I Learned This Long Before I Became a Parent

When I was younger, I read Dale Carnegie's How to Win Friends and Influence People.

One of the ideas that stuck with me was the importance of showing genuine interest in other people.

Ask questions. Let people talk about themselves. Be interested in what they have to say.

People appreciate being heard, and that interest can help build relationships.

I remember reading that section and thinking:

Hey, I do that.

I'd already had several experiences where someone would tell me, seemingly out of nowhere, that I asked really good questions.

I always appreciated those comments.

But reading Carnegie's book helped me recognize that something I'd been doing naturally was actually a valuable interpersonal skill.

I wasn't asking questions because I'd memorized some clever conversation technique.

I was interested.

I wanted to know more about the person I was talking to.

And when they answered one question, their answer usually gave me something else to be curious about.

So when my son asked what made my day good, I recognized a little of that same behavior.

He wasn't just going through the motions of asking Dad about work.

He was interested in the answer.

​That's what made me smile.

A Good Question Is Only the Beginning

Think about a typical conversation with your teenager.

"How was school?"

"Fine."

Conversation over.

Technically, you've asked a question, and they've answered it.

But how much have you actually learned?

Not much.

Now, sometimes that's perfectly reasonable. Maybe nothing particularly interesting happened at school. Maybe your teenager doesn't feel like talking about it.

Not every conversation needs to turn into a profound exploration of their inner world.

But if your goal is to understand your kid a little better, accepting that first answer isn't always going to get you very far.

I've never been particularly good at stopping at "fine."

I might ask:

"Did anything make you laugh today?"

"Did anything make you mad?"

"Did anything interesting happen?"

I'm not necessarily looking for some deep revelation.

I'm looking for a thread.

Something we can follow.

Maybe someone did something ridiculous in class.

Maybe a teacher said something that annoyed him.

Maybe he learned something interesting.

Now we have somewhere to go.

And often, the follow-up question is what turns a routine exchange into an actual conversation.

The Art of Following the Thread

I remember meeting a girl when I was younger who mentioned that she loved to travel.

There were plenty of obvious questions I could have asked.

"Where have you been?"

"What's your favorite place?"

Nothing wrong with either of those.

But instead, I asked:

"Where's the next place you want to visit?"

She thought about it and gave me an answer.

Then I asked:

"What excites you about that country?"

And the conversation continued from there.

I wasn't working through a prepared list of questions.

I was following what she said.

Her answer gave me something new to be interested in.

That's what I think makes a good conversation.

You don't necessarily know where it's going when it starts.

You ask something. You listen. Something in the answer catches your attention, so you ask about that.

Then you follow the next thread.

It's much easier to do when you're genuinely interested in the person you're talking to.

And it's a skill I think our kids can benefit from developing.

Not just because it helps them have better conversations with us.

Because they're going to spend their entire lives interacting with other people.

Friends. Teachers. Coworkers. Employers. Eventually, perhaps, their own children.

Knowing how to take an interest in someone else is a pretty valuable skill to have.

Follow-Up Questions Make Us Think More Deeply

There's another side to this that originally motivated me to create Food For Thought.

Follow-up questions don't just help us connect with people.

They can help us examine our own thinking.

Imagine asking your teenager:

"Do you think it's ever okay to lie?"

They answer:

"Yeah, sometimes."

You could accept that answer and move on to the next question.

But what have you learned?

You know their position, at least in a very general sense.

You don't know why they believe it.

You don't know what exceptions they're imagining.

You don't know whether they've thought about the consequences.

Now imagine asking:

"When do you think it's okay?"

"What if the lie ends up hurting someone?"

"Does it matter who you're lying to?"

"What if telling the truth would hurt someone's feelings?"

Suddenly, they're doing more than stating an opinion.

They're exploring it.

They might discover an exception they hadn't considered.

They might realize that their original answer was too broad.

They might even change their mind.

Or they might become more confident in their original position because they've actually thought through the reasons behind it.

Any of those outcomes can be valuable.

The goal isn't necessarily to arrive at the answer I would have given.

It's to practice examining an idea rather than simply declaring it.

That's why follow-up questions became such an important part of Food For Thought.

The initial question gives everyone something to talk about.

The follow-ups help us discover what's underneath the answers.

They're Also a Pretty Good Way to Sniff Out Nonsense

I've always been skeptical by nature.

When someone tells me something that doesn't quite make sense, I tend to ask questions.

Not necessarily because I think they're lying.

I want to understand what they're saying and whether their explanation holds up.

And sometimes, a very simple follow-up question reveals quite a bit.

Imagine someone confidently declares:

"Everyone knows that's true."

You ask:

"How do we know?"

Or:

"Where did you hear that?"

Or simply:

"Why do you think so?"

Sometimes they have a thoughtful explanation.

Great. Now you understand their reasoning.

Other times, they don't have much of an explanation at all.

Maybe they're repeating something they heard.

Maybe they've never really examined the claim.

Maybe they're more confident in the statement than the evidence warrants.

Confidence and understanding aren't the same thing.

Of course, someone struggling to explain an idea doesn't automatically mean they're wrong. They may simply have trouble putting their thoughts into words.

And someone who gives a polished explanation isn't automatically right.

But follow-up questions give us a way to look beyond the initial claim.

