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The candidate insistently asked about one of the toughest issues a foundation faces. Those questions led to a long conversation about metrics, accountability, and impact. The candidate got the job.

Jean counsels business students to “be fearless” in their job interviews and ask if they’ll have creative running room.

What freedom do I have to step outside the defined role?

How much do you want to hear from me when I am not asked?

What impact do you want to have in the world?

Where does that stand as a priority in your business plan?

I once sent a student to speak to an accomplished friend who was running an exciting startup and looking for promising young talent. The student had done well in class and I thought the two of them might hit it off. About a week after they met, I reached out to my friend to see how things went.

“To be completely honest, it was bad,” he said. “The student was nice, but she had no idea who she was talking to or what we were trying to do here.” She seemed unaware of my friend’s contributions to the field. She never asked how he was applying his experiences or where he wanted to take the business. She did not get the job.

Good job candidates ask serious questions that reflect deep preparation, a grasp of the organization, and a genuine desire for the job. Candidates should study up on the business and its competitive environment. Know about the top people as well as your prospective boss and the interviewer. Ask about the specifics of the job, organizational goals, past experience, and current prospects. Demonstrate informed curiosity about the challenges, opportunities, and culture of the place. What you ask, and how you ask it, projects your knowledge, interest, and engagement. Write down ten smart questions and be prepared to ask them. Make some of the questions open-ended and some very specific. Role-play the likely answers and have some follow-on questions.

You took a hit from the competition last year. How are you dealing with that?

I know there’s been a big shift to online. How has that changed the culture of the place?

Where do you see the biggest challenges and opportunities in the next five years?

Bright Ideas

Job interviews have evolved. In the 1920s, Thomas Edison found himself inundated with job applicants. Being the inventive guy he was, Edison created a test with 141 questions to help him choose the best candidates. They went from the simple to the scientific:

What countries bound France?

How fast does sound travel per foot per second?

Name three principal acids.

Ninety percent of the job applicants failed. The questionnaire prompted an uproar. “Edison Questions Stir Up a Storm,” read a headline in the New York Times on May 11, 1921. “Victims of Test Say Only a Walking Encyclopedia Could Answer Questionnaire.” Still, there’s little doubt that the test winnowed down the number of candidates.

The job interview has progressed since Edison’s day. Now companies use sophisticated “predictive analytics” to measure responses against likely outcomes to forecast retention, learning capacity, leadership potential, and the ability to innovate and make effective decisions. Some companies require candidates to record Skype statements. But determining compatibility—finding Jim Davis’s team chemistry—still depends on human interaction, and that’s driven by the questions that get asked.

Want some practice? You might try the questions at the online dating site eHarmony. Seriously. These questions represent a sort of job interview for romance. More than 100 questions seek insight and reflection on basic traits and hidden quirks.

What adjectives describe you?

How do you rate your emotions?

Do you feel better when you’re around other people?

I’m not recommending hiring by way of online dating. But these compatibility questions, which ask who you are, where you’re headed, and how you describe yourself, are designed to prompt the lovelorn to articulate what they’re all about. They’re great practice for a job interview!

Here’s one everyone should answer:

Do you ask questions when you are in search of information?

CHAPTER 11

THE INSPIRED HOST

Entertaining Questions

BEING A TALK-SHOW HOST IS FUN. You meet interesting people. You get to ask them about their work and their lives, probe their past, and ask them to tell stories. You push them and get personal, test their mettle, and find the funny. You can go for the reflective and thoughtful, or you can be tough and demanding, asking why your guest did what she did when she did it. It’s your call because it’s your show. You set the agenda. You own the space.

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But even if you don’t have a show or will never get near a camera, you can be a host who deftly steers conversation, draws in the guests, energizes an audience. You can do it over dinner, at work, in your social life, or with friends. You can set the agenda and create a mood that serves up ideas and connects people in stimulating, and surprising ways. You can become the maestro whose questions find the high notes that create an invigorating experience that wins rave reviews.

Entertaining questions allow you to engage your audience and keep the conversation interesting and lively so everyone plays. You can be commanding or charming, funny or unpredictable, but the objective always revolves around creating an experience that your guests will enjoy and remember. Use questions the same way a chef uses spices: subtly but deliberately to bring out the flavors of the meal. Basic ingredients?

Know your audience. Who you are talking to? What have they done? Where have they been and what do they care about? Pick questions that intrigue and interest everyone.

Think creatively, choose deliberately. Draw from a menu of topics and questions to create flow and distinctive moments. Sports or politics, fishing or sailing, it’s up to you, but you want a combination of topics that will engage different people on different levels. It’s like the meaclass="underline" plates filled with flavors and colors, veggies and proteins.

Set a mood and set a rhythm. Funny or serious? Provocative or reflective? Set the mood through signals, prompts, words, and timing.

Engage emotion. You trigger emotions through the subjects you pick and the questions you ask. Serious or snide? Funny or flippant? Your call.

I find that if I start with an exchange that is spontaneous and a little unexpected, I can often break the ice, get a smile, and set a tone that is more relaxed and will lead to a more genuine experience.

I was hosting one of my Conversation Series events at The George Washington University, onstage with House Minority Leader and former House Speaker Nancy Pelosi. I had interviewed Pelosi before and knew her reasonably well. I had a bunch of things I wanted to ask her about—politics, the economy, climate change, Washington’s weird ways. In doing my research, I had been warned, very diplomatically, that Pelosi was prone to long, sometimes slightly meandering answers. I didn’t want that. I was looking for a genuine conversation that would cover a lot of ground and illuminate both her politics and her personality. I wanted to draw her out on the polarization in the country and what she could do to change that. I wanted her to talk about how (and why) anyone would go into politics. Mostly, though, I wanted her to engage in a spontaneous and conversational way with me and with the audience.

I decided to start by asking if she’d be willing to begin with a little game.