Narrator: A successful founder of a five-year-old medical device startup sits across from his coach, his company’s rapid growth masking the deep cracks forming within. He’s overwhelmed, exasperated, and finally admits the core of his struggle: "Leadership," he says, "is an unnatural act." This single, honest confession captures the central crisis facing countless entrepreneurs. They build brilliant products and secure massive funding, only to find that the skills that launched their venture are not the ones needed to lead it. The transition from founder to CEO is a journey into unfamiliar, often uncomfortable, territory.

In her book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, executive coach Alisa Cohn provides a practical and deeply human roadmap for this transformation. She argues that while leadership may feel unnatural, it is a skill that can be learned. The book is a masterclass in navigating this journey, structured around three critical domains: managing yourself, managing your team, and managing the company.

Narrator: Cohn’s framework begins with a foundational truth: effective leadership is an inside-out job. Before a founder can manage a team or a company, they must first learn to manage themselves. This requires a radical level of self-awareness, because a leader's blind spots don't just affect them; they become embedded in the company's DNA.

Consider the story of Ronnie, a CEO who confidently told her coach, "I’m extremely strategic." It was her core identity as a leader. To test this, Cohn conducted a mini-360 review, asking Ronnie's team for three words to describe her. The results were a shock. They saw her as "detailed," "focused," and "critical"—all valuable traits, but the word "strategic" was nowhere to be found. This gap between Ronnie's self-perception and her team's reality was hindering her effectiveness. She was so deep in the operational details that her team couldn't see her high-level vision.

This journey of self-management also involves taming the internal demons common to founders, especially imposter syndrome. Cohn tells the story of Matias, an early-stage founder who struggled to articulate his company's vision. He was passionate, but his pitch fell flat. Probing revealed the real issue: Matias didn't truly believe he could build something so big. He felt like an imposter, and this self-doubt was sabotaging his ability to inspire others. Cohn advises founders to build a "highlight reel"—a collection of past successes to consult during moments of doubt—and to actively challenge the negative voices that undermine their confidence.

Narrator: As a company scales, the founder’s role must shift from being the primary "doer" to getting results through others. This requires mastering the art of delegation and creating a culture where people can thrive. Cohn emphasizes that culture isn't about ping-pong tables or free snacks; it's the sum of the behaviors a leader models and tolerates.

A powerful example of this principle in action is the story of Nora, the brilliant founder of an internet security startup. A former trader, Nora was a classic control freak, insisting on having the final word on every decision, no matter how small. Her need for control created a massive bottleneck, slowing growth and demoralizing her talented team. Through coaching, Nora realized the damage her behavior was causing. She learned to identify the very few decisions that truly required her final say and empowered her team to run with the rest. The result was immediate: processes sped up, and morale soared.

Cohn argues that a founder's unexamined flaws often become the company's unintended culture. A leader who avoids conflict creates a "polite culture" where problems fester. A leader who is indecisive creates a "mirror culture" where the whole organization struggles to make decisions. Growing up as a leader means taking responsibility for the culture you create, both intentionally and unintentionally.

Narrator: Of all the relationships a founder must manage, none is more critical or fraught with peril than the one with their cofounder. Cohn describes it as a business marriage, capable of incredible synergy or devastating toxicity. The cancer that eats away at this relationship isn't conflict itself, but the tension that comes from unresolved conflict.

The book contrasts two cofounder dynamics. First, there is the toxic relationship between Sherry and Jennifer. Sherry, the CEO, harbored deep resentment, feeling she did all the work while Jennifer got equal credit. This unspoken anger poisoned their interactions and threatened the company. On the other end of the spectrum are Jason and Jason, cofounders of a digital security company. They explicitly decided to put their relationship before the business, believing that "if we’re good, the business will be good." This foundation of trust allowed them to weather immense challenges, including a hack that nearly destroyed their company.

To prevent the former and foster the latter, Cohn advocates for a "cofounder prenup." This isn't just a legal document about equity; it's an emotional and operational agreement. It forces cofounders to have difficult conversations upfront about their values, goals, decision-making processes, and what happens if one person wants to leave or fails to scale with the company. These proactive discussions build a foundation of trust and alignment that is essential for long-term survival.

Narrator: Many founders resist formal structure, believing it will kill the innovative, free-wheeling spirit of their startup. Cohn counters this with a bold declaration: "Structure is sexy." As a company grows, a lack of structure doesn't create freedom; it creates chaos, confusion, and inefficiency.

This is vividly illustrated by the story of a CEO who was ambushed by five of his employees. They were frustrated because their managers were untrained, deadlines were being missed, and there was no clear process for anything. The root cause? The CEO had assigned the office manager to be the Head of People simply because she was likable, not because she had any HR experience. Without proper systems for management, training, and accountability, the company was floundering.

To avoid this fate, leaders must implement systems. This includes creating a dashboard of key metrics to track progress, as seen with a fintech company that was repeatedly delaying a product launch. When they put all their key metrics on a dashboard, the problems became painfully visible to everyone. It wasn't about blame; it was about creating a shared reality that allowed the team to identify bottlenecks and solve them together. Systems, whether they are dashboards, OKRs, or clear reporting lines, provide the clarity and predictability needed to scale effectively.

Narrator: Cohn opens her chapter on board management with a stark warning: "There are two kinds of founders: those that have had issues with their board and those that will." The relationship between a CEO and their board is inherently filled with tension. However, the CEO's job is not to be a passive subordinate but to actively lead the board.

The most compelling story in the book is that of Charlie, a CEO whose lead investor and board director, Jesse, was demanding his replacement. The company was missing its numbers, and Jesse had lost faith. Instead of fighting back or becoming defensive, Charlie, with coaching, chose a different path. He flew to meet Jesse, led with vulnerability, acknowledged the company's shortcomings, and asked Jesse to personally mentor him. This disarming move completely changed the dynamic. Jesse agreed, and over the next six months, he became one of Charlie's strongest allies, eventually helping him negotiate the successful sale of the company.

Charlie's story demonstrates that the CEO must own the board relationship. This involves building genuine connections with each member, understanding their personalities and motivations, and proactively managing meetings to guide the conversation. It is the CEO's responsibility to transform the board from a group of overseers into a team of strategic advisors.

Narrator: The single most important takeaway from From Start-Up to Grown-Up is that leadership is not a fixed personality trait but a dynamic, learnable skill. The journey from a founder who builds a product to a CEO who builds a company is a profound personal transformation. It requires embracing the discomfort of the "unnatural act" of leadership—of having difficult conversations, of letting go of control, and of holding people accountable.

Alisa Cohn’s work challenges every founder to look in the mirror and ask a difficult question: What does the business need from me right now? The answer often requires shedding old habits and developing new capacities. The ultimate challenge of the book is not just to build a great company, but to build the great leader that the company deserves.