Insights and Strategies
from Dr. Richard Hagberg's New Book:
Founders Keepers:
Why Founders Are Built to Fail
and What it Takes to Succeed.
(Part 2 of The Best Leaders Playbook — Building Trust Systems Series)
(Part 1 of The Best Leaders Playbook — Building Trust Systems Series)
The Leadership Tightrope If you lead long enough, you start to realize something uncomfortable: everything that makes you effective also threatens to undo you. Your drive becomes impatience. Your confidence becomes stubbornness. Your empathy turns into guilt. The longer you lead, the more you realize that the job isn’t about choosing one trait over another — it’s about learning to carry both. That’s what maturity looks like in leadership. It’s not balance. It’s tension well managed. The False Comfort of Either/Or Most leaders crave clarity. We want rules. Playbooks. Certainty. Should I be tough or kind? Decisive or collaborative? Visionary or practical? The insecure part of the brain hates contradiction. It wants the “right answer.” But leadership lives in the messy middle — the place where both truths exist, and neither feels comfortable. The best leaders aren’t either/or thinkers. They’re both/and navigators. A Story from the Field I once coached a CEO who told me, “I’m torn between holding people accountable and being empathetic.” I said, “Why do you think those are opposites?” He paused, then laughed. “Because it’s easier that way.” Exactly. It’s easier to pick a lane than to learn how to drive in two at once. He eventually realized the real question wasn’t which side to choose, but when and how to lean into each. He became known as “the fairest tough boss in the building.” That’s the magic of integration — toughness with tenderness, vision with realism, clarity with compassion. Why Paradox Feels So Hard Contradictions feel like hypocrisy when you haven’t made peace with your own complexity. If you believe you have to be one consistent version of yourself — confident, decisive, inspiring — then every moment of doubt feels like fraud. But the truth is, great leaders are contradictory because humans are contradictory. You can be grounded and ambitious, humble and proud, certain and still learning. The work is not to eliminate the tension — it’s to get comfortable feeling it. The Psychology Behind It Our brains love binaries because they make the world simple. But complexity — holding opposites — is the mark of advanced thinking. Psychologists call this integrative complexity — the ability to see multiple perspectives and blend them into a coherent approach. It’s not compromise; it’s synthesis. It’s saying, “Both are true, and I can move between them without losing my integrity.” That’s where wisdom lives — in the movement, not the answer. Funny But True A client once told me, “I feel like half monk, half gladiator.” I said, “Congratulations. That means you’re leading.” Because that’s what the job demands: peace and fight, compassion and steel. If you can’t hold both, you end up overusing one until it breaks you. The Cost of One-Dimensional Leadership We’ve all worked for the “results-only” leader — brilliant, efficient, and emotionally tone-deaf. And the “people-first” leader — kind, loyal, and allergic to accountability. Both are exhausting. Both create lopsided cultures. When leaders pick a single identity — visionary, disciplinarian, nurturer, driver — they lose range. They become caricatures of their strengths. True greatness comes from emotional range, not purity. The Paradox Mindset Here’s how integrative leaders think differently: They value principles over preferences. They can be decisive without being defensive. They know empathy isn’t weakness and toughness isn’t cruelty. They trade perfection for adaptability. They’re the ones who can zoom in and out — from the numbers to the people, from the details to the meaning — without losing coherence. They’re not consistent in behavior. They’re consistent in values. That’s the difference. How to Practice Both/And Thinking Spot your overused strength. The strength that’s hurting you most is the one you lean on too much. If you’re decisive, try listening longer. If you’re compassionate, try being direct faster. Ask, “What’s the opposite quality trying to teach me?” Impatience teaches urgency; patience teaches perspective. You need both. Invite your opposite. Bring someone onto your team who balances your extremes — not a mirror, a counterweight. Hold paradox out loud. Tell your team, “This decision has tension in it — and that’s okay.” Modeling that normalizes complexity for everyone else. A Moment of Self-Honesty I’ve spent decades watching leaders chase “clarity” like it’s peace. But peace doesn’t come from eliminating tension. It comes from trusting yourself inside it. Once you accept that leadership will always feel contradictory, you stop fighting it — and start flowing with it. You don’t need to be the calmest, toughest, or most visionary person in the room. You just need to be the one who can stay whole while the world pulls you in opposite directions. Your Challenge This Week When you catch yourself thinking, “Should I be X or Y?” — stop. Ask instead, “How can I be both?” Then practice it in one small moment. Be kind and firm. Bold and humble. Fast and thoughtful. That’s where growth hides — in the discomfort between two truths. Final Word The best leaders aren’t balanced. They’re integrated. They’ve stopped trying to erase their contradictions and started using them as fuel. They’ve learned that leadership isn’t about certainty. It’s about capacity — the capacity to hold complexity without losing your center. That’s not chaos. That’s mastery.
