Does it help?
This sounds like they are expected not to waste time, so it might get even harder to ask a stupid question a minute too late, and especially to ask something tomorrow.
But you’re right that it might not be the best technique. I understand the hesitancy to ask questions after a certain amount of time has passed.
I work as a consultant and our time has to be billed to projects. The onboarding stinks, so the new hires often have no concept of billability/utilization nor project budgets. So I’m trying to drill in those concepts, too.
One of the additional lessons here is “the boss doesn’t always know what they’re talking about.” And that’s another hard one for them to accept. Question authority! If the instructions aren’t clear, then they might be nonsense. Have the guts to challenge the boss. And sometimes the challenge can come in the form of a million stupid questions.
As an aside, do you think there is a business opportunity in teaching companies better onboarding? Growing headcount seems like an afterthought most places, and it’s a colossal waste.
The worst example I’ve seen is one company hiring some very expensive onshore consultants to build the basic structure of the application and then quickly hand it off to cheap offshore ones.
What really happened is that the onshore guys created a horrendous mess of untested and undocumented code full of bugs that the offshore ones had no hope of making sense of. And being remote and from a culture of high power distance further exacerbated the problem. It certainly worked out well for the onshore guys who got to bleed the client out of a whole other year’s worth of expensive hours.
So, maybe. It’s risky, like you’ve demonstrated.
Something like this maybe: go to the new person, in the beginning every day, then once a week, then once a month, and say:
"Can you please ask three (3) basic questions about things you're slightly struggling with, and that you think everyone expects you to know, but that you don't?"
At my work, there's a bad combo of senior folks who whip off vague instructions in a single sentence, and junior folks who are afraid to ask questions. I'm in the middle, and I try hard to demonstrate that it's fine to badger the senior folks with questions, and to check in with them constantly. The senior folks like it because it gives them confidence that you're working it out. But some of our straight outta school colleagues just don't do this ("Gotcha. Sounds good!" is a very common email reply from them) and it leads to confusion down the road. After giving them the "ask questions" talk two times, I usually give up on them.
Also, in my position, I often have to review and edit reports that are largely written by electrical engineers and architects, and they all probably think I'm super dumb. I read the reports as the target audience (often non-subject matter experts), and so my comments are things like, "What do you mean by this [basic EE concept]?" I don't preface it with, "I know what this means, but the client might not, please elaborate..."