They help us examine the reasoning, evidence, and assumptions underneath it.

That's an important habit for kids growing up surrounded by confident opinions, persuasive messages, and increasingly sophisticated AI-generated answers.

Sometimes all it takes is one simple question:

"What makes you think that?"

Curiosity and Cross-Examination Are Not the Same Thing

There's an important distinction here.

Follow-up questions aren't automatically helpful just because they're questions.

I could ask my son:

"Why do you think that?"

because I'm genuinely interested in understanding his perspective.

Or I could ask exactly the same question because I'm preparing to dismantle his argument and demonstrate how wrong he is.

Same words.

Very different conversation.

I think the difference often comes down to why we're asking.

Are we trying to understand?

Or are we trying to win?

I've talked about this in another article as Probe, Don't Pounce.

Sometimes parents ask questions when what we really want is confirmation that our kids agree with us.

And when they don't give us the answer we were hoping for, we jump in to correct them.

That's not much different from a lecture with a question mark attached.

Genuine curiosity requires us to be interested in the answer, even when it's not the answer we expected.

It also requires us to pay attention to the person answering.

If a question strikes a nerve, it's usually pretty obvious.

Maybe they get uncomfortable.

Maybe their answers become shorter.

Maybe they simply don't want to discuss that particular topic.

That's okay.

We can move on.

It doesn't mean the subject can never come up again. Maybe it's worth revisiting another day, under different circumstances.

But there's no prize for extracting one more answer from someone who clearly doesn't want to continue.

The point is to understand the person, not interrogate them.

The First Question Still Matters

I don't want to suggest that any question will do as long as you have a good follow-up ready.

The initial question matters, too.

"How was school?" might lead somewhere interesting.

But sometimes school was just school.

Nothing particularly funny happened. Nothing upset your teenager. There isn't much to explore.

You can keep asking follow-ups, but eventually you're trying to squeeze an interesting conversation out of a subject that may not have much to offer that day.

That's one reason I started developing more interesting questions for our family dinners. It's also why the Follow-Up Habit became an important part of the Food For Thought Framework.

Instead of relying on the same routine questions every night, I wanted to introduce ideas that gave everyone something to think about.

Questions that invited opinions.

Questions that created disagreement.

Questions that made us laugh.

Questions where there wasn't necessarily one correct answer.

But even with a great starting question, there's still a difference between asking it and having a genuinely interesting conversation.

You have to listen to the answers.

You have to notice what someone says that deserves a little more exploration.

You have to be willing to follow the conversation somewhere you hadn't anticipated.

The initial question opens the door.

The follow-ups determine how far you go.

I'm Starting to See My Boys Do It, Too

One of the things I've enjoyed watching since we started having more intentional conversations is how my boys interact with each other.

They ask each other questions.

They challenge one another's answers.

They want to know why the other person thinks something.

Are they particularly skilled interviewers?

I don't know.

And frankly, I don't think that's especially important right now.

What matters to me is that they're asking.

They're developing the instinct to hear an answer and recognize that there might be something more worth understanding.

Sometimes that means asking their brother to explain an opinion.

Sometimes it means questioning a claim that doesn't quite add up.

And sometimes it means sitting down to dinner and asking Dad how work was.

Then following up with:

"What made it good?"

I don't know how much of that comes from Food For Thought, how much comes from their personalities, or how much comes from simply growing up.

I'm not going to pretend I can separate those things.

But I love seeing it happen.

Because it suggests that the curiosity I wanted to encourage isn't limited to the moments when I pull out a conversation card.

It's starting to show up in ordinary conversations.

And that's what I hoped for all along.

One Simple Way to Practice

If you want to encourage better conversations with your kids, here's something simple to try.

The next time someone gives you an answer, resist the urge to immediately move on to the next question.

Instead, look for one thing in their answer that makes you curious.

Maybe they say they had a good day.

"What made it good?"

Maybe they say they don't like a particular class.

"What don't you like about it?"

Maybe they express a strong opinion.

"What makes you think that?"

Maybe they tell you about something they're excited about.

"What are you most looking forward to?"

You don't need an elaborate conversation strategy.

You don't need to turn every answer into a philosophical debate.

Just find one thread and follow it.

And when your child asks you a question, give them something worth following, too.

Instead of automatically answering "good" when they ask about your day, tell them a little about what happened.

Give them a glimpse into your world.

You might be surprised where the conversation goes.

The Question That Made Me Smile

When I first started asking my boys more interesting questions at dinner, I was trying to help them become better thinkers.

I wanted them to develop opinions, explain their reasoning, challenge assumptions, and become more comfortable exploring unfamiliar ideas.

I still want all of that.

But something else has happened along the way.

I'm watching them become more curious about other people.

And I think back to that book I read when I was younger.

I remember how good it felt when people told me I asked thoughtful questions.

How satisfying it was to recognize that genuine interest in others was something valuable.

Now I'm seeing a little of that in my son.

He asked how my day was.

I said it was good.

And instead of moving on, he wanted to know why.

It wasn't a particularly profound exchange.

We didn't solve a problem or debate some complicated idea.

We just talked about my day.

But I walked away smiling.

Because the best outcome of asking our kids better questions might be that one day, they start asking better questions themselves.

And sometimes, the most important question is simply:

"What made it good?"