Bringing Up the Boss

Bringing Up the Boss Plot Summary

Introduction

Stepping into the role of a manager for the first time can feel like being pushed onto a stage without a script. One day you're focusing on your individual tasks, the next you're responsible for an entire team's performance, development, and well-being. This transition often comes without proper preparation, leaving many new managers to navigate this unfamiliar territory through trial and error. The challenge intensifies in fast-growing organizations where you might be promoted because you excelled at your job, not necessarily because you demonstrated management capabilities. Suddenly, you're juggling feedback conversations, setting expectations, handling team conflicts, and making decisions that impact not just projects but people's careers. This journey of becoming an effective manager isn't just about mastering technical skills—it's about understanding human motivation, building psychological safety, developing your leadership identity, and learning how to advocate for your team across the organization. Throughout these pages, you'll discover practical approaches to transform these management challenges into opportunities for growth, both for yourself and your team members.

Chapter 1: Set Clear Expectations: The Foundation of Great Management

Clarity is the bedrock of successful management. When team members understand exactly what's expected of them, they can channel their energy toward meeting those expectations rather than trying to guess what success looks like. Yet many managers—especially those new to the role—fail to articulate their expectations clearly, leading to frustration and disappointment on both sides. Consider Diane's experience with her sales team member Lalit. She came to me complaining that Lalit wasn't proactive—he didn't follow up on sales leads mentioned in meetings, came to check-ins without an agenda, and never brought ideas about expanding their client footprint. When I asked if she had communicated these expectations clearly, Diane insisted she had told Lalit multiple times to "be more proactive." The problem wasn't that Diane hadn't mentioned her expectations; it was that she hadn't defined what "proactive" meant to her in concrete, observable behaviors. Lalit was trying to be proactive but had no clear understanding of what specific actions would meet Diane's definition. This situation reveals why expectation-setting is fundamental yet often challenging for managers. Many avoid detailed direction out of fear of being labeled a micromanager. Others fall victim to the Dunning-Kruger effect—as experts, they underestimate how difficult certain tasks are for less experienced team members, assuming instructions are self-explanatory when they're not. Both scenarios leave team members navigating in the dark. Effective expectation-setting answers four essential questions: What's the objective or end goal? What does good look like? What's the timing? What are examples (if possible)? By explicitly addressing these questions—preferably in writing—you create a clear path for your team members to follow. This structured approach ensures you've thought through what you actually want and gives your team concrete parameters for success. When you think your expectations are clear enough, go back and make them even clearer. Push against fears of appearing bossy or micromanaging. Your team members genuinely want to know what success looks like through your eyes, and clear expectations are the map they need to get there. Remember, as Sarah's father wisely said, "An expectation unarticulated is a disappointment guaranteed."

Chapter 2: Give Effective Feedback: Build Growth Through Honest Communication

Feedback is the engine that drives professional growth. Yet despite knowing its importance, many managers avoid giving constructive feedback, fearing awkward conversations or worrying they'll hurt feelings. This avoidance, however well-intentioned, ultimately harms team members by depriving them of opportunities to develop. Josh Hardy, my first manager at a consulting firm, understood this principle well. As a young college graduate, I often bristled at Josh's feedback about seemingly trivial matters—my inconsistent PowerPoint color schemes, arriving ten minutes late to internal meetings, or my haphazard note-taking approach. At the time, I found his constant corrections irritating and unnecessarily detailed. Years later, I came to appreciate that these "little tweaks" early in my career dramatically improved my professional trajectory. Josh wasn't being petty; he was giving me the gift of timely, specific feedback that shaped my development when it mattered most. The impact of early feedback is particularly powerful because behavior becomes more difficult to change the longer it's reinforced. Small corrections early in someone's career can prevent the solidification of poor habits that might limit their growth for years. Withholding feedback doesn't protect your team members—it handicaps them. Well-structured feedback follows a simple three-part formula: Start with objective data ("I observed that you joined the meeting ten minutes late"), explain the impact ("When you arrive late, it disrupts the flow and means we have to recap what you missed"), and suggest a change in behavior ("In the future, please prioritize arriving on time or let me know in advance if you'll be delayed"). This approach reduces defensiveness by focusing on specific behaviors rather than making judgments about the person's character or intentions. Effective feedback isn't just about giving—it's also about receiving. Great managers actively solicit feedback from their teams, creating multiple channels for team members to share their perspectives. This might include anonymous surveys, dedicated upward feedback sessions separate from performance reviews, and regularly asking specific questions about your management style. When you receive feedback, practice responding with openness and gratitude, even when it stings. By embedding honest, structured feedback into your management approach, you create an environment where continuous improvement becomes the norm. Remember that feedback—both giving and receiving it—will feel uncomfortable at first. That discomfort is normal and worth pushing through for the growth it enables in your team and yourself.

