Five Red Team Insights for Leaders and Practitioners

Six months ago I published Red Team: How to Succeed by Thinking Like the Enemy, which attempted to capture, describe, and define a relatively under-examined social phenomenon, red teaming. It is a “90-10 issue,” where 90 percent of people will not grasp what you are referring to, but are deeply curious, while 10 percent know what it is, and often have proprietary and closed minded conceptions of what is authentic red teaming. In the half year since the book release, I have given dozens of interviews with a range of outlets, and book talks at corporations, universities, military commands, and nonprofits. I also continued learning from red teamers who, unfortunately, I encountered only after publication. When you write a book about an obscure issue, the feedback that you receive after it is released makes you realize how little you knew as the author.

For those newly introduced to the concept, or the 10 percent who know it well, there are five new insights that I learned in the past six months about organizations and how they think about, and respond to, red teaming. These findings apply primarily to alternative analysis, or what is known as “decision-support red teaming,” and have less utility for “vulnerability probe red teaming,” such as physical or cyber penetration tests.

First, I have found that government officials, military commanders, and business executives do not believe there is a benefit to hearing or incentivizing challenging viewpoints. I wrote in my book that every senior leader claims to value critical thinking and dissenting viewpoints in the abstract, but remarkably few cultivate it within their organizations. These leaders authentically believe they are omniscient—“I know what’s going on in my organization”—or that they will be warned by someone about any consequential problems far enough in advance to change course. Of course, if you cannot cultivate critical perspectives for small issues, employees will not suddenly offer them for big issues as well. These leaders also believe that however they solicited ideas and processed them throughout their career is precisely how they should in the future. Beliefs of omniscience and unthinking reversion to long-held practices are the characteristics that define a leader unwilling to consider red team approaches or methods.

Second, it is harder to red team ideas than operations. Senior leaders recognize there are undoubtedly problems with how their organizations are structured, how they manage workflow, or the usefulness of their employees’ day-to-day tasks. These leaders are willing to apply red team approaches to such activities to attempt to improve overall performance. Yet, they become resistant to the notion that the ideational basis—the vision, analogies, assumptions—that underlies their institutions’ operations could similarly benefit from red teaming. Metacognition, or thinking about thinking, is inherently uncomfortable and challenging for anybody to do practically. I have found that senior leaders, less so lower-level managers, reflexively avoid ideational conversations, apparently with the belief that they are unneeded or irrelevant to how their organizations function operationally.

Third, it is harder to red team internally than externally. All organizations are more comfortable considering the perspectives of “the enemy” than exploring whether the most critical vulnerabilities lie within. This is especially prevalent within military commands, where many intelligence analysts are trained and tasked to think like the enemy, but no more than a handful actually poke holes in the assumptions of the command’s campaign plan. Similarly, there are teams of competitive intelligence professionals in many Fortune 500 corporations, trying to find information that gives them an edge over competing firms in their marketplace. However, when you ask a senior vice president why they allocate so many resources to better understanding their competitors, and often none to better understanding themselves, they revert back to the omniscient mindset mentioned above. They intuitively understand the need to red team those competing firms, but cannot conceive of why they might need to red team themselves.

Fourth, every organization faces remarkably similar problems. Bosses are unsatisfied with the analyses they receive, but fail to articulate precisely what makes them unhappy. Employees, in turn, attempt to mind-read their bosses, or intuit what they want through limited, often carefully-scripted, interactions. Employees always want more autonomy, more predictable management, and the feeling that their bosses will, at least, sincerely listen to their opinions. However, when this does not happen, almost no employee will speak their mind in front of their boss when it involves internal process matters. At the conclusion of every talk that I give, junior officers, GS-13s, and younger employees will introduce themselves, explain in pained detail their problems, and express their wish to red team their institutions. Though, after asserting enthusiastically “I wish we could do this!” they readily acknowledge it is unlikely. When I do follow-up with them, they cannot report any red team approaches or activities within the organization.

Fifth, senior leaders and managers need practical, simplified handbooks for how to red team. Such a handbook would provide guidance to: identify the most critical issues or vulnerabilities to the organization, answer the frequently-asked questions about the relative pluses and minuses of internal versus external red teaming, give advice for what they should be looking for when hiring an outside red team, present step-by-step instructions on how to most effectively use a red team, and finally provide a methodology to ensure that the problems uncovered by the red team are addressed in a prioritized and thorough manner. These are the sort of viable insights that every leader I have spoken with crave. While most still do not “get” the practical utility of red teams, those that do are open to pursuing them for their organization. But first, they need a handbook to persuade their own bosses that red teaming could be beneficial and is worth pursuing.