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There's a moment in every intelligence officer's career when they realize something uncomfortable: to be effective at their job, they must genuinely connect with people whose values, beliefs, or actions they might find repugnant. Not pretend to connect. Not manipulate. Actually connect.
This realization runs counter to everything we typically believe about empathy. We're taught that empathy flows naturally toward people we like, people who share our values, people who we think of as "good." But in the world of human intelligence, that comfortable version of empathy is nearly useless. What matters is something far more difficult, and far more powerful.
I call it radical empathy: the disciplined capacity to temporarily suspend moral judgment in order to genuinely understand another human being at their deepest level. Not to excuse them. Not to agree with them. But to see them with such clarity that you understand why their choices make perfect sense from inside their own experience.
This skill changed how I operate professionally. It changed how I lead. It changed my relationships. And I believe it's one of the most underdeveloped yet universally applicable capabilities in leadership, business, and life.
The Paradox at the Heart of Intelligence Work
Here's something most people don't understand about recruiting human sources: it's not about deception in the way movies portray it.
Yes, intelligence officers operate under cover. Yes, there are secrets and compartmented truths. But the actual relationship between a case officer and their asset? That has to be real. Authentic. Built on genuine understanding.
Why? Because you're asking someone to do something extraordinarily difficult and potentially dangerous. You're asking them to betray their country, their employer, their colleagues, perhaps even their family. You're asking them to live with secrets that could get them imprisoned or killed.
No one does that for someone they don't trust. Few people will take that risk for a relationship that feels transactional or manipulative (though there have been high-profile espionage cases where money was everything for the spy).
The intelligence officers who succeed at recruitment aren't the ones who are best at lying. They're the ones who are best at understanding. They develop an almost preternatural ability to see the world through another person's eyes, to discover what motivates them at the deepest level, and to position themselves as someone who genuinely meets that need.
This creates a paradox that took me years to fully appreciate: the profession that operates in shadows and secrets requires, at its core, one of the most authentic forms of human connection imaginable.
Finding Humanity in Uncomfortable Places
As a young officer, this was once put to the test when I was working against a major narcotics-trafficking rebel group and recruited one of its members as my source. We had precious little in common, a girl from Northern California and an armed fighter moving opium and heroin into the international market. But we found a way to connect. I learned about his own circumstances, the limited opportunities, the pressures of an armed militia that occupied his hometown, and his desire to do something more, better, with his life.
That experience taught me something I've remembered ever since: every human being, regardless of what they've done, has at least one redeeming quality. Some kernel of humanity that can serve as the foundation for genuine connection. A corrupt official might be a devoted father who would do anything for his children's future.
A disillusioned bureaucrat might be an idealist who once believed deeply in something and now feels betrayed by the system he serves. A person working for an adversarial government might hold private doubts about the direction her country is taking. The skill isn't in inventing these qualities. It's in uncovering them. They're always there. The question is whether you're willing to look past the surface, past your own judgments and assumptions, to discover them.
This is what I mean by radical empathy. It is neither soft nor naive. It’s not about investing my own emotional energy in another person at some supernatural level. It's a disciplined practice of psychological discovery that requires you to temporarily set aside your own moral framework in order to understand someone else's. The term radical empathy could just as well be radical understanding.
The Internal Work Most People Skip
Here's what makes radical empathy difficult: it requires confronting your own judgments, biases, and emotional reactions before you can genuinely see another person.
Most of us don't do this. We don't even realize we're not doing it.
We enter conversations with people already filtered through our assumptions about who they are, what they believe, and what they deserve. We listen for confirmation of what we already think. We interpret their words through our own frameworks. And we call this "understanding." It's not. It's projection dressed up as empathy.
