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Red Team Analysis: How to Think Like Your Opponent

When interviewing pickpockets, crime researcher Paul Ekblom learned they would hang around subway stations looking for victims. Not just anywhere, though. They’d stand near the signs warning the public of pickpockets. People who saw the warning would show the criminals where they kept their valuables by unwittingly checking their wallets. Ekblom’s short anecdote shows the value for analysts to think like their counterparts. It’s the guiding principle behind Red Team Analysis, a method that has applications beyond catching criminals.

Red Team Analysis allows you to better understand a counterpart’s strategy, anticipate their next move and prepare accordingly. As anything worth doing, it’s a skill that must be learned. Let’s dive into the practice at an organisational level before looking at practices applicable to everyday life.

What Is Red Team Analysis?

Red Team Analysis, also known as red teaming, is an imaginative analytical technique that attempts to replicate the thoughts and actions of an adversary. The goal is to examine the plans, processes and inner workings of another group or organisation, typically an adversary. It has its origins in the military but has become a staple practice in intelligence analysis as well. For this article, I’m mainly relying on a simplified version described in the CIA’s Tradecraft Primer.

Red teaming requires a change in perspective. Ordinarily, an analyst’s point of view is that of their own community; the friendly forces or the so-called blue team. As the name suggests, Red Team Analysis puts analysts on the opposing red team, which is a group of analysts who attempt to see the world through the enemy force’s eyes. They switch in their role from being an “observer” of the adversary to being an “actor”.

The method is particularly useful when facing a counterpart with a different culture, set of values, beliefs, mindset or experiences. In other words, it’s always useful because you mustn’t assume your opponent will act or respond the way you would. Red Team Analysis seeks to overcome this bias by tasking a dedicated team to take a perspective other than that of the organisation. But immersing yourself in the world of your opponent is harder than it sounds.

How to Perform a Red Team Analysis

Let’s take a look at how to staff a red team, what basic method the team can use and how they can benefit from changing perspectives.

Assembling a Red Team

If you fancy yourself a red team, you need to staff it. Preferably with people who have cultural knowledge of the entity you’re trying to emulate. Ideally, this knowledge shouldn’t come from books alone. If you want to understand a foreign competitor, it’s best to pick analysts who speak the language, grew up in the country or even worked at the organisation in question. If you’re analysing a criminal organisation, perhaps a former undercover cop can help out.

At the same time, an expert analyst without any subject knowledge can bring a neutral perspective to the table. The goal is to have a balanced team that can genuinely slip into the role of an adversary without getting bogged down in preconceived notions. Regardless of the team’s composition, there are methods to deepen everyone’s understanding of the adversary in question. But more on those later.

A Basic Methodology

Once the team is formed, they can get to work. There are many variations depending on your industry and goals. Here’s a basic five-step method used in intelligence analysis. Let’s consider it with a criminal intel perspective in mind as we try to understand who is behind a series of burglaries:

  1. Define your goals. What are you trying to achieve? What aspects of your counterparts do you want to understand better? What do you hope to learn about your own capabilities or vulnerabilities? For example, the crime analyst may want to gain better insight into where a group of burglars is based and uncover weaknesses in their own organisation and planning.
  2. Immerse yourself in your role. Red teaming is essentially a role play. So aim for realism. You do not pretend to be the adversary. You are the adversary. You respond or react to external stimuli as the adversary would. For example, what will you do if the police are setting up roadside checks in the area you’re doing “business”?
  3. Ask yourself questions. One way to help immersion along is to ask questions from a first-person perspective. It’s an often underestimated but powerful tool. For example: How am I going to execute the burglary? Which neighbourhood should I choose? What problems will I be facing?
  4. Make it concrete. Producing authentic products in your role as an adversary makes your results tangible. When analysing a competitive organisation you’d write policy papers and make recommendations to decide on a course of action. As a burglar, the red team could draft plans, maps and correspondence with associates.
  5. Reflect on lessons learned. Debrief based on your initial goals. What implications do your insights have for your own strategy? Where are potential gaps in training or capabilities? As a crime analyst, you may now better appreciate the planning and risk involved in a heist; an opportunity to provoke the burglars to make mistakes.

Bear in mind that Red Team Analysis is intended as an unapologetic and thought-provoking exercise. It’s supposed to be a raw view into the psyche of the opposing side. Try it. Where would you execute the perfect burglary? If you pick a target in your own neighbourhood, you increase the risk of being recognised and caught. If you pick one in a different town, you increase the risk of being detected while transporting the stolen goods back home. It’s fascinating how your thinking changes when you truly start to think like a criminal.

