The Worst Mistake America’s CEOs Make
Business + Economy

The Worst Mistake America’s CEOs Make


Too many business leaders stink at asking important questions – and as a result, their companies don’t seize market opportunities, push out new products, handle P.R. nightmares effectively or any number of other essential business actions. This absence of critical questioning risks compromising their bottom line, their brand or both.  

“A lot of leaders don’t want to ask the question that needs to be asked,” says Warren Berger, an innovation expert and author of A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. “They feel their role as CEO or company leader is to have all the answers, to be the expert – they’re not comfortable showing the vulnerability that comes with raising important questions.”

Related: How the Right Corporate Culture Can Guarantee Success

But if they don’t ask the questions that need to be asked, they can find themselves behind the eight ball in any number of ways, in today’s hyper-changing marketplace.  

Berger says that the recall-stricken General Motors, for example, could learn a thing or two about how to ask – and answer – key questions.  

“Questioning is an incredibly effective diagnostic tool and companies should use it to anticipate and respond to problems. In the case of GM, the first signs of trouble should have led to many probing ‘Why?’ questions – as well as, ‘What if?’ and ‘How?’ – meaning, ‘What if we take action versus doing nothing?’ and ‘How might we best start to deal with this situation?’”

While it’s possible that people within GM were asking questions but not being heard by decision-makers, Berger says that scenario could highlight another problem. “Companies should have a culture where the people close to the product, such as engineers, feel free to raise uncomfortable questions – as in, ‘Is this car part as safe as it could be?’ – knowing that their concerns will be heard and taken seriously by higher-ups.”  

Related: General Motors Hits Reverse on Its Public Relations

Today’s younger tech company leaders have a lot to teach their elders, says Berger.

“These guys have no problem asking questions, none whatsoever. People like Steve Jobs, Jeff Bezos, the founders of many other tech companies and startups – they ask questions like crazy. They are known questioners. So you have a whole generation today that has been observing leaders who have been very successful by asking questions. Today’s generation of business leaders knows that if you question as a leader and follow through with it, you can lead your company in new directions.”

Berger shares these tips for using questioning effectively:    

  • It’s smart to ask dumb questions. “Innovators, designers and entrepreneurs – the makers and doers – all use questioning as a big part of their process. It starts them on a journey. They ask: ‘Why isn’t somebody doing this?’ Or: ‘Why do we have settle for X?’ Or: ‘What if someone tried to do Y?’ The comfortable expert must go back to being a restless learner – today it’s truer than ever.”

  • Smart leaders reward questioning – they don’t discourage it or inhibit it. “Employees need to feel it’s a good thing to ask questions, that they won’t be seen as troublemakers. Too many executives say, ‘Don’t bring me a question unless you also have the answer.’ That’s a big mistake! Why? Because the answer may involve a team effort; it may involve two years; it may involve many more questions and discussions than one person can create. That doesn’t mean it isn’t a worthy and vital question that could lead to huge success down the line.”

  • Smart leaders break free of conventional wisdom. “Kids excel at this. When the young daughter of Edwin Land, the creator of Polaroid, asked a key question years ago, it revolutionized picture taking. Land was taking his daughter’s picture in 1943 with a regular camera when she asked, ‘Why can’t I see the pictures now? Show me the pictures.’ He explained, ‘No, that’s not how it works. I have to send the film to a lab to be developed and it will take a few days.’ But she pushed: ‘Why do we have to wait for the picture?’ That question got him thinking – and led him to create the instant Polaroid camera.”

Countless breakthroughs, innovations and businesses have started from a single out-of-the-box question. Here’s a sampling of questions and the businesses they sparked, all referenced in Berger's book:      

  • “Why can’t good musicians find the audience they deserve?” (Tim Westergren, Pandora)
  • “What if we could paint over our mistakes?” (Bette Nesmith Graham, Liquid Paper)
  • “Why can’t we find a place for people to crash for a night or two?” (Joe Gebbia and Brian Chesky, Airbnb)
  • “Why can’t everyone accept credit cards?” (Jack Dorsey, the cofounder of Twitter who also cofounded Square)
  • “Why can’t a windshield wiper work more like my eyelid, blinking as much (or little) as needed?” (Bob Kearns, who created the intermittent electronic-sensing windshield wiper)
  • “Why can’t I get the gears on my mountain bike to shift more smoothly?” (Dave Myers, who developed a plastic-coated bike cable product for W.L. Gore)
  • “Why do we want kids to ‘sit still’ in class?” (Abby Brown, designer of a raised-seat school desk that puts the user in a semi-standing position, immediately improving students’ attentiveness)

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