Asking Questions with Frank Sesno

By Dr. Wanda Wallace

Frank Sesno

I recently had the great opportunity to be the one asking questions of a great interviewer, Frank Sesno. I happen to believe leading is really about asking the right question at the right time. Asking questions is how you get your team to think. It is at the heart of delegating and coaching. It’s an incredibly powerful way to motivate. It creates breakthroughs. You cannot lead well without asking good questions.


We don’t spend nearly enough time thinking about what questions to ask. For decades we saw Frank Sesno on TV asking questions of some of the world’s greatest leaders including US Presidents, Nobel prize winners, renowned economists, CEOs and other world leaders. If anyone knows how to ask questions, it’s Frank. He has also written a book about that very subject, called Ask More.


Frank says great leaders are great listeners and great questioners. Nonetheless, no one teaches us how to listen and how to ask questions.


Here are the top takeaways from my interview of him:


Better listening:

  1. Listening drives understanding and engagement. First secret to being a better listener is to ask yourself what kind of listener you are. Am I attentive? Do I listen for data or numbers? Or do I listen for stories? Am I easily distracted? Do I comfortably make eye contact? Eye contact and body language are part of listening.

  2. Listen for a key mood or emotion or a data point to ask more about. That kind of listening drives both understanding and engagement.

  3. Quote people back to them: you are pursuing a deeper level of inquiry. It’s a fundamental and profound level of respect.

  4. Here’s an exercise for better listening: Interview someone for 20 mins on any topic, don’t use the word “I” or “me” once. Force yourself to be focused exclusively on the other person.


Better questioning:

Do some groundwork. Know something about the other person before you sit down. Start with comfortable, non-threatening questions that reflect some knowledge and curiosity. For example, ask: “How did your [current project etc] get started?”

  1. Strategic questions prompt looking over the horizon to see upsides and downsides. These questions look at the longer term. What are we not thinking about? What could trip us up?

  2. Creativity questions or time travel questions. Pose a big hypothetical question – great leaders do this. He gives the example “It’s five years from now, you have the number one program globally, what are you doing?”

  3. Empathetic questions seek to explore what the other person is seeing, thinking, experiencing and feeling. These are the most profound questions. When you do them well, you take a relationship to a new level. For example, Frank asks his neighbor about his wife, who was not well and he was reticent. Then he asked: “How’s your head?” and he started talking about what he was going through.

  4. Bridge building questions help you manage hostile situations and establish rapport. You just want to get the other person talking, to build rapport.

  5. Diagnostic questions lead to exploration of what is going on – they are fact-oriented.

  6. Questions without question marks draw people out. They are designed to get comments. They are non-threatening.

  7. Open ended questions – “How are you feeling today? How’s work?” – allow the interviewee to set the agenda. They help you build rapport. Invite someone to open up and explain what’s going on. This is much better than confronting someone.

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