Chapter 3: Foster Meaningful Work: Connect Tasks to Purpose

Work becomes meaningful when people understand how their daily efforts connect to something larger than themselves. As a manager, you have the unique ability to structure and frame work in ways that help your team members find fulfillment in their roles—even when the core responsibilities remain the same. Consider two hypothetical employees, Kelly and Kiesha, both human resource associates at small companies. Kelly's role is described as supporting HR activities—recruiting candidates, administering benefits, and maintaining files. Her manager assigns daily tasks and expects her to follow instructions. Meanwhile, Kiesha's identical job is framed differently: she helps the company achieve strategic goals by ensuring strong human capital foundations. She works with leadership to determine priorities, then has ownership over activities like recruiting that support those strategies. Though their actual tasks are identical, Kiesha likely derives far more satisfaction from her work because of how it's structured and presented. Richard Hackman identified five key design choices that make work meaningful. First, skill variety ensures work includes diverse, challenging activities rather than monotonous repetition. Second, task identity means completing whole projects rather than disconnected fragments—like researching, conducting, and presenting findings instead of just cleaning data. Third, task significance connects work to its impact on others, such as understanding how tightening screws on airplane brakes keeps passengers safe. Fourth, autonomy gives freedom to determine how work gets accomplished rather than dictating every step. Finally, feedback ensures people know the results and effectiveness of their efforts. Beyond structure, perception matters tremendously in finding meaning. Job crafting, developed by Amy Wrzesniewski and colleagues, helps employees reframe their existing roles to better align with their strengths and motivations. In this process, team members first map their current tasks in a "before" diagram. Then, they create an "after" diagram showing how they'd ideally spend their time, connecting tasks to broader purposes and personal strengths. With your support, they can identify steps to move closer to this ideal. Consider Alex, an executive assistant feeling stuck in his career path. Through job crafting, he transformed his perspective by connecting routine tasks to developmental goals. His calendar management became "creating organizational efficiency," and his meeting preparation transformed into "building strategic communication skills." These shifts didn't change his daily responsibilities but dramatically altered how he perceived their value and connection to his growth. Small management actions can significantly impact how meaningful work feels to your team. Taking five minutes to explain how a project connects to company strategy, acknowledging the impact of someone's work through a specific email, or assigning varied responsibilities that build new skills—all contribute to creating an environment where work feels purposeful rather than pointless.