The Curse of “High Standards” Let’s start with a truth that makes a lot of smart leaders squirm: perfectionism isn’t about excellence — it’s about fear. It starts innocently enough. You want things done right. You have taste. You notice what other people miss. People even praise you for it. But slowly, “high standards” turn into a straitjacket. You can’t hit send until the slide looks perfect. You can’t let someone else finish because “they won’t do it the right way.” You stay up tweaking a comma that doesn’t need tweaking. You call it quality. Everyone else calls it exhausting. Why Perfection Feels Safe Perfectionism isn’t driven by pride. It’s driven by anxiety. It’s the voice that says, “If I can control every detail, nothing bad can happen.” It’s fear of judgment dressed up as professional excellence. The irony is that perfectionists are often the most self-critical people in the room — constantly measuring themselves against an invisible, impossible ruler. They don’t chase perfection because they love quality. They chase it because they hate shame. The Productivity Mirage Perfectionism pretends to be productivity, but it’s actually procrastination with better branding. You tell yourself you’re “improving” the work when you’re really just postponing the moment you might get judged. Every hour you spend obsessing over polish is an hour you could’ve spent creating, delegating, or resting — three things perfectionists are famously terrible at. A Founder’s Wake-Up Call A founder I coached — let’s call him Ryan — was a world-class tinkerer. Every deck, every marketing campaign, every internal email went through him. He’d send back feedback like, “Good, but let’s tighten the phrasing on slide 12.” When his team started missing deadlines, he blamed their “lack of attention to detail.” In truth, they were stuck waiting for his endless revisions. When he finally took a week off, something shocking happened: everything got done. On time. He told me later, “Apparently, I was the bottleneck disguised as quality control.” Exactly. The Neuroscience of “Just One More Edit” Perfectionism lights up the same reward circuits in the brain as addiction. Every time you fix something, you get a tiny hit of relief — like a smoker taking a drag. That’s why you can’t stop. But the more you chase that relief, the narrower your focus becomes. You stop seeing the system. You start obsessing over the pixel. Leadership requires altitude. Perfectionism keeps you at ground level, rearranging the furniture while the building burns. The Lie of the Last 5% You know that feeling when something’s 95% done and you tell yourself, “Just one more pass.” That’s the lie. That final 5% rarely changes the outcome — it just delays it. You’re trading momentum for a false sense of control. I tell my clients, “Your 80% is probably everyone else’s 120%.” Ship it. Learn. Iterate. That’s how progress actually happens. How to Break the Cycle Redefine success. Replace “perfect” with “useful.” Ask, “Will this version move the needle?” If yes, it’s done. Set a timer. Give yourself a fixed window to refine something, then stop — no matter how it feels. Delegate imperfection on purpose. Hand off something messy and resist the urge to “fix” it afterward. That’s your real growth work. Publish before you’re ready. Whether it’s a proposal or a strategy draft, send it early. Feedback beats polish every time. Celebrate iteration. Reward teams for improving quickly, not for getting it “perfect” the first time. Funny but True I once worked with a VP who spent six hours choosing fonts for a quarterly report. When I asked him why, he said, “Details matter.” I said, “To who?” He blinked. Then laughed. “Probably just me.” That’s the moment perfectionism usually breaks — when you realize no one else cares about the thing stealing your sanity. What’s Really at Stake Perfectionism doesn’t just waste time. It kills creativity, trust, and joy. Your team stops taking initiative because they know you’ll re-do their work anyway. You become the bottleneck everyone avoids. And you start confusing fatigue with dedication. Excellence inspires. Perfectionism suffocates. The Emotional Shift: From Control to Curiosity Progress requires permission to experiment — to be wrong. When you trade “perfect” for “better,” you re-open the door to learning. And that’s where real innovation lives. Great leaders don’t aim for flawless execution. They build systems that learn faster than their competitors. That’s progress. Your Challenge This Week Take something you’ve been over-polishing — a presentation, a product feature, an email draft. Send it at 80%. Breathe through the discomfort. When your team improves it, resist saying, “See? I would’ve done that.” Instead, say, “That’s better than I imagined.” Because it is. Final Word Perfection feels like power. But real power is progress — messy, iterative, unfinished progress. Leadership isn’t about getting everything right. It’s about getting the right things moving. So send the draft. Launch the feature. Let good enough be great — and watch your world expand.
