Bringing Up the Boss

Have you ever suddenly found yourself in charge—responsible for others—yet painfully uncertain how to lead them well? In Bringing Up the Boss, Rachel Pacheco argues that great management is a learned practice, not an innate talent. The book is a coaching manual for those who, like Sandy from the introduction, have been thrust into management without a roadmap. Pacheco contends that being a boss means far more than delegating and evaluating—it's about guiding human beings through the messy realities of work, growth, motivation, and meaning.

Drawing on years of coaching and organizational leadership—particularly in fast-moving start-ups—Pacheco unpacks management into three distinct but overlapping arenas: managing individuals, managing teams, and managing yourself. By breaking down each sphere into bite-sized concepts, vivid anecdotes, and research-backed tools, she creates a realistic playbook for anyone learning to lead without losing their sanity (or their humanity).

Why Management Feels So Hard

Pacheco begins by debunking a myth that plagues new managers: that good management is common sense. It isn’t. Managing is difficult because it encompasses dozens of discrete behaviors—feedback, performance evaluation, motivation, hiring, team dynamics, self-awareness—and each draws on psychology as much as process. Most organizations promote high performers into management roles without teaching these skills, creating the classic tragedy of the promoted top performer who makes their new team miserable. Like learning a sport, management requires repetitions, reflection, and errors along the way. You can’t just read the rules; you need to practice.

Building a Management Muscle

Pacheco likens management to a muscle—one built through practice under pressure. A key insight is that your managerial practice happens in public: every decision and conversation directly impacts others. So she supplies frameworks and templates so that readers can rehearse key actions—like setting expectations or conducting a performance improvement plan—before they’re under the spotlight. The book’s tone is reassuringly realistic: you will make mistakes, people may quit, and that’s part of the job. What distinguishes great managers is the willingness to learn quickly from missteps.

A Lens of Inclusion and Humanity

Because Pacheco wrote during the twin upheavals of the pandemic and racial reckoning of 2020, inclusion and empathy are baked into her definition of effective management—not bolted on as separate diversity chapters. She argues that managing across differences (of identity, privilege, or geography) is not optional; it is the essence of leadership. True competence includes anti-oppressive and psychologically safe practices, because people do their best work only when they feel valued and respected.

The Book’s Structure: From People to Purpose to Self

The body of the book proceeds in three parts. In Managing an Individual, you explore how to guide one person’s performance, motivation, and meaning. Pacheco teaches how to clarify expectations, offer feedback that actually changes behavior, coach development, and handle underperformance with fairness. In Managing a Team, she turns outward—to hiring, firing, team norms, conflict, and dialogue—laying out how to create psychological safety and avoid the dysfunctions that make teams implode. Finally, in Managing Yourself, she looks inward: how you manage your own self-doubt, power, and relationship to your boss, and how to recognize when it’s time to move on.

Each section ends with humor and humility—an anecdote of failure or surprise—reminding readers that management is both serious work and profoundly human work. Pacheco’s goal is not perfection but growth: to transform bosses from accidental managers into deliberate leaders who understand that leadership begins with managing themselves.

Key Premise: Great management is learned through tools, reflection, failure, and feedback—not innate charisma or authority. The “boss” is built, not born.

In short, Bringing Up the Boss is not a manifesto of abstract leadership virtues but a hands-on human guide. It’s messy, funny, and practical—like management itself. Whether you’re running a start-up team, leading a nonprofit, or managing your first intern, Pacheco wants you to remember: you will be a terrible manager before you become a great one. The only way forward is to begin, screw up, learn, and get better—together with your team.

Why are so many managers chronically disappointed by their teams? Because, Pacheco argues, unspoken expectations guarantee disappointment. In the chapter “Great Expectations,” she shares a witty but painful truth: managers often feel frustrated not because their people are incompetent, but because they are guessing what success looks like. As her friend’s father puts it, “An expectation unarticulated is a disappointment guaranteed.”

Why Managers Fail to Set Expectations

Pacheco identifies two obstacles. First is the fear of being a micromanager. Many new managers, desperate to be liked, err on the side of vagueness. They think autonomy means hands-off leadership. The result? Anxiety and confusion. The second is the Dunning-Kruger effect—the bias that makes experts assume tasks that feel easy to them must also be easy for others. So both sides overestimate the other’s understanding, and work goes awry.

The Four-Question Formula

To clarify expectations, Pacheco offers a simple template every manager can use when assigning work:

• 1. What’s the objective? Define the end goal and why it matters.
• 2. What does good look like? Paint a picture of quality and success.
• 3. What’s the timing? Be explicit about deadlines and interim milestones.
• 4. What are examples? Provide models or past work to illustrate standards.

