Becoming the Boss

Becoming the Boss Plot Summary

Introduction

I was twenty-four years old when I was abruptly handed my first leadership role. After a company restructuring, I found myself managing a team of five people, most of whom were older than me. The morning of my promotion, I sat at my desk feeling a peculiar mix of pride and panic. While I had excelled as an individual contributor, I had no idea how to lead others. What if my team didn't respect me? What if I made terrible decisions? That evening, I called my mentor in tears, convinced I would fail spectacularly. Leadership is a journey that transforms not just your career but your entire identity. Whether you're a first-time manager, an entrepreneur launching a startup, or someone taking on a volunteer leadership position, the transition from individual contributor to leader represents one of the most significant challenges you'll face in your professional life. The path is rarely straight, often confusing, and filled with unexpected obstacles. Yet this journey also offers extraordinary rewards – the chance to amplify your impact, develop others, and create lasting change in your organization and community. Through stories of both triumph and struggle, we'll explore the essential skills and mindsets that will help you not just survive but thrive as you become the leader you're meant to be.

Chapter 1: The Leadership Journey: From First-Time Manager to Seasoned Leader

Liam McGee started his career as a junior salesperson at Wells Fargo, essentially "dialing for dollars" as he described it. Naturally shy, he was so terrified before his first in-person sales call that he actually drove away before walking through the client's door. Slowly, he began to overcome his fear – he knew he wouldn't keep his job otherwise – and worked his way up through the ranks. One day, on his way to meet with his mentor, he overheard the mentor say to a colleague, "I think that McGee kid can be on the twelfth floor someday," referring to where the top executives sat. "That changed my life," McGee recalled. "It confirmed to me that my goals were possible." McGee went on to mention "five very important mentors who were very tough on me and gave me sometimes-too-candid feedback. They saw something in me and I trusted them." McGee's journey illustrates a crucial reality of leadership development: it rarely follows a straight line. The path from individual contributor to seasoned leader involves false starts, moments of doubt, and critical points where someone else's belief in you becomes the catalyst for your own self-confidence. For McGee, that overheard comment became a pivotal moment that transformed his career trajectory. Jeremy Lade, a U.S. Paralympian in wheelchair basketball and coordinator of wheelchair athletics at the University of Wisconsin at Whitewater, describes how he constantly seeks new ways to build team atmosphere. "I get ideas from everyday life," he says, "from surfing the Internet, talking to people, watching commercials. I look outside of wheelchair basketball. I'll watch football or soccer practice or talk to the leader of a fellowship of Christian athletes. You can always find some kind of benefit from every experience or conversation." What both McGee and Lade demonstrate is that leadership development requires an open, learning mindset. The journey isn't just about acquiring technical skills or formal authority. It's about developing emotional intelligence, building relationships with mentors, remaining curious about diverse perspectives, and maintaining the humility to continuously improve. The most successful leaders never stop learning or expanding their horizons, understanding that leadership is not a destination but a continuous evolution.

Chapter 2: Building Your Personal Brand as a Leader

When I asked dozens of successful leaders what they believed to be the most important characteristics of a leader, their answers converged around four essential elements: visibility, differentiation, consistency, and authenticity. These elements form the foundation of what leadership experts call your "personal brand" – the reputation and impressions you create in your professional world. Tom Peters, the management guru who first introduced the concept of personal branding in a 1997 Fast Company article, wrote: "We are CEOs of our own companies: Me Inc. To be in business today, our most important job is to be head marketer for the brand called You." This perspective places your reputation and career management almost entirely in your control. It's empowering and quite different from the days when you had to wait and hope that a high-level person would notice you, realize you had potential, and decide to groom you for a leadership position. Alexandra Lebenthal, CEO of financial firm Lebenthal & Co., learned this lesson early in her leadership journey. "Managing people can be a daunting task and a new manager might have preconceived ideas about all of a sudden becoming someone else, but the best leaders I have known are the ones who let their true personalities shine through by being open and approachable," she explains. When she first became CEO, Lebenthal felt that to get respect she had to act more authoritative. "In doing so I made a decision and communicated it in a way that was far from my usual way of dealing with people. As a result, someone left the company. Had I handled it differently, she might have stayed. It was a real wake-up call for me." Authenticity forms the cornerstone of leadership presence, but that doesn't mean being unfiltered or unprofessional. It means aligning your external actions with your internal values and strengths. Jeremy Lade, the wheelchair basketball coach, shares that he is constantly seeking new ways to build team atmosphere: "I need to figure out each individual's strength to get the most out of them to best help our team. This takes a lot of communication." The most powerful personal brands aren't manufactured – they're cultivated through consistent actions that reflect genuine values and strengths. When you understand what makes you effective and valuable as a leader, you can consciously develop those qualities while remaining true to yourself. Your leadership brand isn't about creating a perfect image; it's about becoming aware of your impact on others and intentionally shaping that impact to align with your leadership goals and values.