You’ve probably sat in that meeting—the one where everyone nods, the plan sounds brilliant, and something inside you whispers, “This feels off.” Then six months later, the numbers tank, the team fractures, and nobody remembers who actually decided. In my long coaching career, I’ve seen it too many times. Great ideas and inspiring vision coming down to smoke and ash. Smart, driven executives—people who built companies, raised rounds, changed industries—still fall into predictable judgment traps. Not because they’re careless. Because they’re human. The Hidden Architecture of Bad Decisions Every bad decision has two layers. On the surface: logic, data, and justification. Underneath: emotion, fear, and ego. Most leaders debate facts and models, but what really drives the call is the invisible need to feel safe, competent, or in control. When you miss that layer, you mistake momentum for clarity and conviction for truth. That’s how companies derail while leaders are still congratulating themselves for being decisive. 1️⃣ The Speed Illusion Speed feels powerful. It gives relief from ambiguity. But urgency isn’t strategy—it’s self-medication for anxiety. Founders equate slowing down with weakness. They move fast because stillness feels unbearable. Yet every “fast” decision eventually slows the company—rework, reversals, lost trust. Real speed comes from reflection. Pausing to ask, “What problem am I actually solving?” is the fastest move you’ll ever make. 2️⃣ The Confidence Mirage After enough wins, confidence starts masquerading as accuracy. The brain confuses familiarity with truth. It’s seductive. You’ve seen this pattern before; you know how it plays out. Except this market is different. This team is different. You are different. Overconfidence blinds leaders to nuance and punishes curiosity. The antidote is humility baked into process: someone on your team must be paid to prove you wrong. If no one can, your culture’s too polite—or too scared. 3️⃣ The Echo Chamber Nothing kills judgment faster than agreement. When everyone smiles and nods, it feels like alignment. It’s actually avoidance. Teams stop challenging you not because you’re right, but because it’s unsafe to be honest. That’s sunflower bias: people orienting to the boss’s preference like plants to the sun. If you want better decisions, be the last to speak. Reward the person who changes your mind. 4️⃣ The Emotional Hijack Anger, pride, and fear are terrible decision tools—but exquisite disguises. They look like conviction. They sound like leadership. When emotion drives the bus, judgment rides in the trunk. I’ve seen executives make firing decisions in rage and acquisitions in euphoria. Both felt certain. Both collapsed later. Emotional regulation isn’t soft skill—it’s cognitive hygiene. If you can’t calm your nervous system, you can’t access your wisdom. 5️⃣ The Binary Trap Under pressure, complexity collapses into yes/no. Hire or fire. Launch or kill. Acquire or walk away. It feels efficient—but amputates imagination. The danger isn’t choosing wrong; it’s never seeing what else was possible. My rule: three options minimum. If you can’t name three, you’re not deciding—you’re reacting. 6️⃣ The Hero Complex Many founders believe leadership means having the answer. It doesn’t. It means designing the system that gets to the answer. Heroic decision-making doesn’t scale. It breeds dependency and fear. When every big call runs through you, the company stops learning. Leadership maturity is letting go of being right so the organization can be smart. 7️⃣ The Reversal Loop Some leaders can’t stop re-deciding. They add “one more thing,” change direction midstream, or quietly undo yesterday’s call. It feels adaptable. It’s actually destabilizing. People stop believing you because they’re waiting for the next reversal. Write down the decision, the rationale, and the success indicator. Revisit it only if assumptions change—not if your anxiety does. 8️⃣ The Overload Fallacy The modern executive disease is information addiction. We convince ourselves that more data equals better judgment. It doesn’t. It equals paralysis. “Let’s gather more data” is often code for “I’m afraid to decide.” Define the minimum information needed for a quality call. Then decide. You’ll make faster mistakes—and faster progress. 9️⃣ The Politics of Preference Many bad decisions aren’t analytical—they’re social. Leaders favor the messenger over the message. Bias hides in plain sight—in who gets airtime, forgiveness, and credit. If your decisions correlate with who you like most, judgment has already left the room. 🔟 The Culture of Silence The most dangerous phrase in business isn’t “We failed.” It’s “No one told me.” When truth becomes expensive, companies go bankrupt buying harmony. People stop telling the truth long before the numbers reveal it. Psychological safety isn’t comfort—it’s accuracy. The day your team stops disagreeing with you is the day your decline begins. The Fear Beneath It All Beneath every bad decision is fear. Fear of being wrong. Fear of losing control. Fear of being seen as weak. And fear always demands speed, certainty, and dominance—the three enemies of judgment. The Discipline That Saves You Better judgment isn’t a personality trait; it’s a design choice. Build systems that slow thinking without killing action. 🟦 A pre-mortem before launch. 🟦 Three options before closure. 🟦 One dissenting voice before consensus. 🟦 A decision journal reviewed quarterly. These small rituals do what ego can’t—they make you wiser before experience humbles you. The Mirror Moment Every leader eventually faces it—the moment you realize the enemy isn’t chaos. It’s your own certainty. Maturity is learning to pause in that quiet space between knowing and not knowing. That’s where judgment lives. Before your next big call, ask yourself: What if the part of me that’s most confident is also the part most afraid? Because in my experience, that’s where the truth usually hides.
