The Secret to Better Ideas and Better Leadership? Asking Incisive Questions

UPDATED: June 3, 2024
PUBLISHED: June 4, 2024
David Novak

Reprinted by permission of Harvard Business Review Press. Excerpted from How Leaders Learn: Master the Habits of the World’s Most Successful People by David Novak with Lari Bishop. Copyright 2024 David C Novak. All rights reserved.

I always tell people that the best thing about being new in any job, company, role or project is that you have carte blanche to ask questions. It’s the only way to learn. The trick is to be secure enough and curious enough to keep asking questions—as many as possible.

How to ask better questions at work

Warren Berger, author of A More Beautiful Question, has explained that our questioning peaks at about age 4. “Why does that 4-year-old… begin to question less at age 5 or 6?” he asks. “And why aren’t we trying to stem or reverse that decline?”

I believe one reason is that, as we age, we become overly confident in our knowledge or overly worried about looking like we don’t know something.

“As you become more senior as a leader, it’s even trickier to be curious—because you think you know a lot and other people think that you know a lot,” Michael Bungay Stanier, author of the bestselling books The Advice Trap and The Coaching Habit, said to me. “But if you think to yourself, my role as a senior leader is to use my wisdom not to have the fast answer but to enable the others around me to figure out the problems, come up with their own solutions and make sure that they’re not doing anything stupid—if you bring your advice in at the right time—then you unlock something amazing.” 

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The “advice monster”

Active learners make the effort to stay curious first and dole out advice second so they don’t fall victim to what Stanier calls the “Advice Monster,” which grows from our need to tell it, save it or control it. “All of them are impossible,” he says. “It’s impossible to know everything. It’s impossible to save everybody or everything. It’s impossible to control everything.” 

Instead, active learners redirect that energy to keep exploring and discovering. When I was on the board of JPMorgan Chase, I was elected to compile the feedback from the board and give CEO Jamie Dimon his annual performance review because of my focus on people development. Dimon asked several questions about every piece of feedback I gave: “If the board thinks I should focus more on X, how can I get more efficient at Y?” “How do you think I could improve at this or that?” “What else am I missing in that area?” And Brian Cornell, the hugely successful CEO of Target, told me he fights to stay curious through literal language metrics. He tries to communicate in a question-to-statement ratio of 3:1. 

A flood of poorly thought-out questions that don’t advance your thinking or learning isn’t the answer, though. The key is to ask better questions. In my book, Taking People with You, I taught the importance of asking questions that promote insight. Berger believes the antidote is to ask more beautiful questions, which by his definition, “shift the way we perceive or think about something—and that might serve as a catalyst to bring about change.” 

How leaders learn

Author and public speaker Nancy Kline, the winner of the International Listening Association’s Listener of the Year Award, uses the term “incisive questions.” “Between you and a wellspring of good ideas is a limiting assumption,” she writes in her book, Time to Think. “The assumption can be removed with an incisive question.”

A perfect example is the difference between asking, “What should we do?” and the more incisive, “What could we do?” Researchers have even studied the difference and found that when we use “should,” we limit everybody’s thinking to the most obvious or safest options.  When we use “could,” we open our minds to a broader world of possibility. I used that technique when asking people how we could grow the business. People often think in terms of modest growth and develop plans to achieve it. I liked to ask, “Instead of shooting for 5% growth, how could we grow the company by 10%?”

“What if” questions are a powerful way to kickstart people’s imaginations and break away from limiting assumptions. When I’m trying to break away from my own assumptions, I often ask, “If some hotshot came in to take over my job, what would she do?” 

I love to ask, “What would you do if you had my job?” I’ve posed it to people from all backgrounds, from line cooks to corporate board members. You can’t believe the insights that one question has generated over the years. A common answer I’d hear on the front lines was a diplomatic version of “I’d fire my boss.” That helped me spot needed coaching and leadership development and sometimes people who weren’t a good culture fit. From restaurant managers, I’d hear things like, “I’d cut out half of the bureaucracy we have to deal with” or “I’d stop trying to reduce our food costs. It’s getting in the way of producing good products.” Asking those questions was a great way to let people know I valued what they thought and what they cared about. 

Whether you want to call them incisive questions, more beautiful questions or questions that promote insight, active learners use them to get past the blocks and biases the brain creates, cut through the BS and help people generate better thinking, better ideas and better learning.

Photo by Lgmmedia/Courtesy of David Novak

David Novak is the founder of David Novak Leadership, a leadership development organization and platform, and the cofounder and former chairman and CEO of Yum! Brands, one of the world’s largest restaurant companies with over 1.5 million team members working in more than 135 countries.

His mission is to make the world a better place by developing better leaders. He pursues this passion through courses, workshops, philanthropy, and especially his top-ranked podcast, How Leaders Lead, where he interviews high-profile leaders in business, sports, health care, and government. David is also the author of four leadership and personal development books: the New York Times bestseller Taking People with You (based on his original leadership development program), Take Charge of You, O Great One!, A Little Story About the Awesome Power of Recognition, and The Education of an Accidental CEO.