Chapter 3: Mastering Communication: The Key to Leadership Success

Liam E. McGee, who rose to become chairman and president of The Hartford, observed: "Nothing prepares you to be a CEO. The buck truly does stop with you. You have to be careful of what you say. People take what the CEO says differently." His insight captures a fundamental truth of leadership: words matter enormously, and the higher you rise, the more weight your communication carries. A fascinating study by researchers at the University of Texas at Austin found that leaders use the word "I" less than non-leaders, dispelling the commonly held belief that leaders are self-centered or egotistical. According to the researchers, "There is a misconception that people who are confident, have power, have high status tend to use 'I' more than people who are low status. That is completely wrong. The high-status person is looking out at the world and the low-status person is looking at himself." This research highlights one of the most important shifts new leaders must make: moving from an "I" perspective to a "we" perspective. Instead of saying, "I believe this is the right strategy because..." simply say, "This is the right strategy because..." Or, even better, "We need to implement this strategy because..." Remember that as the leader of a team, you are still a member of that team. "We" is one of the most powerful words in your leadership vocabulary. Julie Daly Meehan, executive director of Hartford Young Professionals and Entrepreneurs, emphasizes that effective communication requires listening: "Communication is half listening. If you are just thinking about the next thing coming out of your mouth, you are missing a lot of key information—not only what other people are saying, but how they are feeling about it. When I'm more actively listening, I'm able to recognize the holes in the information I'm receiving and ask questions, rather than getting back to my desk and realizing I'm missing something." Angela Lee, assistant adjunct professor at Columbia Business School, offers practical advice for becoming a better listener: "Start with your audience. What is their perspective? Taking five minutes to ask yourself about your audience's objectives, goals, and biases will prime you to listen." She also recommends releasing your agenda: "Don't listen for what you expect to hear; listen to what the other person is actually saying." Effective leadership communication isn't about being a polished speaker or prolific writer. It's about creating understanding, building connection, and inspiring action. The most influential leaders communicate with clarity and purpose, adapting their approach to their audience while maintaining authenticity. They recognize that how they say something is often as important as what they say, and they take full responsibility for ensuring their message is received as intended.

Chapter 4: Managing People: Strategies for Different Generations

Early in my career, I worked at a start-up called WorkingWoman.com. After about a year, I received my first-ever promotion and was told to hire a junior person to handle some of my workload. I chose a friendly, eager, recent college graduate named Alex. It was my first experience managing someone, and I was excited to become a mentor to my brand-new protégé. I managed to read about ten seconds of The One Minute Manager before my employer went bankrupt. I had been a manager for three whole weeks. This brief experience taught me one of a new boss's most important lessons: succeeding as an individual contributor is not the same as succeeding as a manager. While I did a fairly good job of teaching Alex the importance of our company's partnerships, I continued to do all of the work I'd been doing previously myself. I assigned Alex a few administrative tasks, but I kept all of the important stuff for myself and wondered why he didn't seem that busy while I was more slammed than ever trying to manage him and do all of my work, too. Michael "Dr. Woody" Woodward, PhD, an organizational psychologist, explains this common challenge: "When you are going into a role that requires people management, the key is your ability to operate through other people. And it's not always fun! Your natural inclination is often to fall back on your expertise and do what you do well, which is being an individual contributor. Any new manager struggling to get the result they need will tend to jump in and do the work themselves." In 2009, Laszlo Bock, senior vice president of people operations at Google, launched an empirical study called Project Oxygen to figure out the differences between the best and worst bosses at Google. The company had always believed that because they hired really smart people, all a boss needed to do was leave people alone and provide technical wisdom when requested. They couldn't have been more wrong. The study found that technical expertise ranked last among the predictors of a boss's effectiveness. Instead, employees most wanted "even-keeled" bosses who made time for one-on-one meetings, helped them solve problems, and took an interest in their lives and careers. One of the most significant challenges facing today's leaders is managing across generational differences. For the first time in American history, four distinct generations are sharing the workplace: Traditionalists (born 1922-1945), Baby Boomers (1946-1964), Generation X (1965-1981), and Millennials (1982-2000). Each brings different expectations, communication styles, and work preferences. Effective management requires understanding these differences while avoiding stereotypes that might limit individuals. The most successful people managers today recognize that leadership is not about control or authority but about creating environments where diverse individuals can contribute their best work. They build genuine relationships with team members, communicate clear expectations, provide meaningful feedback, and create opportunities for growth. Above all, they understand that management is not a secondary task but a primary responsibility – perhaps the most important contribution they make to their organization's success.

