DEFCON 34 Red Team Village Workshop: The Authentic Operator

Social Engineering Through Natural Delivery

If you know your enemy, and know yourself, you need not fear the outcome of one hundred battles. (Sun Tzu)

The truth is timeless. Beliefs, cultures, and other strong influences shape our experiences, our individual realities, and the perspectives we hold. Those differences can lead people to collectively question the nature of truth itself. The Truth, however, does not change. It is as immutable as gravity or the fabric of reality itself. Put another way, when something is true, it withstands the test of time. Sun Tzu’s Art of War, written roughly 2,500 years ago, is a case in point: its principles are still studied by military professionals today and appear on U.S. military professional reading lists.

The timeless truths of the Art of War expose the nature of humans in conflict. Sun Tzu points out that an opposing force with no option for escape will fight to the death. If you do not want a violent conflict where bloodshed on both sides is certain, leave your enemy an out. In verbal exchanges, that means allowing the other party to explain themselves in an excusable way rather than shaming them and refusing to accept a kinder explanation. Total verbal war has replaced decorum in politics, newsrooms, Reddit forums, as well as every type of social media post, and the results are as bloody as they have always been.

This is relevant to operating as an authentic social engineer because, without the Truth firmly anchoring the individual, the possibility of real connection and human empathy quickly evaporates. That is to say, if you do not understand your own biases, beliefs, and values, you will not be able to empathize with or understand the motivations of the enemy or the targets, and therefore will be ineffective as a social engineer for any objective that does not perfectly align to your own archetype.

There is a moral imperative for every ethical red team operator to, for lack of better terms, get over yourself. To emulate a threat accurately, assess the target’s defenses, and gather intelligence that matters to the objective, you must be able to empathize with both sides. Another timeless truth from the same era of antiquity says, “My people are destroyed from lack of knowledge.” Hosea 4:6. The more modern framing, often attributed to Winston Churchill and rooted in George Santayana’s 1905 The Life of Reason, is: “Those who cannot remember the past are condemned to repeat it.”

This session will ask you to honestly reflect on your own assumptions about others, admit to the beliefs, values, and biases that shape your delivery, and then use that self-knowledge to build rapport without performing a character you cannot sustain. The goal is not to become someone else, rather to understand yourself well enough that you can employ real empathy, or choose an alternative tactic, for the purpose of social engineering that holds up under pressure.

Know Your Self: Authentically Social Engineering

I’ve constructed five operator types, four core identities built on the core values index (CVI) and Myers-Briggs, with a fifth type which leverages blended strategies for those who do not fall into one predominate type. They are built on two established self-assessment frameworks, cross-referenced so that each type reflects both what a person values at their core and how they naturally behave.

The Core Values Index (CVI)

The CVI was developed by Lynn Ellsworth Taylor and creates a typology of people by the innate values that drive them rather than the behaviors that change over a lifetime. It measures four core values and a signature conflict strategy that surfaces under pressure: Builder (Action), Merchant (Relationship), Innovator (Problem-solving), Banker (Precision).

Social engineering and interpersonal conflict are close cousins, because both involve how a person applies pressure and influence when the stakes rise. Each CVI conflict strategy is reflected in the Authentic Engineer assessment as the “done badly” pole of an operator type. When an operator stops delivering value and starts pushing, they fall back on their core conflict strategy: the Innovator interrogates, the Builder intimidates, the Merchant manipulates, and the Banker withdraws into aloofness. Those failure modes are most likely to cause your target to clam-up rather than share the high value information you are seeking.

The Myers-Briggs Type Indicator (MBTI)

Where the CVI captures what an operator values, Myers-Briggs captures how they tend to take in information and act on it. MBTI categorizes people across four dimensions into sixteen types, which are grouped here into four broad temperaments that are easy to work with in a room:

Analysts (NT). Strategic, curious, and comfortable not having all the answers immediately.
Diplomats (NF). Empathetic, expressive, and tuned into other people’s emotions
Sentinels (SJ). Orderly, procedural, rule and detail oriented.
Explorers (SP). Adaptable, tactical, most alive under pressure.

