Book Review: “Red Teaming” by Bryce Hoffman

4 min readSep 10, 2019

Groupthink or complacency can be devastating when developing great products. Having someone who plays or is a devil’s advocate is often a welcome aspect of the product development process. So-called “red teams” take playing devil’s advocate to the next level; the mission of such teams is to force businesses and people to think differently. Red teams will push businesses to consider alternative points of view or contemplate worst case scenarios. Red teaming makes us aware of our assumptions and cognitive biases, and offers us a means of overcoming them. “Red Teaming” is the brilliant book by Bryce Hoffman in which he examines the origins of red teaming and offers an abundance of red teaming techniques.

Red teaming exercises are applied in a wide range of contexts:

Cybersecurity — Companies hiring specialised red teams to attack their technology and exploit security vulnerabilities. Going beyond standard penetration tests, red teams will act as aggressively and unrestricted as any hacker would.
Intelligence — Whether it’s NATO, the CIA or the Israeli army, they all have teams dedicated to doing “alternative analysis”, set up explicitly to challenge prevalent assumptions within intelligence bodies.
Business — When developing a business strategy, companies often consider a best case scenario, assuming that everything will go to plan. Red teaming exercises can help in laying bare any strategic gaps or flaws, helping companies scan the business environment for both threats and opportunities.

Whatever the context, red teaming is all about rigorous questioning and thinking unconventionally. Red teams consists of people who’ve proven to be contrarian thinkers. These are the three phases of a typical red teaming exercise:

Using analytical tools to question the arguments and assumptions that too often go unquestioned during the regular planning process.
Using imaginative techniques to figure out what could go wrong — and what could go right — with the plan, in order to expose hidden threats and missed opportunities.
Applying contrarian thinking to challenge the plan and force the organisation to consider alternative perspectives.

Hoffman argues that adopting a red teaming mindset means that you’re not taking anything for granted, challenging everything and thinking the unthinkable. Red teaming is about looking at the future, and not getting burdened by the past. In the book, Hoffman also explain what red teaming is not:

A challenge to leadership — The red team’s role is to empower leaders and managers to make better decisions by providing them with a more objective analysis, a more comprehensive picture of the business environment, and alternative options to consider.
A creator of new plans — Hoffman stresses that red teams don’t make plans. In contrast, their purpose is to make existing plans better.
Always right (or has to be right) — Red teams don’t need to be right to be effective. They work more effectively in those environments where it’s ok to be wrong.

The question arises when it make sense to create a red team. Hoffman explains that although all red teaming starts out with a problem, not all problems require red teaming. David Snowden’s Cynefin framework is great tool to figure whether it’s worth doing a red teaming exercise:

Fig. 1 — David Snowden’s Cynefin framework — Taken from: https://www.researchgate.net/figure/The-four-contexts-of-the-Cynefin-framework-When-in-disorder-the-actual-context-is-not_fig2_283194976

If problems fall in the “complicated” or the “simple” quadrants of the Cynefin framework, they can be solved through a more straightforward, reductionist approach to problem solving. Problems that are “complex” or “chaotic” tend to be much more open ended and fluid, thus benefiting from a more radical problem solving approach. Ideally, red teaming should begin after a plan has been created but before it has been approved, while there’s still time to approve it.

Finally, Hoffman’s book contains a range of valuable techniques to consider as part of a red teaming exercise:

Problem Restatement — When faced with a challenge or problem, one of the best first steps in solving — even before you start thinking up possible solutions — is to examine and restate the problem.
Think-Write-Share — This technique is a way of ensuring that the red team begins with divergent thinking and moves to convergent thinking. The technique works like this: Start by asking team members to think about a problem or question, then write down their thoughts and share them with the group.
1–2–4-All — 1–2–4-All enables you to engage all team members simultaneously — irrespective of team size — in generating questions, ideas, and suggestions.
Argument Dissection — Dissecting an argument involves asking a number of questions of any argument that is used to justify a particular course of action, or that is offered as an explanation for a problem.
Key Assumptions Check — Hoffman explains how in red teaming, it’s essential to differentiate between facts and assumptions. Facts are things that are objectively true right now. However, most plans fail because they rely on unstated or unexamined assumptions.

Main learning point: Red teams or red teaming exercises can be extremely valuable for businesses, whether you’re creating a strategy or developing a new product. Red teaming breaks through groupthink and inertia, and will offer important alternative perspectives to consider.

Related links for further learning:

Book Review: “Red Teaming” by Bryce Hoffman

Written by MAA1