We ask:
“Do you have any questions?”
“Do you understand?”
The irony is that more often than not, when you ask “Do you have any questions?” people will say no, when they mean YES. And when you ask “Do you understand?”, they’ll say YES when they mean NO.
Then we hit a wall and don’t understand why.
That’s to it. It's not because they’re lazy or checked out. It’s usually due to one or both of the following reasons: either
- they haven’t sufficiently processed the information yet to have figured out the real answer, so they give a “placeholder” response, or
- they’re afraid of looking foolish and embarrassing themselves by confessing their own ignorance—especially in front of other people who also aren’t speaking up.
In other words: those two questions are incredibly common… and more often than not, completely useless.
Reconditioning deeply-rooted patterns (you're not in high school anymore)
I learned this years ago when teaching English in a Japanese high school. I was trying to run an American-style classroom in a very traditional school system that did not typically encourage students to ask questions.
On the contrary—asking was seen as selfish, taking the teacher’s time to answer your question instead of using that time to disseminate more information to everyone.
And culturally, the need to “save face” and not embarrass themselves in front of others was socially paramount.
A common Japanese expression is deru kui utareru—“the nail that sticks out gets hammered down.”
In other words: keep your mouth shut and your head down. Only a fool would demonstrate their own ignorance, so keep your questions to yourself.
So when I asked those two questions, I got the publicly acceptable (though often untruthful) answers.
How do I know they weren’t truthful?
Because as soon as the bell rang, there would be a line of students at my desk, each waiting to ask questions privately. And half the time, most of them were asking some version of the same question or two.
They needed to understand that there was a >90% chance whatever question was in their mind was also in other students’ minds—and to ask it was demonstrating generosity and courage, not ignorance or selfishness.
But that was a huge mental paradigm shift to catalyze in whole classrooms of students.
And here’s the punchline: this is not just “a Japan thing” or even “a high school thing.” This is a human thing.
The smallest change that unlocked the biggest movement
One of the smallest changes I made that yielded the biggest movement was in how I solicited questions after giving instructions.
It starts with shifting from yes-or-no questions to open-ended questions.
Instead of “Do you understand?” or “Do you have any questions?” I reframed the invitation:
“I know I gave you a lot of information. What parts aren’t clear yet? What questions do you have?”
The underlying assumption is that things aren’t 100% clear right away, period. Confusion is normal. Questions are expected. Of course something is unclear… I just needed their help to identify it.
Then came the hardest part: I had to stay SILENT and WAIT.
That’s a leader’s perpetual internal battle: the moment's silence gets uncomfortable, the leader’s instinct is to rescue everyone (self included) from the discomfort by filling the silence themselves.
The students were masters of the waiting game. If I only gave them 3–5 seconds before saying, “No questions? Okay, let’s move on,” they’d keep their heads down, avoid eye contact, and wait me out.
But if I could resist the urge to break my own silence—10 seconds… 20… 30…—eventually a hand would go up.
When “fine” isn’t fine
Ironically, this is not different from many teams and individuals who are long out of high school.
Many reflective (vs. reflexive) thinkers—especially if they lean introverted and/or shy—have a whole internal protocol they run before asking a question:
- Do I feel like I understand it enough to do what I need to do?
- Will everyone look at me if I ask a question?
- Will I look foolish if I ask this?
- What is the “right way” to ask?
- Will someone else ask so I don’t have to
- Can I just email later?
Now layer in power dynamics (you’re the boss), group dynamics (everyone else is quiet), and speed (the meeting is moving), and suddenly silence doesn’t mean comprehension. Silence often means calculated self-defense.
So if you want more proactive clarification requests from your team, you have to stop asking questions in ways that compel people to hide instinctively.
Leadership communication tips: the better prompts to ask instead
Here are a few swaps I share with clients during coaching and training engagements —simple language changes that dramatically increase clarity, accountability, and psychological safety.
Start by shifting from “yes-or-no” questions to open-ended ones:
1) Replace “Do you understand?” with “What parts aren’t clear yet?”
You’re normalizing ambiguity and inviting specificity.
2) Replace “Any questions?” with “What questions do you have?”
Same goal, totally different social signal.
3) Use a “teach-back” prompt.
Instead of yes/no comprehension checks, try:
“Just so I know whether or not I explained it clearly, how would you describe the next step?”
“What are you going to do first?”
“What should success look like by Friday?”
This isn’t a pop quiz. It’s an executive communication skill: confirming shared understanding without shaming anyone.
4) Give people processing time on purpose.
“Take 30 seconds—write down one question or one risk you see.” Then ask for responses.
5) Make it safer to speak up than to stay quiet.
Thank the first person who asks a question—out loud, and be specific:
“Thanks for asking that, Chris; no doubt others are wondering that too.”
You’ve just rewarded necessary risk team-oriented generosity, not bravado.
The other roadblock to getting good questions
The problem is that our instinct reaches for questions designed for speed and closure. On the surface they look like they are seeking input, but underneath they feel different.
“Do you understand?” sounds like, “Can we move on?”
“Any questions?” sounds like, “Please don’t slow this down.”
Your facial expressions and vocal tone can make the questions sound rhetorical—even if you don’t mean them that way.
If you want to institutionalize a culture in which people speak up proactively (before issues become expensive), meetings produce alignment instead of polite nods, and execution doesn’t rely on mind-reading, then your questions have to do more than seek information.
They have to create safety. And yes, you have to stay silent long enough for the room to trust you mean it.
Want to build this into your leadership culture?
The next step is turning these small language shifts into consistent habits—especially in high-stakes contexts like change management, performance conversations, or cross-functional alignment. If you’re ready to add this to your leadership skills inventory, let’s talk.
Start being the leader who knows how to ask the question that brings the best answers to light.
