Have you ever thought about how only humans can ask questions?
Animals can’t.
Even chimpanzees who’ve been taught sign language to communicate their needs and emotions have never been observed to ask a question.
But what’s so important about questions?
We ask them every day, mostly without thinking twice about it.
I’ve become fascinated by the hidden art of asking great questions…
Mostly because I realized that I suck at asking them.
Can somebody suck at asking questions?
In my MBA program, I’d observe my classmates go up to the professor during the break, asking them a question.
And I wondered…What are they asking?
My mind was still processing the lecture and didn’t produce any queries.
Was there something wrong with me? I felt like I should be asking something and was afraid this meant that I wasn’t curious or learning enough.
When I started to take online courses, something similar happened.
I admired the courage of my fellow students, who raised their hands and asked clever questions, often in front of hundreds of people.
I didn’t even know I had the same question until they said it out loud.
Again, by not asking questions, I felt like I was missing an opportunity.
So I became obsessed with questions and figuring out how to ask better ones.
Questions are the answer
On the surface level, questions are just a vehicle we use to get a piece of information.
Sometimes, they even annoy us. Think of your children torturing you with a repeated “But why?” or your spouse quizzing you with a “What’s wrong?” when you just don’t want to talk about it right now.
But when you look one level deeper, questions are darn powerful!
They can reframe our thinking, unlock a new perspective, and fuel memorable conversations.
They challenge limiting beliefs and the status quo, and lead us to a new solution we hadn’t even thought of before.
A great question asked at the right time can be a gift to someone and make us look smart in front of an important person.
How do we harness the power of questions?
This is just another thing we’re never really taught when growing up. School is all about giving better answers, not asking better questions.
For me, getting better at asking questions started with realizing where they truly make a difference.
I found four areas…
Conversations
Great questions are the difference between forgettable small talk and a conversation you think back on days after.
And they’re especially important when you talk to introverts (like me).
I often don’t feel comfortable bringing up topics in conversations…even when I’m talking to my closest friends.
I want to share something that happened in my life or that’s bothering me badly, but I don’t know how to bring it up without feeling awkward or interrupting the flow of the conversation.
In my head I’m thinking: Just ask me the right question and I’ll tell you!
Asking better questions in conversations with your friends/siblings/parents/partner can deepen your relationships.
You might discover a new side in someone you’ve known for years.
And even become more popular. After all, we like people who are interested in us.
Job interviews
Questions are the means to determine if a candidate and an organization are the right fit for another.
Standard “What are your strengths/weaknesses?” aren’t going to cut it if you want to find the perfect person for the job.
It’s on the interviewer to lead the conversation and dig into the candidate’s motivations and skills.
As an interviewee, asking great questions is equally important. It’ll demonstrate that you’ve seriously considered the role.
One of my favorite questions to ask at the end of the interview is: Is there anything about my background or skills that makes you question whether I am a good fit for this role?
Marketing
As a copywriter, I learned that getting to know your audience insanely well is the key to effective marketing.
If you want to write copy that resonates, you have to uncover what’s inside their head.
In surveys and interviews, I’d ask customers about their challenges, goals, and why they’ve bought the product.
I also interview the business owner to uncover their story and what makes their product unique and different.
The right questions unlock insights that customers and business owners didn’t even know they had.
Journaling
A coach asks you questions to uncover the answer that’s already within you.
What if you could be your own coach?
That’s what journaling does for you!
The right prompt can help you reflect, work through roadblocks, and open up new answers.
I’ve found that journaling in the morning is one of the best ways to start the day.
If you want fresh questions in your inbox, Chris Harry sends Journal Prompts on the regular.
How to get better at asking questions
Easy! Borrow great questions from others. Imitate, then innovate (H/T David Perell).
Whenever I come across a powerful question, I save it immediately in my Second Brain and pull it out when needed.
Here’s a glimpse into my repository, categorized by what objective you want to achieve.
If you (or someone you’re talking to) feels stuck…
- Is that so? (to challenge a belief)
- Can this situation be seen in a different way?
- What answer am I missing because it seems too stupid?
- If your life was a movie, what would the audience be yelling at you to do?
- How am I making things more complex than they need to be?
- What would the you in 10 years’ time advise you to do now?
- What keeps you up at night?
If you want to expand your horizon…
- What would I work on if money didn’t matter?
- If you could be paid to do absolutely anything on earth, what would you do for a living?
- What am I holding back on?
- What would I do with my life if I could start all over again?
- What is something that I want to do that scares me?
If you want to dig deeper…
- What’s that like for you?
- How did it feel like?
- Tell me more about that! (Not a question, but still a powerful prompt to get someone to keep talking.)
If you want to reflect and draw out the lessons learned…
- What advice would you give to your 18-year-old self?
- What book has had a profound impact on my life?
- What is a mistake you seem to repeat each year?
- What did you learn this year about the world?
If you want to assess your own path…
- Am I living intentionally?
- What do I need to let go of?
- Who am I trying to please?
- What activities do I miss when they are not a part of my day?
- If you keep living the way you are, what will your life look like in 20 years?
- What do I dislike but know is good for me?
If you want to feel happier in the moment…
- Who are you grateful for?
- What is good enough for me?
- Who could I reach out to provide help with today?
- What was the highlight of your day/week/month/year?
- What makes you happiest in your life?
If you want to see your progress…
- What have you stopped caring about this year?
- What have I enjoyed learning about recently?
- What have you gotten better at this year?
Pheww…That’s a lot of questions!
What if you could only remember one?
Well, here’s the most important question you can ask to unlock whatever you’re stuck with:
Why?
Simple, yet powerful.
Now, I’m curious to know…
