Power Questions: Build Relationships, Win New Business, and Influence Others

Suggestions for How to Use This Question
“Is it a yes or a no?”
When you are trying to pin someone down on an issue, or determine their commitment,
there are many ways you can ask the question. There are soft, inquiring approaches like
“What would you think of. . .?” Sometimes, you must leave no room to wiggle.
A closed-ended question is potent when you want a direct, unvarnished response. Is it
a yes or a no? When asked purposely, in an appropriate way, the closed-ended question
is a powerful and demanding ally to the asker.
When to use the question
To find out whether or not someone is fully committed.
To draw out any doubts or hesitations.
Alternative versions of the question
“Can you commit fully to this?”
“Are you on board or not?”

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“Can you make a final decision now?”
Follow-up questions
“What excites you most about this?”
“What are your biggest doubts or reservations?”

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13
Bury the Clichés
“I threw him out of my office.”
“What?”
I'm with Fred, the chief executive of the North American operations of a
multinational corporation. Fred was formerly the chief information officer
(CIO) of one of the world's largest banks. He's had hundreds of salespeople
call on him over the years.
“You name the company,” he tells me. “Goldman Sachs, IBM, Accenture,
McKinsey, EDS, and then every bucket shop between here and the West
Coast as well. They've all tried to sell me something.”
Fred is smart and tough and doesn't tolerate fools. But I have a hard time
picturing him throwing someone out of his office.
“You literally kicked him out? You're kidding?”
“I'm not kidding,” says Fred. “He asked the question.”
“Which one?”
“What keeps you up at night?”
He continues, shaking his head: “You see, it's a terrible question.
Overused. Clichéd. Stale. And worst of all, lazy. I hate lazy salespeople. At
a certain point it seemed that every salesperson, banker, and consultant was
asking that question. They were like lemmings. They'd come and call on me
and invariably ask, ‘What keeps you up at night?’
“They thought that by posing that question I would—as if by magic—
immediately volunteer to tell them all about my toughest issues. Then they
could say, ‘Ah, we have a solution to fix that.’ I started escorting them from
my office.”
“And it doesn't work that way with you?” I ask. (I know that it doesn't
work that way with most people, but I want to understand how Fred thinks
about it).

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“No, it doesn't. Nor with anyone else. Look, let's get some more coffee
and I'll explain why. I'll tell you what the really smart ones do that is
effective.”
Fred's executive assistant brings us two fresh cups. We move from his
desk to a small sitting area with a couch, a coffee table, and an easy chair.
We settle in.
I can't believe my good fortune. I'm like a 14-year-old again, listening to
my cigar-smoking, cognac-sipping Uncle Morton discuss his philosophy of
good living. But now, I'm going to school with the world's best instructor on
how to have a great first meeting with an executive prospect.
Sir Isaac Newton, referring to his extraordinary scientific breakthroughs,
said, “I stood on the shoulders of giants.” I feel like Fred is lifting me onto
his back, and I'm definitely going along for the ride.
“Here's why,” Fred explains, “‘What keeps you up at night?’ is a terrible
question. First, it's a shot in the dark. It doesn't demonstrate to the other
person that you've done your homework, researched the organization, and
thought about the issues they face. It's a question that requires zero
preparation. That's why it's evidence of laziness.”
I'm scribbling furiously.
“Second, if someone doesn't already know you pretty well, they are
probably not going to tell you what is really on their mind. Teasing that out
requires that you first build some trust and credibility. Come on! Think
about it. Am I going to immediately share my innermost cares and concerns
with some salesperson I've never met before? Are you kidding?
“Third—and this is especially true if you're talking to a CEO or a really
senior executive—this is a problem question. At my level, I'm focused on
growth and innovation, not operational problems. I have operating
executives who are paid to worry about those problems. Ultimately,
executives like me are paid for growth and innovation. ‘What keeps you up
at night?’ doesn't actually help you get at the most fruitful issues.”
“So, what do the smart ones ask?”
“You have to approach a meeting with me as a balancing act. You must
prepare. Read my annual report. Search the web. Read my speeches. Watch
the videos of me being interviewed. Review analysts’ reports. Learn about
my priorities and strategies before you walk in the door.

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“But then—and this is really important—when you sit down in front of
my desk, don't presume to know what my real issues are. Be confident, but
be humble. Probe and possibly suggest, but don't walk in here and tell me
what I'm concerned about.”
“The great salespeople ask indirect questions that show they know their
stuff. They say things like, ‘Fred, how are you reacting to the merger of two
of your biggest competitors? Or, ‘I was intrigued by what you said at the
investors conference in New York last month. How is your push into Asian
markets going to impact your financial controls and risk management
requirements?’
“The other day, someone had carefully read our proxy statement, and she
asked me some very intelligent questions about our executive compensation
plan. She wanted to know why we had made certain choices. It was an
engaging discussion. She kept gently probing, asking questions. She learned
a lot about what is on my mind and about my talent management and
retention strategies. We were satisfied with our existing provider, and had
no intention of giving her any business. But she was so artful—I believe her
firm will get a project from us.
“In other words, ask me questions that implicitly show you are
knowledgeable and experienced. Talk about your view of my competition,
and how you think the industry is evolving. Get me involved in that
dialogue. Then, I'll start to open up. Once that happens, you can be a little
more direct.
“You might even say: ‘Given all that we’ve discussed—x, y, and z—
where do you wish you were making faster progress? Which of these issues
are proving to be the toughest nut to crack?'”
We wrap up, and I'm beaming. In one hour I've just had a semester's
course in advanced salesmanship.
“Fred, this has been terrific. And thanks for the coffee.”
“I enjoyed the discussion. And by the way, you're a darned good listener.
Call anytime.”
The meeting reminds me that powerful individuals like to help the people
in their network. They enjoy doing favors for others. Sometimes, asking a
client or colleague for advice creates an opportunity for them to feel good
about your relationship—and for you to learn.

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When you want to understand a leader's issues, don't ask tired cliché
questions like “What keeps you up at night?” Engage them in a discussion
about their critical challenges. Ask about the impact of current events. Ask
about the future.
Let me give a few examples that will stimulate your thinking:
“Where will your future growth come from?”
“How do you think your current strategy is going to change, given. . .(e.g., the success of new
competitors, the rise of low-cost imports, deregulation, etc.)”
“If you had additional resources, which initiatives would you invest them in?”
“Sometimes a ‘breakthrough’ requires a ‘break-with.’ Are there any things you need to
deemphasize or stop doing?”
“Why have you been successful so far? How will that change in the future?”
“Which organizational or operational capabilities do you need to strengthen in order to achieve
your goals?”
“As you think about the future of your business, what are you most excited about? What are
you most concerned about?”
Don't ask lazy clichés like “What keeps you up at night?” Instead, ask
informed questions about the future. Questions that capture the
imagination. Questions about the other person's aspirations, priorities,
and reactions to the world around them.