This checklist might sound obvious, but Pacheco insists it’s transformative. Each question forces clarity and shared accountability. Even seasoned employees appreciate knowing exactly what’s expected—and most new hires crave it.

From Micromanaging to Empowering

Being clear isn’t the same as micromanaging. Micromanagers dictate how to climb the mountain; good managers describe what summit they want reached and let the team chart the path. Research from Google’s “Project Oxygen” confirms this—clarity of goals correlates with higher autonomy and satisfaction. (Similarly, Kim Scott’s Radical Candor posits that caring personally means also challenging directly.)

Expectation Setting as a Culture

Pacheco urges managers to normalize expectation discussions as part of everyday work, not just project kickoffs. Teams should revisit expectations midstream and openly adjust them as conditions change. To make this a habit, she includes an Expectation-Setting Template in her appendix for ongoing performance check-ins.

If you think you’re being clear, be clearer. Clarity isn’t control—it’s kindness. Every line of direction is a lifeline against confusion.

When managers define what good looks like, they give employees both safety and stretch. The result is fewer re-dos, fewer frustrations, and—most importantly—greater trust. As Pacheco repeats, you can’t read minds. So stop expecting your team to.

In one of the book’s funniest chapters, “Feedback Is Like Underwear: It’s a Gift You Need, Maybe Not One You Want,” Pacheco teaches managers to view feedback as both essential hygiene and leadership duty. Avoiding feedback, she argues, is not kindness—it’s negligence. Without it, small missteps compound into career-derailing habits.

Breaking the Fear Loop

Why do managers avoid feedback? Because they want to be liked and dread awkwardness. But as Pacheco’s story of the VP “Justine” shows, withholding critique backfires. Justine avoided feedback to spare an employee’s feelings—only for him to be blindsided when fired. Thus, she became the “mean manager” she feared being. Great bosses give feedback precisely because they care.

A Simple Feedback Formula

Her super-simple three-step model makes conversations less painful:

• Start with data: “I observed you arriving ten minutes late.”
• Explain impact: “That delayed the client meeting.”
• Suggest change: “Let’s agree you’ll aim to be five minutes early next time.”

Grounding feedback in observable behavior, not judgment, reduces defensiveness. It’s structured, kind, and actionable—the management equivalent of brushing twice a day.

Receiving Feedback Without Flinching

Managers must also model openness to criticism. Pacheco explains that our brains interpret negative feedback as a social threat—our “reptilian” survival brain flares up. To override it, she suggests asking often, listening silently, and thanking always. Create separate meetings for upward feedback (so employees aren’t anxious about critiquing you during reviews).

She even provides sample survey prompts, like: “What’s one thing I could do to make your job easier?” This normalizes a two-way feedback culture. (Amy Edmondson’s research on psychological safety supports this: teams that voice mistakes learn fastest.)

Avoid the “feedback sandwich”—don’t sugarcoat critique between fake praise. Say what needs saying, clearly and respectfully, then move on.

Pacheco ends the chapter with Nike-level bluntness: just do it. Feedback will always be awkward, but perfection isn’t the goal—frequency and honesty are. Like the gym, consistency matters more than form. Every tough conversation today prevents a firing later.

Pacheco insists that most “bad employees” are actually victims of bad management. Her story of “Michael,” a team member she mishandled early in her career, proves the point. When he underperformed, she failed to set expectations or coach him. By the time she acted, it was too late. Years later, Michael was clerking for the Supreme Court—while her firm went bankrupt. Lesson learned: performance issues are often management issues.

From Feedback to Coaching

Coaching, Pacheco explains, is distinct from feedback. It’s about asking questions that help the employee think, not telling them what to do. After attending a yoga retreat where a guru used probing questions to spark epiphanies, she realized great managers do the same. They build employees’ muscles of ownership, proactivity, and trust by asking, “What’s your ideal outcome?” or “What worries you about this?”

She provides dozens of practical “beautiful questions”—from “What fears hold you back?” to “What would success look like six months from now?”—to guide these development conversations. The aim is not advice but awareness.

Performance Improvement as a Partnership

When coaching does not yield results, Pacheco turns to Performance Improvement Plans (PIPs). Though maligned, PIPs can save careers when used early and clearly. A good plan lists three to four key areas of improvement, concrete actions, metrics, and check-in dates. Most importantly, nothing in a PIP should be a surprise—it crystallizes months of prior feedback.

She counters the “PIP as prelude to firing” myth with the story of “Marie,” who turned her plan into a promotion. Once expectations became visible, Marie improved rapidly. A PIP, Pacheco argues, is a roadmap, not a verdict.

Use performance tools as mirrors, not weapons. The goal isn’t to corner employees—it’s to show them what improvement looks like and walk beside them there.

