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The Facts: Were you there when this went down? Did you say this? Sometimes you start with these inquiries, sometimes you circle around to them, but these are the questions that establish the connection between the person you’re questioning and the activity at hand. They may be simple yes-or-no questions. They confront your adversary with an event, an act, with words or facts, and they ask about this person’s connection to them. You probably already know the answer because often it is public knowledge.

The Accusation: Did you do it? Did you mean it? Why didn’t you stop it? Take the allegation, add a question mark, and throw it at the accused. This question demands a response—a denial, an admission, or an obvious dodge. It asks explicitly about the wrongdoing you are alleging. The question is intended to put the accused on the defensive. It frames the confrontation.

The Deniaclass="underline" Do you own a red convertible? Did you drive that car on the day in question? Did you stop for gasoline? Since denial, quasi-denial, or obfuscation is often the first response, you must anticipate a nonanswer and be prepared to come back at it in persistent ways. Take the incident apart piece by piece. Ask about the evidence, the timeline, eyewitness reports, the person’s own words, or the historical record. Use them to reveal inconsistency or hypocrisy, lies or misbehavior. These questions can force a response, make a point, or simply call out your adversary.

For the Record: When are you going to tell the staff about the layoffs? Will you agree to testify publicly? Why did you lie? Sometimes the best confrontational questioning is less about the answer and more for the record. The question becomes a point of reference, significant for having been asked. What did the president know and when did he know it? Senator Howard Baker famously asked in the middle of the Watergate hearings. The question led to damning testimony that put Richard Nixon squarely in the middle of the cover-up. For-the-record questions can be retrieved, replayed, and revisited as a snapshot in time, a moment of accountability.

The Audience: Confrontational questioning is often directed as much at the audience—a jury, a review board, the general public—as it is at the individual. Use your questions to articulate and illustrate acceptable versus unacceptable behavior. Draw the line in the sand. Even if you do not elicit much new information, your questions can focus attention and get noticed.

The Risk: Confrontational questions can be dangerous. They don’t build bridges, they often destroy them. Ask these questions carefully, deliberately. Calculate and be sure you’re right. Falsely accusing someone can kill your credibility, make you look foolish and empower your adversary. Whether a brutal dictator or a rebellious teenager, a certain swagger flows from having survived a challenge and defied authority.

Listen: When you ask about wrongdoing, listen for evasive or distracting language or words that change the subject or shift blame. Listen for uncomfortable silences that suggest someone is searching for just the right words. If you hear that, pounce. Listen for a shred of admission, revelation, or remorse. That’s when you lean in and ask more.

Try: Attempt some confrontational questioning. A college student stands accused of plagiarism. She turned in a paper on dying coral reefs. She is a solid student and has never been in trouble, but a plagiarism app revealed whole sections of the paper lifted from Wikipedia—word for word. A committee will hear the case. You’re the prosecuting professor. Write ten questions. Make them short and precise, each focused on a specific element of the allegation. Do not ask flatly if the student admits to the charge. Build the case a step at a time.

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CREATIVITY QUESTIONS

Creativity questions encourage people to think about things that go beyond the familiar. They encourage originality and risk-taking. They ask people to consider new ideas and imagine new scenarios. They put us in the future tense. They push boundaries. Creativity questions ask people to imagine ambitiously and think independently.

The Dream: What would you change? What if there were no limits? What is your dream?

These are opening questions that grant license and unleash the imagination. You are asking people to put convention to the side, to set their sights high and try something new or experiment. These questions inspire people to think big, over the horizon to imagine new approaches, new definitions. They are the questions that frame the challenge, set the bar, and loosen the rules.

The Frame: What’s the next Big Thing? How can we eliminate poverty? What will it take to beat cancer? What’s the unexpected twist in the story? Frame your question to inspire and to invoke the future. Ask people to imagine a different and better place. Make the questions inspirational, to shift our gaze from the weeds to the sky.

Role-Playing: What if you were CEO? What would you do? What if you were the director making the movie? What would Jeff Bezos think about this situation? Ask your collaborators to try on another pair of shoes—the shoes of the decision maker. Ask them to assume responsibility. Your question puts them in another place. Now they are invested, thinking in a different context and imagining at another level.

Your Sunglasses: When should you take them off? You can direct the action and tell people precisely when to take off their sunglasses or you can ask people to invest themselves in the decision and think about what they are doing, why and to what effect? Invite them to be part of the creative process instead of just handing them a script. These questions challenge people to take ownership of the script and the creative process.

Time Traveclass="underline" You succeeded. You’re in the future. What are you doing? What’s it like? What do you see? Skip past the particulars, the details, and the distractions. Forget the fear and the can’t-do white noise. Pretend money doesn’t exist. Ask people to boldly go where no one has gone before: the future. Ask them to look around and try it on. Then look in the rearview mirror to see how you got there and what it took.

The Superhero: What would you do if you knew you could not fail? That’s Gavin Newsom’s question. Ask it to help people embrace risk and understand that fear of failure should not stand in the way of brainstorming, big ideas, and worthy goals.

Listen: Be alert to the brave and the different, and for ideas that spark imagination and enthusiasm. Listen eagerly for originality and boldness. If you hear a germ of an idea, fascinating but not fully developed, draw it out with a series of questions that nurture the thought process.

Try: Run the “future test” with a roomful of colleagues, friends, or family. It is five years from now. We achieved our goal. What does that look like? What are we doing? What are we proud of? The questions are about the future but asked and answered in the present tense. The future is now. Your time machine worked.

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MISSION QUESTIONS

Mission questions ask us to find shared purpose and turn a challenge into a common goal. They ask us how we can contribute and accomplish something worthy and needed. These questions connect mission to people. They inspire generosity and help us come together, give of ourselves, and accomplish good things.

Discovery: What do you care about? What do you stand for? What are your passions in life?

Start by asking about what matters and why. If a friend is interested in childhood obesity, find out why. If they’re passionate about global hunger, is it because they were in the Peace Corps and helped feed a village or because they have been to New Delhi and witnessed hunger up close? Discover the mission and understand where it comes from.