Worried That You’re Boring Your Audience? Demand Interesting Questions!

UPDATED: May 22, 2023
PUBLISHED: May 15, 2013

During the Australian Open Tennis Championships in 2011, when she was ranked No. 1 in the world, Caroline Wozniacki got wind of the fact that the media found her press conferences boring because she always gave the same answers. “I find it quite funny because I always get the same questions,” she told the press at her next opportunity. Then she proceeded to give answers to all the questions she was always asked. She then said, “Hopefully this was a little bit different than usual, and now you can maybe give me some questions that are a little bit more interesting.”

She’d thrown down the gauntlet, and the reporters rose to the challenge. The questions that followed ranged from how she enjoyed her visit to a cricket game the day before to how the world should solve global warming, from whether or not her parents kept scrapbooks to how well she played the piano. Each answer was new, and therefore was news. And the press conference itself was news. Major score for Wozniacki PR.

The investor Warren Buffett recently chose to enliven his generally predictable annual meeting at Berkshire Hathaway by handpicking a designated gadfly, Douglass A. Kass, a hedge fund manager who maintains a short position on the stock and is often found poking at Berkshire’s weak spots. Buffett was tired of the annual weekend of adulation, it seems, and wanted to be tested.

Mr. Kass told The New York Times that he had winnowed a list of 25 potential questions down to six, none of which had been asked before, he said, and two of which would be big news if Mr. Buffett answered them.

The questions focused on what the company would look like after the 82-year-old Mr. Buffett leaves. Mr. Kass invoked the story of Henry E. Singleton, who ran Teledyne, one of the world’s largest conglomerates, in the 1960s and ’70s, and who broke it into three companies because he felt it had become too big, before he died in 1999, aged 82. Then he asked his question: “What is the advisability of restructuring Berkshire into separately traded companies organized along business lines?”

What’s wonderful about the exchange that followed is that Mr. Buffett paused before replying, and during his answer he both smirked and scowled. He wasn’t reading from a song sheet. He wasn’t trotting out a well-practiced answer. He’d asked to be tested, and he was ready to come up with answers on the spot. Sure, he thinks about the future of his company all the time, but this question hadn’t been asked in public before, and it hadn’t been asked in this way. After both he and his vice chairman took turns expressing the conviction that breaking the company up would create a poorer result, Mr. Buffett saw the opportunity to offer some of his down-home humor: “If you come to a day when the Dow has fallen 1,000 points a day for a few days and the tide has gone out and you find some naked swimmers, those naked swimmers will call Berkshire.”

There were no big surprises in the answers, but the fact that Mr. Kass, dubbed the Berkshire Bear, was asking different questions made for a change in the content, and was stimulating to the participants. Advantage Buffett.

And that’s what you want. Sometimes, to get your listeners going, you have to be willing to swim out into uncharted waters. Make sure there are a few sharks in there with you, and let them flash their teeth. Because that’s what the audience will see—danger—and it will be exciting. But you’ll be cool, because you’ll know that they’re not really sharks at all. They’re just people, and you’ve asked them to be there, whatever they decide to ask. They’re happy, because they get attention. You’re happy, because you get attention. And the audience is happy, because this time, they stayed awake.

Alison Lester is a writer and communication skills coach based in Singapore. Her books include a guide to more creative and comfortable presentation skills called Present for Success, and a collection of essays called Restroom Reflections: How Communication Changes Everything. She blogs at RestroomReflections.com, and her first novel, Lillian on Life, will be published by Amy Einhorn Books in January 2015.