Asking Better Questions
Recently, I realized that I mostly get paid to ask questions.
- As a consultant, advising companies
- As a podcast host
- In calls with potential clients
The curious thing is that, like most people in a similar position, I never had any formal training in asking questions! I basically just wing it and try to get better over time.
That got me thinking: What makes a good question?
The other day, I reflected on that. Here’s what I came up with.
1. Good Questions Are Open-ended
Recently, we did a survey about our podcast, and someone mentioned that some questions I asked the guests were “either-or” type of questions.
Q: “Do you prefer dogs or cats?”
A: “Dogs.”
Ouch, not a very interesting conversation!
A better one might have been “What’s your favorite pet?”. It allows for surprising answers.
Q: “What’s your favorite pet?”
A: “Tarantula!”
We have to ask ourselves what we want out of the answer, which leads me to my second observation:
2. Never Ask A Question If You Don’t Care About The Answer
Or to rephrase it, “Only ask things you care about.” If you don’t care about the other person’s answer, why even ask? Ask something else you care about instead!
For example, when you ask someone if they prefer dogs or cats, what are you really asking?
- Do you wonder if the person is nice?
- Do you care about the logistics of owning a pet as a full-time employee?
- Or do you rather want to hear a certain answer from the other person that happens to fit your narrative? (The obvious correct answer is “cats”.)
Be honest!
Dig deeper into “why” you’re asking the question. If it’s one of the former two questions, get straight to the point:
Q: “Are you a nice person?”
A: …
Q: “How do you manage having a pet if you have to work all day?”
A: …
It will lead to better answers.
If it’s about your own agenda and you’re just looking for someone to give you the answer you’re hoping for (confirmation bias): don’t. Again, allow them to surprise you!
Who knows? You might learn a thing or two about your preconceptions.
Which leads to…
3. Good Questions Reveal Something About The Person Who Answers; Bad Questions About The Person Who Asks
It’s very easy to slip into a role where you’re framing people, and that lets your bias speak more about you than the person you’re talking to. Be conscious about that so that you can avoid it when it happens.
Q: “Why do you love X?”
A: “I don’t.”
Better:
Q: “Tell me something you truly believe about X”
A: “I believe that…”
The more unique the answer, the more you learn about the person. So I would even say that a good question is one that reveals something unique about the person who answers.
- What is it that only they can say?
- What is it that they have unique insight into?
Q: “As an expert in X, who has been in the field for 20 years, what is one thing that people always get wrong about X?”
A: “People always think that X is about Y, but it’s really about Z.”
4. Good Questions Are Stacked On Top Of Each Other
Do you know the Five Whys technique? It’s simple: Ask “why” five times to get to the root of the issue.
Q: Are you happy with your job?
A: No.
Q: Why?
A: It drains my energy.
Q: Why?
A: I have to do boring things.
Q: Why?
A: My boss thinks they must be done by someone.
Q: Why?
A: No one got around to automating them.
Q: Why?
A: We don’t have the skills to automate boring tasks.
Aha! If they learn how to automate things, this might lead to better job happiness! That’s insightful.
What’s nice is that it was a purely mechanical process. With every step, we dug deeper into the underlying question. At some point, the truth revealed itself.
I love this technique. Good questions are built on top of each other. The questions themselves don’t have to be complicated. It can actually be the same question asked a few times in a row – even a child could do that.
In fact, they do. A lot! This is how they learn about the world around them.
As grown-ups, we should not unlearn this technique. “It’s rude to ask that.” “Don’t pry.” “Don’t be nosy.”
We should relearn it! Ask follow-up questions to get to the root of things.
But also! Hold the other person accountable.
Q: “How can we fix poverty?”
A: “I will do everything in my power to fix it.”
Q: “But how?”
A: “I will try countermeasures which were discussed with…”
Q: “Can you give me a concrete example?”
A: “…”
When someone answers your question, ask yourself if the answer really covered everything you wanted to know. Often, the most interesting pieces are omitted. Sometimes on purpose. But this is the most revealing part, the part at the verge of uncertainty and insecurity and you have to uncover it to get to the heart of the matter! If you don’t do this, conversations stay shallow.