Ultimately, managing performance requires courage, compassion, and a steady habit of asking hard questions early. Done right, feedback leads to coaching, coaching leads to growth, and plans lead to clarity. Done poorly, silence leads straight to firing.

If you think pay solves motivation, think again. Pacheco’s motivation chapters dismantle the fantasy that cash alone inspires loyalty. Drawing on David McClelland’s needs theory, she shows that every employee is powered by a unique blend of achievement, power, and affiliation. Like love languages, everyone values them differently—and good managers learn to speak all three.

Three Drives, Three Personalities

The Achiever (Katie) lives for goals, progress, and visible wins. Recognize her publicly, set measurable objectives, and celebrate milestones.
The Power Player (Mary) thrives on influence and competition. Reward her with responsibility, not just praise. Let her lead projects or mentor others.
The Affiliation Seeker (Laura) treasures connection and belonging. Build team rituals and offer roles centered on collaboration and culture.

No one is purely one type—every team blends these motives. The art of management is tuning your style to match each person’s dominant drive.

The Pay Paradox

In “The Complications of Compensation,” Pacheco explores how money can backfire. Drawing on behavioral economics, she outlines three psychological traps:

• Loss Aversion: people hate losing bonuses more than they love gaining them.
• Equity Theory: we care more about fairness than absolute pay (we’d rather earn $100k when peers earn $100k than $110k when they earn $120k).
• Procedural Justice: we accept disappointing pay decisions when the process feels transparent and fair.

Thus, being open about how salaries and promotions are decided builds more motivation than simply raising salaries. Clarity is currency.

Learning as the Ultimate Motivator

Pacheco concludes this section with a beautiful insight: the deepest motivation isn’t money—it’s learning. Like the South African dog who regained his purpose by dragging a tire on the beach, humans need to feel useful and challenged. Managers must design work that provides skill variety, autonomy, and meaning. That’s where true engagement—and joy—live.

So before you plan bonuses, plan growth. Pay your people fairly, yes—but fuel them with progress, purpose, and the chance to get better every day. That’s what keeps them running long after payday.

After performance and motivation come the soul questions: what makes work worth doing? Pacheco devotes Part I’s final chapters to meaning—both the capital-M Meaning (life purpose) and the small-m meaning of daily satisfaction. Managers, she argues, have a duty to help people find both.

Job Crafting and Design

Drawing from organizational psychologist Richard Hackman, she shows five ways to design meaningful roles: skill variety, task identity, task significance, autonomy, and feedback. The story of Kelly and Kiesha—two HR associates with identical jobs but opposite fulfillment—proves the point. Kiesha’s work felt vital because she saw how it connected to strategy and people’s lives. Kelly’s felt mechanical because no one showed her the link.

To bridge that gap, Pacheco recommends “job crafting”—literally redrawing one’s role through reflection. Employees map their current tasks (“before”) and reimagine their ideal mix (“after”), connecting daily work to personal values. The manager’s job is to make small shifts that move the employee closer to the “after” version.

Emotion at Work

In “There’s No Crying in Baseball,” Pacheco dismantles the myth of emotionless professionalism. Suppressing emotion drains energy and authenticity. Drawing on sociologist Arlie Hochschild’s concept of emotional labor, she shows how forced cheer or forced calm (especially in service work) leads to burnout. Yet emotions also spread—through emotional contagion. The manager’s role is to allow true feelings but contain negative spirals.

She encourages “What’s up below?” check-ins that invite authenticity without chaos, and modeling vulnerability herself. “Feelings are everywhere,” she concludes. “Be gentle.”

Meaning, then, isn’t mystical—it’s manufactured through clarity, connection, and compassion. If you help your team understand how their work matters and feel safe being human while doing it, you’ve given them what every employee secretly wants: purpose with permission to feel.

Part II tackles the full life cycle of a team—recruiting, onboarding, and letting people go. Here Pacheco blends humor (“Always lock the bathroom door during interviews”) with rigor, insisting that consistency beats charisma in every hiring decision. Good recruiting isn’t about gut feel; it’s about structure.

Hiring by Science, Not Vibes

Her antidote to bias is a structured interview process applied “Every. Single. Time.” Each role should have clear must-haves, standardized behavioral questions (“Tell me about a time when…”), and written assessments testing real skills. She mocks the infamous “airport test”—“Would I want to be stuck with this person at an airport?”—as shorthand for affinity bias. When you rely on likeability, you hire versions of yourself and shrink diversity.

Onboarding as Integration

Being the “new kid on the block” is universal agony, she writes. So managers must actively script a welcoming process: coffee chats, peer buddies, early projects, and explicit first-week and first-month checklists. This isn’t bureaucracy; it’s inclusion. Structured onboarding reduces burnout and signals respect. As Pacheco quips: “Don’t make newbies raid the fridge wondering whose yogurt they just ate.”

