Works Well With Others

Have you ever walked into a meeting, party, or new job and felt like everyone else had the rules—and you didn’t? In Works Well with Others, Ross McCammon turns that awkward, insecure feeling into the foundation of confidence itself. Drawing from his unlikely journey from a small in-flight magazine in Texas to becoming an editor at Esquire in New York, McCammon argues that professional success isn’t about being perfect, connected, or even particularly polished—it’s about learning to act human in strange environments, and to use your anxiety and outsider perspective as fuel rather than a flaw.

At its heart, McCammon’s book is a survival manual for impostors—people who think they were let into the building by mistake. He reveals that everyone, from new interns to pop stars, is at least a little bit nervous and weird. Success, he argues, comes not from faking confidence but from developing comfort with discomfort, and learning how to play the small social games that make big opportunities possible. He calls these moments—the handshake, the first-day introduction, the awkward work lunch—the “microtransactions” of professional life. Master them, and you’ll seem confident even when you aren’t.

From Chicken Sandwiches to Esquire

McCammon opens his story sitting in a parking lot outside Dallas, eating a Chick-fil-A sandwich and feeling a dull dissatisfaction with his work editing Spirit, Southwest Airlines’ magazine. Minutes later, he receives a call from a New York recruiter inviting him to interview at Esquire. The conversation captures the book’s main thread—opportunity never feels like opportunity when you’re terrified of blowing it. Convinced that the call is a scam, he still agrees to the interview, and soon finds himself in Manhattan, worrying that he’s not wearing the right jacket and that everyone will find out he doesn’t belong.

This experience becomes the prototype for nearly every chapter: McCammon places himself in uncomfortable, often ridiculous scenarios (shaking hands with Kanye West backstage, surviving fancy lunches with executives, buying his first acceptable pair of shoes) and extracts from each a principle for how to function when you feel like a fraud. Each failure or faux pas—like introducing himself to a coworker in the men’s room—becomes a lesson in human behavior and humility.

The Power of Small Things

Unlike typical self-help books promising life hacks or business frameworks, Works Well with Others focuses entirely on little social rituals—how you shake hands, order lunch, email, smile, and talk about clothes. McCammon treats these as vital signals of how you see yourself and others. Small talk, for example, isn’t meaningless—it’s civilization in miniature. Knowing how to exchange pleasantries shows empathy, curiosity, and confidence, and it sets the tone for more consequential conversations later. Similarly, a good handshake (firm but brief, with eye contact and enthusiasm) establishes respect faster than any résumé.

His point isn’t that outward performance replaces substance, but that behavior precedes belief. Dressing well, he argues, actually makes you feel more capable (“enclothed cognition,” as researchers call it). Smiling lifts your mood by activating brain circuitry linked to joy. Taking small confident actions makes confidence follow, not the other way around. As with Amy Cuddy’s research on body language or Brené Brown’s writings on vulnerability, McCammon shows that how we carry ourselves changes how we experience ourselves.

The Art of Awkwardness

Perhaps the most reassuring theme of the book is that awkwardness isn’t a liability—it’s a resource. Anxiety indicates that you care. Feeling like an outsider can sharpen your awareness and empathy. In the workplace, the people who quietly wonder whether they belong often overprepare, notice details others miss, and take nothing for granted. Self-doubt, McCammon says, gives you an advantage if you use it for motivation instead of paralysis.

He develops this into a broader professional philosophy: confidence and humility are not opposites but partners. To work well with others, you must project both—enough certainty to inspire trust, and enough insecurity to stay teachable. When he eventually learns this, McCammon stops worrying about “fitting in” at Esquire and realizes that everyone there, even the most accomplished editors, are improvising too. That’s the paradox of professional life: no one ever really knows what they’re doing, but those who accept that fact do it best.

Why It Matters

In a world obsessed with hustle culture and performative confidence, McCammon offers something subtler and more humane. His message is that success isn’t about erasing insecurity—it’s about managing it with grace. You don’t “fake it till you make it”; you learn it as you make it. By reframing discomfort as progress, embarrassment as data, and awkwardness as humanity, you unlock the real secret to working well with others: being a little kinder—to them and to yourself.

The rest of the book builds out this philosophy through short, funny, and often profound essays on professional etiquette, communication, style, and mindset. From the rules of lunch to the art of profanity, McCammon provides a playbook not for perfection but for presence. If you’ve ever second-guessed your handshake, your outfit, your small talk, or your whole career, this book—and this summary—will help you do all of it better, without being someone you’re not.

At the book’s core is a recognition of something most professionals secretly feel: the fear of being found out. McCammon experienced it blatantly when he got the call from Esquire. He couldn’t believe he was being considered, convinced the recruiter had dialed the wrong number. That disbelief—what psychologists Pauline Clance and Suzanne Imes first defined as “impostor phenomenon” in 1978—became a lens through which he viewed every aspect of his success. His realization that everyone around him felt the same way becomes the book’s first crucial insight.

