From Start-Up to Grown-Up

Have you ever launched an exciting new venture only to realize that the leadership skills that got you started aren’t enough to keep you growing? In From Start-Up to Grown-Up, Alisa Cohn argues that founding a company isn’t just about vision—it's about evolution. The inner transformation from entrepreneur to CEO is a journey that involves mastering yourself, your people, and your organization. Cohn contends that being a great founder requires creativity, passion, and energy, but being a great CEO demands reflection, emotional intelligence, and disciplined systems. The very traits that make you fearless at the starting line can trip you up later if you don’t learn to adapt.

Drawing from twenty years of coaching founders of companies like Venmo, Foursquare, Etsy, and DraftKings, Cohn maps out a practical leadership roadmap for scaling yourself as effectively as your business. She organizes her playbook around three dimensions of growth: managing you, managing them, and managing the company. The first is internal—dealing with your self-doubt, triggers, and stress while learning to lead with honesty and awareness. The second focuses on relationships—the messy, unpredictable world of managing employees, building culture, and handling hiring and firing with both rigor and compassion. The third addresses the systems you need—operational discipline, metrics, meetings, and governance—to turn a chaotic start-up into a stable, well-run enterprise.

The Unnatural Act of Leadership

Cohn opens with a powerful truth: “Leadership is an unnatural act.” Founders often feel contradiction between their instinct to act and the need to pause and reflect. One CEO jokes that every day he must “commit an unnatural act”—communicating differently to different people, managing his own defensiveness, or opening a company-wide meeting with a story instead of data. This paradox sets the tone for the book: leading isn’t about doing more, but doing differently. Emotional maturity and self-regulation—the ability to see yourself clearly and choose your response—are the first milestones of growth.

Why This Evolution Matters

Cohn insists the founder-to-CEO leap is one of the hardest transitions in business. Early success rewards hands-on action and control, but scaling means letting go. Your behaviors become your culture, and your blind spots become the company’s weaknesses. As serial investor Randy Komisar notes in his foreword, “Your company needs a CEO, but you don’t need to be that CEO—unless you’re ready to be coachable.” The message is clear: growth is a choice. Reflecting deeply on who you are, how you lead, and what the business needs from you right now is a lifelong discipline.

Leadership maturity determines whether you’ll stall or scale. Marshall Goldsmith (author of What Got You Here Won’t Get You There) echoes this idea—what propels a founder through the early stages often hinders them later. In Cohn’s coaching framework, emotional growth precedes strategic growth. Until you manage yourself—your anxiety, impatience, or perfectionism—you can’t manage the people or the company effectively.

The Three Growth Dimensions

Cohn structures the book in three major parts, representing the concentric circles of a founder’s development. Managing You deals with self-awareness, stress, imposter syndrome, and personal habits that sustain high performance. You learn that leadership begins with the mirror—people see you amplified, not as you imagine yourself. Managing Them turns outward: building psychologically safe environments, giving praise, setting expectations, and delegating effectively. And Managing the Company addresses the strategic architecture of scaling—hiring senior managers, establishing clear metrics, running effective meetings, and working productively with your board and cofounders.

This triple focus shifts the perception of leadership from heroic command to disciplined practice. It’s not about becoming someone else—it’s about growing into the next version of yourself. Each phase serves as a mirror: how you handle conflict reveals your triggers; how you delegate reveals your trust; how you manage the board reveals your maturity. The process is emotional as well as tactical.

A Guidebook for the Lonely CEO

Founders often confess loneliness—the sense that everyone looks to them for answers, but no one understands their doubts. Cohn’s coaching voice feels like a steady hand on your shoulder. She combines empathy with tough love, urging CEOs to ask for help, develop rituals to manage stress, and build a “village” of mentors, peers, and coaches. Problems never go away, she reminds us—they just evolve. Her mantra, repeated throughout: “The work is in you.”

Ultimately, this book isn’t just about business—it’s about personal transformation. You start as an entrepreneur chasing an idea and, through reflection and discipline, become the leader of an enduring institution. That’s the heart of Cohn’s message: if you want your company to grow up, you must grow up first. The organization can’t outgrow its founder. The question she leaves us with is deceptively simple and utterly profound: What does the business need from you right now?

