Bookshelf with Harvey SchachterBusinessManagement
January 11, 2019

Bookshelf: The Book of Bountiful Questions

Carpenters and electricians have tools: hammers, saws, pliers, plungers and flashlights. So, do managers: questions. But we often fail to see them as tools – fail to arm ourselves in various situations with the right questions.

In The Book of Beautiful Questions, journalist Warren Berger helps, offering a host of questions for better decision-making, sparking creativity, connecting with others, and stronger leadership. “Having strong questioning skills has always been important. But in a time of exponential change, it’s a 21st Century survival skill. From an individual career standpoint, continued success will depend on having the ability to keep learning while updating and adapting what we already know. We must continually invent or reinvent the work we do every day. None of this is possible without constant questioning,” he writes.

But we resist or forget. A prime enemy of questioning is fear. As youngsters, we were fearless questioners. But then parents, teachers and other kids sent us a message that asking questions carries risks. So, we hold back, afraid of asking the wrong question.

Another big enemy of questioning, ironically, is knowledge. “The more you know, the less you feel the need to ask,” he notes. Of course, we don’t know as much as we think we know, and we lose the chance to improve.

Time also holds us back. We assume there isn’t enough time for questions. “We’re under pressure to make quick decisions and render snap decisions, and to do, do, do – without necessarily asking why we’re doing what we’re doing or whether we should be doing it at all,” he says.

Calling himself a “questionologist,” he urges you when facing decisions to think of your questioning skills as a flashlight and the decision ahead of you as a dark room. Every question illuminates a new area, and the better the question, the more light it sheds.  Snap decisions can go awry, and so he suggests in such situations asking these four questions to check up on yourself:

  • What am I inclined to believe on this particular issue? Start by trying to articulate your beliefs.
  • Why do I believe what I believe?  Nobel-Prize winning physicist Amos Penzias called this the “jugular question” because it forces you to consider the basis of your beliefs.
  • Why would I like it to be true? Wishing and hoping does not lead to great decisions, so examine your real motivation.
  • What if the opposite is true? In the 86th episode of Seinfeld, George Costanza met some success doing the complete opposite of what he would do normally. You can benefit from the same formula.

To deal with hubris, he has four intellectual humility questions that help bring you down to earth:

  • Do I tend to think more like a soldier or a scout? Julia Galef, co-founder of the Center for Applied Rationality, says a soldier’s job is to protect and defend against enemy, whereas a scout’s purpose is to explore and discover. Which mindset tends to prevail in your decision-making? Asking this question routinely can illuminate when your mindset is leading you in a bad direction.
  • Would I rather be right, or would I rather understand? Wanting to be right leads to defensiveness and can wall you off from learning and understanding. This question blends well with Stephen Covey’s recommended habit: Seek first to understand, then to be understood.
  • Do I solicit and seek out opposing views? “Don’t ask others if they agree with you – ask if they disagree and invite them to say why,” Berger urges.
  • Do I enjoy the “pleasant surprise” of discovering I’m mistaken?  Finding out you’re wrong can lead us to feel ashamed. But you can also choose to embrace being mistaken as a pleasant surprise, one of openness and growth.

He has another series of questions that help you with the common situation of being presented with nonsense or shaky information:

  • How strong is the evidence? Demand substance for every claim.
  • What are they not telling me? Sometimes the problem is not the information and evidence before you, but what is being hidden. Focus on that.
  • Does it logically follow? When people are trying to persuade you, they often offer flawed reasoning. It’s important to suss out logical fallacies.
  • What is the opposing view? As with Seinfeld’s Costanza, consider the opposing side of what is being suggested, weighing it with an open mind. It may reveal important insights or even offer a better path.
  • Which of the conflicting views has more evidence behind it? Choose that option.

When faced with a problem, he suggests asking four “why’s”: Why does this problem matter? Why does this problem exist? Why hasn’t this been solved already? Why might that change now?

Moving on to creativity, he notes we often complain we can’t be innovative since we lack the time. If you say (or think) that, here are four questions to ask yourself:

  • If I began to see my attention as a precious resource, how might I better protect it?
  • How can I shift from a “manager’s schedule” to a “maker’s schedule”? Managers tend to spend their lives in meetings, and usually the workday for everyone revolves around that kind of schedule. But makers – those who create reports and other important office output – need solid, uninterrupted blocks of time to concentrate. Creativity is more likely to arise in that second schedule.
  • Am I pruning the vine? Consider cutting back some tasks to provide more time for the truly important ones.
  • What if I trade the morning news for the “morning muse”? The morning can be a prime time for creative thinking. Slow down, avoid the news and other morning bustle, and unleash your mind.
  • Instead of taking a break from social media, what if I reverse that? Take breaks – but few of them – in which you engage with social media. Otherwise, stay away.

To find your big idea, he recommends asking: What stirs me? What bugs me? What’s missing? What do I keep coming back to? What is ripe for reinvention?

Connecting with others often starts at a first meeting with the perennial “What do you do?” Junk that question and instead try, “What are you most passionate about?” or “What problem do you wish you could solve?” or “What did you want to do when you were growing up?”

Instead of the ritualistic “How are you?” when encountering a friend or colleague, try: “What’s the best thing that happened to you today?” Or: “What are you excited about in your life right now?” It opens the door for  a more interesting answer.

He has many questions to help your leadership. Four – drawn from legendary management guru Peter Drucker and other luminaries – are intended to sharpen your focus: What is the one thing I can do that would make everything else easier or unnecessary? What should we stop doing? What do I want to go big on? At this moment, what is the highest, best use of my time?

There are many opportunities for what he calls “ambulatory inquiry” as you walk around the office and connect with subordinates. Instead of resorting to ineffective questions like “How’s it going?” or “Who screwed up here?” he recommends:

  • “What’s the biggest challenge you are facing?” This can be made specific by adding on “this project” or more general, with the words “in your job.”
  • “Are you making progress?” If they aren’t, frustration will occur, so you should know.
  • “Help me understand what led to….” This is a less accusatory way of delving into a problem than asking who screwed up.
  • “Is it clear what we’re doing and why?” A vital, often unasked question. People can’t be aligned with your strategy or current efforts if they don’t understand it.
  • “How can I help?” Former Campbell Soup Company CEO Doug Conant calls this the “ultimate leadership question.”

The book is probably the ultimate collection of questions for managers and executives. Yes, there are too many of them to digest in any one sitting. But it can be a valuable resource to turn to in your morning muse.

About this author

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HARVEY SCHACHTER

Harvey Schachter is a writer, specializing in management and business issues. He writes three weekly columns for the Globe and Mail and The Leader’s Bookshelf column for Canadian Government Executive, and a regular column and features for Kingston Life magazine. Harvey was editor of the 2004 book Memos to the Prime Minister: What Canada Can Be in the 21st Century. He was the ghostwriter on The Three Pillars of Public Management by Ole Ingstrup and Paul Crookall, and editor of Getting Clients, Keeping Clients by Dan Richards. A McGill commerce graduate, Harvey spent more than 15 years in a variety of positions at The Kingston Whig-Standard, including editor and planning and promotions manager. He won two National Newspaper Awards for his writing and a national Owl Award for a marketing program he created at the newspaper.

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