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Entertaining questions can turn your boring dinner into a theater of wit and ideas and provocative conversation. Be your own talk show host. In Chapter 11, you’ll learn ways to draw out memorable dialogue and keep the conversation moving, using ideas from one of the most engaging and curious people I’ve ever met. Invite Socrates to supper—if you dare. Serve this recipe at your next meal and you’ll have everyone talking.

Finally, what does it all mean? Chapter 12 asks legacy questions that reveal your life story and craft an uplifting narrative of accomplishment and gratitude. These questions from the edge will help you step back and take stock of what you have done and the people you have known. Here, you meet the rabbi who gets asked about God’s intentions and read the curious words of a twenty-five-year-old who questions her future. I introduce you to one of the bravest people I’ve ever met.

At the back of the book, I provide a guide that summarizes the question categories and their component parts, with a few ideas you can try to become a more effective questioner.

This book is not prescriptive. It doesn’t tell you how to ask in every situation. But it does offer examples that demonstrate the power of questions and the benefits of deep, nuanced listening. The categories reflect a range of curiosity. As you will see, each enlists different asking skills in search of distinct outcomes. Humans are built to be curious, that much is in our DNA. This book illustrates how some of the most successful people have honed their curiosity and developed an ability to ask and to listen that has served them extraordinarily well.

Our questions reflect who we are, where we go, and how we connect. They help us learn and they help us lead because effective questioning marshals support and enlists others to join. After all, asking people to solve a problem or come up with a new idea turns the responsibility over to them. It says, “You’re smart, you’re valuable, you know what you’re doing—what would you do about this problem?”

My aim in writing this book is to show you the power of questions and how it can be applied effectively and freely. Enjoy and learn from the exceptional questioners you meet here.

And then, ask more.

CHAPTER 2

SOMETHING’S NOT RIGHT

Diagnostic Questions

THERE ARE DAYS REPORTERS DREAD, but they come with the territory. A rumor, a phone call, and then a pit in your stomach, no matter how seasoned you are. A passenger jet has disappeared. Air traffic controllers lost contact with the crew. The plane vanished from radar screens. Airline and aviation authorities are racing to figure out what’s gone wrong. So are we.

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In the newsroom, we are scrambling, preparing to go on the air with the story. What exactly will we say? What do we know? Where will definitive information come from? And when? We deploy reporters. We’re all over the FAA and the FBI and the airline. We’re using new flight-tracking apps. We’re working sources, contacting anyone who might have heard anything. We brace ourselves for the most perilous time in live TV—that period after something happens but before anyone in authority can confirm what actually happened. If we get it wrong, we spread misinformation, scare innocent people, and may even affect the actions of first responders. We tarnish our credibility and outrage our viewers.

A lot of our work will unfold in real time, right in front of the audience as we ask the questions that track what’s going on and what went wrong.

What airline and flight number?

How many were on board?

When and where did it disappear?

These are the first harried questions we ask in those early, frenzied moments—the who, what, when, and where questions of a breaking story.

Was there mechanical trouble?

Was anyone on a watch list?

What did witnesses see?

We need to know what happened and what went wrong. Until those questions are answered, the rest of the story will remain a mystery.

What’s the Problem?

Fortunately, most planes land safely, and life does not unfold in a TV newsroom. But our need to identify problems so we can act on them is an ingredient of daily existence. The reporter’s rapid instinct, like the clinician’s expertise in connecting symptoms to illness, is a skill you can develop and incorporate into your questioning to become better, faster, and more precise when you have to diagnose a problem. Whether it’s a life-threatening condition or a leak in the basement, a pain in the shoulder or an issue at work, you have to figure out what the problem is before you can do anything about it. You have to ask the right questions, accept bad news, and roll with the unexpected to get the answers you need in a timely fashion.

Since human beings first stepped out of our caves, we realized that if we were to survive, we had to identify peril and then avoid or overcome it. That still holds true, although these days, with Wi-Fi in our caves, we often call the experts. Still, we can hone our skills so that our diagnostic questioning is sharper. We can be better questioners of the doctor or the mechanic or the boss when they think they have the answers to our problems. We can challenge our political leaders when they speak with certainty about a simple problem and an easy solution.

Diagnostic questioning is the ground floor of inquiry. It is the foundation on which other questions are built. It pinpoints a problem and provides a roadmap for a response.

What’s wrong?

How do we know?

What are we not seeing?

What should we do?

Diagnostic questioning identifies a problem then burrows down to its roots, especially when those roots are not instantly obvious.

Your tooth is killing you. You go to the dentist. She asks where it hurts, when it hurts. When you chew? When you drink? She taps, pokes, and applies cold water till you leap out of the chair. Oh sorry, did that hurt? Yes, you grunt, through the junkyard that litters your palate. She says the problem is this other tooth. You’re feeling “referred pain.” An X-ray confirms it. A filling fixes it.

Your company recently introduced a new product. It isn’t selling. Everyone thinks it’s a flop. You’re not so sure, so you hire some consultants to figure out what’s going on. They conduct focus groups. They ask lots of questions about this product and similar ones. They discover that people actually like it and several of them say they’d buy it—if they knew about it. Turns out the marketing was the problem.

Diagnostic questions, whether they are directed at a company or a cavity, progress systematically to describe the problem and identify it.

Connect symptoms and specifics. Start with big, broad, what’s-the-problem questions and then narrow down, zero in. Get past the generic to identify the symptoms and describe related observations in detail.

Ask for the bad. Don’t duck the issues or avert your eyes. Ask direct questions in search of direct answers. It may get ugly, but if you want to fix a problem, you have to acknowledge it to deal with it.

Study history. Look back. Ask about similar experiences, events, and patterns. They provide a baseline. Look for similarities to other situations.

Ask again. The mere existence of a problem means there is something unknown or unanticipated. To be sure you’re on solid ground, ask several times and several sources. Confirm and corroborate.

Challenge the expert. We rely on experts to diagnose our disease. But that doesn’t mean they’re right or that they’re off the hook in explaining what’s going on. Before you accept a diagnosis, ask what it is, what it means, and where it’s coming from. And reserve the right to get another opinion.