Being Human
How To Ask A Great Question
A practical insight on asking better questions, creating deeper connection, and helping people find more honest answers.
Create better connection and get better answers with these 3 simple hacks.
Not only is asking good questions one of my favorite things to do, it’s what I do for a living.
Many people think hiring a life coach is about paying someone to tell you what to do or who to date. But most of the time, my clients already have the answers. They just need to be asked the right question to find them.
“If this person you’re dating ended up being the mother of your kids, how would you feel about that?”
“If you could be twice as happy but make half the money, would you leave that job and go work for yourself?”
The reason you ask a question is to learn something new. Now if you ask someone a question about themselves and they don’t know the answer, then the process of discovering it reveals something new for both you AND them. They just learned something about themselves simply because you suggested there was something worth learning. What a gift.
But not all questions are made equal.
Most questions suck.
Most people are asking boring questions in the hope that they accidentally get interesting answers.
“So what do you like to do for fun?”
“Do you have any brothers or sisters?”
“Where do you work?”
*cue vomit*
Ask boring questions, get boring answers.
We all know what a bad question is. They are the ones that immediately put us on autopilot, regurgitating answers we’ve said a thousand times. Sometimes we can even tell that the person asking them doesn’t actually care about the answer.
But a good question…oh man.
Not only can you get more interesting answers but a good question can literally change a life. I’ve seen it.
A friend of mine who was once the star-child CEO of one of the fastest growing companies in America was once asked, “Who would you be if you weren’t the CEO of this company?”
He didn’t have an answer.
That prompted a life-altering journey of introspection where he ended up leaving his company, leaving the country, and having a child with the woman who asked the question. He realized he didn’t have an answer and so he had to go find one.
So what makes a good question?
Good question.
A good question has 3 key characteristics:
It’s unexpected.
It comes from curiosity.
It demands truth.
Let’s break those down.
1. Great Questions Are Unexpected.
We all know the script. We’ve run the play a thousand times.
“Hey!”
“Hey, nice to meet you.”
“Nice to meet you too. So what do you do for work?”
“Oh, I work at *****.”
“Oh, that’s cool! Do you like it?”
Jesus. My fingers are cramping even just typing that out.
Where are we going with this? Chances are, nowhere interesting. And if it’s getting somewhere, it’s going to take quite some time to get there.
So, break the pattern.
Instead of starting at level 1 and making your long and laborious way to level 2, just start at level 3. Instead of asking “So, what’d you do today?” on a first date, try “What made you want to come on a date with me?” Some people may be turned off because they’re used to being asked about traffic. That’s ok. If you’re reading this article, the chances are those people aren’t for you.
The majority of the time I’ve taken this approach I’ve been met with relief and gratitude because most people have been waiting for the pattern to be broken. They’re craving connection and are exhausted of talking around the things that matter rather than the things themselves. Ask an unexpected question and you might just shock them into being honest.
2. Great Questions Come from Curiosity.
Don’t ask things you don’t care about.
Simple.
I don’t ask my mailman what his favorite flavor of ice cream is because I don’t care. And when you care about something, it shows. People can feel it. Especially when it’s them.
When you ask people good questions you’re making a statement. You’re saying, “You are interesting enough to be curious about.” When you ask them about the things that matter to them, you’re declaring that those things matter to you. A good question makes someone feel valuable.
9 times out of 10, if you’re asking one of those “what do you like to do for fun?” questions, you’re dancing around the thing you actually want to know. Why are we playing on the sand if we came to the beach to swim in the ocean? Lean into your curiosity. If you want honest answers, ask honest questions. What do you actually want to know?
For example, “What do you like to do for fun?” is actually the topsoil question to “Are you more of a Netflix and Chill kinda girl or Ketamine and Clubbing kinda chick?”
“Where do you work?” is actually the Walmart version of “Do you feel inspired by what you do for a living?”
Before you ask them anything, first ask yourself what you care about. You’ll end up doing both of you a favor. When you ask what you really want to know you learn about who they are through their answers and they learn about you through the curiosity you have and the questions you ask.
3. Great Questions Demand Truth.
This one is my favorite. Great questions demand truth.
Notice I didn’t say “THE truth”, I just said truth. There’s a difference between the right answer and an honest one. You can ask a question as an interrogation which would make someone feel like they have to say the right answer or you can ask it as an invitation which makes them feel like they should give an honest one.
Sometimes, questions are asked so poorly that the answers don’t create any sense of depth or new level of understanding, which is the exact opposite of what you’re trying to do when you ask a question.
This is why specificity helps.
It’s the difference between, “How was your day?” and “What was the hardest part of your day?”
One of those questions carries the conversation forward, one of them kills it. If a question makes them stop and think — you’re on the right track.
**Pro tip: Don’t ask questions that someone can give an automatic answer to.**
When you ask me a specific and unexpected question, I have to find the answer within myself. I have to think. That process alone makes it so much harder to give a boring answer and almost impossible to lie. Like my friend who left his company. When you’re asked a question you’ve never been asked, you have to go into a part of your brain you’ve maybe never been and connect things you’ve never connected. This is called learning. And it’s kinda fun. Especially when you’re doing it together.
How To Ask A Great Question
Remember, it’s not just the words of the question, it’s how they’re asked.
Watch your tone. Mind your body language. Lean in, never away.
Raising your eyebrows, crossing your arms, and asking “What could you possibly like about Donald Trump?” is very different than a curious tilt of the head and “What are your favorite qualities about Donald Trump?” It’s not the question that feels like an interrogation, it’s the energy behind it.
If you want to connect with someone, you have to learn about them.
If you want to learn about them, you have to ask questions.
If you have expectations of their answers or scoff at their responses, it’s only a matter of time before they shut down and the connection that could’ve been is locked behind fear.
Be ready to understand rather than to judge and the person might have an answer that surprises you about not just them but maybe even yourself.
Stay curious, stay on your toes, and don’t ever settle for anything less than the truth.
* Imari
Key takeaways
- Great questions help people discover something new about themselves.
- Boring questions usually create automatic answers.
- A great question is unexpected, comes from genuine curiosity, and demands truth.
- Specific questions make it harder for people to hide behind autopilot responses.
- The energy behind the question matters as much as the words themselves.
- If you want to connect with someone, ask questions that show you are ready to understand rather than judge.
Questions this insight opens
How do you ask a great question?
Ask something specific, unexpected, and rooted in genuine curiosity. A great question should make someone pause, think, and tell the truth rather than repeat an automatic answer.
What makes a question powerful?
A powerful question reveals something new. It can help someone notice what they feel, want, fear, value, or know but have not yet said out loud.
Why do boring questions get boring answers?
Boring questions often put people on autopilot. When someone has answered the same question hundreds of times, they usually give the same rehearsed response unless the question breaks the pattern.
How can better questions improve connection?
Better questions communicate care. They tell the other person, “You are interesting enough to be curious about.” When asked with warmth and presence, good questions can make people feel seen, valued, and safe enough to be honest.
How can coaching help me ask better questions?
Coaching can help you develop the curiosity, presence, and emotional precision required to ask better questions. For creative leaders, founders, and high-achievers, better questions often lead to clearer decisions, deeper relationships, and more honest leadership.
If this insight named something you’re navigating in your own life or leadership, explore coaching with Imari.
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