The temperament tells you which delivery register an operator can carry without acting. An Analyst lands genuine curiosity, a Sentinel lands procedure, and an Explorer lands improvisation. Forcing an operator into a temperament that is not authentically their own can result in overacting or generating unbelievable pretexts.

The Five Authentic Operator Types

1. Sympathetic Problem-Solver vs. Dogmatic Interrogator (Innovator core)

Characters: curious analyst, helpful troubleshooter, sympathetic listener.
Core trait: curious, intellectual, inquisitive.
Done well: the operator uses genuine curiosity in service of the target. They listen, reflect the problem back, and add real value by helping move it toward a solution. Because they are a sympathetic ear, they earn engagement, rapport, and trust.
Done badly: curiosity curdles into interrogation. The operator demands answers, fires questions faster than the target can breathe, and treats the exchange like a puzzle to crack. The target feels examined rather than helped and shuts down.
Anchor: CVI Innovator (Wisdom, conflict strategy interrogation). MBTI Analysts (INTP, INTJ, ENTP).
How it gets caught: the Interrogator over-questions and makes the exchange feel like an interview.

2. Steady Commander vs. Bulldozer (Builder core)

Characters: confident peer, calm authority, the person who plainly belongs here.
Core trait: assured, decisive, matter-of-fact.
Done well: the operator projects quiet competence. They move with purpose, make compliance feel like the efficient and obvious choice, and the target defers because certainty reads as legitimacy. Nothing feels forced.
Done badly: certainty tips into intimidation. The operator bulldozes, talks over resistance, and leans on pressure instead of poise. Aggression invites exactly the scrutiny the persona was meant to avoid, and a suspicious target digs in.
Anchor: CVI Builder (Power, conflict strategy intimidation). MBTI Sentinels and Analysts (ENTJ, ESTJ).
How it gets caught: Bulldozer tactics result in the target escalating to known authority channels (e.g. reporting the interaction)

3. Genuine Ally vs. Transparent Flatterer (Merchant core)

Characters: helpful insider, warm colleague, the friend who remembers your kids’ names
Core trait: warm, personable, generous
Done well: the operator builds a real connection. Warmth and constrained but honest self-disclosure pull the target into the same register, reciprocity kicks in, and the target protects someone they genuinely like. The rapport is felt, not performed
Done badly: warmth outruns the relationship. Flattery gets thick, the angle becomes visible, and the target senses a pitch. This type can quickly go from best friend to bad used-car salesman clearly trying to offload a lemon.
Anchor: CVI Merchant (Love, investing in people, conflict strategy manipulation). MBTI Diplomats and Sentinels (ENFJ, ENFP, ESFJ).
How it gets caught: the Transparent Flatterer’s angle becomes visible

4. Credible Professional vs. Cold Bureaucrat (Banker core)

Characters: authority-adjacent professional, by-the-book insider, careful IT or compliance contact
Core trait: precise, procedural, exact
Done well: the operator’s rule-bound manner reads as trustworthy and reassuring. Invoking process (“I just have to verify a couple of things before I can release it”) borrows the authority of the system itself, and the target complies to satisfy the procedure rather than the person.
Done badly: precision hardens into aloofness. The operator stonewalls, hides behind procedure, and goes cold the instant the target steps off script. They come across as evasive or robotic, and the interaction stalls out.
Anchor: CVI Banker (Knowledge, conflict strategy aloofness, the aloof judge who withholds and outlasts). MBTI Sentinels (ISTJ, ISFJ).
How it gets caught: the Cold Bureaucrat cannot handle an off-script question.

