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The Superior Red Teamer’s Learning Checklist

Imagine for a moment that we can enter the head of an average red teamer. We might find a stream of thoughts that runs like this: “They were sure impressed with my red teaming. Too bad everyone doesn’t know how to red team. The world sure would be a better place. I see things other people miss. Too bad everyone doesn’t red team. I wonder why they don’t? It kind of makes me special, doesn’t it? I think I’ll get some new shoes today.”
      While we don’t know a single red teamer who wouldn’t mind getting some new shoes today, we also don’t know a single red teamer who doesn’t fall prey to this line of thinking, at least now and then. While we acknowledge that red teamers are indeed a superior breed, we also know that this type of thinking can hinder a red teamer’s ability to learn, because—shocking though it may be—red teamers don’t know everything, and they do make mistakes.
      We therefore encourage all red teamers to submit regularly to a learning checklist. It doesn’t have to be this one, but it should aim to get at similar points.

  1. What mistakes in judgment have I made recently? How did these affect my red teaming?
  2. What are my biases? How do they affect my red teaming? How can I moderate them?
  3. If I could go back in time, how would I change my red team assessments from a year ago? From five years ago?
  4. What do I still need to learn that would make me a better red teamer?
  5. What is the weakest part of my red teaming toolkit? What can I do to improve it?
  6. What single thing can I do every day to improve my red teaming skills and perspective? Am I doing it? Why not?

      Your goal should be to note improvement every time you run through the checklist. Of course, if the checklist leads you to believe that you would change nothing and have nothing to learn, you have a much deeper problem. Superior red teamers don’t focus on being superior; rather, they focus on learning and improving, and the best red teamers we know know they still have a lot to learn.