Chapter 5: Time Management and Work-Life Integration

In the old days (like, twenty years ago), most people had dial-up Internet, we used fax machines to crank out documents page by page, and we waited three days to receive an important item in the mail. The only instant communications were the phone and tapping someone on the shoulder. There were very few cell phones, so if you commuted to and from work, you usually listened to the radio in the car or read a book on the train or bus. If you wanted to get work done over the weekend, you went back into the office. Believe it or not, people thought they were busy then. Today we are regularly sending, receiving, and processing information by e-mail, text, IM, phone, voice mail, messenger, overnight mail, FTP, LinkedIn, Twitter, Facebook, blog comments, live meetings, teleconferences, videoconferences, Skype, shared folders, wikis, and whatever technology is invented tomorrow. Plus, when you're the boss you're exposed to the stress and busyness of all the people you oversee in addition to your own. When I first started my career, I remember being really impressed by people who were "slammed," "buried," "overloaded," "getting killed," or "completely maxed out." "They must be so important!" I thought, as I chugged my third Diet Coke of the morning. But now I know better. Being busy is not a badge of honor. Yes, the world moves much faster today, and yes, leaders have a lot to deal with. But managing it all is part of your job. If you are a leader and you are "slammed" all the time, then you are: (1) not delegating enough, (2) not organized enough, or (3) being dramatic. Management guru Stephen Covey tells a famous story about a teacher giving a lecture about time. The teacher places a wide-mouth gallon jar on the table and adds three fist-size rocks to the top. He asks if the jar is full, and the students say yes. He then adds gravel, which fills the spaces between the rocks. Again, he asks if the jar is full, and the class says yes. Next, he adds sand, which fills the gaps between rocks and gravel. Finally, he pours in water. The lesson? If you don't put the big rocks in first, you will never get them in. If you want to accomplish big things in your life—building a sustainable company, having a happy family, launching a new product, or writing a book—you have to schedule the steps related to those big things before anything else. When you plan the big things, you are so focused and committed to your major goals that the smaller things tend to fall into place. Effective leaders understand that time management isn't about cramming more activities into each day – it's about making deliberate choices about how to invest limited time and energy. They create systems that allow them to focus on their highest priorities while delegating or eliminating activities that don't significantly contribute to their goals. They recognize that their most valuable resource isn't money or talent but attention, and they protect it accordingly.

Chapter 6: Networking and Relationship Building

Liam E. McGee, whose leadership journey we've followed throughout these chapters, attributes much of his success to "five very important mentors who were very tough on me and gave me sometimes-too-candid feedback. They saw something in me and I trusted them." His experience highlights a fundamental truth about leadership development: no one succeeds alone. When I was in college, a very successful family friend told me that the most important thing I could do for my career was to keep building my contacts. I've followed that simple but profound advice ever since. In those days, networking consisted of either a phone call, a face-to-face meeting, or an old-fashioned snail mail letter. As a leader today, you have countless additional methods—LinkedIn, Twitter, Facebook, Skype, FaceTime, Google+ Hangouts—to leverage in relationship building. The most successful networkers use all tools—online and offline—available. The rise of social media has transformed networking, but the core principles remain unchanged. Angela Lee, the Columbia Business School professor and founder of 37 Angels, receives many requests from her MBA students for introductions to people in her extensive investor network. She doesn't mind these requests "when I sense they are truly passionate about what they're going after, and that they have done their research on me and know they are asking for my core competency. It's about knowing your audience and having done your research and making that person feel like an individual and not a big Rolodex." Congressman Aaron Schock explained how relationship building contributes to legislative success: "I spent much of my first year in Congress getting to know my colleagues who were part of my freshman class and the more seasoned members of Congress who understood how the House works. This effort to connect with my colleagues helps when I need support for a bill I am introducing, so I know which members might be interested in joining me, and it's not the first time they have heard from me. Making the personal connection is a huge part of persuading people to support the goals you have in front of you." Effective networking isn't about collecting business cards or LinkedIn connections – it's about building genuine relationships based on mutual value and trust. The most successful leaders approach networking with a "give first" mindset, looking for opportunities to help others without immediate expectation of return. They build diverse networks that extend beyond their industry or function, recognizing that innovation often emerges from unexpected connections. Most importantly, they understand that relationships require regular maintenance and invest time in nurturing their most important professional connections.