True radical empathy requires a different thought process: First, acknowledge your judgments. Don't pretend you don't have them. If you're meeting with someone whose politics you find abhorrent, whose business practices you consider unethical, or whose personality rubs you the wrong way… acknowledge it. To yourself. Clearly. You can't set aside what you don't recognize. Second, summon genuine curiosity about their internal logic. This is the key move. Ask yourself: What would have to be true for this person's choices to make perfect sense? Not sense by your standards, sense by their standards, given their experiences, their information, their pressures, their fears, their aspirations. Dig deep to understand the other person’s “why” or sense of purpose. Everyone is the hero of their own story. Everyone's choices feel rational from inside their own experience. When you can't understand why someone does what they do, the limitation is usually in your own understanding, not in their rationality. Third, find the universal human element. Beneath the surface differences, what basic human needs are they trying to meet? Security? Recognition? Belonging? Purpose? These needs are universal even when the cultural context or strategies for meeting them diverge radically.
Finally, let genuine connection emerge. When you've done this work, something changes. The person in front of you stops being a caricature or a problem to be solved and becomes a full human being. Connection is truly possible, not because you've manipulated it, but because you've created the conditions for it. Your own curiosity and open mind promote trust, and trust is the foundation of real connection.
Why This Feels Uncomfortable
I've shared these ideas with others over the years, and occasionally encountered resistance. The concern usually sounds something like this: "If I empathize with someone whose behavior is harmful, aren't I excusing or enabling that behavior? Doesn't understanding become complicity?" This is an important question, and the answer is no, but only if you understand what radical empathy actually is. Radical empathy is not agreement. It's not approval. It's not moral relativism. And it’s not, again, pouring all of your own emotional energy into the other person.
It’s about understanding. You can fully understand why someone made a destructive choice and hold them accountable for it. You can genuinely empathize with the pressures that led someone to act unethically and still insist on consequences. You can see the humanity in someone and oppose everything they stand for. In fact, I'd argue that empathy strengthens your ability to respond effectively. When you truly understand someone's motivations, you're better positioned to influence them, negotiate with them, counter them, or help them adapt their behavior. You're operating with full information rather than fighting a caricature. The intelligence world taught me this viscerally. We weren't in the business of excusing bad actors. We were in the business of understanding them so well that we could anticipate their moves, identify their vulnerabilities, and, when possible, recruit them or change their behavior.
Understanding is not endorsement. It's power.
The Shift That Changes Everything
I remember another moment from late in my career when I sat across the dinner table from a former communist insurgent who had since risen to some prominence in his government. Decades earlier, we would have been committed adversaries. He still harbored deep animosity for the United States and, by extension, me as our government’s representative.
The conversation was tense and stilted at first, but shifted over time as we spoke about our families, our mutual desire for equality in our countries, our values of independence, self-reliance, and patriotism. He realized that I sought understanding, not judgment, and that changed everything. It ended up being one of the most fascinating dinner conversations I had enjoyed in years.
What I've learned is that radical empathy creates a particular kind of shift in how other people experience you. When someone feels genuinely seen, not judged or evaluated, not managed, but actually understood at some level, something in them opens. Defenses lower. Authentic communication becomes possible. Trust builds faster than it otherwise would. This isn't mystical. It's psychological. Humans are fundamentally wired to respond to being understood. We crave it. And we can tell the difference between someone who's performing and someone who actually gets us. Intelligence officers become skilled at creating this experience for others because recruitment depends on it. But the skill needs to be real to work. The curiosity must be sincere, and your humanity must be felt.
Beyond the Shadows: Where Radical Empathy Transforms Results
For years, I cultivated this capability in classified contexts, assuming it was specialized, something unique to the peculiar demands of intelligence work. Obviously, that’s not the case. Radical empathy is a master skill that amplifies effectiveness in virtually every domain that involves human beings.
Leadership and Management
The leaders I most respect share a common trait: they understand their people at depth, and they can set aside judgment as they seek to build that understanding. They can appreciate someone else’s skills and performance, but also their aspirations, pressures, and private struggles.