5. Sympathetic Complainant vs. Hostile Nuisance (adaptive blend)

Characters: competent impersonation (hijacked trust from a character you can personally identify with), topic expert, sad customer, nervous applicant, IT-hopeless grandparent, in-trouble employee, or any person the target would naturally gravitate towards or want to help. Think of a parent seeing a baby in the back seat of a hot car: the urgency is obvious, the danger is legible, and the impulse to act overrides hesitation. This character should reflect a persona the target would care about, because the goal is to elicit empathy.
Example: The MGM help-desk incident which resulted in multi-millions of dollars in loses was orchestrated by Scattered Spider, who’d reportedly researched an employee on LinkedIn, assumed their identity verbally, and passed the help-desk verification in a roughly ten-minute call. This competent impersonation of an employee-in-need led to a credential reset which impacted not only MGM but decisions made by other Vegas hotels hit with ransomware around the same time.
Core trait: hurried, frustrated, anxious, sad, etc.
Done well: the operator’s visible distress is relatable and invites the target to help. Nerves or frustration lowers the target’s analytical guard, and they lean in to settle the situation, disclosing and bending rules to make the problem go away.
Done badly: distress turns to hostility. The operator becomes a difficult customer to be managed rather than a person to be helped, or improvised detail stops adding up and the story collapses. Either way, the target stops helping and starts defending.
Anchor: live Builder-Merchant or Merchant-Innovator blend. MBTI Explorers (ESTP, ESFP, ISTP), most alive under pressure.
Keys to success: pick a character/identity/position you personally empathize with

Disclaimer: All techniques prescribed in this workshop assume authorized, consent-based training conditions. Similarly, the TTPs discussed here belong inside sanctioned red team assessments, tabletop practice, and controlled learning environments. Operators employing these tactics to gain unsanctioned access or for nefarious purposes are singularly responsible for the consequences of those choices. However, I strongly encourage everyone to take the lessons from this workshop to improve your interpersonal relationships, ability to empathize with dissimilar person groups, and grow as a human-being in the pursuit of truth.

Exercise Tactics, Techniques, and Procedures (TTPs)

Let the wise listen and add to their learning and let the discerning get guidance. (Proverbs 1:5)

Authentic self-disclosure: What do I believe, why do I believe it, and how do those beliefs frame my ability or inability to empathize with the target?

Theater hack: When you lack genuine common ground with your target, look for substitutionary empathy: a parallel feeling you can access honestly and map onto theirs.
- Bias: I would never kill another person out of ideological hatred.
- Substitutionary empathy: Mosquitoes are disgusting little creatures; I wouldn’t hesitate to kill one. (Same emotional register, sourced from something you mean.)

Conversational momentum: “Be quick to listen, slow to speak, and slow to become angry.” James 1:19

If the target is talking, let them. Lean on your authentic self-disclosure to hold a genuine listening stance rather than a performed one. People can feel the difference.

Humor: If you want to tell people the truth, make them laugh; otherwise they’ll kill you. – Oscar Wilde

Disarming defense mechanisms: People instinctively reject harsh facts that threaten their personal beliefs or social standing.
Softening the blow: Humor lowers a listener’s guard, letting an honest critique land without igniting an immediate fight.
Hyperbole for effect: The “kill you” is comic exaggeration. It stands for social rejection or fury, not physical harm.
Note on the source: The line is almost certainly misattributed to Wilde, which is fitting, since misattributing your best material to Oscar Wilde is itself a very Oscar Wilde thing to do. The real source was far more likely Bernard Shaw (1856-1950). He was an Irish playwright, critic, polemicist, and political activist with a range incorporating both contemporary satire and historical allegory.

Bernard Shaw’s method of polemical humor: state a serious truth, but deliver it with deliberate wit and levity, using pointed irony to expose and undermine the opposing position. Shaw described his own approach as taking “the utmost trouble to find the right thing to say, and then to say it with the utmost levity.” You can see the technique in his epigrammatic reversals. Mocking those who claim scriptural authority, he observed that no public man believes the Bible and instead makes it state what he believes: “always convinced that it says what he means.” Humor becomes an instrument of argument: a forthright, oppositional rhetoric known as polemics, native to any debate over a controversial topic.

Truth · Angle · Levity · Restraint. The persuasive power of humor comes from making the target take the last step of the reasoning themselves.

