, it’s often because there is more pressure on the boss-person than usual: because there’s a Christmas sale, because they’re expecting a review, or something like that. So it’s likely to be the case that you actually DO understand the situation, but are inclined to second-guess yourself because it seems like a strange question. When that happens, it’s worth considering whether there’s a reason they might be more worried than usual about a routine task. (And it’s usually NOT a good idea to ask them directly, although it can be, depending on the relationship).