Firing with Humanity

When separations come—whether voluntary or not—clarity and compassion rule. Managers must overcommunicate plans, act swiftly, and treat exits as part of the team’s story, not a hush-hush failure. Celebrate top performers who move on; support those who part ways for performance reasons; and when layoffs occur, “cut once, cut deep,” then rebuild trust.

Never ghost departing employees—acknowledge, thank, and help them land well. How you handle exits defines your team’s culture more than any poster on the wall.

Finally, she references William Bridges’ model of transitions—endings, neutral zones, and new beginnings—to remind managers that everyone processes change differently. Managing departures isn’t about paperwork; it’s about shepherding emotion from loss to renewal.

Teams, Pacheco admits, can be heaven or hell. She recounts a disastrous project in Kazakhstan to prove it: unclear roles, infighting, and one colleague who—literally—brought a gun to a trust-building dinner. Yet from this chaos she extracts two universal truths: high-performing teams depend on explicit norms and psychological safety.

What Makes a Real Team

Referencing Google’s “Project Aristotle” research, Pacheco emphasizes that successful teams share behavior patterns, not personalities. They define their operating rules early (“How do we decide? How do we handle conflict?”), practice empathy through exercises like “Journey Lines,” and ensure conversational balance so every voice is heard. Managers should invite junior members to speak first, appoint devil’s advocates, and directly manage airtime hogs.

Encouraging Dissent

In “Getting Your Team to Speak Up,” she revisits the Abilene Paradox—where everyone agrees to a bad decision no one wants (like driving to Abilene in the Texas heat). To prevent this, managers must reward dissent and “speak last.” Written brainstorming before meetings helps quieter voices shine without social pressure. Cultural context matters too: not everyone’s comfortable interrupting; inclusion demands multiple avenues to contribute.

The Good Fight

Not all conflict is bad, Pacheco insists. Task conflict—debating ideas—is healthy. Process conflict—debating logistics—is necessary. Relationship conflict—disliking people—is cancerous. Great teams keep the first two high and the last low. If conflict turns personal, rebuild trust through empathy and shared purpose, not avoidance.

Culture vs. Community

In her final reflection on team life, she flips a corporate cliché: “Don’t build a culture. Build a community.” Culture, she says, dictates behavior; community generates belonging. Replace slogans with shared experiences. Welcome newcomers, celebrate departures, and maintain alumni networks. Culture makes people act; community makes them care.

It’s a simple but radical shift: manage your team less like a machine and more like a neighborhood. When people feel they belong, performance follows naturally.

In the final section, Pacheco turns the mirror around. You can’t lead others if you can’t lead yourself. Self-management requires emotional intelligence, humility, and self-boundaries—especially when your power increases. Her last chapters feel almost like therapy sessions for managers who’ve lost sleep over tough calls.

Confidence and Vulnerability

The best management advice Pacheco ever heard came from a friend: “Show confidence up and vulnerability down.” To your boss, project competence and ownership; to your team, admit mistakes and fears. Vulnerability builds trust when paired with competence. Fake bravado breeds distance; openness breeds loyalty.

Power Without Corruption

Once promoted, beware the subtle arrogance power brings: favoring those like you, ignoring dissent, protecting your turf. She playfully coins terms like “manator” and “bosspressor” for leaders who rule instead of lead. If you find yourself managing friends, address the awkwardness honestly and set boundaries together. Friendship and authority can coexist only with disciplined empathy.

Managing Up

Your boss, like you, is overwhelmed. Between high cognitive load and short memory, they’re not thinking about you nearly as much as you think they are (the “spotlight effect”). So take charge of the relationship: drive agendas, anticipate needs, communicate progress, and adapt to their style. Don’t resent disorganization—complement it. Great employees make their bosses look great without servility.

When It’s Time to Go

Eventually, every manager must face a crossroads. Should you stay or should you go? Pacheco reframes job offers as mirrors: they show you whether you need to fix your role, take the offer, or start a new search. Using micro-exercises—writing career intentions, envying wisely, crafting an elevator pitch—she encourages thoughtful self-renewal over impulsive exits.

Her parting advice is both sobering and liberating: “Don’t love something that can’t love you back.” Your job can inspire you, but it cannot reciprocate. Love your people; manage your company; protect yourself.

In short, Bringing Up the Boss ends where it began—with humanity. Leadership isn’t about mastering others; it’s about managing your own ego, emotion, and energy so your people can thrive. As Pacheco reminds readers, everyone starts as a terrible boss. What matters is that you decide to become a better one.