There’s always someone in every meeting who keeps yapping the majority of the time. There’s also somebody else who says almost nothing, then asks one question that stops the room cold. Think back to the last presentation you sat through. Which one of those two individuals do you remember a week later?
Asking questions is a skill, and it can be learned. So, today, we break down the art of asking questions and understand why some questions land and most do not.
You already give better advice than you take
Ask a friend what they should do about a stalled project, a bad boss, or a relationship in trouble, and the answer usually comes quickly and clearly. Ask yourself the same question about your own stalled project, and the clarity disappears.
Psychologists Igor Grossmann and Ethan Kross documented this phenomenon and named it after King Solomon, a ruler famous for sharp counsel about everyone's life except his own. Their research found that people reason more wisely about a friend's dilemma than their own and that the wisdom gap closes the moment someone is guided to view their problem from a distance, as if watching a stranger deal with it.
This finding explains why a good question outperforms a good answer in a meeting. A question forces distance. It pulls the group out of its tangled context and asks it to see the problem as an outsider would, which produces sharper thinking and better brainstorming.
It also explains why asking thoughtful questions makes you look sharp, not just sound polite.
Harvard Business School researchers Alison Wood Brooks and Leslie John studied thousands of conversations, including speed dates where participants were randomly assigned to ask either many questions or very few.
People who asked at least nine questions in fifteen minutes were rated as more likable by their partners and remembered more accurate details about them. On the dates, high question askers were more likely to get a yes to a second one. So it’s not just your workplace. Asking good questions helps you make yourself more likable in your social circle as well.
What makes a question great
Asking questions is great. We have established that already. But asking a “question” just for the sake of asking questions can sound pretty lame. If you ask your colleagues, "What is your favorite color?" right before an important meeting, your impression will definitely suffer, no matter what.
A sharp question passes three tests:
- It names a specific stake,
- It cannot be answered yes or no.
- It aims at something you do not already know.
Drop any one of the three, and the question collapses into small talk or an interrogation.
Take a manager who is checking on a project. "How's it going?" fails all three. It names no stake, invites a one-word answer, and gets forgotten within the hour.
Swap it for "What part of this is most likely to slip, and what would it take to catch that this week?" and the same two minutes produce something worth acting on, because the person answering has to commit to a specific claim instead of a mood.
The stake test works because it removes an escape hatch. A vague question lets someone hide behind a vague answer. A specific one does not. This is also why the outsider framing from Solomon's Paradox makes such a reliable question generator: Asking what a person with no history would do automatically forces a specific, checkable claim instead of a comfortable shrug.
Run any question you are about to ask through those three filters before it leaves your mouth. It costs three seconds and changes what comes back.
Steal the outsider question
The outsider question runs on a fixed formula: name a role, strip it of history, then ask what it would change about one specific thing. "If [a person with no history here] looked at [this one specific decision], what's the first thing they would change?" Fill in the brackets, and the formula does the rest.
For a stuck decision, ask:
"If someone took over my role tomorrow with zero history here, what's the first thing they would change?"
Write down the honest answer before you talk yourself out of it.
For managing up, replace "What do you want me to do?" with a question that hands your manager a frame instead of a blank page:
"Here's what I think success looks like on this by Friday. What would make you wish we had flagged the issue sooner?"
This version signals judgment instead of helplessness.
For giving feedback in a group, resist the instinct to state your read of a problem directly. Ask the room the outsider version first:
"If a new hire looked at this process with no context, what would confuse them?"
People defend a process less when the question is framed around a stranger's confusion instead of their own competence.
Layer in one more habit from the Brooks and John research: whatever question you ask, follow it with a genuine follow-up that references a specific detail the other person just gave you. This move, more than any clever opener, is what signals you were actually listening.
Ask this before Friday
Pick one decision you have been avoiding this week, a hire, a pricing call, or a conversation you keep postponing. Write down the outsider question exactly as scripted above, then ask it out loud in your next meeting or send it in writing before Friday. Do not soften it into a suggestion. Ask it as a question and let the silence that follows do the work.
Until next time, Future Leader…