Chapter 4: Build Team Psychological Safety: Create an Environment of Trust

Have you ever been part of a team that looked great on paper but somehow couldn't function effectively together? A collection of talented individuals who, despite their skills, formed what might be called a TINO—Team In Name Only? This disconnect often stems from missing the foundational elements that transform a group into a true team. Google's Project Aristotle, which studied 180 teams across the organization, discovered that high-performing teams weren't distinguished by diversity, personality types, or even working styles. Instead, they shared two crucial ingredients: explicit norms and psychological safety. These elements formed the bedrock upon which effective teamwork could flourish. Explicit norms are the shared "rules of the game" that guide how team members operate together. Interestingly, Google found that the specific norms didn't matter as much as everyone knowing and following them. A team that spends twenty minutes chatting before diving into work can be just as effective as one that starts promptly with a structured agenda—provided everyone understands and operates within those expectations. Problems arise when team members have different, unspoken assumptions about how things should work. Psychological safety, a concept developed by Amy Edmondson, means team members feel secure taking risks without fear of embarrassment or punishment. This safety emerges from two components: empathy (understanding others' perspectives) and conversational turn-taking (ensuring everyone has a voice over time). When psychological safety exists, people feel comfortable sharing ideas, admitting mistakes, asking questions, and challenging the status quo—all behaviors that drive innovation and prevent costly errors. Building these foundations requires deliberate action. Start by gathering your team to explicitly document your working norms. Discuss communication preferences, decision-making processes, and how you'll handle disagreements. Create a written record that new members can reference and revisit periodically as the team evolves. To build empathy, use tools that help team members understand each other's perspectives. This might include personality assessments like StrengthsFinder or exercises like Journey Lines, where each person maps their year's highs and lows to share with the group. These structured conversations help people see beyond workplace roles to understand colleagues' experiences and motivations. For balanced participation, establish practices that encourage everyone to contribute. Appoint devil's advocates for important decisions, have junior team members speak first in discussions, or "warm call" quiet participants by asking specific questions. These approaches help prevent dominant voices from controlling conversations while building the team's collective intelligence. Remember that creating psychological safety isn't a one-time event but an ongoing practice. The small actions you take consistently—acknowledging vulnerability, responding supportively to mistakes, demonstrating curiosity rather than judgment—gradually build an environment where everyone can bring their best thinking to the team's challenges.

Chapter 5: Develop Your Leadership Identity: Balance Confidence and Vulnerability

One of the most powerful pieces of management advice comes in just six words: "Show confidence up and vulnerability down." This simple guidance encapsulates the delicate balance required in effective leadership, particularly for new managers navigating their emerging leadership identity. Showing confidence "up" to your own manager means demonstrating your capability to execute work, lead your team, and serve as a thought partner. It involves anticipating your manager's needs, taking initiative on problems before being asked, and presenting solutions rather than just challenges. This confidence assures those above you that you can handle the responsibilities entrusted to you. Meanwhile, showing vulnerability "down" to your team creates the psychological safety and trust essential for high performance. When you admit what you don't know, acknowledge mistakes, or share appropriate concerns, you model the authenticity that allows others to do the same. This vulnerability builds connection and demonstrates that perfection isn't the standard—growth and learning are. However, new managers often struggle with this balance. Christina, preparing for an important organization-wide presentation, considered two approaches with her team. She could say, "I'm going to bomb this TED Talk. I didn't prepare at all," or "Public speaking still makes me nervous despite giving lots of presentations. I memorize every big presentation to feel prepared." The first statement conveys incompetence (and likely inauthentic incompetence at that). The second shows vulnerability while maintaining competence—revealing the very human nervousness even experienced speakers feel while demonstrating the professionalism to prepare thoroughly. Similarly, when Fatima needed to discuss potential layoffs with her anxious team, she could have said, "I'm in the dark just as much as you and petrified about losing my job," or "I'm also anxious about the uncertainty. It's scary making decisions when things aren't clear. I'm working to get answers for our team as soon as possible." The first approach might seem transparent but undermines confidence in her leadership during a crisis. The second acknowledges genuine feelings while maintaining her role as the team's advocate and guide. Vulnerability as a manager often means being comfortable saying "I don't know" when you don't have an answer, admitting when you've made a mistake, or acknowledging when you're facing a new situation. This honesty builds trust far more effectively than pretending to have all the answers. New managers frequently delay difficult conversations until they feel prepared for every possible question—an impossible standard that prevents necessary communication. The courage to be vulnerable pays unexpected dividends. When teaching a graduate class, I unexpectedly became emotional during a discussion and started to cry—something I feared would destroy my credibility. Instead, it deepened my connection with students and created a level of trust previously absent. While crying in front of a class isn't on my list of favorite activities, that authentic moment bridged the gap between teacher and students in ways careful planning never could. In developing your leadership identity, remember that vulnerability builds trust when coupled with competence. The balance of showing confidence up and vulnerability down creates the foundation for authentic leadership that inspires both respect and connection.

