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This column is part of Globe Careers' Leadership Lab series, where executives and experts share their views and advice about leadership and management. Follow us at @Globe_Careers. Find all Leadership Lab stories at

Thirty years ago, renowned author Edward de Bono compared a high-powered car driven to human intelligence: the car underperforms if the driver's skills are underdeveloped; intelligence underperforms if it does not have proactive, skilled thinking to direct it.

I would like to extend this analogy to team discussions: a cognitively diverse group of people bring enormous intellectual potential to problem solving, but this power is lost if it is not managed. Groups are vulnerable both to the mental failings of each individual and to the weaknesses that are particular to teams (such as groupthink and group polarization). High quality conversations do not self-generate any better than a fast car drives itself. "Thinking together," as author William Isaacs describes it, does not come as naturally to us as "thinking alone." When we think alone, we advocate for and defend our positions. When we think together, we seek deeper understanding. So what are the skills required to generate productive conversations?

Of the many, there are three that stand out, in large part because they don't come easily to us.

1. Spend 50 per cent of your time asking questions

Complex problems are defined more by what we cannot see, than what we can. Complexity is deciphered by buried cues that reveal intricate underlying causal relationships. But because our default is to simplify everything we think about, we are prone to disregarding the missing information that is hidden but crucial in assessing a complex problem. The only way around this vulnerability is to proactively ask questions – a lot of questions; more than we are accustomed to asking in our typical hurry to draw conclusions and jump to action.

In groups, we are even more reluctant to ask questions, for fear of looking ignorant or uninformed. Asking questions can be viewed by others as using up precious time that could otherwise be allocated to advocating an opinion. But effective team conversations are balanced between question asking and opinion stating. And just as important as the quantity of questions is their quality. We are adept at masquerading our opinions and judgments as questions, even if we are not consciously aware of it. We pose questions with preconceived assumptions that we are merely seeking to validate (the "don't you agree?" type of questions) or to influence (the "do you really think that will work?" type). The authenticity of a question – the degree to which it is legitimately truth-seeking – is a function of how willing we are to resist premature conclusions.

2. Suspend judgment

We rush to conclude because we have a built-in addiction to certainty. But complex problems defy definitive conclusions because they are always shifting and evolving as we interact with them. In other words, there is always missing information, so it behooves us to suspend judgment until we can determine that we have gathered at least enough information to make a reasonable guess about the outcomes of our decisions. Even then, after concluding and taking action, we have to retain the flexibility to revisit and revise. Complex problems demand a different kind of notion of truth than the everyday one that serves our straightforward problems. Complexity requires a notion of truth as provisional – always subject to revision.

Conversations that keep in mind the provisional nature of truth are more effective in seeking out alternative explanations that might fit the data better.

3. Think probabilistically

Probability keeps us and others honest. It's not specific probability estimates that are important; it's a probabilistic mindset that is key because it encourages us to assess our uncertainty. Assigning an approximate probability to the likelihood of our conclusions being correct forces us to estimate how much information we are still missing. For example, "This strategy will expand our customer base," is less meaningful than the same claim with an additional qualification, "With an estimated 60-per-cent likelihood."

We do not typically quantify our certainty in explicit terms that can be challenged by others. Yet provisional truth requires that our claims be qualified with an estimate of our certainty. Group participants should always be asking themselves, "How high a probability can I assign to my interpretation of events?" Likewise, they should challenge others to quantify the certainty of their claims.

High quality conversations are characterized by the kind of "thinking together" that takes practice, because skilled thinking (together or alone) does not just happen on its own. In fact, the unifying principle that underlies the three conversation strategies is humility. But not simple-minded, perfunctory humility. Tackling complex problems requires a deep and profound acknowledgement that each of us is not as smart as we typically think we are. When we think we have got things figured out, we rarely do. Edward de Bono wrote, "The biggest enemy of thinking is the feeling that our thinking is pretty good and we do not need to do anything about it." Only by maintaining awareness of our cognitive vulnerabilities can we unleash the power of conversation to deal with complexity.

Ted Cadsby is a corporate director, consultant, best-selling author, researcher and speaker on complexity and decision making. Formerly he was an executive vice president at Canadian Imperial Bank of Commerce. His latest book is Closing the Mind Gap: Making Smarter Decisions in a Hypercomplex World.

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