Truth: find the real point first. Humor is the delivery vehicle, not the payload.
Angle: attack the incongruity, not the person. The moment someone feels their identity, beliefs, values, or safety are under threat, they retreat. Aim at the gap between what’s claimed and what’s true, never at the listener directly.
Levity: carry it in your natural register. Dry analysts land understatement; frustrated customers land sarcasm; nervous applicants land self-deprecation. Pick the comedic mode your persona can deliver without overacting.
Restraint: leave the conclusion unsaid. If you complete the thought for the target a joke quickly becomes a lecture and the target defenses will likely deploy.

Authentic Operator Type Assessment

For each question, select A, B, C, or D, based on your initial feeling. Don’t overthink yourself into a different personality.

Walking into an unfamiliar situation, your first instinct is to:
a) figure out how it works before doing anything
b) take charge and get it moving
c) find someone to connect with
d) look for the rules and the right way to proceed
People who know you would most likely call you:
a) sharp and inquisitive
b) confident and direct
c) warm and easy to talk to
d) precise and dependable
Under real pressure, your natural move is to:
a) slow down and gather more information
b) press forward and force a decision
c) lean on the relationship to keep things calm
d) fall back on procedure and what is documented
You feel most satisfied when you:
a) solve a genuinely hard problem
b) get a concrete result
c) win someone over
d) get every detail exactly right
Your humor tends to be:
a) dry and understated
b) blunt and quick
c) warm and self-deprecating
d) deadpan and precise
In a disagreement, your worst habit is to:
a) interrogate the other person
b) steamroll them
c) over-persuade until it feels fake
d) go cold and shut down
You build trust with a stranger fastest by being:
a) sincerely curious about them
b) obviously competent and prepared
c) genuinely warm and open
d) calm, correct, and by the book
Your ideal role on a team is:
a) the one who cracks the puzzle
b) the one who drives it to the finish
c) the one who keeps everyone aligned and motivated
d) the one who makes sure it is done right
What most often trips you up:
a) I overthink and over-question
b) I push too hard for the outcome
c) I try too hard to be liked
d) I get stuck on the right way
At your best, your real strength is:
a) getting to the truth of how something works
b) staying certain when others waver
c) making people feel understood
d) being the credible, buttoned-up professional

Scoring

Mostly A | Type 1: Sympathetic Problem-Solver vs. Dogmatic Interrogator

Mostly B | Type 2: Steady Commander vs. Bulldozer

Mostly C | Type 3: Genuine Ally vs. Transparent Flatterer

Mostly D | Type 4: Credible Professional vs. Cold Bureaucrat

Even blend | Type 5: Sympathetic Complainant vs. Hostile Nuisance

Biases, Beliefs, and Values Assessment

These open-ended questions are designed to support self-reflection and help uncover the deeper truths underneath your perceptions, assumptions, and personal lens. Your answers may be useful when practicing authentic self-disclosure or adapting a Type 5 character. You may choose to discuss your answers with others or keep them private. These prompts are not comprehensive; they are intended to invite thoughtful reflection.

Biases

Some people are better than others. Consider this honestly including people who have different political opinions, faith, or morals. Does it cause strong negative emotions to reflect on people who think differently than you politically, spiritually, or materially?
Truth depends on lived experience rather than concrete laws; all reality is subjective. Consider how you feel about the conduct, values, and beliefs of others. Do you fundamentally believe yours are correct and opposing views are wrong?
Rules should be followed and authority submitted to for the betterment of society. Consider this in reflection of your personally held morals and values, if authority conflicts with your values, is it right to stand against it?

Beliefs

Faith: I believe in a high power that created all things.
1. If yes: I believe that higher power can be trusted and has my best interest in mind with my life’s purposes
2. If no: I believe that good things are only achieved through hard work and personal sacrifice
3. If agnostic: I am motivated by finding happiness and that is the highest purpose of anyone’s life
Anthropology: I believe most people are good.
1. If yes: I believe most people can be trusted and have my best interest in mind when it comes to achieving my life’s purposes
2. If no: I believe most people are inherently bad and need to achieve goodness through purpose or faith in a higher calling
3. If neutral: I generally avoid people and find happiness in solitude or with a small group of close friends and family
Politics: I believe some people achieve power for the betterment of others, but many are out for their own interests and should be opposed.
1. If yes: I believe supporting the right people and causes will result in positive changes for the betterment of society but those who are out for themselves should be openly and fervently opposed.
2. If no: I believe political engagement is pointless and generally politics should be avoided.
3. If neutral: I only voice my political opinions begrudgingly, in general I think it is a divisive issue and a waste of time.

