The Annoying Red Teamer: A Philosophical Approach to the Problem

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Painting of Diogenes and the Lantern.Red teamers can be annoying. Sometimes the annoyance is justified, sometimes not. After all, who likes to be told that they overlooked a key assumption or failed to implement a sensible practice? It’s not surprising that many people resist even the idea of red teaming.
      As red teamers, we often lament the shortsightedness of this resistance. What we don’t discuss very often is the uncomfortable fact that we often aggravate and perpetuate it. Yes, we can be self-satisfied and snobbish. And why not? We spend our days thinking about important things other people ignore, neglect, and overlook. Even when we’re not snobbish and condescending (honest!), we have to work twice as hard not to be perceived as such. That’s just the nature of the game.
      David L. Hall notes that philosophers must endure a similar burden. It’s worth reviewing some of his insights. Hall, for example, tells us that “philosophers seem always somewhat smug and condescending.”1 Much like red teamers, “We philosophers are far more aware than the rest of you of the dangers of bartering abstractions. You may rise to the level of critic, but we are the critics’ Critic.”2
      He continues,

Given the duties of this office, it should not be surprising that philosophers who do their job well just “can’t get no respect.” Besides the fact that nobody likes a critic, however dispassionate and solicitous are his or her aims, the critical nature of the philosophical task suggests that philosophers have no subject matter of their own. Philosophy is a stance taken with respect to this or that. This is but to say that philosophy is philosophy of. It is not so much propositional as prepositional: philosophy of being (metaphysics); of knowledge (epistemology); of art (aesthetics); of moral behavior (ethics); of history; of religion; of politics; of culture.3

      Again, that’s not unlike what we do as red teamers. We’re usually red teaming someone else’s system, someone else’s process, someone else’s ideas, which leads to this inescapable conundrum: “With respect to the practice of philosophy, it is always the case that someone else’s ox is being gored—be it one’s own colleagues or members of the extra philosophical world.”4
      As if that’s not enough, Hall concludes,

Perhaps the most unattractive feature of philosophy is that, unlike those mainstream scholars who are in the business of gathering new knowledge to extend the boundaries of our understanding, philosophers are excessively proud of what they do not know and powerfully committed to the task of persuading others that they ought to be at least as humble.”5

      While the people we red team are doing their best to build and operate things, we arrive to show them how the thing they have spent time and energy building can so easily be broken. If only they (the builders) could be as humble as us (the breakers), the world would be right (and we would be out of work).
      It leaves us in a tough position. Even if we’re not arrogant by nature, we can unintentionally project arrogance in our red teaming role. (Of course, fundamentally arrogant red teamers do exist, but that’s a topic for another post.) What can we do?
Foremost, we need to adopt a collaborative attitude (at the right time). When we’re “playing red,” we should be hardheaded and uncompromising. We’re not there to be nice or accommodate the client’s ego. That said, when we take our “red” hats off and talk to the client, we’re on the same team. A little tact and empathy goes a long way.
      Speaking of empathy, it’s worth remembering that the typical client has much more to do than red team his or her operations all day, every day. Try working as a full-time red teamer while also ensuring that the hiring process for the new HR manager is on track, your presentation to the board sets the right tone, and the new fleet maintenance contract avoids the pitfalls of the previous one. Oh, and by the way, the union is not happy with your latest contract proposal.
      Along these same lines, remember that when dealing with clients, we should always couch stories of previous red teaming engagements in appropriate terms. It’s tempting to show our clients how smart we are, but perceptive clients will wonder what stories you’ll tell about them once your work is done. As entertaining as they might be, the stories of how we totally exposed previous clients’ idiocy might best be reserved for private discussions among our fellow red teamers. Even then, we should respect OPSEC requirements.
      Another issue is how we, as a red teaming community, describe our art. This is a concern that transcends discrete red teaming engagements. Yes, we find problems, and yes, we uncover poor thinking, but there’s usually a better, less critical way to say the same thing. The last thing we usually want to do is stride confidently into the client’s office and assert that we’re there to find and fix his or her problems, implying that we’re going to find all the things that he or she should have already uncovered. It’s better in most cases to describe our role as a troubleshooter, mediator, or advisor—there to do all the things that the client would do if the client had the time and inclination. Indeed, the client who hires or staffs a red team effectively acknowledges just that.
      Finally, we need to recognize that we suffer from most if not all the same human biases and cognitive frailties as our clients. Our experiences as red teamers are worth something, to be sure, as are our toolkits and approaches, but it’s not as if our minds are inherently superior. It’s worth recalling as well that even the most sublime red teamers among us must someday die (memento mori); we’re certainly not above the Roman generals who were told, during the celebrations of their triumphs, “remember that you have to die.” An occasional dent to a red teamer’s pride can be a good thing. We should always be conscious that red teaming can become a conceit if not balanced by some humble, self-directed red teaming—a willingness to gore our own oxen, you might say.
      It’s a little grim to close with a reminder of our mortality and the goring of our own oxen, so let me close instead with a reminder of the valuable service we perform. Red teaming is coming of age, and an ever-increasing number of people recognize it as a valuable, necessary activity. In the past 20 years, red teaming has gone from an esoteric, frequently misunderstood virtuosity to a well-known skill. All of us can appreciate that; we just shouldn’t let it go to our heads … and heaven forbid that we ever evolve a philosophy of red teaming—now that would be truly annoying.

  1. David L. Hall, “What Has Athens to Do with Alexandria?”, Early China, Ancient Greece: Thinking Through Comparisons, 2002, p. 16. []
  2. Ibid. []
  3. Ibid. []
  4. Ibid. []
  5. Ibid. []

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