Perspective, Tactical Empathy & Mirroring

As I’ve alluded to above, analysts performing a Red Team Analysis can easily fall for the so-called mirror image problem. This occurs when they “impute to a foreign actor the same motives, values, or understanding of an issue that they hold.” Analysts must be able to overcome this mindset and truly see the world through the adversary’s eyes. Let’s dive a bit deeper into this concept by discussing perspective, tactical empathy and mirroring.

Perspective

According to former CIA covert operative (read: spy) Andrew Bustamante there’s a crucial difference between perception and perspective. Perception is you sitting across someone, making casual judgements from a distance. Trapped in your own view of how things are and how they should be. It’s when you shift your mind to their perspective that things change.

Now you’re “observing the world from outside of yourself”. You begin to think about what their life is actually like. What it means to be them with all their feelings, hopes and fears. Based on how they present themselves, their living circumstances, jobs and families. What you gain from making this shift, Bustamante explains, is a considerable information advantage.

The US Army’s The Red Team Handbook describes two methods that are of interest here. One of which is the applied critical thinking tool called Four Ways of Seeing. Developed by the army’s own University of Foreign Military and Cultural Studies it’s ideal to analyse two groups; how they view each other and interact. Each point of view is explored. In the end, we can examine what they both have in common, how they differ and where there might be misunderstanding.

How Team Bob
Sees Team Bob
How Team Bob
Sees Team Sally
How Team Sally
Sees Team Bob
How Team Sally
Sees Team Sally

A complementary method is the Cultural Perception Framework. It’s designed to “discover another culture’s underlying tendencies, habits, values, and beliefs and avoid mirror-imaging”. The method expands on the Four Ways of Seeing by asking how land, climate, water, food or natural resources impact the culture in question. Given the physical environment, what effect do those circumstances have on the culture’s economy, the prevailing social structure, the political and the belief system?


Tactical Empathy

Former FBI hostage negotiator Chris Voss takes this idea to the realm of negotiation. Dubbed tactical empathy, he teaches this skill as a means to explore a counterpart’s state of mind through conversation. This can be useful when you’re having regular exchanges with a competitor. Again, the information advantage is gained by reflecting people’s words, thoughts and feelings back to them to make them feel understood.

Compared to Bustamante’s perspective, tactical empathy is a much more methodical approach. It entails mastering several communication skills such as labelling and calibrated questions. Check out my review of his book and MasterClass online course if you want to learn more. Beyond that, the main takeaway is this: The ability to grasp someone’s point of view is not to be confused with agreement.

Mirroring

A similar concept is mirroring. It’s the art of studying your counterpart closely and reflecting back their words, actions and characteristics. As Robert Greene points out in The 48 Laws of Power, “everyone is wrapped up in their own narcissistic shell”. Holding up a metaphorical mirror to them lowers people’s resistance. There are three different levels of mirroring that are of interest in Red Team Analysis.

First, there’s the mirror of physical appearance as a gateway to someone’s mind. The way people dress, their body language or ticks. As Edgar Alan Poe once pointed out, merely mimicking someone’s facial expressions can be a portal into their mind.

When I wish to find out how wise, or how stupid, or how good, or how wicked is any one, or what are his thoughts at the moment, I fashion the expression of my face, as accurately as possible, in accordance with the expression of his, and then wait to see what thought or sentiments arise in my mind or heart, as if to match or correspond with the expression.

Edgar Allan Poe

Second, we can mirror what’s beyond the surface of appearances. People’s mindsets, values, worldviews, ideals, thoughts and experiences. As Voss points out, there’s tremendous value in figuring out someone’s (metaphorical) religion; i.e. their deepest-held beliefs. These can be mirrored through words and actions. And yes, this is all quite reminiscent of method acting.

Thirdly, we can mirror the actual words and actions of others. In warfare, mirroring actions is used to better understand what the enemy is up to. When it comes to penmanship, instructor Gary Provost recommends copying other people’s writing. This way you become aware of the choices they had to make and gain valuable insights into their creative process and decision-making.

Risks & Benefits of Red Team Analysis

As you can tell by now, you can really nerd out on Red Team Analysis. Careful, though. Here are some risks and benefits you should consider before going too deep down the rabbit hole.

Risks

One of the main risks of Red Team Analysis is overconfidence in the results. The more authentic the end product, the more convincing it will seem. Even though the results cannot project all possible courses of action of an adversary. Bear in mind: You can’t even predict the behaviour and decisions of your own boss with certainty. So make sure you compare findings with real-life developments and whether they actually take shape.