Everyone Is an Impostor

From Supreme Court Justice Sonia Sotomayor to actress Meryl Streep, even public icons have admitted to feeling fraudulent in their own roles. McCammon concludes that impostorism isn’t weakness—it’s a shared condition of ambition. Those who question their worth often push hardest to prove it. Outsiders, by definition, are observant; they notice power dynamics insiders take for granted. Their sensitivity equips them to read rooms, disarm egos, and forge genuine relationships, which are far more powerful assets than innate confidence.

In this light, the impostor isn’t a fraud but a learner in motion. Self-doubt, harnessed correctly, becomes a kind of drive—a “productive paranoia” that keeps you humble and alert. (This insight echoes Carol Dweck’s work on growth mindset: successful people aren’t those who never fail but those who treat failure as feedback.)

When Doubt Becomes Fuel

When McCammon starts at Esquire, he walks into what feels like a movie set of cool confidence. Surrounded by sharp dressers and fast talkers, he feels both invisible and exposed. But over time, that anxiety forces him to pay attention—to style, timing, gestures, and the subtleties of communication. His insecurity becomes his superpower. He learns faster precisely because he fears failure. As he puts it later, “When you have doubt, you have more. You have the problem plus doubt.”

Reframing Success

By the book’s end, McCammon redefines success not as mastery but as a continuous balancing act between readiness and unpreparedness. You are always both ready and not ready, because growth never stops. This is why, he says, you should always remain an outsider—to keep your curiosity, your perspective, and your edge. What once felt like inadequacy becomes identity. The goal is not to fit in, but to belong on your own terms.

One of McCammon’s funniest and most instructive insights comes from something as simple as entering a room. Science shows people form impressions within milliseconds, often before a single word is spoken. The author turns this anxiety-inducing fact into a strategy. Whether you’re walking into a job interview or a meeting, those first thirty seconds belong to you. Even if everyone outranks you, you set the tone by establishing warmth and curiosity.

The Eye Contact Rule

McCammon’s golden rule for every professional situation is simple: look everyone in the eye. Eye contact communicates control, honesty, and interest more effectively than any verbal flourish. Its power lies in suggesting that you’re paying attention—to them, not to your own nerves. He even points to research indicating that high levels of eye contact make interviewees seem more confident and capable. It’s not about dominance—it’s about engagement.

Handshake Philosophy

His entire meditation on the handshake, hilariously framed around Kanye West’s expertly executed greeting, drives the same point home. The best handshake combines efficiency, confidence, and human warmth. A quick, firm grip, direct gaze, and a genuine smile can make you more “hireable” (supported by a University of Iowa study he cites). Hold too long, and you seem needy; too lightly, and you seem timid. Kanye’s “Westian pump”—a perfect one-second rhythm with a compliment—perfectly illustrates grace under pressure. (“Even with greetings,” McCammon jokes, “Kanye has flow.”)

Knowing how to initiate contact—whether by handshake, smile, or small talk—isn’t about performance; it’s about making others comfortable in your presence. McCammon suggests small things like observing the view out a conference room window, remarking with curiosity, or asking a genuine question. Curiosity, he insists, is the most underrated virtue in business. It opens people up more than confidence ever could.

Failure, McCammon argues, is over-celebrated and under-understood. The startup mantra of “fail fast” sounds inspiring, but actual failure is miserable. What truly matters is screwing up productively—making small mistakes early and learning from them before they compound. For him, that meant giving bad presentations, writing clumsy emails, and staying up too late refining headlines no one would notice. Only after he accepted that these mistakes weren’t catastrophic did he start improving quickly.

Fixed vs. Growth Mindsets

Drawing from psychologist Carol Dweck’s research, McCammon contrasts “fixed” thinkers, who avoid risk to protect their image, with “growth” thinkers, who see error as fuel. Most new hires, he says, suffer not from incompetence but shame—they hide mistakes instead of exposing them to correction. You don’t need to apologize constantly; you need to improve publicly. Progress, he says, happens when you stop trying to seem perfect and start getting feedback faster.

The Rule of Early Failure

His “Failure Rule” is simple: you must screw up at least ten times early in a new job to know you’re learning. The checklists he shares—handshakes gone wrong, overtalking in meetings, pretending to know cultural references you don’t (like Werner Herzog)—show that embarrassment is an education. The real mistake is pretending otherwise. “You’re supposed to do bad work,” he writes. “Everyone wants you to do bad work. It’s how we know you’re trying.”

McCammon’s lesson: failure only teaches when met with curiosity, not despair. If you can laugh at your errors while analyzing them, you turn shame into data. That shift—from humiliation to humor—is the difference between suffering and growth.

Few chapters in the book are as unexpectedly profound as McCammon’s thoughts on clothes. Initially self-deprecating about his lack of fashion sense, he eventually learns from Esquire’s fashion director Nick Sullivan that style is about ideas, not fabric. The right clothing isn’t vanity—it’s a tool for confidence and psychological performance.