This understanding doesn't make them soft. It makes them effective. They can deliver hard feedback in ways that the other person can receive because they've earned trust through genuine connection. They can motivate individuals differently based on what actually drives each person. Radical empathy allows you to lead people as they actually are, not as you assume them to be.
The "Likeability" Trap Leaders Must Escape
Here's a leadership mistake I have seen repeatedly over my long career. Too many leaders fall into the trap of filtering their teams through the lens of personal likeability. They gravitate toward employees they find pleasant. They invest more energy in people who are affable, who share their communication style, who feel easy to deal with. And they unconsciously distance themselves from those they find difficult, abrasive, awkward, or simply different. This is a fundamental leadership failure, and radical empathy is the antidote.
Bottom line? You don't have to like everyone you lead. It’s not a friendship. It isn't a marriage. It's work. The question isn't whether someone's personality delights you; it's whether you can understand them well enough to connect, build trust, and lead effectively. Some of the most valuable people I've worked with were not people I would have chosen as friends. They were prickly, or intense, or operated on a wavelength different from mine. Early in my career, I might have kept them at arm's length, managing them transactionally rather than leading them fully. That would have been my loss, and the organization's loss. Because frankly, genius does not always come in convenient packages. Radical empathy strips away the likeability filter. It asks a different question: Can I understand this person deeply enough to lead them well? The answer is almost always yes, if you're willing to do the work.
This becomes especially critical when you're leading people from outside your own field of expertise. If you're a business leader managing engineers, or a military officer leading intelligence professionals, or an executive suddenly responsible for a function you've never worked in, you can't rely on shared professional language or common technical background to create connection. You have to build it another way.
That way is radical empathy. It begins with genuine curiosity and an open mind. It requires you to ask questions you don't know the answers to, to listen without feigning expertise you don't have, and to understand what drives people whose work you may never fully comprehend. When you do this, something interesting happens: people forgive your lack of specialized expertise in their field. They trust you anyway. Because what they really need from a leader isn't someone who understands their work better than they do. It's someone who understands them. Connection precedes credibility. And connection begins with empathy.
Negotiation and Conflict Resolution
Every negotiation book talks about "understanding the other side's interests." Radical empathy takes this further. It's not just understanding what they want, it's understanding why they want it, what fears drive their positions, what pressures they face, and what success looks like from inside their world.
When you achieve this level of understanding, creative solutions emerge. You see trades that weren't visible before. You can frame proposals in language that resonates with their values rather than yours. You can anticipate objections and address them before they surface.
I've watched negotiations transform when one party makes the effort to genuinely understand the other. The shift is palpable. Suddenly, the conversation moves from positional warfare to joint problem-solving.
Sales and Client Relationships
The best salespeople I know aren't persuaders in the traditional sense. They're understanders. They invest time in genuinely comprehending their client's world… the pressures they face, the internal politics they navigate, the fears that keep them up at night, the outcomes that would make them heroes within their own organization.
From this understanding, they don't have to "sell" in the pushy sense. They simply present solutions that genuinely fit. The client feels understood rather than manipulated, and trust builds accordingly.
This is exactly what intelligence officers do with potential sources. We seek to understand their world so thoroughly that when we finally present an opportunity, it feels like the natural answer to their problem, because often it is.
Cross-Cultural and International Contexts
Radical empathy becomes even more critical when operating across cultural boundaries. Different cultures have different frameworks for understanding the world. Very different assumptions about hierarchy, relationships, time, honor, and obligation.
Effective cross-cultural engagement requires the ability to temporarily adopt another cultural framework, to see the world as your counterpart sees it, and to communicate in ways that make sense within their context rather than your own.
This was the daily work for intelligence officers working abroad. But it's equally essential for global business leaders, international negotiators, diplomats, and anyone working across cultural lines in our increasingly connected world.
