Will Anyone Follow a Leader Who Embraces Uncertainty?

Excerpted with the permission of the author from Chapter Four

Note from Bob:  My friend Warren Berger has just released his newest book, A More Beautiful Question.   This is a “Must Buy”  for every leader who wants to “Sharpen Their Leading with Questions Skills.”

Will Anyone Follow a Leader Who Embraces Uncertainty?

“The most important thing business leaders must do today is to be the ‘chief question-asker’ for their organization,” says the consultant Dev Patnaik of Jump Associates. However, Patnaik adds a cautionary note: “The first thing most leaders need to realize is, they’re really bad at asking questions.”

Most business execs rose up through the ranks because they were good at giving answers

That shouldn’t be surprising . Patnaik notes that most business execs rose up through the ranks because “they were good at giving answers. But it means they’ve had little experience at formulating questions.” The questions they are accustomed to asking are more practical and interrogative:

  • How much is this going to cost us?
  • Who’s responsible for this problem?
  • How are the numbers looking?

That kind of practical , give-me-the-facts questioning has its place. Such questions can help in running a business, but not necessarily in leading it.

Adam Bryant, who writes the New York Times Corner Office column, featuring weekly interviews with top CEOs, says the best leaders understand that asking open, exploratory questions can help them figure out what’s coming and where new opportunities lie, so that they can lead their company in new directions.

Ron Shaich of Panera observes, “When you’re leading a team, a start-up, or a public company, your primary occupation must be to discover the future. A compelling and even subversive question is an effective tool for navigating uncharted terrain.”

The problem with asking questions, for some business leaders, is that it exposes a lack of expertise and, in theory, makes them vulnerable. That many of today’s most successful CEOs are questioners, as documented in the research of Hal Gregersen and Clay Christensen, would seem to disprove that theory. But the myth lingers that business leaders must be all-knowing, decisive, and in possession of infallible “gut instincts,” all of which leaves little room for questioning.

Randy Komisar, a leading Silicon Valley venture capitalist, says the best business leaders and entrepreneurs have a different attitude toward “answers.”“They understand that answers are relative. You can have an answer for right now, but it changes.”

Because change is now a constant, the willingness to be comfortable with, and even to embrace, ambiguity is critical for today’s leaders. The consultant Bryan Franklin has observed that effective leaders today may not appear to be entirely decisive because they are forced to reconcile conflicting forces and paradoxes in the current marketplace. Such leaders often find themselves “standing at the intersection between seemingly contradictory truths”: How do you balance growth with social responsibility? How do you enrich your offering while streamlining production? And so forth.

In the midst of such complexity, leaders need extraordinary “sensemaking” capabilities , according to Deborah Ancona, the director of the MIT Leadership Center. Ancona defines this as “the ability to make sense of what’s going on in a changing and complex environment.” To do this, she maintains , leaders must be able to get beyond their own assumptions, take in vast amounts of new information, and figure out how to apply all of that to their business, sometimes doing that via experimentation. This adds up to a lot of Why, What If, and How questions.

The leader needn’t, indeed shouldn’t, be asking these questions alone.

“One of the most important things to know about becoming more of a questioning leader is that the questions don’t all have to come from you,” says Patnaik. If others are given permission and encouraged to question, they can contribute a range of perspectives and help raise the kinds of Why and What If questions that might never occur to the person at the top.





Warren Berger


Warren Berger has studied hundreds of the world’s leading innovators, entrepreneurs and creative thinkers to learn how they ask questions, generate original ideas, and solve problems.  His writing and research on questioning and innovation have appeared in Fast Company, Harvard Business Review and Wired.  His website is AMoreBeautifulQuestion.com


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