Enclothed Cognition: Dressing for Confidence

Citing research from Columbia University, McCammon describes “enclothed cognition,” the phenomenon where what you wear changes how you think and perform. Participants wearing a doctor’s coat, for instance, paid closer attention to detail. For McCammon, a new pair of cap-toe Oxfords became his version of the doctor’s coat—shoes that made him feel capable and self-assured. By investing in his appearance, he wasn’t pretending to be someone else; he was signaling to himself that he was worth taking seriously.

Sprezzatura: Effortless Nonchalance

The Italian concept of sprezzatura, from Baldassare Castiglione’s The Book of the Courtier, becomes McCammon’s mantra: the art of studied carelessness. It means giving a damn—and then loosening your grip slightly. A slightly askew tie, mismatched patterns, or visible wrinkles can make you appear comfortable and confident. Sprezzatura liberates you from perfectionism, not only in dress but in demeanor. “Give a shit,” McCammon paraphrases. “And then slightly less of a shit.”

Confidence by Conduct

Over time, he learns that confidence is cumulative—a feedback loop between outer polish and inner assurance. You don’t have to look like a model to carry yourself with poise; you have to communicate competence through intention. Conversations, meetings, and even posture are part of your outfit. (Think of Tom Wolfe’s belief that style is character made visible.) The takeaway: dress and act the way you’d behave if you already felt confident—and in time, you will.

Much of Works Well with Others reads like a comedic anthropology of office life: what to say over email, how to behave at lunches, meetings, or bars. McCammon’s humor masks deep insight into how civility and attention keep workplaces sane. His rules—don’t over-cc, don’t “grab coffee,” don’t talk about your dreams at work—are really about one principle: respect others’ cognitive bandwidth. He suggests that professionalism isn’t about formality; it’s about clarity + courtesy.

Speech, Silence, and Small Talk

Learning when not to talk is a skill. In meetings, he says, your job is to say less and listen more. The most underrated tactic in the workplace, he insists, is silence. Brief but confident answers like “It’s great” communicate authority without ego. At the same time, he defends small talk—as dull as it feels, it’s how civilization stays stitched together. A comment about the weather isn’t filler; it’s empathy in disguise.

Emails, Drinks, and Toasts

His “De Niro Method” of emailing—reply as if you’re Robert De Niro (“Sure.” “Perfect.” “Sorry.”)—teaches economy of tone. At drinks, one drink is enough; past two, your judgment goes soft. And his rules for toasting are unexpectedly moving: keep it short, skip the clichéd Irish verse, and aim for kindness over comedy. Sentiment, he says, beats humor every time. When you stand to speak about others sincerely, people remember it forever.

Each of these micro-lessons points to a single truth: the most impressive professionals are those who make their colleagues feel seen, not dominated. Etiquette, then, isn’t artifice—it’s empathy in slow motion.

Late in the book, McCammon tackles the toxic side of professionalism—how to deal with assholes, intimidators, and underminers. His taxonomy of jerks is both hilarious and alarmingly precise. There are assholes (predictable and self-absorbed), pricks (anxious but redeemable), and underminers (the scheming saboteurs). His cure for all of them involves three principles: accept, embrace, and engage.

Acceptance and Embrace

You can’t reform assholes, he warns. They thrive on predictability and lack of self-awareness. The best defense is awareness: see them, anticipate them, and limit their impact. Their presence, ironically, creates moral contrast—you seem more grounded and reasonable next to them. That recognition alone can reduce their power.

Engage, but Calmly

When confrontation is inevitable, McCammon prescribes one magical question: “Why would you do that?” It forces the offender to account for their behavior—a task most bullies can’t handle. The key is tone: bemused, not furious. Outrage gives them fuel; curiosity drains it. Self-awareness, to an asshole, is like sunlight to a vampire. (Compare this approach to Kim Scott’s Radical Candor, which advocates a similar blend of honesty and care.)

Building Credibility

Through it all, McCammon reminds you that your reactions define your reputation. Power doesn’t come from dominance but from discretion—knowing when to speak, when to smile, when to leave. Even intimidation, he says, can be useful when paired with empathy. True authority comes from competence plus kindness. The rest is noise.

The book closes with a deeply personal return to McCammon’s outsider identity. Even after years at Esquire, he admits he never felt totally “inside.” That unease, he decides, is a gift. Self-doubt keeps you hungry, observant, and adaptable. When he revisits the Central Park bench where he used to hide after turning in work, terrified of being fired, he realizes something profound: being uncomfortable is the surest proof that you’re growing.

The Power of Perspective

For McCammon, outsiderhood means seeing both the system and its absurdity. It’s what allows him to notice details others miss—like the choreography of a business lunch or the quiet theater of a meeting. Outsiders make organizations better precisely because they haven’t gone numb to their contradictions. They care enough to notice, and curiosity is contagious.

Belonging Without Assimilation

He distinguishes between belonging and blending in. To belong means to contribute without erasing what makes you different. To blend in means surrendering individuality. The healthiest workplace, McCammon suggests, welcomes people who feel like they don’t deserve to be there—because they’ll do the hardest work to stay. Success, he concludes, is not comfort but contribution. You never stop being an outsider; you just learn to use the view.