Chapter 7: Growing Through Success and Failure

My toddler daughter's favorite movie is Toy Story. She especially loves the scene in which the brand-new astronaut toy Buzz Lightyear tries to prove to the skeptical, old-fashioned cowboy Woody that he is not a toy but a real astronaut who can fly. He proceeds to jump off a bedpost and, through a series of lucky accidents, he appears to fly gracefully around the room. Buzz lands proudly, raises his arms in triumph, and all of the other toys applaud. A frustrated and irritated Woody says: "That wasn't flying! That was falling with style!" The toys ignore Woody and proceed to worship Buzz Lightyear all the same. This is how I recommend handling the inevitable mistakes you will make in your career. You're going to make mistakes and fail sometimes. So do your best to fall with style. In the early years of building my speaking business, I worked as an independent consultant for a corporate training company. I taught courses on business writing and grammar, and I soon learned that one of the biggest mistakes professionals make in their writing is overuse of the passive voice – e.g., "This book is being read by you" vs. "You are reading this book." The reason to avoid passive voice is that it places emphasis on the action taken rather than the person taking that action. And in many instances, you can use the passive voice to avoid mentioning the action-taker at all. The prime example we shared to explain why business leaders should avoid passive voice was this: "Mistakes were made." The phrase, popular with politicians, admits something went wrong but totally avoids taking any blame. Using an evasive phrase like this would be the opposite of falling with style. Leaders take responsibility not just for wins, but also for losses. Congresswoman Tulsi Gabbard offers this perspective on leadership challenges: "As long as you are motivated by a desire to make a positive impact, you cannot fail and will overcome the naysayers and the inevitable obstacles. You won't win every single battle, and there will be challenges. But every battle and every challenge is actually an opportunity—an opportunity to learn, to expand, to change course, to build character, and ultimately, to be a better servant leader." JetBlue Airways chairman Joel Peterson has said that "Most Likely to Bounce Back after a Fall" would be a much better yearbook category than "Most Likely to Succeed." The ability to persevere through failure, learn from mistakes, and maintain optimism in the face of setbacks differentiates exceptional leaders from average ones. True resilience isn't about avoiding failure – it's about how quickly you recover, what you learn, and how you apply those lessons moving forward.

Summary

Throughout our exploration of leadership, we've witnessed the transformative journey from individual contributor to inspiring leader. We've seen how Liam McGee overcame his fear of sales calls to become a chairman and president, how Jeremy Lade continuously seeks new ideas to build team spirit, and how Congresswoman Tulsi Gabbard views every challenge as an opportunity to become a better servant leader. These stories remind us that leadership is not about perfection but about continuous growth, authentic connection, and resilient response to both success and failure. The path of leadership offers profound lessons for anyone willing to embrace its challenges. First, true leadership begins with self-awareness – understanding your strengths, acknowledging your limitations, and remaining committed to ongoing learning. Second, effective leadership requires genuine connection with others – communicating with clarity, listening with empathy, and building relationships based on mutual trust and respect. Finally, transformative leadership demands resilience – the ability to maintain perspective in difficult moments, to learn from mistakes, and to keep moving forward despite obstacles. As Dan Black of EY Americas observed about the rising generation of leaders: "I am so bullish on this generation. They have so much to bring to the table... They are diverse, culturally aware, connected, and networked in ways my generation never knew how to be. These kinds of skills make them uniquely prepared to be successful in the coming decade or two."

About Author

Loading...

Lindsey Pollak

Lindsey Pollak is a New York Times bestselling author and one of the world’s leading career and workplace experts, with a special focus on early career success.She was named to the 2020 Thinkers50 Radar List, which honors 30 global management thinkers whose work is shaping the future of how organizations are managed and led. Lindsey’s next book, a response to the Covid crisis, "Recalculating: Navigate Your Career Through the Changing World of Work," will be published in March 2021. Her other books include "The Remix: How to Lead and Succeed in the Multigenerational Workplace," "Becoming the Boss" and "Getting from College to Career." Lindsey’s speaking audiences and consulting clients have included more than 250 corporations, law firms, conferences and universities.She has been featured in such media outlets as The TODAY Show, The New York Times, The Wall Street Journal, CNN and NPR.

Read more