The brilliance of asking incredibly naïve questions; Most workplace conversations discourage real dialogue — the kind you get when people feel free to challenge plans, ideas, even one another.

The brilliance of asking incredibly naïve questions

February 10, 2014: 12:27 PM ET

Most workplace conversations discourage real dialogue — the kind you get when people feel free to challenge plans, ideas, even one another.

By Megan Hustad

FORTUNE — I was about to get on a conference call and asked the call organizer if he had scheduled a hard stop. No, he said, but he hoped the call would be over in 45 minutes.

The call started, and after 70 minutes I hung up knowing I could always pretend Skype had dropped the call. But no one complained. It seems I wasn’t the only one frustrated.

It wasn’t just that the call was long, or that in an hour and 10 minutes nothing noteworthy had been accomplished. Nor was I irritated because time had been wasted. The more I thought about it, the more convinced I was that conference calls rarely satisfy because we join them hoping to enjoy meaningful collaboration when, in fact, the whole set-up trains our minds toward loss-prevention and saving face. We talk because not talking will lower our status in the group. We keep talking because we worry we haven’t yet proven our value. And everyone becomes so focused on sounding smart that we often don’t give others the recognition we ourselves crave.

Experiences like these amply demonstrate the need for a “questioning culture,” Warren Berger argues in his forthcoming book, A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas.

Many workplaces, Berger writes, discourage real dialogue — the kind you get when people feel free to challenge plans, ideas, even one another. He argues that office cultures that encourage group questioning gain an edge. Google’s (GOOG) “sometimes chaotic” weekly TGIF sessions, during which all employees are invited to ask Larry Page and Sergey Brin questions, gets a nod from Berger, as does MIT’s Media Lab, where engineers experiment widely and fail, fail again, and fail better on the way toward a solution.

In such settings, not knowing isn’t penalized. “I consistently position myself as an idiot,” Paul Bennett, of the design firm IDEO, tells Berger. He believes this willingness to ask what he himself calls “incredibly naïve questions” has helped their firm thrive.

By incredibly naïve Bennett means those painfully elementary questions that in some audiences would get him branded a dim bulb. Called to speak to Iceland’s parliament in the wake of the country’s financial crisis, he asked, “Where’s the money?” Not to be disrespectful, he later explained, but because first-things-first questions prompt an audience to explain things simply, and with that simplicity comes clarity.

Incredibly naïve questions “work” because they lower defenses. They also force us to put aside stock answers. This can slacken a conversation’s pace — but that’s all for the good, Berger argues.

“In most meetings — and in most everything we do in business — we are usually trying to keepthings moving forward and just ‘get things done.’ This is a natural impulse, and of course it’s important to get things done and stay on schedule. The problem is, this leaves little time to question assumptions, as in, Why are we doing this particular thing? Have we really thought it through, and considered other possibilities?

Berger recommends instituting a pause for questions that challenge the group’s basic operating assumptions. (Among my questions would be, “What do we hope to accomplish in 70 minutes that could not be done in 45?”)

There is no ideal formula for how to engineer this pause. But over time, a group develops a tolerance for it. “And while it may seem as if this is slowing progress, what you’re actually doing is making sure that your ‘progress’ isn’t taking you down the wrong path.”

Achieving such a questioning culture would be easy, I thought, if enlightened CEOs stood behind it, demonstrating by confident example that incredibly naïve questions are not necessarily a sign of weakness, stupidity, or lack of team spirit. But what about people who report to insecure middle managers who don’t like the idea — or the questions?

Berger isn’t worried.

“Leaders must signal to holdouts that this is now part of what’s expected of them: to question and welcome questions. And also to encourage a kind of questioning that is ambitious, positive, thoughtful, and potentially actionable.” (As opposed to people just asking about vacation policies.)

This might mean rewards for beautiful questions. It also means a new collective responsibility for the outcomes of questioning sessions. “Don’t punish [the asker] by saying, ‘Okay, you raised this question, now it’s on you [alone] to find the answer.'”

Most good questions don’t have tidy answers. But only in embracing that messiness — and sometimes rudeness or foolishness — do we fumble our way toward brilliance.


About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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