Healthcare, Counseling, and Helping Professions
Professionals who work with people in crisis (doctors, therapists, social workers, counselors) depend on the ability to understand without judgment. A physician who can truly understand a patient's fears and lifestyle constraints will be more effective at encouraging treatment compliance. A therapist who can enter a client's frame of reference can facilitate change that would otherwise be impossible.
The radical empathy developed in intelligence work is structurally identical to the "unconditional positive regard" that therapists cultivate. Both require the capacity to understand without judgment, to see the logic in choices that might otherwise seem irrational or self-destructive.
Politics, Policy, and Civic Life
In an era of intense polarization, radical empathy offers something our public discourse desperately needs: the ability to understand positions with which we disagree without portraying counterparts as caricatures.
This doesn't mean abandoning your principles or treating all positions as equally valid. It means understanding why people on the other side believe what they believe. What experiences, fears, and values drive their positions.
From this understanding, persuasion becomes possible. Common ground becomes visible. And even where agreement is impossible, respectful coexistence becomes more achievable.
The Practice: How to Develop Radical Empathy
Like any skill, radical empathy can be developed. Here's how I'd suggest approaching it: Start with low-stakes practice. Before attempting this with someone who triggers strong reactions, practice with neutral encounters. The barista who seems rude. The colleague whose communication style irritates you. The family member whose choices confuse you. Ask yourself: What would have to be true for their behavior to make perfect sense?
Notice your judgments without fighting them. You don't need to eliminate your moral reactions. You need to notice them clearly enough that they don't unconsciously drive your behavior. Judgment observed is judgment that can be temporarily set aside. Ask questions you don't think you need answered. The most powerful understanding often comes from exploring areas where you think you already know the answer. You probably don't. So, ask anyway. Listen for what's underneath the surface. When someone expresses a position, seek to understand what need it serves. When they describe a behavior, think about what fear or aspiration drives it. Keep digging beneath the presenting content.
Practice with people you disagree with. This is where the growth happens. Find opportunities to genuinely understand (not debate, not convince, just understand) people whose views differ from your own. This is uncomfortable and becoming increasingly rare in our polarized political climate. Do it anyway. Debrief yourself. After important conversations, reflect: Did I genuinely understand this person's perspective, or did I project my own assumptions? What did I miss? What would I do differently?
The Person You Become
Here's what I didn't expect when I began developing this capacity: it changed me.
Radical empathy doesn't just make you better at understanding others. It makes you more aware of your own biases, assumptions, and blind spots. It develops your intellectual humility and a kind of cognitive flexibility, or the ability to hold multiple perspectives simultaneously, to see situations from different angles, to resist the allure of your own certainty.
It also, somewhat paradoxically, makes you more secure in your own values. When you've genuinely understood perspectives different from your own and chosen to maintain your positions anyway, those positions are no longer defaults. They are consciously chosen. And that's a different kind of conviction.
This focus on empathy is something our country desperately needs more of today. It’s core to the work I conduct on Mind Sovereignty™, since the collapse of civic empathy is so closely tied to filter bubbles, algorithmic amplification, and the resulting affective polarization we see in society. But empathy can be rebuilt, and it starts at the individual level.
An Invitation
We live in a time when understanding across divides feels increasingly rare. Political polarization, social media echo chambers, and the pace of modern life all conspire against the slow, patient work of genuinely seeing another person.
And yet this capacity has never been more valuable. In leadership, in business, in diplomacy, in life… the ability to understand without judgment, to see without agreeing, to connect across differences, remains the master skill that amplifies all others.
I was fortunate to develop this capability in an unusual crucible. But the skill itself isn't classified tradecraft. It's available to anyone willing to do the internal work.
The question is whether we're willing to set aside our own sense of certainty (and often, moral superiority) long enough to actually see the person sitting across from us.
In my experience, what we find when we do so is almost always more interesting (and more human) than what we assumed.
The Cipher Brief is committed to publishing a range of perspectives on national security issues submitted by deeply experienced national security professionals. Opinions expressed are those of the author and do not represent the views or opinions of The Cipher Brief.
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