Before you manage anyone else, Alisa Cohn says, you have to learn to manage yourself—the toughest, most elusive employee you’ll ever have. Founders are often brilliant and driven but also impatient, insecure, and prone to burnout. Being your own boss means confronting the committee in your head: self-doubt, perfectionism, and fear. To grow from start-up to grown-up, you must turn radical self-reflection into a daily reflex.

Seeing Yourself Clearly

Cohn begins with a simple exercise: ask people to describe you in three words. One founder told her she was “strategic,” but her team described her as “detailed, focused, critical.” That mismatch revealed the first truth of leadership—intention isn’t impact. You think you’re inspiring, but your team might find you intimidating. The only way to grow is to hold up a mirror, get real feedback, and reconcile those two realities.

She guides founders through a practice called the mini 360-feedback. Ask peers and employees what three words come to mind when they think of you. The courage to hear it—and then change—is foundational. One CEO, stunned to learn his people saw him as a bully, walked out angry but came back forty-five minutes later calmer, saying, “I asked my wife. She said it was true.” Self-awareness starts with humility.

Demons, Doubts, and Imposter Syndrome

Nearly every founder wrestles with imposter syndrome: “Who am I to make this real?” The higher you climb, the louder the voice of doubt. Cohn reminds you that it's normal. Chamath Palihapitiya, investor at Social Capital, confessed, “The more successful I am, the more I have imposter syndrome.” Cohn’s antidote is compassion paired with evidence. Make a highlight reel of your past successes. One CEO who felt fraudulent remembered he had raised tens of millions and rescued a faltering product—proof that capability wasn’t the issue, confidence was.

Cohn also encourages positive self-talk (a common practice among Olympic athletes and BetterUp CEO Alexi Robichaux). Instead of rehearsing failure narratives, repeat rational affirmations rooted in past wins: “We’ve solved harder problems before,” or “Every mistake teaches us the code.” Replace self-bullying with mental training for resilience.

Stress, Health, and Habits

Leadership is physically and emotionally exhausting. Founders work twelve-hour days, skip meals, and confuse motion with progress. One CEO collapsed after yelling at his team—not from rage but from hunger. Cohn’s remedy is basic but profound: eat and sleep like a leader. The most valuable asset of your company, she insists, is you. Personalized routines—morning gratitude, midday exercise, evening reflection—prevent burnout and sustain clarity.

Cohn calls habits, routines, and rituals “training for the mind.” A founder who began every morning listing five gratitudes and three priorities found calmer focus and better perspective. Another started doing jumping jacks twice a day, prompting laughter and team bonding. These micro-practices create stability amid chaos. She quotes Aristotle: “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”

Building Your Village

Finally, no founder survives alone. The job is too demanding and isolating. Cohn insists on building a network—a “village” of mentors, peers, friends, and coaches. A coach offers unbiased reflection; peers offer solidarity. Together they rebuild perspective when crises shrink it. She reminds CEOs that seeking help isn’t weakness—it’s the only way to keep growing. As venture capitalist Randy Komisar says, “Before you engage a coach, you must be coachable.” The work, once again, starts with vulnerability.

This first stage—managing you—is about self-awareness, self-care, and self-trust. Master yourself, Cohn writes, before you try to master your company. Founders spend endless energy fixing external problems, but every issue in the business eventually leads back to one question: What does this situation reveal about me?

After you manage yourself, the second leap is managing others. Alisa Cohn calls it the move from “doing to leading.” As your company grows, your job shifts from personally solving problems to creating the conditions for others to do their best work. You must learn the counterintuitive skills of psychological safety, praise, accountability, and delegation—the invisible architecture of leadership.

Creating Psychological Safety

People perform best when they feel safe. Google’s famous research on team effectiveness—building on Harvard professor Amy Edmondson’s work—proved that psychological safety is the number one predictor of success. Cohn illustrates this vividly through Suzy Batiz, founder of Poo~Pourri, who learned to handle chaos with humor and transparency. When she’s triggered, her team calmly says, “You’re triggered,” and she owns it. Emotional honesty becomes organizational strength.

