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ARMSTRONG: Yes.

Having gotten the fallen hero to acknowledge his guilt, Oprah then took him through an extended conversation on his motivations and the consequences of his actions, along with the prevalence of doping in the sport he betrayed.

Armstrong may have hoped the exchange would provide some made-for-television redemption. It did not. But the interview clearly showed how effective yes-or-no, guilt-or-innocence questioning can be when the case is airtight, the prosecutor is disciplined, and the questions are precise and based on information you can bank on.

“It’s an art, it’s psychology, it’s brains, it’s communication, and it’s theater,” Olson counseled. For the record.

Blunt Force

It’s not often you get a Lance Armstrong confessing to his sins. Donald Trump certainly didn’t recant when Jorge Ramos pressed him. Mary Landrieu wouldn’t assign fault, no matter how many times Anderson Cooper asked. I can’t think of a single occasion when a politician dropped to his knees after being asked tough questions to say, “Thank you for grilling me like this … YES, I am a hypocrite. YES, I lied to the public. OF COURSE, I don’t believe half the stuff I say in public.”

But we ask these questions to get answers where we can. We use them to make a case, to say, “What you have said or done is not acceptable and you will be held accountable.”

Whether you’re taking on your boss or your mayor, your mother-in-law (which I don’t recommend) or the hapless customer representative at the airline that just left you stranded midway through your journey, your questions matter and make a point.

But you don’t want to pick a fight needlessly and you don’t want to be wrong. Accountability questions cannot be shots in the dark. They must aim at a real target. When you question and confront, draw from the knowledge you have and set the agenda. Listen closely to control it. If you hear a speech, stop it. If you hear dissembling, call it. If you detect weakness, zero in on it. Where you detect evasion, challenge it. If someone talks in circles or ignores the question, reassert control and ask again.

Confrontational questions entail risk because they put relationships and reputations on the line. Before you confront anyone, ask:

Is confrontation called for?

Are the questions clear and compelling?

Am I willing to stake my reputation on them?

After all, if you’re wrong or if you sound ill-informed or like a bully, the questions will boomerang and hit you, not the person you are trying to hold to account.

Ask yourself when and where. Is it appropriate to confront a subordinate in a staff meeting? With others present? Over lunch? Or in a private meeting in the office? Timing, venue, and atmospherics of this type of questioning define the dynamic.

Reflect on exactly how you want to frame your questions. Should they come in a series of short, sharp yes-or-no queries? Or should they be preceded by a recitation of the evidence to frame the issue and establish the premise? Think of tone and whether the questions should be served up with sarcasm or delivered with solemnity, posed in sadness or in anger. The theatrics of confrontational questioning matters, sometimes as much as the answers you get.

Consider the value of the relationship. I didn’t really care if I angered Yasser Arafat or if I ever saw him again, though I was keenly aware that my hosts probably did not want him to storm out. Anderson Cooper isn’t planning on having lunch with Mary Landrieu, and Donald Trump probably won’t be buying Jorge Ramos a vanilla milkshake. If you’re going to ask for accountability or confront someone with accusatory questions, consider the cost and be sure you’re willing to pay it.

Confrontational questions are the blunt force instruments of inquiry. But they are necessary if we are to live in a place where everyone respects and plays by the rules and is accountable for their actions.

CHAPTER 7

IMAGINE THIS

Creativity Questions

CREATIVITY QUESTIONS INVITE US to pull out the paintbrush, throw away the coloring book and think differently. They prompt our imaginations. They ask us to get out of the way, break rules of convention, and exceed the bounds of the possible. They encourage us to rally to greatness or peer into the future, to see a new world. They invite us to daydream.

?

What would it be like to ride around like a millionaire?

What a great question. It asks us to envision wealth and comfort replacing the common chore of getting from one place to another. It prods us to imagine how special we’d feel if a deferential driver did the navigating and if convenience replaced stress. No wasted time finding a parking space or hailing a cab. No digging through your pockets for money. (Millionaires don’t carry money, anyway.) You stretch out in the back seat, comfortable and relaxed, managing the empire. Absolute efficiency. Pampered success.

It is the question that animated a couple of techie dreamers in a late-night brainstorming session. Travis Kalanick and Garrett Camp were “jamming on ideas, rapping on what’s next.” Camp came up with a Big Idea: a solution to the horrible taxi service in San Francisco. Camp was stuck on creating a car service that was so efficient people would feel like they were riding like millionaires. In the summer of 2010, the pair launched a tiny company. They called it Uber.

Within four years, Uber reported that riders were taking more than one million trips a day in more than fifty countries. Five years after it started, the company was valued at as much as $50 billion. It inspired the “sharing economy,” as companies like Airbnb, Snapgoods, and Task-Rabbit remade the way people travel, work, buy, and do business around the world. So now we know. If people are given an opportunity to ride around like a millionaire, they’ll do it, millions of times over.

Questions that drive creative thinking are out-there questions. They are big and bold. They ask people to transport themselves to a different time and place and state of mind. They open the door to aspiration and disruption. They challenge the status quo. They reframe issues around visionary, maybe even revolutionary, ideas.

You find inspiration in these fun questions because they invite fresh and original thinking. But you may also feel uneasy when they challenge conventional wisdom and the world you know. Whether you’re trying to invent the next big thing, make a crazy video to sell cars, or write the next inspiring chapter in your life, this line of questioning can help you hatch ambitious new ideas and bring people along for the ride to collaborate and create alongside you. Creativity questions ask you to pretend as they connect you to an imagined reality, where horizons are brighter and where limitations are lifted. They are questions that suggest everything is possible.

That’s what it’s like to ride around like a millionaire.

Creativity questions may not hand you the next $50 billion business, but they will help you put together the best brainstorming session you’ve ever imagined. They will help you reset the dial and think about new ways to get the kids to be on time or eat their broccoli. They will help you bring divergent viewpoints together and think about new ways to address a problem in the community or in the country. Creative questions can become a collaborative quest for answers.

What’s the magic wand idea?

We’ve arrived. What are we doing?

There are no obstacles. Now what?

Creative questioning asks people to close their eyes and imagine. It welcomes crazy ideas, shrugs off the obvious, and seeks alternatives. Creative questioning asks fellow travelers to:

Set sights unreasonably high. Ask more of yourself and others without being limited by the laws of gravity. There will be plenty of time to come back to earth later. If you don’t aim high, you will never go into orbit.