How to Talk to Anyone

Oct 16, 2023

One person who is a savant of asking questions (Doug), and another who is mediocre at answering them (me).

Asking better questions can improve your conversations, make you more likable, and increase your success in business, relationships, and life.

You’ll learn: The power of asking questions and four ways to ask better questions.

Quick Housekeeping:

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How’s this month’s Burn the Ships going? My legs are feeling like pistons.

Scarcity Brain is out now wherever books are sold.

I’ve done a lot of interviews about my books. I’ve spent even more time on the other side, where I’m the journalist interviewing someone for my books and stories.

So I think a lot about questions. The questions I’m going to get in interviews, the questions I’m going to ask in interviews.

Many interviewers approach questions like a checklist—ask and move on. But the best interviewers bake them into a free-flowing, spontaneous conversation. And yet, at the end, the interviewer has gotten the interviewee to say everything they want him or her to say far better than he or she could have imagined.

I recently had the opportunity to talk about my new book, Scarcity Brain, with a person I consider a genius at interviewing.

I appeared on NPR’s RadioWest, hosted by Doug Fabrizio.

Growing up in the Rocky Mountain West, RadioWest has always been one of my favorite shows. It’s an hour-long interview show on Salt Lake City’s NPR affiliate that covers a wide range of fascinating topics. For example, issues relevant to the West, culture, science, history, and (insert anything). Fabrizio has interviewed subjects like the Dalai Lama and Desmond Tutu.

Fabrizio is one of the best, if not the best, interviewer I’ve encountered.

He’s like a chess grandmaster of asking questions—he knows exactly how to get you to say things better than you otherwise would, and he can see downfield better than any interviewer I’ve encountered. He’ll ask you a question five minutes into the interview that sets him up to ask another question 40 minutes later. It’s wild.

Here’s the episode:

We can all learn something from Fabrizio.

To understand why he’s so good, we need to understand something about human conversation and asking questions, which is this: We could all be better at it.

Today’s post covers:

Why asking better questions can get you ahead in life.
Four tactics to ask better questions.

Let’s roll …

The case for questions

In short

Research shows that people who are better at asking questions are more likable and have more success in business, relationships, and life.

The details

The Harvard researcher Alison Wood Brooks has spent a career asking questions about questions. She studies the psychology of conversations.

Her big finding is that people don’t ask enough questions. And this applies to all of our conversations—the ones big and small that we have with colleagues, friends, family, and even adversaries.

As she wrote in the Harvard Business Review:

Among the most common complaints people make after having a conversation, such as an interview, a first date, or a work meeting, is “I wish [s/he] had asked me more questions” and “I can’t believe [s/he] didn’t ask me any questions.”

There are many reasons we aren’t good at asking questions. For example:

We may spend too much time talking about ourselves.
We may think we already know the answer.
We may not care.
We fear we’ll ask a “dumb question.”

Those are all factors. But Brooks thinks the main reason is that most people don’t quite understand just how powerful questions can be.

Asking Questions Increases Your Likability

In 2017, Brooks and four colleagues from Harvard set up a series of experiments to investigate how asking questions impacts how others perceive us.

Like, does asking a lot of questions make you seem nosey or endearing?

Past studies had suggested the latter. For example, one study found that people who draw more information out of others are better liked. Another study found that patients gave better ratings to doctors who asked more questions.

In the first experiment, Brooks and the other Harvard scientists put 430 people into groups of two, so there were 215 pairs of people. They randomly assigned one person in each pair to ask their partner either a lot of questions or just a few questions.

In the second experiment, outside participants analyzed transcripts of the conversations the 215 pairs of people had in experiment one.

In the third, they looked at speed dating success rates. They analyzed transcripts and results from a speed dating session involving 110 people.

The findings:

In study one, the people who asked more questions were rated more likable because they were seen as more responsive.
In study two, the people who answered the most questions were rated highest. The scientists explained, “when you are participating in a conversation, you like people who ask more questions. But when you are observing a conversation, you like people who answer more questions. These results suggest that people like question-askers when the questions are directed toward them personally.”
In study three, the people who asked more follow-up questions got more second dates.

Other research suggests that people who ask more good questions are better able to get jobs, secure investment funding, sell you something, get ahead in the office, and have better relationships.

Ok. Great. But how do you ask good questions?

The art of asking good questions

In short

Have questions ready for common encounters, ask follow-up and open-ended questions, and change topics frequently.