Cohn’s case studies show safety under pressure. Suzanne, founder of a networking company, stayed overnight with her team during a customer crisis, repeating, “We can fix this and we will fix this.” Her composure built trust. As Cohn summarizes, “Your behavior is the baseline of a high-performing company.”

Praise Is Strategic Fuel

In start-ups hungry for speed, praise often vanishes. Yet Cohn calls praise a CEO’s “secret superpower.” One founder never told his team they were doing great because he assumed silence meant approval. His employees wasted hours second-guessing his judgment. Another leader’s designer was near quitting until he heard that his boss thought he was a “creative genius.” The simplest words can restore commitment. Praise costs nothing but builds massive social capital.

Even underperformers should hear recognition for what works—confidence grows from acknowledgment. Cohn uses the “Moneyball principle”: a baseball coach turned a hopeless player into a competent first baseman purely through encouragement. When people feel valued, they risk more, learn faster, and follow you through tough times.

Accountability Without Blame

Cohn’s coaching formula for accountability is deceptively simple: say what you mean and mean what you say. Clarify expectations, make commitments visible, and course-correct calmly. Her “G-O-D” tool—Goal, Outcome, Do-over—helps leaders dissect missed results without shame. One CEO realized she snapped at her marketing chief not from strategy but from frustration. When she rewound the tape using Cohn’s framework, she replaced blame with curiosity: “Why did this happen? What should we do differently?” Problems, after all, are the price of progress.

Delegating and Developing Others

Founders struggle most with delegation. They pride themselves on being the fastest, smartest problem solvers. But growth requires giving away your Legos, as First Round Capital puts it. Cohn uses Ken Blanchard’s “Will and Skill” framework to teach leaders how to match guidance to maturity: high-will, low-skill employees need coaching; high-skill, high-will ones need autonomy. Dennis Crowley of Foursquare admitted that handing over product design—the work he loved—was daunting but necessary. “When you delegate the thing you’re best at,” he said, “that’s when real leadership begins.”

Delegation isn’t abdication—it’s orchestration. When you entrust people, define the playing field, coach their growth, and let them surprise you. The founder’s evolution from expert to enabler marks the real passage to CEOhood.

Leading others, in Cohn’s model, is emotional work. You juggle empathy with firmness, grace with growth. Founders who get it right build cultures of trust and performance—companies that thrive not because of the founder’s brilliance but because the founder taught others how to shine.

Alisa Cohn doesn’t romanticize hiring—it’s where most founders fail. She cites Mo Bunnell’s maxim: “Hiring wrong costs years; hiring right compounds.” Start-up hiring is often driven by chemistry instead of clarity. Founders choose people they like rather than those with the right values and skills. The antidote is intentional recruiting anchored in purpose, process, and evidence.

Hiring for Values, Not Just Skills

Every hire reshapes your culture, so hiring is cultural architecture. Cohn warns that if you haven’t defined what your culture is, you’ll build it by accident. Jocelyn, a healthcare founder, hired doctors for expertise but ignored teamwork. Her company became hyper-smart and dysfunctional. Values—like collaboration, curiosity, drive—must be screened explicitly. Ask candidates: “Tell me about a time you solved a hard problem with others.” The story reveals whether they think collectively or alone.

Alexi Robichaux of BetterUp showcases precision hiring through “balloon interviews.” Founders train select employees to test for cultural fit—grit, empathy, playfulness—independent of technical skill. A candidate may pass all technical screens but fail the culture test if they lack mission alignment. BetterUp treats its first 500 hires as “cultural cofounders.” That level of rigor creates long-term coherence.

The Mechanics of Hiring

Cohn’s hiring checklist starts with restraint: don’t hire until you must. Many staffing needs can be met through systems or smarter processes. Define the job with precision—list measurable results, not vague adjectives like “good communicator.” Gather evidence through stories (“Describe a time you turned around a failed project”) and fact-based references (“Would you hire them again?”). This method replaces intuition with structured insight.

