How to Ask Good Questions

One of my favorite life philosophies: “Everyone, everyone, has something of value to teach you. It’s just a matter of finding the keys to unlock it.”

I stand by this adamantly. It’s absolutely true. Everybody has something to share that’s of interest to you — an experience, a philosophy, a skillset, a recommendation, an entire paradigm.

Those keys I reference? They’re questions.

Asking good questions allows you to connect more deeply with people. It also allows you to glean valuable information. I approach interactions with the mentality that everyone has something valuable to teach me. All I have to do is identify where that value lies, and then figure out which questions unlock it.

Asking good questions isn’t just a skill. It’s an art form.

So — How Do You Ask Good Questions?

Step 1: Start by asking “why” — not vocally, but internally. Ask this question of every single thing you hear people say. Make it a habit. People’s sentences and phrases are the surface of a well that runs very deep. There are a myriad of suppositions, philosophies and experiences laying the foundation beneath it.

Asking questions helps you identify the depth beneath the sentence. Why did they do something? What thought process led them to make a certain decision? What underlying philosophy dictates the way they interact with the world?

Asking why becomes a habit. Once you’ve practiced enough, you no longer have to consciously ask why to every statement. Rather, you’ll begin to identify which questions will lead you most directly to the gold you’re looking for.

Step 2: Take notes. If you’re able, take physical notes; writing things down on paper keeps your head clear to identify more questions. Always listen fully to the people who are talking to you, to the best that you’re able.

If you can’t take physical notes (and in some contexts you can’t), then take mental notes of important points to come back to.

Step 3: Learn to recognize what people like to talk about. People love talking about their passions.

Step 4: Start somewhere. Figure out your in, and then slowly work the conversation until you land on the information you’re looking for. The most important step is to engage.


“When my daughter graduated homeschooled high school, I had a lot more free time to devote to my marketing research.”

Break this down. How old is your daughter now? How long ago did she graduate? Is she your only child? Why did you homeschool? Did you homeschool all the way through? What was your homeschooling philosophy? Did you homeschool other children? What’s she doing now? What kind of marketing research do you do? Did you do it while you were still homeschooling? Do you do it full-time now? If not, what else do you do? Why are you interested in marketing research? How are you applying it? Can I find examples of your marketing work anywhere?

These questions aren’t necessarily all relevant. Most of them likely aren’t even things you’ll ask, or care about. But if you make formulating questions a habit, you’ll come up with a few gems.

Learn How to Deliver

Even when you understand what makes a good question, sometimes the act of asking shuts people down. It’s intimidating to ask someone a question. You’re afraid of sounding stupid. You’re afraid of taking the leap to engage. What if you come across as being stupid, or naive? What if it’s a bad question? What if it’s a good question, but you sound inarticulate when you voice it?

These nerves make you more self-aware, and the self-awareness makes you stumble. It’s a vicious cycle. (As a side note, the best way to deal with stumbling is to laugh it off. Confidence covers most blunders. As Churchill said and the hipsters adopted, keep calm and carry on. People don’t scrutinize casual interactions nearly as much as we think they do. If you present confidence, people will read confidence — and confidence is impressive.)

A few good rules of thumb to keep in mind for question delivery:

  • Don’t overexplain. Keep it as simple and direct as possible.
  • In the vein of keeping it simple, don’t ask a conglomerate question, with too many pieces. Keep the points you want to get at punchy, and hit one per question.
  • Look for natural segues, and utilize whenever possible, but don’t be afraid to gracefully change the subject.
  • Act legitimately engaged — body language, eye contact, tone of voice, etc. The more engaged you are, the more likely someone is to want to take the time to divulge information.

Follow-Ups are Golden

The hardest part is the beginning — finding a starting question and opening up a dialogue. Once you’ve begun, continuation is easy. When listening to someone answer your question, follow the same methods above again. Take notes. Ask why. Formulate questions.

Follow-ups allow you to delve deeper into specific branches of a topic and hone in on the information you’re looking for. Usually they’re what uncover the real gold.

Leave a Reply