Speaking of which…
5. Good Questions Run Deep
- “Why is the sky blue?”
- “How do people fall in love?”
- “Are you happy?”
These are simple questions! But they touch on the very foundation of what we know, our perception of the world, and ourselves.
The simpler the question, the deeper the answer. Answering with “I don’t know” is totally fine. The important part is to stay curious and to be genuinely interested in the answer.
6. Let The Winners Run And Cut Your Losses Short
Sometimes, no matter what you try, there’s just nothing in a conversation. You might have ended up in that weird space where people are simply out of their depth and you turn circles.
Cut the cord.
Just acknowledge it and move on.
Trained conversationalists do it all the time without anyone noticing. The conversation gets boring, so they just move on to the next topic. There doesn’t even have to be a transition.
Q: “So, what do you do for a living?”
A: “I’m a plumber.”
Q: “Oh, interesting. So, what are your plans if you win?”
A: …
Once you notice that, you will see it everywhere. We do it all the time in our daily lives, too, for example on the phone. Just cut your losses, move on to the next topic.
Similarly, if you notice that you both are really into a topic, just run with it.
7. Give People Space To Think
Pauses are powerful.
Ask your question and then… wait. Just wait.
Don’t fill the silence with your own thoughts or insecurities. Let the question speak for itself.
If you’re truly interested in a deeper thought, you need to give people time to unpack it - for you and for themselves.
If you’re not willing to wait, you’ll miss out on the best part of the conversation.
We are trained to give quick answers. If someone asks you “How’s it going?”, the expected answer is “Good, you?”. People are surprised when I take a moment to answer and give them a truly honest answer, which might be deeply personal.
Similarly, let people give you their quick answer first. Then wait. Often, they will stop and follow up with a much more personal answer.
Use pauses to your advantage.
8. Obvious Questions Can Be The Best Questions
If you look close enough, which question to ask becomes obvious.
- “Why are we still working on this?”
- “Should we split up?”
- “How do you feel after the diagnosis?”
You’re addressing the elephant in the room!
But just because you have an obvious question, that doesn’t make it easy to ask!
You might know that the question could hurt. Or that the answer is uncomfortable to handle. And yet, it’s still the right question to ask.
What I noticed is that oftentimes multiple people have the same “obvious” question in mind. They are just too afraid to ask.
Most people dance around the topic because they want to be polite. They don’t address problems head-on because it’s easier! The result is small talk.
Especially if you get paid to ask questions, your job is to ask questions that no one else wants to ask. Often, politics, infighting, and hidden agendas make it very hard for people to break out of their role and ask the obvious question.
If you’re not afraid to ask the obvious question, you will look like Houdini.
Suddenly, an avalanche of follow-up questions gets unleashed. An honest, constructive conversation emerges.
The thing is, just because you don’t ask the uncomfortable question, it doesn’t make the problem go away. In fact, you might make it worse in the long run. It’s easier to get it out of the way and move on!
Q: Why are we still working on this?
A: Actually, I have no idea. Let’s find something else.
Q: Should we split up?
A: Yes, I think so. Let’s talk about it.
Q: How do you feel after the diagnosis?
A: I’m scared. I don’t know what to do. But I’m glad you asked.
The truth is hidden in plain sight. If no one dares to ask, these questions stay unanswered. The trick is to accept the answer for what it is. Don’t be mad or angry at people who honestly answer your question. Be mad or angry for not asking sooner.
If You Don’t Understand The Answer, Ask Again
In the past, I would often gloss over an answer and pretend I understood it. Turns out that it was a bad strategy: In the best case, I would have missed out on a great opportunity to learn something new. In the worst case, I wouldn’t have a good question to follow up with.
Funnily, I’m rarely alone with this problem. There’s usually more than one confused person in the room. So don’t be afraid to refine your question to clarify any misunderstandings.
Q: “Can you explain that differently?”
A: …
Q: “Am I correct in understanding that you mean…?”
A: …
Q: “Can you give me an example?”
