Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

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ENTERTAINING QUESTIONS

Entertaining, three-course questions spice up conversation and bring out the interesting and the fascinating. Fun, irreverent, or probing, these questions can be served up in healthy portions around the table or in the office to help people connect, engage, and learn more about one another. Ask these questions well and you’re the master of your own ceremonies!

The Theme:

What is the one thing in the world that blows you away?

This is how you set the theme and steer the conversation. Start with a question that will intrigue and engage everyone. Ask in a way that is not threatening or intimidating. Frame the question so everyone can chime in somehow—with an experience or an opinion, a factual observation, or a personal story. You can make the theme question serious or fun, big or little.

Riddles: If we went to Mars, what would change? If you had three wishes, what would the second one be? What will be the big breakthrough of the next twenty years?

These are game-show questions, imagination starters. You’re asking people to weigh in on a riddle that has no right or wrong answer. But in answering, they reveal some of their thinking and personality. These are brainteasers, guaranteed to produce surprises along the way.

Trendsetters: What happens when two-year-olds have smartphones? What would it take for you to buy an autonomous vehicle? Why should we still teach handwriting?

Really? Trends provoke thought and commentary about our time and condition. Questions like these capture the zeitgeist and the human dynamic. They intrigue, surprise, amuse, and captivate. Ask about the present and the future. Invite your guests to close their eyes and imagine.

The News: Is America still capable of doing great things? How will China change the world? What will it take for the home team to win the World Series?

A three-course question gains caloric content if the stakes are real and some people in the room actually know something about it. Ask about the world. Look at your guest list for the gold mines of interesting experience or expertise. These questions make headlines and invite people to talk, think, learn, debate, and disagree.

Supper with Socrates: What is success? Do you need success to be successful? Is success always good? Is it a virtue?

Pick an issue or an attribute. Ask a series of poignant questions to pick it apart, define, and debate it. Challenge conventional wisdom, standing definitions, and just about anything that people take for granted. Ask what is true, how we know, why we care. Steer people away from the personal or anecdotal and toward fact, reason, and experience. This could go deep—or just plain exasperate. So keep the conversation focused, bringing participants back to the core questions. This is some of the most thought-provoking stuff you can serve up.

Laugh: What’s your most embarrassing experience? If you could erase one day in your life, which day … and why? If you made a commercial, what would you be selling?

Questions that point at ourselves show that we don’t take ourselves so seriously. Asking for the funniest, weirdest, or most unexpected can prompt a laugh or entertain a crowd.

Listen: These questions can delight or they can ruin your party. Listen to keep the conversation moving and amazing. But also listen for hints of annoyance, resentment, or impatience. Some topics, framed the wrong way, can be poisonous—religion, politics, money come to mind. You need the right crowd and the right host to come in for a soft landing. Listen to determine when you should exercise the host’s prerogative to change the subject.

Try: Select questions as you’d select a meal: appetizers, a main course, and dessert. Make note of the interests and experiences your guests bring to the party. Pick your courses accordingly, starting with something light, moving into the stuff you can sink your teeth into, and ending with something sweet. Don’t overdo it. Let it breathe. Leave room for coffee.