The details

When I started analyzing the research on questions, I realized that Fabrizio was leveraging all the techniques Brooks and other researchers say works to:

Make you more likable.
Get great responses from the person you’re speaking with.

Here’s what you should do:

1. Do your homework

Fabrizio had an iPad in front of him during the interview. It contained a document of notes and quotes from Scarcity Brain. He’d occasionally eye it to read me a line from the book or pull a specific stat I’d referenced.

Everyday conversation is obviously different than an NPR interview. You won’t have talking points.

But a little homework goes a long way.

Brooks found that when people went into everyday conversations with “even just two or three bullet points of ideas” of what to talk about, the conversations were much more enjoyable and productive.

The takeaway: Keep a sort of “running list” of topics you can chat about with people you’re likely to run into. For example, co-workers, neighbors, friends at a party, and more.

This also works for meetings. Brooks’ research found that meetings with an agenda were rated as more enjoyable compared to those that didn’t have an agenda.

2. Ask follow-up questions

Whereas a novice interviewer asks questions seemingly at random, Fabrizio laid questions out like dominos—one question led to another led to another. Each took a slight turn or went deeper—like peeling an onion—which got better information out of me.

If you take one thing from this piece, it should be this: Ask more follow-up questions.

The researchers found that follow-up questions are the most powerful questions we can ask. Brooks wrote:

(F)ollow-up questions … signal to your conversation partner that you are listening, care, and want to know more. People interacting with a partner who asks lots of follow-up questions tend to feel respected and heard.

But you have to ask them right. The researchers wrote, “Follow-up questions are only possible if an individual asks an original question, listens to the answer, and probes for more information (i.e., understands the answer, validates the partner, and cares to know more—the definition of responsiveness).”

The worst conversationalists, on the other hand, don’t ask follow-up questions. They may even ask their first question in hopes that it will then be directed back to them—so they can in turn blabber on about themselves. For example, they ask a neighbor how their kids are doing so they hopefully brag about how their own kid got into Yale.

3. Switch topics frequently

Asking follow-up questions is a must. But a handful go a long way.

Eventually, your follow-up questions will run their course, and the topic will begin to get stale.

When we experience a lull in conversation, we often feel awkward changing the topic. Don’t.

Brooks’ research discovered that switching topics frequently leads to better conversation. It keeps both parties engaged.

Fabrizio didn’t linger. Once he’d asked a series of questions that got me to say what he knew his listeners would find useful, he pivoted fast and hard to a new topic.

This is something Joe Rogan is also excellent at. Here’s a hilarious example.

4. Ask open-ended questions

Fabrizio’s questions sometimes didn’t feel like questioning.

Here’s what Fabrizio frequently did: He’d repeat a statement I made or talk briefly about something I wrote in the book.

Then, instead of asking a pointed question, he’d quickly say, “… so tell me more about that.” It was a sort of statement-question hybrid.

Brooks wrote, “Open-ended questions … can be particularly useful in uncovering information or learning something new. Indeed, they are wellsprings of innovation—which is often the result of finding the hidden, unexpected answer that no one has thought of before.”

Fabrizio’s open-ended questions worked because instead of directing me into a specific lane with a specific question, he was just sort of winding me up and letting me go in the direction I felt was most important. I’d find myself going into a deeper answer that was richer in context than I’d given in my previous interviews.

He didn’t use this technique for every question — he seemed to use it in places where a more free-form answer, driven by my own voice and thought patterns, would better serve the listener.

In chatting about this, another friend told me he had an old boss who would say “say more” anytime someone would assert a new idea in a meeting. And it always got the person talking and laying out her thought process.

After my first RadioWest interview in 2021, I stole this tactic from Fabrizio. For example, I used it a bunch at a neighborhood party. “Oh, you (insert something the person just said). That’s interesting. Tell me more about that…”

Try all these tactics yourself, then tell us more about that experience in the comments.

Have fun, don’t die, ask questions.

-Michael

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How to Talk to Anyone

Asking better questions can improve your conversations, make you more likable, and increase your success in business, relationships, and life.

You’ll learn: The power of asking questions and four ways to ask better questions.

Quick Housekeeping:

The case for questions

In short

The details

Asking Questions Increases Your Likability

The art of asking good questions

In short

The details

1. Do your homework

2. Ask follow-up questions

3. Switch topics frequently

4. Ask open-ended questions

Sponsored by Maui Nui Venison

Sponsored by Momentous​

Sponsored by GORUCK​

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