Book Review – Red Team How to Succeed By Thinking Like the Enemy

The truth is, I’m only partially through reading this book, but it is so good that I need to share this with you now to remove the mental “Blogging tic” and be totally free to absorb its goodness.

The book is: Red Team How to Succeed By Thinking Like the Enemy, published in November and written by Micah Zenko.

Zenko has a lucid, logical, vivid, easy writing-style, and the book is grounded in facts and littered with real-world examples, borne out of hundreds of interviews with Red-Team practitioners.  .

Zenko has piercing observational skills, which enables him with sniper-like precision to highlight what works, what doesn’t, and why.

Zenko begins with laying out the Red Team raison d’être by deftly employing the narrative of the Catholic Advocatus Diaboli. An elegant and succinct idiom is used to frame the theme of the book: “You cannot grade your own homework”.

Zenko details how Red Team’s should conduct themselves and it was personally revelatory and heartening to read the traits of a good Red Teamer – some of which I had previously considered more a hindrance for me personally.

Here’s some examples:

Fearless Skeptics with Finesse

its members should be somewhat outside of the norm.

The best red teamers tend to be self-described “oddballs” and “weirdoes,” as well as critical and divergent thinkers inherently skeptical of authority and conventional wisdom.

Able to break free from biases and subjective mores that constrain our thinking.

Able to question the “existence bias” otherwise known as the Status quo bias.

Successful red teamers tend to be quick on their feet, adaptive, self-motivated, and fearless in pursuing what they believe to be true, yet also innately curious and willing to listen to and learn from others

Able to identify and internalize the motives and values of an adversary so that they can become that adversary.

An additional element in the mix of traits necessary to successful red teaming is that team members tend not to be “climbers,” Unlike those who are willing to do or say whatever is needed to advance their careers, they should prioritize speaking their mind over being a team player, or they have accepted that they have hit a ceiling above which they will not be promoted.

The second variable that correlates to successful red teaming has to do with experience. There is a reliable, recognizable set of educational and professional experiences that lend themselves to the skills required for red teaming: being widely read (especially in history), having held multiple postings in a profession, and demonstrating the ability to brief and write exceptionally well. A common refrain enunciated by red teamers across a number of fields was that, to adequately convey and emphasize their points, effective practitioners of the art of red teaming have to be able to tell a story.

The third and final attribute that accompanies successful red teaming is that its practitioners must possess tacit interpersonal communication skills that enable them to work well with each other. Several directors of red team units use the phrase: “You must be able to play well in the sandbox with others.” Retired Air Force Colonel James Baker directed the Chairman of the Joint Chiefs’ Chairman’s Action Group (CAG) from 2007 to 2011, which, among its other duties, conducts alternative analyses for the military’s most senior uniformed official. Baker pointed out the contradictions in finding good red teamers: “you bring someone on board who is used to being the smartest person in the room, but now they aren’t, and they have to be willing to listen and learn.” Moreover, “you want to hire people who are outsiders and think differently, but haven’t given up on the institution yet.”

OK, I’ll stop there, I’ve already lifted too much of Zenko’s text and could go on all night.

Zenko goes on to detail seventeen Red Team case studies drawn from the military and national security field, but that have “profound applications for the private sector as well.”

This is a super and thoroughly enjoyable read, it’s not dry and academic, but immensely informative, vibrant, alive and most importantly – real.

Zenko’s passion, knowledge and enthusiasm for Red Teaming positively vibrates from the pages and is delightfully infectious.

This book came at just the right time for me and I’d encourage you to grab a copy.