How To Ask Better Questions

Child Asking Question
Kids are great at asking questions. Why do we lose that as we grow older?

Think back to when you were a kid.

Or think of a time when you had kids or were around kids.

I’m talking from about three years old to about 10 years old.

What do many kids at this age have in common?

They ask a lot of questions.

Here’s a typical interaction between a parent and child at the grocery store:

Child: What are those?

Mom: Eggs.

C: What are eggs?

M: We eat them for breakfast.

C: Why?

M: Because they’re good for you.

C: Why?

M: Because they have healthy vitamins and minerals.

C: What are vitamins and minerals…

Have you been there?

Sure, it can get annoying, but those kids are in a period of their lives when they’re really looking to soak in as much information as possible.

Adults sometimes like to say that kids today don’t want to learn anything. They just want to play video games on their phones all day.

Well, when kids are young they’re very willing to learn. They’re probably more willing to learn than at any point in life.

Losing The Ability To Ask Questions

I don’t know why it happens, but it seems that as we get older we become afraid to ask questions.

It almost seems like we’re more likely to offer unsolicited advice when having a conversation with a friend. Wouldn’t a question be a better way to go? The friend probably doesn’t want your advice, but they would love if you asked questions and allowed them to share more detail.

I don’t know why adults lose the ability to ask questions, but whatever the reason, it’s beneficial to get back into the daily habit of asking more questions.

It’s a great way to learn and those that continuously learn throughout life seem to be more successful.

It’s good for life. It’s good for business.

But now the question is how you learn to ask better questions. Here are some tips I could find.

Tip #1. Ask More Questions

I’m a fan of quantity. I believe the theory and the stories and studies seem to prove that quantity builds quality. I listen to country music and a big artist even today is John Rich of Big & Rich. He was originally in the band Lonestar in the ’90s before he kind of kicked around a bit and then hit it big as a songwriter and then Big & Rich broke.

Somewhere around that songwriting/B&R period Rich gave an interview and made the comment that he had written 800 songs since coming to Nashville.

800 songs…

That’s pretty incredible to me. You have to be pretty dedicated to just churning out songs to make it to that number.

I’m sure John was worried about quality, but he knew that he for him to get good at songwriting that he had to learn the craft. He had to write a lot and write a lot of bad songs in order to write good songs.

The same is true in what I would say is most if not all areas of life. If you want to improve you need to do something over and over.

The same is true with asking questions.

Get in the habit of asking more questions.

But it does help to have a little direction so let’s look at some additional tips.

Tip #2. Remove Judgment

Do you like when people judge your actions, thoughts, beliefs?

I know that it bothers me. I’ve always had this tendency to kind of shut my brain off when I feel like I’m being judged.

Now, on the other side of things I know that I have done and still do my fair share of judging. I try to stay away from it because I know how much it bothers me, but I’m still guilty of it.

On the road to asking better questions it’s important to remove judgment from the tone of your voice and from the questions you’re asking.

For example, the question Why did you do that? can come across in a couple of ways. It can be judgmental if you use one tone, but it can be sincere if you ask it in another tone.

It is about asking different questions, but it’s also about asking questions with the right tone. Removing judgment allows you to get better answers and have better conversations.

Tip #3. Get People Thinking Critically

Let’s say you’re talking with a mentor-type person. Maybe it’s a parent or grandparent. Maybe it’s someone you have admired in the business world.

They may want to help you out of the goodness of their heart, but you’re more likely to have an engaging relationship if you ask questions that makes them think critically.

You could start with a question like: What is a business deal that you’re proud of?

That’s a good start, but you can really take it to a new level if you ask: Why do you think that was such a success?

Maybe the person has thought about this question before. Maybe they haven’t. It gets them thinking about their own successes and experiences and they’re likely to open up to you and together you can kind of discover the really enlightening information.

Tip #4. Open-Ended

Closed questions can be good in certain occasions. Maybe something like: What’s your recommendation for buying a truck?

The person might say: I’d definitely recommend the Ford F-150.

That’s some good information, but you could perhaps get even better information with a second, open-ended question that asks:

Why would you recommend the F-150?

Why is a good way to go. How is another good way to get things going on an open-ended answer. What and Can may work in certain situations, but they open you up a bit for one-word answers.

Open-ended questions are tricky depending on the situation. I think of sportswriters and their dealings with players that have just lost games. Those situations are tough. The best reporters seem to be able to come in with the right asking tone and the right open-ended questions that lead to the best and most insightful answers.

Tip #5. Keep It Positive

I’m a big believer in keeping it positive. Studies show that employees benefit more from positive feedback than they do from negative feedback.

The same is true with asking questions. If you ask a question that makes the other person feel negative then you’re not likely to get a good response. The person will probably feel threatened, bad about themselves and the conversation probably won’t go anywhere.

This reminds me of the movie Apollo 13 when the NASA team leader back in Houston is getting a rundown of the status of the mission from his team. They’re telling him everything that’s wrong and finally he says:

What do we got on the spacecraft that’s good?

This mindset completely changed the outlook. It went from focusing on the negative to focusing on a way to solve a short-term problem and a way to get the crew home.

It’s a quick reaction to ask the question:

How could you make such a poor decision?

You could use the right tone, but it might be better to ask:

What can we do to improve for next time?


In my experience, the best leaders have always been ones that have asked questions. My first boss out of college was really a curious guy. He was always asking his team questions. And at that same company I interacted with the CEO a few times and he was another guy that was always asking questions. He asked business questions. He asked more personal questions and things like that. It was great and really revealing about the value of asking questions.

If you’re looking to get more out of your conversations then hopefully these tips will help you ask better questions. It starts with the right mindset and learning a few ways to switch things up a bit. From there, you can learn more about life and business.

And who doesn’t want that?

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