THE ART OF ASKING A SINGLE GOOD QUESTION
The ability to ask a good question at the right moment is a superpower. Whether you’re solving a problem with intelligent people, getting to know your significant other’s family, or trying to figure out what to do with your life, questions direct the flow of conversation. The quality of a question makes the difference between a meaningful conversation and one that feels like a waste of time.
You, too, can become a better friend, a more critical thinker, and an engaging interviewer by mastering this esoteric art.
So, what makes a good question?
Good questions often start with “What“, “How“, and “When“
As I’ll define it, a good question strikes the right balance between empowering and challenging the other person. The question is one that calls them to attention, to fully engage with the conversation, but doesn’t leave them stuck or wallowing to give you an answer.
To empower someone, the question needs to consider who they are and what they’ve already said. Before you’ve even begun thinking about what to ask, you need to understand a little bit about who the person is, how they think, and what they have to say. Get curious about the context, content, and terms they’ve used. When you are genuinely curious about someone else, you invite them to share and engage.
Instead of asking a complex or clever question, strive to empower and encourage your conversational partner with a question that makes it obvious you are more interested in their genius than your own.
Your question is challenging if it calls for more thought, for others to get curious alongside you. If your question can be answered with a single word, especially “Yes” or “No”, it doesn’t require much curiosity.
Questions that inspire curiosity, to revisit what we thought we already understood, start with words like “What”, “How”, and “When.”
“I’ve heard you mention 'the things that are most important' a few times. What are they for you?”
“When that happened, how did you react? [...] What are you thinking and feeling about it now?”
“I’m hearing you haven’t found a solution to this problem. What have you tried so far? [...] How has that played out?”
“With all of that in mind, how can I be helpful?”
“What’s obvious to you that I’m not seeing here?”
Curiosity is your superpower. You’ll ask powerful questions, and the other person will feel seen, intelligent, and excited to keep the conversation going.
Good questions are easy to answer
Notice your reaction to the following question, considering it as if you were in conversation with a group of people: “What is your favorite book of all time?”
The question is so broad that it leaves most people slogging through a difficult consideration process. You need to think about all of the books you’ve read, and then you need to think about the criteria you’ll use to determine which is the best… And then you doubt whether you’ve actually considered every book.
If you take the time to answer the question thoroughly, the flow of conversation is lost.
On the other hand, consider what it would be like to respond quickly with the first thing that comes to mind. You’d be left with the underlying dissatisfaction of knowing you answered with too little deliberation.
So, that was a hard question to answer. A better question would be more specific, giving you less to consider: “What are three books you’ve recently read that you would recommend and why?”
How does this question land with you instead? Notice how the specificity of the question gives you metaphorical bowling lane bumpers. It’s easy to quickly begin answering the question and feel good about your answer..
These are broad, overwhelming questions that stall a conversation:
What should I do?
What do you want out of life?
What’s your favorite memory?
What are the steps I need to take to succeed?
What are your criteria for a significant other?
These are specific questions about the same issues that are easier to answer:
What experiment can I run to learn what I should do?
What’s one thing in your life that’s non-negotiable?
What’s one of your favorite memories from elementary school?
What step could I take that’s sure to be beneficial?
What is your love language?
Each of these questions could flow into more questions that collectively create a big-picture answer for one of the broader questions. Getting to that big-picture answer takes time, and it requires you to stay curious about the answers you’re getting, adjusting your questions and chasing your curiosity as the conversation unfolds.
Good questions are one clear question
In the spirit of making it easy for someone to answer your question, ask a single question and then shut yer trap 🙂
Even if it’s not exactly what you meant to ask, just wait and see what happens. Asking a single question provides clarity and specificity. Asking multiple questions at the same time creates the additional task of discerning what the actual question is before they even begin thinking about how to answer.
Don’t: “What led you to leave your last job? I mean, I get that you were unhappy, but was there anything else? Were you interested in a different industry, or was it more that you were sick of your boss? And what jobs are you applying for now?”
Do: “What led you to leave your job?”
A good question has no agenda
Let’s say you ask a single question and shut your trap, but you know you could have asked a better question. You realize the question you asked will be misinterpreted, and the answer you get is not an answer to the question you wish you’d asked.
Instead of interrupting their answer or (just as bad) waiting for them to finish so you can course-correct and ask the right question, follow their lead instead. Lean into what they thought you asked and ask a follow-up question to their answer. Instead of focusing on what you wanted to ask or where you want the conversation to go, focus on what they wanted to tell you and where the conversation naturally leads.
Bonnie Stith, one of my favorite coaches, summarizes this well: “If you don’t have an agenda for them and you’re holding their agenda, the only thing left for you is curiosity.”
A good question doesn’t pass judgment
Unlike questions that begin with “What” or “How”, a question that begins with “Why“ can more easily be misinterpreted as judgmental.
“Why did you do that?” is objectively a fair question, but it’s easily interpreted as “You’re an idiot, you screwed up, and I want to shame you for it.” Sure, it’s not true for any question that starts with “Why” - if you ask someone, “Why is the sky blue?”, they’re not likely to take offense.
So, more specifically, Why questions about someone’s process, thinking, or actions should be considered carefully. For that matter, “What” and “How” questions could also get you in trouble: “What were you thinking?” or “How could you do that?” are both questions that could be easily received as judgmental.
Bottom line: check yourself before asking. If the question is received as judgmental, the conversation will become contentious. Judgmental, contentious conversations shut down collaboration, curiosity, and productive problem solving.
What are the worst and best questions you’ve been asked? What else is missing here?
I’d genuinely love to hear from you. What are your thoughts on this article? What’s missing? What do you disagree with? How can we get more nuanced about asking a good question?
