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Ask More The Power of Questions to Open Doors, Uncover Solutions

CHAPTER 11
THE INSPIRED HOST
Entertaining Questions
B
EING 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.
?
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 meal: 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.
She looked at me quizzically. “Whatever you wish,” she said warily.
Okay, I said, “I’ll give you a name or a topic, you get a one-word response.”
“Do I get the same?” she asked with a grin.
“Absolutely!” I responded. The audience laughed in anticipation.
Pelosi leaned forward, watching intently, not knowing exactly where this
was going. I wasn’t going to pounce or embarrass her, but I was trying to put
some energy in the exchange and drive some spontaneity to the conversation.
Just the night before, Pelosi had been on the front lines of a big budget deal.
It was Republican House Speaker John Boehner’s swan song achievement, his
last big act before retiring. It passed with votes from Republicans and Democrats
alike—a rare event in Washington. Pelosi had rallied support from her side.


That’s where I started.
“Budget deal?” I asked.
“Hooray,” was her reply. She smiled proudly.
The presidential campaign was under way and an unlikely candidate was
leading the Republican field. I invoked his name.
“Donald Trump?” I asked.
“Performer.” She grimaced.
Abroad, Vladimir Putin was rattling sabers, deploying his military.
“Russia?”
“Careful.” She scowled.
Democrats are perennially on the defensive about big government. Their
adversaries like to refer to them as tax-and-spend liberals.
“Taxes?”
Pelosi paused. “Investment.”
Democrats wanted to raise taxes to pay for a range of government programs,
so that one word captured their rationale perfectly. In less than a minute, we’d
covered several topics—and with an amusing economy of Qs and As. Our
political word association game opened the conversation with a few laughs and
no speeches, and it established an informal and approachable relationship
onstage. It encouraged spontaneity and set Pelosi’s internal clock and her
expectations for how I was going to proceed. I think she enjoyed it. I know the
audience did because I heard their reaction and laughter and I knew my
questions touched on a variety of issues they were following in the news.
Opening with scene-setter questions can help you get people talking, set the
pace, and frame the conversation. Figure out what you want to talk about and
how, factor in the personalities you have in the room, then map out questions
and anticipated responses. You can excite the imagination or you can prompt
reflection. It’s your show.

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