Then there are other risks the British Ministry of Defense describes in their very own red teaming handbook. Red Team Analyses tend to be “time-consuming” and “resource hungry”. Their antagonistic nature can lead to resentment and mistrust within an organisation. You should also consider the danger of a red team being weaponised to further a personal agenda. That smug manager on floor six…let’s get his project red-teamed to put him back in his place.

Benefits

There are clear benefits, though. It’s become a truism that we’re prone to a plethora of cognitive biases such as the Endowment Effect. We’re much more attached to ideas if we own them. That makes it hard to give them up, that is to change our minds. Then there’s groupthink, the tendency to sacrifice critical thought on the altar of group cohesion. An external and unbiased team with no involvement in a project can bring in fresh and contrarian perspectives.

Red Team Analysis prompts a team to take ownership of new, often controversial views. Even if the group is staffed by people who had prior involvement. Similar to Tenth Man Rule or Premortem Analysis, the method legitimises criticism and dissent. If established with Fingerspitzengefuehl, red teams can expose shortcomings and weaknesses in planning and decision-making. Without the critics being branded as troublemakers.

Red Team Analysis in Everyday Life

A proper Red Team Analysis works best for organisations with lots of resources. As a civilian, you’re not going to get a bunch of analysts together to form a clandestinely operating red team that spends an ungodly amount of time putting themselves in the shoes of the used car dealer who’s trying to sell you a station wagon.

But you can use red teaming principles to give you an edge in everyday life. Let’s see what such a perspective change could look like. Forget the car dealer, though. We’re going to put ourselves in the shoes of a stormtrooper on Death Star duty and cross our fingers that this example won’t turn out as cringe as it sounds.

A Stormtrooper’s Perspective

Congratulations, you’re now a stormtrooper on the Death Star. You wake up in the morning and put on your armour, a black body suit with pieces of white plastic stitched onto it. You’re sweating as soon as you’ve geared up. Your blaster doesn’t come with a sling so you will have to carry it the whole day. Your helmet is light but bulky. Get used to it. You’ll rarely be allowed to take it off during your ten-hour shift.

The Empire Strides Back and Forth

Your ten-hour shift consists of patrolling the endless, cold and sterile corridors of a 160 km wide orb floating in space. Up and down. Back and Forth. The orb’s purpose is to bring death to whole planets. But for you, most days are boring and quiet. The only actual faces you see are those of your superiors. Nothing happens. That is until the enemy suddenly appears. In the form of a space wizard mind-controlling you and killing your comrades with a lightsaber. A bloody sword.

Generally, your enemies seem to be good shots, which can’t be said of your peers. How are you supposed to restore order to the galaxy if you can’t hit a blast door? Hundreds of your comrades have already died next to you. You lost faith in your training and equipment a long time ago. The Empire is a bureaucratic behemoth. They can build a Death Star in no time. But the procurement of more effective body armour and blaster slings is taking forever.

A New Cope

Lunchtime is the best part of your day. When you get to enjoy your Penne all’Arrabiata in the Death Star canteen. Other than that, your boss is a tyrant who reports to a tyrant who reports to yet another tyrant. In turn, that tyrant reports to his boss; a lord in a black mask who chokes people to death without even touching them. You’ve never met the guy but rumours are the boss reports to a big boss who can shoot lightning from his hands.

You can still bear this dreadful job. But only because you were indoctrinated since the moment you were born. And there’s really no way out except death. However, you’ve retained a small bridgehead of good. All hope is not lost. If the opportunity came up, you’d defect in a heartbeat. You’ll join a resistance. Even if you’d only end up playing a goofy, underused supporting role in a botched trilogy.

Everyday Red Teaming

You’ve made it through the example. Excellent. Now imagine your personal real-life equivalent to a stormtrooper. The coworker who’s giving you the vibes of a psychopathic bully. Or that shifty-looking car salesman you don’t trust. Imagine what you could accomplish if you spent less time judging and debating them. And more time exploring the little slices of heaven and hell their minds inhabit.

Closing Thoughts

A thorough and well-executed Red Team Analysis is an extreme way of putting yourself in the shoes of your opponents. Such a complete immersion into someone else’s world requires skill and experience.

The basic red teaming principles, however, can be easily applied every day. Maybe don’t start by thinking thief in a heroic attempt to bust the pickpocket gang at your local train station.

But if you meet someone who suspiciously looks like your next arch-nemesis, put yourself in their shoes with a bit of imagination and empathy. They may end up not looking like an opponent after all.