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Leadership and the art of the difficult conversation

Talk matters

The complexity of our times requires a new form of leadership. Instead of the all-knowing decision-maker, today’s leader must be practiced in the fine art of facilitating productive discussions.

Tweet thisToo many leaders default to consensus as an indicator of good decisions and to ending meetings on-time as an indicator of efficiency. But premature consensus and being ahead of schedule often yield superficial thinking and poor decisions. To be successful, the leader-as-facilitator must do battle with three obstacles in the path of productive conversations, each of them related to how people think.

Obstacle #1: Oversimplifying Cause and Effect

Global warming, financial crises, epidemics – these systemic issues contain many interacting factors that make them difficult to assess and predict. The structure of many corporate and public policy problems is not much different.

We are now living in two worlds simultaneously: World #1, characterized by problems that are structured in simple ways for which we are well-suited, and World #2, characterized by complex problems to which our basic intuitions are not well-adapted. Today’s leaders must be ever-cognizant of World #2. They must be ruthless in probing for complexity, and refuse to accept simple cause-effect explanations.


“Leadership is not about finding consensus. An effective leader needs to have the courage to embrace complexity.”

-Ted Cadsby, former executive vice-president of CIBC Tweet this


Obstacle #2: Jumping to Conclusions

We are accustomed to speedy thinking, because, historically it has been so successful for us. (For more on this, read Blink by Malcolm Gladwell.) Whereas the key to blinking is the speed with which close enough conclusions are drawn, the key to assessing complexity is the time-consuming exploration of multiple interpretations.

We are not accustomed to slowing the pace of our thinking and we are not designed to explore multiple interpretations once we’ve arrived at one that seems to make sense. This is compounded by the fact that we operate in a frantic environment driven by instant communication, where speed seems the only way to survive.

That’s why leaders must become adept at facilitating slow thinking, to coin a term from Nobel Laureate Daniel Kahneman's book Thinking Fast and Slow. Since the rush to certainty is deeply embedded in us, the job of the leader-as-facilitator must be to slow the pace of conversation, allowing for the time it takes to analyze complexity.

Leaders can become expert in avoiding the race to premature certainty by adopting a mindset of provisional truth. As the keepers of provisional truth, they keep in mind that explanations are always hypotheses – interpretations that are subject to being revised or rejected as new information becomes available. This mindset slows a team down and keeps thinking flexible by encouraging skepticism about the first reasonable explanations. Obstacle #3: Succumbing to Groupthink

The term groupthink was coined by Irving Janis in the early 1970s to describe the tendency of individuals in discussion to move toward unanimity: the motivation to conform overpowers the motivation to critically evaluate ideas that are supported by others. Groupthink expedites the rush to conclude by discouraging the use of the most important tool we have for complexity: challenging our interpretations and conclusions.

Leaders must therefore become facilitators of cognitive diversity. By leveraging different perspectives, they can manage groupthink out of conversations. They work hard to pull conversation from the brink of premature consensus by harnessing the power of other minds to challenge each other.

In today’s organizations, the quality of conversations determines the quality of decisions, and complexity is making the need for high-quality conversations all the more pressing. To be truly effective, leaders must learn to be facilitators. They must foster deeper and more nuanced analyses of cause and effect; to pace conversations in the spirit of provisional truth; and to leverage cognitive diversity to subvert groupthink.


Ted Cadsby, MBA, CFA, is a corporate director on both for-profit and not-for-profit boards, and principal of TRC Consulting. He is a former executive vice-president of CIBC, having run a number of Canadian and international wealth management businesses, as well as the retail branch network in Canada. He is the author of two books on investing.

Read the full article in Rotman Management Magazine. 

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