The Grand Inquisitor — Can Great Questions Improve Both Strategy & Culture?

Weekly reflection

Jack Ma applied for thirty jobs and was rejected for all of them. He later said, “I even went to KFC when it came to my city. Twenty-four people went for the job. Twenty-three were accepted. I was the only guy who was not…” His first company, Hangzhou Haibo Translation Agency, failed in 1994. In 1995, he launched China Pages, one of the first Internet companies in China, which later became Alibaba.

In 1898, Henry Ford developed a self-propelled vehicle he called the Quadricycle. He launched Detroit Automobile Company in 1899 with angel funding, but the car was of poor quality and the company failed in 1901. Ford tried again with the Henry Ford Company, but that, too, ended in disappointment. On his third try, he founded what became Ford Motor Company in 1902.

What would induce an investor to back a failed entrepreneur? Investors have little patience for poor performance, much less failure. Jack Ma and Henry Ford might never have gotten a first meeting with most investors. An investor would need to have patience, open mindedness, and the inquisitiveness to look beyond resume-level indicators to see the intrinsic capabilities of these high potential future leaders.

“Investors have little patience for poor performance, much less failure.”

How does one do that? I was pondering this question as I read the following passage from David Brooks in his book, The Second Mountain: The Quest for a Moral Life: “I have a friend…who is an amazing listener. I’ll describe some problem to him, and he’ll ask me some questions. There comes a moment in the conversation, after he’s asked four or five questions, when I expect him to start offering his opinions and recommendations. But then he surprises me and asks six or eight more questions, before eventually offering counsel or advice. Real listening, whether to others or yourself, involves that unexpected extra round of questions, stretching the asking beyond what feels natural.”

Is the ability to ask great questions an innate or learned skill? Meyers Briggs classifications would suggest that the perception and sensing qualities of a good questioner are innate. But Jim Collins, author Good to Great: Why Some Companies Make the Leap…And Others Don’t, believes otherwise. He describes an early experience as a new Stanford faculty member. At that time, he thought the way to prove he belonged was though insightful observations, so he prepared for faculty meetings accordingly. Eventually, Jerry Porras, a senior faculty member and statesman, pulled Jim aside and tactfully suggested that great questions, not great answers, were more highly valued. From that day forward, Jim changed the way he prepared for meetings. Jerry and Jim would later coauthor the bestseller Built to Last: Successful Habits of Visionary Companies.

The Art of the Question

At Stanford, I was fortunate to represent our student body at various board and investor functions. After one such dinner with Tom Clausen, CEO of Bank of America and the World Bank, I reflected to a friend that perhaps I get along better with CEOs. My friend smiled wisely and said, no, they get along better with you. It was just the kick in the butt I needed. Like Jim Collins, I was forced to reckon with and understand the superpowers that enable executives to rise to the top. Sincere questions and active listening often distinguish these leaders. John F Kennedy was reputedly a sponge for information, who had the knack of sucking his counterparts dry for information. To varying degrees, successful corporate CEOs have mastered the art of the question.

“Sincere questions and active listening often distinguish these leaders.”

Are questions an art form? Great oratory is readily appreciated as an art. A great questioner is harder to discern because the best of them hide their art form. Clarity and transparency are hallmarks of a good commentator rather than a good interrogator. There are a couple methods, however, that are worth considering.

One early mentor taught me a simple approach: Ask questions like water flowing through a funnel. You may know where you want to go (or think you do), but never start there. Instead, start several layers higher with broader, open-ended questions. See where they take you. They may take you to a better place. And they will surely tell you more about the person and the business.

Active listening is essential. Search executive Geoff Smart describes this in Who: The A Method for Hiring as Getting Curious: What, How, Tell Me More. He explains, “After a candidate answers one of your primary questions, get curious about the answer by asking a follow-up question that begins with ‘What,’ ‘How,’ or ‘Tell me more.’ Keep using this framework until you are clear about what the person is really saying.” GH Smart partner, Michael Haugen, demonstrated this for us effectively at one of our CEO Summits a few years ago. This technique produces a lot of added information quickly. In informal settings, great conversationalists use a softened version of this to create flow in a conversation while honoring one’s guest with center stage.

