Red Team Wisdom From Experts

My book Red Team: How to Succeed by Thinking Like the Enemy will be “launched” in one week. One lasting impression that I got from reading the red team literature broadly, and speaking with over two hundred individuals in the field, is the vivid and memorable phrases that red teamers use to describe their work. This colorful language was especially remarkable because it was not at all rehearsed; most of the people who I spoke with had never been interviewed about their professional experiences or insights into red teaming. Many red teamers lack public profiles because they are in the military or government (where interviews not controlled by public affairs officers are discouraged), in the private sector (where proprietary concerns and non-disclosure agreements prohibit much real transparency), or have no personal or professional need for attention.

One of the most impressive professionals who I was fortunate to learn from was Ellyn Ogden, worldwide polio eradication coordinator at the U.S. Agency for International Development. She was exposed to an intensive red teaming effort, which I detail in my book, by way of the University of Foreign and Military Cultural Studies (i.e. “Red Team University”) at Fort Leavenworth, Kansas. She summarized her impressions of red teaming to me as: “It definitely changed me. It helped me envision failures, and made me more confident and bold to raise matters with seniors…there’s this internal pressure on myself to speak when nobody else will.” That is a consistent characterization of the under-appreciated impact of red teaming: it changes, even temporarily, an individual’s meta-cognition (how they think about thinking) and awakens their obligation to question and challenge conventional wisdom.

I open each chapter in my book with a quote that I both loved and that summarized the central theme of the chapter: best practices, military, intelligence community, homeland security, private sector, and conclusion, “modesty, misimpressions, and the future of red teaming.” See the six quotes below:

“When you hear ‘best practices,’ run for your lives. The Titanic was built with best practices. It was faithfully operated in accordance with best practices.”

—Retired U.S. Army Colonel Gregory Fontenot, director of the University of Foreign Military and Cultural Studies (Red Team University), 2011

“When I pinned on my fourth star in December of ’08, I had a four-star coming through the receiving line to congratulate me and he leaned over and he whispered, ‘You realize that, from this point forward, no one will ever tell you the truth again.’”

—General Martin Dempsey, chairman of the Joint Chiefs of Staff, 2011

“A better channel should be established to convey speculative and/or unorthodox views of experienced analysts to the upper echelons of the various intelligence agencies. This might be done by means of gists of only a paragraph or two. Acquaintance with such views could provide officials with a better grasp of Soviet options and also serve to warn them of possible Soviet actions or intentions.”

—Robert Gates, Central Intelligence Agency analyst of the Soviet Union, 1973

“The one thing I learned doing red teaming was that no matter what technological barriers were in place, with just a little bit of surveillance you can figure out how to beat every single defensive system.”

—Bogdan Dzakovic, former head of the Federal Aviation Administration Red Team, 2013

“The best way to get management excited about a disaster plan is to burn down the building across the street.”

—Dan Erwin, security officer at Dow Chemical, 2000

“I have never learned anything from any man who agreed with me.”

—Dudley Field Malone, defense attorney in The State of Tennessee v. John Thomas Scopes, 1925

I would greatly welcome your recommended quotes as well.