Be Questionable; The Antidote to Expertise Addiction

Hi, my name is Jay and I’m an expertise addict. It’s been 30 minutes since I acted like a know-it-all.

I was raised to value intelligence, but somewhere along the way I confused intelligence with having a ready answer for any situation. I see now that aspiring to be the foremost authority on anything is a fool’s errand.

Knowing things is becoming an obsolete advantage

in 2011, IBM’s artificial intelligence platform Watson famously beat the best human players at Jeopardy. Ken Jennings, one of the humans who lost to Watson delivered a TED Talk about the experience in which he refers to himself as an “obsolete know-it-all.” Watson has redefined what it means to be a know-it-all, but it has not yet figured out how to parlay its vast stores of information into world-changing outcomes and predictions. For example, Watson already has consumed everything published on the subject of cancer but hasn’t yet improved patient outcomes.

Watson may have an answer for any question about cancer, but Watson still can’t tell the difference between a useful question about cancer and an unproductive question about cancer. I suggest that we cede knowing things to artificial intelligence (AI) and instead stake our future on developing our questionable intelligence (QI). Of course, I’m playing with the word, “questionable,” but my use of the word is consistent with its original meaning. Before “questionable” connoted something deprecatory, it simply meant something that may be interrogated or something open to dispute.

How do we create readiness for key roles in our organizations?

Earlier this week I had an opportunity to share my work at Unstuck Minds with the Leadership Development Council of the Conference Board at a meeting in New York. Eliška Meyers, The Program Director and I agreed that we would have the group fast cycle through the methodology on a relevant topic as a way of learning by doing. I asked Eliška for a headline question that council members would immediately recognize as a shared dilemma. We chose to focus on the question: How do we accelerate readiness for key roles in our organizations? Are you already thinking about how you would respond to the question? You may be addicted to expertise too. Let me suggest that we first probe the question for thinking traps.

First, the idea of “accelerating readiness” seems to suggest that we know what “readiness” looks like. If we know what it takes to be ready for key roles, then the question is ultimately about getting the right people into that future state faster. If we don’t know what it takes to be ready, then asking how to accelerate readiness doesn’t seem like the place to start.

It’s as if we’ve been preparing our future leaders in a conventional oven and now, we’re looking for the microwave. We get trapped by the question when we successfully find ways to speed up the process only to discover that we no longer have a taste for what we’ve prepared.

Another subtle trap in the question has to do with the idea of “key roles.” For the most part, our current organizational structures remain hierarchical and role specific. We tend to organize around highly experienced individuals who have tremendous authority to set direction and make investment decisions. One of the reasons people in Human Resources and Talent Development feel pressured is that in many cases our most highly tenured senior leaders are retiring and taking with them decades of accumulated expertise and experience that those left to fill their roles lack.

At the end of the session with the council, we considered a different question: How do we make our organizations less dependent on an individual’s talent and experience?

Counterproductive Expertise

If we can’t accumulate expertise through tenure on the job, what’s the next best substitute? Maybe we should start by questioning the value of accumulating expertise in the first place. Consider Jerry Useem’s July 2019 article for The Atlantic, At Work, Expertise Is Falling Out of Favor. Useem described the U.S. Navy’s “Minimal Manning” experiment in which a large number of specialized workers are being replaced with fewer problem-solving generalists. After describing several conversations with organizational leaders about the pitfalls of mastering a narrow specialization, Useem mused, “It would be supremely ironic if the advance of the knowledge economy had the effect of devaluing knowledge.”

David Epstein in his 2019 bestseller, Range; Why Generalists Triumph in A Specialized World, also makes the case that expertise can be counterproductive. Epstein offers examples and research that seem to fly in the face of recent advice based on Angela Duckworth’s work on Grit or Malcolm Gladwell’s writings on mastering a skill through 10,000 hours of dedicated practice. For example, Epstein writes about the work of Erik Dane of Rice University who coined the term, “cognitive entrenchment” to describe the downsides of domain expertise. Dane conducted research to demonstrate that accumulated domain expertise is associated with a loss of flexibility in problem-solving, adaptation and creative idea generation.

Be Questionable

Apply Questionable Intelligence to make sure you are asking better questions. Anyone who has been frustrated by the volume of useless options returned from a poorly worded Google search inquiry understands the importance of thinking clearly about what you want to ask. When experts frame questions, they inevitably infect the question with their world-views. If you go to an ear, nose, and throat Doctor (ENT) with a complaint about pressure behind your cheeks, you’ll be asked very different questions than if you went to a dentist with the same complaint. Unless that is, the dentist and the ENT had enough QI to set their expertise aside long enough to pose a few broad, open-ended questions.

If our future depends on leaders who can be effective under conditions of uncertainty and complexity, maybe it’s time society deemphasized knowing and expertise in favor of discovering and inquisitiveness.

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