The Power of a Good Question
“He who asks a question is a fool for five minutes; he who does not ask a question remains a fool forever.”
— Chinese Proverb
CEOs ask lots of questions. They have to. As their company grows, they become further removed from what’s happening on the ground. Talking to customers directly becomes less frequent. Meetings with individual contributors dwindle. The last batch of product features might launch without the CEO even knowing they were coming.
This is not another post on founder vs. manager mode. If you’ve been reading our material, you already know our stance on that debate. The point here is different:
CEOs have access to all sorts of data — financial reports, product engagement metrics, sales performance dashboards — but making sense of it requires more than just reading the numbers. And that means asking questions — a lot of them.
In fact, if there is one high-leverage yet dead-simple skill for CEOs to improve, it’s the ability to ask a good question.
What’s a Good Question?
“The ability to ask good questions is the foundation of all learning.”
— Confucius
We often overcomplicate this. A good question is simply one that elicits a useful and honest answer.
Let’s imagine a scenario that every startup CEO reading this post has encountered.
An employee enters your office (or pops up on your screen) to tell you that the absolutely, positively, no-matter-what crucial project that had to be done by Friday . . . won’t be.
The CEO’s goal at that moment should be to gather intelligence, understand the implications, and then direct resources, but how does the CEO respond?
You can imagine one scenario where the CEO says, “Okay, who fucked up? Why did they fuck up? Why am I only hearing about this fuckup now?”
Now, how do we think that the employee will respond, knowing their answer could get them or a colleague chastised at best or fired at worst? And they’re not just being asked to report the issue; they’re being asked to name the perpetrator, judge what went wrong, and explain why they didn’t escalate sooner, all under an implied threat.
Were those good questions to elicit a useful and honest answer? And the next time something goes wrong, will that same employee want to be the one to deliver the news?
Now imagine, instead, the CEO asks, “Help me understand what happened. What do you believe caused the issue? What were the earliest indicators that this project might be in jeopardy?”
Would the messenger feel safer? Might they be more open and candid about the situation and the available options?
Striking a Balance
Let’s be clear: Being a CEO doesn’t mean being a pushover.
Pleaser CEOs avoid hard conversations to keep the peace. They tiptoe around problems, afraid to disrupt harmony. Those CEOs don’t last, and for good reason.
But the CEO who shoots the messenger, implies threats, and scares the hell out of their team during high-stakes moments can be just as ineffective.
So where does that leave us?
Practice Good Questions
I even made a list to help you get started reframing prosecutorial questions as inquisitive ones.
| Prosecutorial Questions | Inquisitive Questions |
| “Why is this project behind schedule? Who dropped the ball?” | “I noticed the timeline has shifted. What challenges are we running into?” |
| “Why are our numbers down? What went wrong?” | “We’re tracking below plan. What are you seeing in the data that might explain this?” |
| “Did you even think through the risks before making that decision?” | “Let’s go back to the beginning. Take me through what the thinking had been, and how we assessed risks?” |
| “Why hasn’t this problem been fixed yet?” | “What’s preventing us from resolving this issue, and what help is needed?” |
| “Why is [team member] underperforming?” | “How is [team member] doing? What support might help them improve?” |
| “Why are we losing deals to competitors?” | “What are we learning from lost deals, and how can we adjust our approach?” |
| “Do you even have a plan to fix this?” | “What are the possible solutions on the table?” |
| “Why is morale low? What’s going on with the team?” | “I’ve been sensing some shifts in the team. What are you feeling?” |
| “Why did you take so long to escalate this?” | “When did we first know this was an issue? Please walk me through what we knew and when.” |
| “How did you let this happen?” | “Let’s explore how we got here. What factors led to this outcome, and what can we learn from it?” |
The Power of Tone
“People may hear your words, but they feel your attitude.”
— John C. Maxwell
Words alone are insufficient. Your energy is the context for your content (h/t to Tony Robbins).
My wonderful three-year-old daughter is flexing her independence in all sorts of utterly adorable ways, including that she is lying about everything. She will look me straight in the eye, ask for candy for lunch, and claim, “Mommy said I could,” when, in fact, Mommy isn’t even in the house.
Yes, my daughter is terrible at lying, which is both hysterical and terrifying.
When she does fib, I can return her gaze and say, “You’re lying.” But I say it with love, sweetness, and a touch of humor. More often than not, my gentle accusation is met with a giggle.
Now imagine I’m driving down the highway, and a police officer pulls me over. The officer asks how fast I thought I was going, and I reply, “Sixty-five miles per hour.” If he then locks eyes with me and sternly says, “You’re lying,” I promise you, the moment won’t feel quite as playful.
The words are the same. The tone changes everything.
For CEOs, asking good questions is only half the equation. How you ask them determines the response. And that’s not easy.
A Skill That’s Free to Improve but Costly to Neglect
CEOs are constantly buffeted by a thousand winds — customers, employees, investors, board members, competitors — all while likely operating on too much stress and too little sleep. It’s a lot to handle.
And yet, the job demands awareness of their mood, their energy, and their words.
Because, at its core, being a CEO boils down to a simple cycle:
Review data. Ask good questions. Evaluate responses. Make a decision. Review data. Ask good questions. . .
And if that’s the job, perhaps make each question count?