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Becoming the Boss

11 min

New Rules for the Next Generation of Leaders

Introduction

Narrator: Imagine being promoted to your first management role. You're excited, but also terrified. You read a bit of a classic management book, hire your first employee, and then, just three weeks later, the company goes bankrupt. The head of the company hands you your laptop and says, "Keep it. Use it to go start your own business." This isn't a hypothetical scenario; it's the real-life story that launched Lindsey Pollak's career and became the foundation for her book, Becoming the Boss: New Rules for the Next Generation of Leaders. The book argues that the leadership advice of the past is no longer enough. To succeed today, a new generation of leaders must navigate a world transformed by unprecedented demographic, economic, and technological revolutions.

The Old Leadership Playbook Is Obsolete

Key Insight 1

Narrator: The core principles of leadership—confidence, ethics, drive—are timeless. However, Pollak argues they are insufficient for the modern workplace. Today's emerging leaders face three simultaneous revolutions. First is a demographic revolution: by 2020, millennials were projected to make up half the U.S. workforce as baby boomers retired in droves. This shift requires leaders to manage multigenerational teams with vastly different expectations and work styles.

Second is an economic revolution. The United States faces a "post-employment" economy where companies thrive with fewer workers, and rising powers like China and India challenge its global dominance. Millennials are saddled with historic levels of student debt, with college tuition having surged over 1,120 percent since 1978, making financial stability a major concern.

Finally, a technological revolution is accelerating at an extraordinary pace. It took landline phones 45 years to reach 50 percent household penetration; mobile phones did it in just seven. Leaders must now manage virtual employees, navigate the etiquette of new communication tools, and prepare for a future where experts predict 45 percent of American jobs are at high risk of being replaced by computers. The old rules simply weren't written for this reality.

You Must Lead Across the Generational Divide

Key Insight 2

Narrator: For the first time in history, four distinct generations share the workplace, and understanding their unique characteristics is no longer optional—it's a diversity issue. Traditionalists, shaped by the Great Depression and World War II, value loyalty and formal hierarchy. Baby Boomers, who grew up in post-war prosperity, are optimistic, competitive, and have dominated corporate culture for decades.

Generation X, the "latchkey kids" of the 70s and 80s, are independent, skeptical, and tech-pioneering. They often feel overlooked, caught between the massive Boomer and Millennial generations. As one Gen Xer described it, "Think of us as older siblings, resenting the fact that our younger siblings seem to have things so much easier and get so much more attention than we ever did."

Finally, Millennials, raised by "helicopter parents" and immersed in technology, are self-expressive, group-oriented, and globally minded. While they are poised to take over leadership roles, they face a significant perception gap. One study found that while 82% of millennials see themselves as loyal employees, only 1% of HR professionals agree. To lead effectively, millennials must understand these different worldviews and bridge the communication gaps between them.

Your Professional Reputation Is a Brand You Must Actively Manage

Key Insight 3

Narrator: The concept of a personal brand is about actively managing your professional reputation. Pollak emphasizes that every action, or inaction, communicates the value of the brand called "You." This brand is built on four pillars: visibility, differentiation, consistency, and authenticity. It's not enough to be good at your job; you must be known for it.

This brand management extends to handling uncomfortable, age-related comments. Pollak shares a story of being at a conference when a man in his sixties, after a brief chat, patronizingly touched her nose and said, "Boop!" In that moment, she had to decide how to react to protect her professional authority. She chose to ignore it, but in other situations, she has used deflection or direct confrontation. The key is to have a strategy for protecting your brand when it's challenged. This also applies to your online presence, where you must curate your social media to reflect the leader you want to be.

Management Is a Skill, Not an Extension of Your Old Job

Key Insight 4

Narrator: The skills that make someone a great individual contributor are not the same skills that make them a great manager. Pollak learned this the hard way in her first management role at WorkingWoman.com. She was excellent at her job, but when she was promoted and hired an employee named Alex, she continued doing all the important work herself, delegating only minor administrative tasks. She was overwhelmed while Alex was underutilized.

This is a classic trap for new managers. As organizational psychologist Dr. Michael "Woody" Woodward notes, "Your role as a manager is to develop your players and lead them to success. It’s about working through others by influencing action." This requires a completely new skillset focused on delegation, communication, and empowerment. Google's "Project Oxygen" study confirmed this, finding that technical expertise was the least important quality of a good boss. Instead, employees valued managers who made time for them, helped them solve problems, and took an interest in their careers.

Prioritize the 'Big Rocks' to Master Your Time

Key Insight 5

Narrator: Pollak argues that "busy is not a badge of honor." Effective leaders aren't constantly "slammed"; they are in control of their time. To achieve this, she points to Stephen Covey's famous "big rocks" analogy. Imagine a jar you need to fill with big rocks, gravel, sand, and water. If you start with the sand and gravel, you'll never fit the big rocks in. But if you place the big rocks—your most important priorities—in first, the smaller items will fill the spaces around them.

This means leaders must identify their most critical tasks and schedule them first. On overwhelmingly busy days, Dan Black, a director at EY, takes just 15 minutes to plan and triage his priorities. This small investment in planning prevents him from being consumed by urgent but unimportant tasks. Leadership is a marathon, not a sprint, and managing your energy by focusing on what truly matters is the only way to finish the race.

Build Your Network Before You Need It

Key Insight 6

Narrator: Networking is not just about collecting contacts; it's about building a diverse and authentic "personal advisory board" to guide your career. This board should include a traditional mentor, a co-mentor (a peer for mutual support), a sponsor who will advocate for you, a peer sounding board, and even your parents, who can offer a unique, long-term perspective.

A core principle of modern networking is to "give first." Pollak tells the story of a college student who, after an informational interview with a CEO, asked if there was anything she could do to help. The CEO admitted she was struggling with her new iPhone. The student spent the next 30 minutes giving her a tutorial. That small act of generosity built a memorable, positive connection that a simple thank-you note never could have. By building relationships before you need them and offering value to others, you create a powerful support system that will be there when you need it most.

Learn to Fall with Style

Key Insight 7

Narrator: Mistakes are inevitable in any leadership journey. The key isn't to avoid them, but to handle them with grace. Pollak uses an analogy from the movie Toy Story, where the character Buzz Lightyear attempts to fly but instead careens around the room in a series of lucky accidents. His friend Woody dismisses it, saying, "That wasn't flying! That was falling with style!" For leaders, "falling with style" means owning your mistakes, processing the frustration privately, learning from the experience, and bouncing back quickly.

This means avoiding evasive language like "mistakes were made" and instead taking direct responsibility. It means not throwing a public tantrum like a boss Pollak once had who threw a printer on the floor in anger. And it means sharing the lessons from your failures with others. As the late Nora Ephron said, if you slip on a banana peel, you're the butt of the joke, but if you tell the story of slipping on a banana peel, you're the hero.

Conclusion

Narrator: The single most important takeaway from Becoming the Boss is that modern leadership demands a fundamental shift in mindset. It's a transition from being an individual star performer to becoming a developer of people; from seeking stability to embracing constant change; and from hoarding information to practicing radical transparency. The old, hierarchical model of command-and-control is being replaced by a more collaborative, authentic, and adaptable style of leadership.

Ultimately, the book challenges a new generation to not just occupy leadership positions, but to redefine them. The real question it leaves us with is not whether you are ready to be a boss, but whether you are willing to do the continuous work of learning, growing, and connecting that is required to become the kind of leader the future needs.

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