Chapter 6: Manage Up and Around: Navigate Organizational Relationships

Being an effective manager isn't just about leading your team—it's equally about managing relationships across and above you in the organization. Your ability to influence, communicate, and collaborate with peers and superiors directly impacts your team's success and your own effectiveness as a leader. Managing up—building a productive relationship with your own boss—often receives less attention than managing direct reports, yet it's crucial for your team's success. Consider my experience with my boss Samaiyah. Every Monday night, I'd contemplate how to approach our Tuesday morning meeting, sometimes canceling last-minute with a breezy "Nothing new!" Other times, I'd manufacture a "crisis" to discuss or attempt to redirect the conversation to office gossip. This approach reflected my uncertainty about how to use these meetings effectively—a common challenge in managing up. Two key factors make managing up challenging. First, there's the collision of cognitive load and the spotlight effect. Your boss juggles numerous responsibilities that tax their working memory, while you naturally overestimate how much they think about your work. The reality is that your boss likely isn't thinking about you or your projects nearly as much as you assume. Second, many managers hit what I call the "expert inflection point"—the moment when you become more knowledgeable about your functional area than your boss. This shift requires a fundamental change in how you approach the relationship, moving from seeking answers to providing expertise and solutions. To manage up effectively, focus on two key principles. First, own the execution of the relationship. Take charge of every aspect—come to meetings with prepared agendas, proactively provide updates rather than waiting to be asked, and present solutions alongside problems. Second, understand and adapt to your boss's style. Rather than expecting them to change their approach, identify how you can complement their strengths and weaknesses. If your boss is disorganized, bring structure; if they're detail-oriented, provide concise summaries with supporting documentation available. Beyond your boss, lateral relationships with peers and other departments critically influence your effectiveness. These relationships provide resources, information, and support that help you advocate for your team and navigate organizational complexities. Start by mapping the stakeholders who impact your work, then intentionally build connections through regular check-ins, shared projects, or informal conversations. When conflicts arise with peers—as they inevitably will—approach them with curiosity rather than defensiveness. Ask questions to understand their perspective, look for shared interests beneath opposing positions, and focus on solving the problem together rather than assigning blame. Remember that these relationships persist long after specific disagreements fade, making the "how" of resolution as important as the outcome. Finally, recognize that navigating organizational politics doesn't require compromising your integrity. Politics simply means understanding how decisions are made, who influences them, and how resources are allocated. By building strong relationships based on mutual value and trust, you position yourself to effectively advocate for your team's needs while contributing to broader organizational goals. Managing up and around requires intention and adaptability, but mastering these relationships amplifies your impact beyond what you could achieve through direct authority alone. As you develop these skills, you create an environment where your team can thrive with the support and resources they need to succeed.

Summary

Throughout this journey into effective management, we've explored the foundational elements that transform good intentions into great leadership. From setting crystal-clear expectations to fostering psychological safety, from delivering growth-oriented feedback to navigating complex organizational relationships, the path of management requires both technical skill and emotional intelligence. As Rachel Pacheco reminds us, "Being a manager is simultaneously an art form, a scientific discipline, and an innate gift. But coaching itself is a basic tool that you can start implementing immediately." Your growth as a manager starts with a single action today. Choose one practice from these pages—perhaps conducting a team norms discussion, scheduling feedback conversations with direct reports, or mapping stakeholder relationships—and implement it this week. Remember that management excellence isn't achieved through perfection but through consistent practice, genuine care for your team's development, and the courage to balance confidence with vulnerability. The impact you'll have as you master these skills extends far beyond tasks completed—you'll shape careers, build confidence, and create environments where people can do their best work.

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Rachel Pacheco

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