“After a candidate answers one of your primary questions, get curious about the answer by asking a follow-up question that begins with ‘What,’ ‘How,’ or ‘Tell me more.’”

These first two are easy methods that anyone can use and perfect over time. Doing these first two things alone at a high level can go a long way. The next two methods are art forms and rare gifts; few executives do even one of them well.

The first is the logical non sequitur or bridging question. This is the question that logically shifts the conversation into a wholly different direction in an unexpected way, changing the perspective and the course of our thinking. Nick Lovegrove, in The Mosaic Principle The Six Dimensions of a Remarkable Life and Career, describes people who offer this perspective as ‘T-shaped’ — with deep expertise in one subject but a breadth of perspective that enables them to relate this expertise in new and unexpected ways. Board members such as this are a rare gifts, as they can alter both company strategy and board culture. I recall one such board member who had a real gift for the bridging question. He spoke rarely and he only asked questions, yet he influenced management as much as or more than anyone. The whole board would listen intently when he spoke, in anticipation of his course-altering questions.

“I recall one such board member who had a real gift for the bridging question.”

Would these tools help us identify a Jack Ma or Henry Ford from among a stream of meetings with entrepreneurs? Jack Ma maintains that Masayoshi Son, an early investor in Alibaba, can discern the ‘scent of an entrepreneur.’ Donald Lucas, seed investor in nine unicorns back in the 70s-90s, when a unicorn was a rare species, had an uncanny ability to identify talented entrepreneurs. He was the first to back Larry Ellison, and, as Oracle’s only investor, was Chairman for nearly 20 years. He found Joe Costello from three levels down in Cadence; as CEO, Joe turned the company around, making it the dominant EDA player in the semiconductor industry.

One of the great talents of an interviewer is opacity: a good question should not tip off the desired answer. A good entrepreneur (or a charlatan) will reverse-engineer any question if tipped off, even in some non-verbal way. Don Lucas intentionally tipped his questions using the art of misdirection. His line of questioning would lead one to think he wanted one answer. Only a confident CEO, steeped in their field, could resist the flow and give the unexpected, but desired, response. This method enabled Don to develop a clear view of an entrepreneur in just a brief meeting. He was not always right, but his hit rate for reading people was amazingly high.

“One of the great talents of an interviewer is opacity: a good question should not tip off the desired answer.”

Can a firm adjust its collective mindset about questions? A small proposal…

Spain, currently the reigning FIBA World Cup title-holder in basketball, has a method for teaching passing and teamwork from a young age. Spain plays a beautiful brand of basketball, with great team chemistry: everyone learns to pass well and move instinctively — without the ball. My children once trained under a Spanish coach, which gave me some insight into how they instilled those skills at a young age. Every practice, they ran a passing drill, requiring each team to make at least ten passes without any dribbles before taking a shot. Play was balky at first. Players would crowd around the ball in a scrum. Turnovers were rampant. Rarely did a team get to make a shot, much less make one in the initial practices. But new patterns emerged with each successive practice. Players learned to move the ball quickly before the defense converged. They learned to move without the ball to get open. They spaced the floor to expose weaknesses in the defense. Teams gelled and developed rhythm. They not only got shots, they learned to work together for easy shots. At the highest level, great passing teams like Spain can dismember the stingiest defenses.

What if decision meetings required ten questions before commenting? I surmise that a similar process would emerge. Discussions would be balky and awkward at first, as teams learned and honed new skills. Pregnant pauses would replace interruptions. A different team dynamic would emerge. Monologs would get shorter. The pace of discussion would accelerate. More information would surface. Occasionally, teams might arrive at different conclusions. Decisions would garner broader support.

Might one be more open to the next Jack Ma or Henry Ford? Hard to say, but good questions — and honing the ‘art of the question’ — could stack the odds in one’s favor.

Originally published at https://www.linkedin.com.