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Red Teaming

By Bryce Hoffman

Crown Books, 278 pages, $37.00

The Roman Catholic Church calls it the devil's advocate: When Mother Theresa was being considered for beatification, atheists Christopher Hitchens and Aroup Chatterjee were invited to testify against that honour being granted. For the Israeli Mossad, the country's intelligence agency, it's called the 10th man: If nine people in a critical meeting arrive at the same conclusion, the tenth person must disagree, no matter how improbable that line of thinking. For the CIA, it's the red cell, a group of contrarian thinkers who are urged to challenge conventional wisdom. For the U.S. and Canadian armed forces, it's called red teaming.

And your company should consider adopting the same concept, ensuring second thought in a time when complexity and psychological biases can get you in deep trouble. "Red teaming works. It works for small California tech start-ups and Japanese wealth funds. It works for old, iconic corporations and innovative disruptors. It works for non-profits and hedge funds. And it can work for your company too, if you let it," consultant and former journalist Bryce Hoffman writes in Red Teaming.

Mr. Hoffman wrote American Icon, about Alan Mulally's overhaul of Ford Motor Co., in which a critical ingredient was pressing senior executives to continually examine their plans and assumptions, fighting against complacency and group think, which had gripped that company and so many others. There were no formal red teams – just a no-nonsense CEO. But for many organizations, creating a formal team – whether ad hoc or permanent – makes sense to ensure critical thinking is unleashed.

Ideally, red teaming should begin after a plan has been developed but before it has been approved. You want time to modify it. The red team needs healthy discussion and a free flow of ideas. That is best achieved with divergent thinking, looking at alternatives, which ultimately morphs into convergent thinking. In that vein a good deal of the book is devoted to sharing techniques to achieve that balance.

Think-write-share involves everyone on the team thinking about the problem and writing down their ideas on index cards before sharing it with others. "By requiring a short amount of time for silent reflection at the beginning, team members have a chance to consider their responses before sharing them with the group. Writing those responses down is important, too, because it forces people to 'own' their answers. It is far easier to equivocate when people are just blurting out the first thing that comes to mind. This method also forces people to pre-commit to an idea and not modify their thinking based on what they hear from the rest of the group," he explains.

Another technique is Being Your Own Worst Enemy, a role-playing exercise in which the red team assumes the role of a competitor and tries to figure out how to react to your organization's plan. Ideally, the effort mimics real life, with the red team fed information in little bits, as your competitor might learn about the situation normally. That shows how your rival might react to counter your efforts.

The devil's advocacy approach requires the red team to take a belief that is central to your organization's strategy and develop the most compelling case that the opposite is true. It starts by the red team reviewing all the information the regular staff used to reach its conclusion and, if time, allows the group to conduct its own fact-finding.

"The red team does not have to be right – and just like a high school debate team, it does not have to believe in the position it is taking. The conclusion your organization has already reached may, in fact, be correct. But by conducting a rigorous Devil's Advocacy analysis, you will find out if that is really the case," he observes.

Red teaming started to develop its modern popularity after the Israeli military was caught flat-footed in the early days of the 1973 Yom Kippur War, due to a flawed strategy widely and fiercely embraced. The stakes of your own planning may not seem as high but red teaming still makes sense. This book captures the best ideas of this burgeoning new movement

Mark Mortensen of INSEAD discusses his findings about teamwork and how knowing what teams others are on can improve workflow

Special to Globe and Mail Update

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