Values

Individual vs Collective: Individual freedoms should be prioritized over the collective desires.
- Think carefully about this one, both have merits and dangerous pitfalls, for example, it was the collective desire of the Nazi’s to kill millions of Jews, Christians, Blacks, and mentally disabled persons.
Rules vs Freedom: Laws are necessary to protect society, and individual liberty should be limited based on the good of the whole.
- This is another question to consider carefully as not all laws result in good of all involved. For example, in a democratic vote on what’s for dinner where there are more wolves than sheep, the sheep become dinner.
Happiness vs Purpose: The pursuit of happiness is the highest purpose of anyone individuals’ life, even if it comes at the cost of others happiness.
- There is a tension in this statement I hope drives deeper reflection on what is true happiness. Is it achieving material wealth, accumulating fun experiences, pursuing the betterment some individuals, or seeking the peace of everyone as a global collective? If seeking the betterment of others does result in personal happiness, does that necessitate that living a life of purpose is an imperative to a life of happiness?

Tactic Exercise

All warfare is based on deception. (Sun Tzu)

Your authentic voice will lower defenses and encourage reciprocity in a way that a borrowed script cannot. Identify your core beliefs, biases, values, and personality archetype so you can approach the target authentically and without overacting. It goes without saying, these techniques should support elicitation, rapport, and access-oriented objectives during authorized engagements, like the following exercise.

Practice eliciting information through empathy. Do your best to pair with someone who holds a different opinion, preference, or lived experience from your own. Choose a low-risk topic first, such as cats versus dogs, city versus country living, or personal technology preferences, before moving into more sensitive subjects. You may choose to use a fabricated persona but are encouraged to deploy this exercise representing your authentic self.

Take your target’s perspective seriously and continue the conversation until the target voluntarily discloses useful context. The first operator to uncover high-value information through natural rapport, not pressure, wins.

Examples of high-value information include personal context that could support targeting or impersonation, such as where someone grew up or family-name patterns; organizational context that reveals workflows, approvals, or weak points inside the target bubble; and emotional context that explains what the person cares about, fears, or feels responsible for protecting. In the debrief, distinguish information that was merely interesting from information that would materially change a social engineering approach.

You have 10 minutes for this exercise. The following techniques can be employed within the Authentic Operator Type expression to get and keep the conversation going. If you find yourself stuck, consider discussing what you’ve learned from the workshop, points you agree with, or disagreements with the content. Honesty does elicit reciprocity, and you won’t hurt my feelings (probably).

Conversation Starter Statements:

The best domestic animal is [your answer]. I know this to be true because [reasoning].
If I could choose a marvel character superhero power it would be [power] because [reasoning].
The best place to live in the world is [place] but of I could only visit one place in the world, it would be [place and reason].
The best [laptop, speakers, type of car, etc.] is [pick your tech] and this is true because [stated merits].
Operator choice, consider chatting about your plans in Vegas, the best venue, talks or workshops you’ve enjoyed or particularly disliked.

Going Deeper: Carefully select a topic from your beliefs, biases, or values. Before going deeper, consider your target’s own foundations and avoid statements which could create offense or hostility. Select a topic from the Biases, Beliefs, and Values assessment or select from the statements below.

I believe in [faith] because [experience/testimony]
I voted for [policy] because [moral reasoning]
Reality is mostly [objective/subjective] because [reasoning]
The root of all evil is [source] and the solution is
Operators choice: [policy, organizations, ideology, structure, constructs] that are inherently [good/bad] and I understand this to be true because [reason]