A: …
There’s an old Chinese proverb that goes like this:
He who asks a question is a fool for five minutes; he who does not ask a question remains a fool forever.
Good Observations Yield Good Questions
I noticed that many people who ask great questions have exceptional observation skills. They notice things that others don’t.
Q: “Why are you still working here?”
A: “I need the money.”
Q: “Tough luck. What’s for lunch?”
A: …
vs.
Q: “Why are you still working here?”
A: “I need the money.”
Q: “I noticed that you have this book on your desk. What’s that about?”
A: “Oh, that’s my passion! I’m reading up on sales because I want to start my own business.”
Q: “Nice! What is it about sales that you find so interesting?”
A: …
See how this tiny observation about a book on the desk led to a much deeper conversation? Suddenly, you’re talking about someone’s passion and dreams. You might inspire them to have more conversations with customers during work time to get some practice.
If you want to improve your observation skills, come prepared. Learn more about the person you’re talking to.
- What are they passionate about?
- Who’s their role model?
- What are they doing in their free time?
- What are they reading?
- Which projects are they working on?
If you come prepared, you’ll have an easier time asking good questions. Context makes good questions obvious.
The Best Follow-up To An Answer Is A Question
Okay, you got an answer. Now what?
Many people follow up with a statement about themselves.
“Oh, I also like that!”
“Yes, I also did that!”
“Let me tell you about my experience!”
“You should do this!”
This shows that you’re not interested in the other person, only in yourself.
Instead, what if you could only follow up with a question?
Q: “What’s your favorite sport?”
A: “Table tennis.”
Q: “How did you get into that?”
A: “My dad played it when I was young.”
Q: “What’s your favorite memory of playing table tennis with your dad?”
A: “We used to play in the basement. It was so much fun!”
Q: “What made it so much fun?”
A: “I don’t know. It was just the two of us. It was our thing.”
Q: “What did you learn from your dad about table tennis?”
A: “He taught me how to serve. He was really good at it.”
Q: “What’s the most important thing about serving in table tennis?”
A: “You have to hit the ball at the right angle. Otherwise, it’s easy to return.”
Q: “What’s the most difficult angle to return?”
A: “The one that goes straight to the corner. It’s hard to reach.”
See how this conversation unfolded? It’s like peeling an onion. You get deeper and deeper into the topic. You learn more about the person. You learn more about the topic. Step by step, you tap into someone else’s hard-earned wisdom. Look at all the things you learned in such a short time! Their favorite sport, their childhood memories, their relationship with their dad, how to serve in table tennis, the most difficult angle to return a serve. If you had followed up with “I like that too,” you would have missed out on all of this and probably never learned about it.
All just because we kept asking questions instead of making statements.
Think about all the people you know. Who do you like to talk to? I bet it’s the people who ask you questions and listen to your answers instead of talking about themselves all the time.
Interestingly, it’s entirely selfish to ask questions. You learn more about the other person than they learn about you. You’re in control of the conversation.
Summary
I’m still not good at asking questions. I wrote this mostly as practice for myself. Maybe it helps someone else too.
Here’s a summary of what I wrote:
- Good Questions Are Open-ended
- Never Ask A Question If You Don’t Care About The Answer
- Good Questions Reveal Something About The Person Who Answers; Bad Questions About The Person Who Asks
- Good Questions Are Stacked On Top Of Each Other
- Good Questions Run Deep
- Let The Winners Run And Cut Your Losses Short
- Give People Space To Think
- Obvious Questions Can Be The Best Questions
- If You Don’t Understand The Answer, Ask Again
- Good Observations Yield Good Questions
- The Best Follow-up To An Answer Is A Question
Don’t be mistaken! Asking good questions is hard work! You have to be present, you have to listen, you have to reflect. It helps to take mental notes while you’re talking to someone. After a while, you will get better at spotting the patterns.
Asking good questions is a skill that can be learned and improved upon. Asking more questions can’t hurt along the way.
So, how do you ask better questions?
Thanks for reading! I mostly write about Rust and my (open-source) projects. If you would like to receive future posts automatically, you can subscribe via RSS.