She also warns about hiring friends. Friendship clouds judgment. As Noam Wasserman notes in The Founder’s Dilemma, most startups that hire friends eventually strain or lose those relationships. Have a “friend prenup”: define roles early, commit to professionalism, and agree you’ll choose the business over the friendship if needed.

Onboarding and Quick Wins

Once you’ve hired, success hinges on onboarding. New hires must see what success looks like in 30, 60, and 90 days. Cohn urges CEOs to share a “personal operating manual”—how you think, decide, and communicate. Your new executive should craft their own. She also insists on quick wins: visible achievements that signal competence and build early trust. Listening sessions with cupcakes sometimes qualify as quick wins—they show presence and empathy.

Letting People Go

Firing is every leader’s nightmare, but delaying it poisons the team. Most CEOs, Cohn says, fire months too late. Use facts, not feelings. Clarify expectations, measure results, then act decisively. When Brian Berger of Mack Weldon ignored warnings about a toxic hire, he learned his cofounder’s rule: “If there’s doubt, there’s no doubt.” The replacement process was painful but freeing—culture improved instantly. Treat departures with dignity; the goal is not punishment but protection of the mission.

Cohn also details how to handle layoffs humanely—communicate transparently, express empathy, and reaffirm stability. The goal is to preserve trust among those who remain. “Layoffs suck,” she admits, “but clarity rebuilds confidence.” Hiring and firing, she concludes, are expressions of leadership maturity—moments when vision meets accountability.

Growth changes everything—including what leadership looks like. In part three of her framework, Cohn argues that running a startup of ten people and leading a scale-up of 200 require different muscles. Founders who refuse to evolve from ad-hoc improvisation to structured management risk collapse. Success, she says, “earns you the right to play again.”

Building Management Capacity

The first step in scaling is to build managers who can manage. Founders often promote individual contributors who lack training, leading to micromanagement or chaos. Cohn redefines management as “getting results through others.” Managers must learn role modeling, coaching, and cascading information. They should be emotionally steady, not moody peers. One newly promoted manager failed because he partied with some teammates and mocked others. Cohn coached his CEO to separate friendship from leadership—a crucial rite of passage.

The Role of HR and Performance Systems

When you have fifty employees, you need a Head of People, not an office manager. HR should train managers, design performance reviews, and build career paths. Cohn rehabilitates performance reviews from “corporate bureaucracy” into developmental dialogue. They’re not grades—they’re growth conversations. A good review, she says, includes accomplishments, strengths, developmental opportunities, and inspiration. In her words, “Feedback is a gift.” Alexa von Tobel echoes this: “It’s not mean—it’s kind.”

HR also drives structure. Spotify’s “squads, tribes, guilds” and HubSpot’s “pods” exemplify small teams with clear missions. Cohn calls structure “sexy”—not stifling but energizing. Without it, leaders drown in firefighting and staff feel lost.

Metrics, Process, and Meetings

The grown-up company runs on rhythms. Cohn teaches CEOs to track key metrics (“dashboard thinking”), adopt OKRs—objectives and key results—and hold effective executive meetings. Each meeting should open with humanity (“How are you feeling?”), move to clarity (“What did we decide? Who does what by when?”), and close with reflection. Regular metrics show progress and expose bottlenecks—without blame. Her favorite cultural tool, the RACI matrix, clarifies who is Responsible, Accountable, Consulted, and Informed on each project, eliminating turf wars.

Operating systems, she insists, don’t dull creativity—they free it. As coach John Wooden told his players, “It’s the little details that make big things happen.” Rituals and process give emotional safety to teams under pressure.

As your company expands, your own role transforms again. You stop managing people and start managing managers. You become a developer of leaders—a conductor of an orchestra rather than a soloist on stage.

Once the internal growth systems are in place, the final test of leadership maturity is external: managing governance and partnership. Alisa Cohn helps CEOs navigate two high-stakes relationships—the boardroom and the cofounder dynamic. Both require the same skills she’s taught throughout: emotional stability, communication, and trust.

