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What Separates Good Red Teamers from Poor Ones?

The intangible qualities that characterize a good red team can be difficult to measure but are arguably just as critical to success as a team’s technical proficiency. In fact, a technically proficient but arrogant red team may actually be less useful than a less proficient but more humble and adaptable one. After all, the less proficient but adaptable team can always contract the expertise it needs, particularly if it is first willing to consider and ask the right questions.
      In the following points, I identify some of the qualities that I think characterize good red teamers and good red teams. Don’t expect to find individuals who exhibit all of these criteria equally well, but do plan to avoid red teams that fail as a whole to embody these qualities.

  • It almost goes without saying that good red teamers are willing to question assumptions. They aren’t deterred by strong-willed experts, although good red teamers seek expert opinion as necessary (and it usually is).
  • Good red teamers are willing to consider arguments contrary to their own. They don’t “cherry pick” the evidence to support individual or organizational mindsets but seek and weigh evidence as objectively as possible.
  • Good red teamers know when to push and when not to push. Over time, an organization is likely to marginalize a red teamer who always claims the sky is falling. Maintaining credibility as a red team requires good negotiation, communication, and listening skills.
  • Good red teamers have thick skin. They can take and give criticism without getting upset. As above, this requires good negotiation, communication, and listening skills.
  • Good red teamers accept real-world constraints. They understand that perfect answers are usually not available and that the eighty percent solution is often the best course.
  • Good red teamers are naturally curious. They want to know how and why things do and don’t work.
  • Good red teamers don’t think in terms of simple cause-and-effect logic. They consider systemic interactions and higher-order consequences.
  • Good red teamers learn and adjust as they go. They are willing to acknowledge their mistakes.
  • Good red teamers have integrity. They are hard to bend and bully.

      Poor red teamers tend to lack several of these qualities. Particularly poor red teamers may strongly exhibit the opposites of these qualities. A very poor red teamer, for example, would accept the most common assumption as valid and would validate this assumption by finding only evidence to support it. Poor red teams tend to (1) lack the methods and tools necessary to red team effectively or (2) possess a myopic overconfidence that prevents them from learning and growing. I’ve seen both kinds.