Frank Sesno | The Power of Questions (Episode 651)

Frank Sesno (@franksesno) is an award-winning journalist with more than 30 years of experience, and the author of Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change.

“If you want to confront a problem, you have to go looking for it — and cannot avert your eyes when you find it.” -Frank Sesno

The Cheat Sheet:

  • Knowing how to ask good questions is a springboard to understanding others and making better connections.
  • Why we should think of our line of questioning as a diet — and ensure that it’s balanced.
  • Which of eleven categories of questions we should ask (e.g. diagnostic, empathetic, strategic, creative, etc.) when we seek a certain outcome.
  • How to get through to people who don’t want to connect — and build trust and rapport in the process.
  • What it means to maintain intimate distance when questioning someone — and how it allows us to really listen to what they’re trying to tell us.
  • And so much more…


(Direct Download Episode Here)

There are countless courses and books that teach us how to speak — but not many that teach us how to listen to others and ask questions effectively to reach a desired outcome.

To remedy this, we’re joined by Frank Sesno, former CNN correspondent, director of the School of Media and Public Affairs at The George Washington University, and author of Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change. Listen, learn, and enjoy!

Please Scroll down for Full Show Notes and Featured Resources!

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More About This Show

You don’t need to be a therapist, lawyer, police officer, or journalist to benefit from knowing how to ask good questions. After more than 30 years of interviewing people from all walks of life — including world leaders from Ronald Reagan to Yasser Arafat — Frank Sesno shares what he knows in his new book Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change.

“I would always go into these interviews curious,” says Frank. “I would always go into these interviews knowing that I wanted to get an answer to something, but I didn’t really have what I call a question strategy. I would block by themes. I would think about how I posed a question because I knew someone would try to duck it or something. But I thought and I wondered, ‘Is there something more to that?'”

He concedes that most of us are crummy at asking questions because we simply don’t know how. It’s not something that’s taught in schools. Even in his own experience as a journalist whose job it is to ask questions, it took him years to really feel like he was doing it effectively.

One of the first things he would like to change is the Q&A (question and answer) format to Q&L (question and listen).

“[Q&A] implies that I’m going to ask a question and then you’re going to give me an answer — and then I can move on. But if it’s really Q&L — I’m going to ask a question and I’m really going to listen. I want to know what you’re going to say. I’m going to use that as a springboard to deeper understanding. To a deeper knowledge. To a deeper purpose. I’ve got these eleven categories of questions and each connects with a very specific outcome; that listening is critical, and I think the best leaders are the best questioners. The best interviewers are the best listeners. The best therapists are both!”

Categories of Questions

Frank details eleven categories of questions in Ask More; here are six of them.

Diagnostic: These are the questions we ask when something’s gone wrong so we can figure out how to fix it. “We’re opening our minds, we recognize there’s a problem, we understand something needs to be done about it, but we don’t know what,” says Frank. These are the questions a doctor will ask when trying to cure what ails you, or a mechanic trying to pinpoint exactly why your car only makes that curious rattling noise whenever it rains on a Wednesday. Frank calls this “the ground floor of questioning.”

Strategic: These are the big picture questions that help us look over the horizon. “They’re meant to challenge yourself and those around you — and conventional wisdom,” says Frank. As an example, he lays out the eight questions Colin Powell said must be answered affirmatively before military action is taken by the United States (and what happened when we ignored them).

Empathetic: These questions seek to uncover the feelings and emotions that motivate a subject and view the world in their shoes. Frank brings up NPR’s Terry Gross as a host who expertly uses this category of questioning to get to the essence of artists, musicians, authors, and other creative people.

Creative: These are the questions that prompt the subject to tap into their creativity and share their own unique ideas. When Hollywood showrunner Ed Bernero had trouble capturing the right shot — a dramatic scene in which two characters visually connected for the first time when one removed his sunglasses — he asked the actor when he felt the sunglasses should come off. It challenged the actor to think of the scene differently, and they got the shot right on the very next take.

Bridge-Building: When someone doesn’t really want to open up to us (like a hostage-taker, a would-be assassin, or a teenager), we need to establish trust and rapport — build bridges with gentle, softball questions that give the subject an opportunity to open up on their own terms and us the opportunity to listen. These “questions without question marks” are designed to comfort, not provoke.

Confrontational: In contrast to bridge-building, confrontational questions — like the ones dominating the media these days — are meant to provoke answers for the official record rather than comfort or build trust with the subject.

Listen to this episode of The Art of Charm in its entirety to learn more about why we better remember what we say than what we hear, how desired outcomes guide us toward the category of question we should be asking, why empathetic relationships pay dividends in virtually every case, the benefits of developing intimate distance when questioning someone, a few practical exercises that help us get into someone else’s head and try to understand the world from their perspective, the Commander’s Rule, how to get through to people who don’t want to connect — and build trust and rapport in the process, and lots more.


If you enjoyed this session with Frank Sesno, let him know by clicking on the link below and sending him a quick shout out at Twitter:

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Jordan Harbinger - author of 952 posts on The Art of Charm

Jordan Harbinger has spent several years abroad in Europe and the developing world, including South America, Eastern Europe, and the Middle East, and speaks several languages. He has also worked for various governments and NGOs overseas, traveled through war zones, and been kidnapped -- twice. He’ll tell you the only reason he’s still alive and kicking is because of his ability to talk his way into (and out of) just about any type of situation. Here at The Art of Charm, Jordan shares that experience, and the system borne as a result, with students and clients.


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