Managing the Board

Every founder eventually faces a reckoning with their board. There are only two types of CEOs, Cohn quips: those who have had issues with their board and those who will. Boards bring power and personality—alphas, micromanagers, and general-fighting-the-last-battle directors abound. The solution is proactive relationship management. Think of your board as another team you lead. Meet members individually, learn their motivations, and shape the culture of meetings with clear norms (no laptops, all voices heard).

One of Cohn’s clients turned a hostile board director into a mentor by flying out to meet him face-to-face, leading with vulnerability: “I need your help to become a better CEO.” That candor melted resistance. “The work is in you,” she reminds all founders. Your triggers—defensiveness or shame—are leadership lessons disguised as conflict.

Cofounder Alignment

Your cofounder relationship, Cohn says, is like a marriage. It can empower you or exhaust you. Most conflicts spring from misaligned growth rates and unclear roles. She gives clients a “Cofounder Prenup,” a checklist covering values, decision rights, conflict style, and succession. Discuss uncomfortable questions early: What if one of us stops scaling? What if one wants to sell and the other doesn’t? These talks create emotional infrastructure for future turbulence.

Cohn’s case studies range from lifelong friends who imploded under stress to siblings who thrived through transparency. One founder lamented his cofounder’s stagnation until coaching uncovered her grief—she missed the intimacy of the early company stage. Honest dialogue defused anger and led to an amicable exit. Sometimes parting ways is growth too.

Healthy partnerships, she says, require regular “conflict nights” or alignment rituals to talk openly about tensions and goals. As serial entrepreneur Michele Romanow observes, “Cofounders are supposed to fight—it’s how progress happens.” What matters is respect and mutual mission. Trust, revisited again and again, is the glue that holds a company together.

Cohn’s closing section feels particularly modern: how do you lead in a world where the office has dissolved? The pandemic accelerated remote work, exposing the fragility of team connection. Managing culture and communication virtually is now a permanent skill of grown-up leadership.

Recreating Human Connection

In physical offices, connection happens organically—casual chats, shared lunches, laughter in hallways. Remote work erases those micro-interactions. Cohn urges leaders to recreate them intentionally through rituals: “virtual coffees,” scavenger hunts, trivia hours, and small talk at the start of meetings. Humanity must be built into digital routines. She notes, “If you think small talk wastes time, wait until you see what happens without it.”

Communication Without Misinterpretation

Digital channels multiply confusion. People Slack, email, and text across mismatched threads. Cohn prescribes communication hygiene. Define which medium serves which purpose—Slack for internal coordination, email for cross-team updates, text for urgent matters. Accompany every message with context and warmth. She draws on Erica Dhawan’s Digital Body Language: politeness cues (greetings, emojis, punctuation) prevent misread tone and build trust remotely.

Also, over-communicate goals. Weekly “snippets” summarizing progress help replace the hallway visibility of physical offices. Clarity cures anxiety.

Remote Hiring and Onboarding

Hiring remote employees extends trust across screens. Cohn recommends double diligence—more interviews, deeper reference checks, and at least one face-to-face meeting if possible. Once hired, onboard with celebration: swag boxes, personal notes, and virtual lunches. Leaders must ensure day-one connection, not confusion. A company that neglected to onboard its remote VP of Product saw Slack channels mocking him within weeks—proof that culture fails silently online.

Structure and Mental Health

Structure becomes survival in a virtual world. Shared file systems (no solitary spreadsheets) and clear decision protocols prevent chaos. At Leverage, founder Nick Sonnenberg defines collaboration as ending the “scavenger hunt”—everyone should know exactly where information lives. Remote work also heightens mental health risks. Cohn compassionately notes that anxiety and depression can spike in isolation. Encourage employees to set boundaries, take walks, and seek support. Psychological safety matters more than ever when the workplace is a Zoom screen.

Leading remotely distills everything Cohn teaches: self-awareness, transparency, empathy, and systems. Physical distance magnifies the need for emotional closeness and operational clarity. Growing up, even in the digital era, still starts with you.