The Charisma Illusion Charisma gets all the press. It fills conference rooms, wins funding rounds, and dominates the LinkedIn highlight reel. We treat it like the gold standard of leadership — as if volume equals vision. But charisma is a sugar high. It spikes energy, then crashes trust. Composure, on the other hand — quiet, grounded, centered composure — is the kind of influence that lasts. It doesn’t light up a room; it settles one. When things go sideways, it’s not the charismatic leader people look for. It’s the calm one. The Crisis Test Picture this. The product just failed. The client’s furious. Your team’s pacing like trapped cats. Two leaders walk in. One storms into action — loud, fast, “What the hell happened here?” The other walks in slowly, looks around, and says, “Okay, let’s breathe. What do we know so far?” The first one gets attention. The second one gets results. That’s emotional geometry — the calmest person in the room reshapes everyone else’s state. Why Calm Is the Real Power When you stay composed, you’re not just managing your emotions — you’re regulating the entire system. Here’s the neuroscience behind it: people mirror the nervous system of whoever has the most authority. If you’re grounded, they sync to your rhythm. If you’re frantic, they sync to that instead. You don’t need to lecture anyone on resilience. You just have to model it. It’s not charisma that makes people trust you; it’s the quiet sense that you’re not going to lose your mind when things get hard. Charisma’s Half-Life Charisma is a spark. It can ignite a team — but if there’s no composure beneath it, the whole thing burns out. You’ve seen this movie before: the leader who rallies everyone with a passionate all-hands speech, then disappears into reaction mode when things get messy. Charisma without composure is like caffeine without sleep. You’re awake, but you’re not steady. Composure doesn’t get the applause. It gets the loyalty. A Founder’s Story One founder I worked with — I’ll call him David — was known for being a “high-voltage” guy. He could pitch an investor, fire up a crowd, or talk anyone into anything. But his team? They were walking on eggshells. His energy filled every room, but it left no oxygen for anyone else. During one session, I asked, “When you raise your voice, what happens to theirs?” He went quiet. That was the moment he understood that his passion — the thing he was most proud of — had become the team’s anxiety. A year later, his team described him differently: “He’s still intense, but steady. We trust him more now.” He didn’t lose charisma; he layered it with composure. The Calm Before the Influence Here’s what composure actually looks like: You listen longer. Because real influence starts with attention, not argument. You breathe before reacting. That pause isn’t weakness; it’s power management. You let silence do the work. Charisma fills every space; composure creates space for others to step in. You own your tone. You realize your sighs, your speed, your face — they’re all communication tools whether you intend them or not. You choose steadiness over certainty. People don’t need you to know everything. They just need to know you’re okay not knowing. Funny But True A client once told me, “When I’m calm in a meeting, people assume I’m hiding something.” I said, “Good. Let them wonder.” That’s how unfamiliar calm has become. In some cultures, composure looks radical — even suspicious. But it’s exactly what people crave in a world that never shuts up. Why Charisma Is Easier (and More Addictive) Charisma gets feedback. You see the energy rise, you feel the applause. It’s visible. Composure feels invisible — until you lose it. No one thanks you for staying calm during a crisis. But they remember it when deciding whether to follow you into the next one. That’s why maturity in leadership means getting comfortable with the quiet wins — the meeting that didn’t spiral, the argument that didn’t happen, the team that stayed focused because you did. The Emotional Geometry in Practice Think of composure as geometry because emotions move through space. When you enter a room, you alter its emotional shape. If you radiate calm, people’s shoulders drop. Their thinking widens. They start contributing. If you radiate stress, the room contracts. People shrink. Ideas vanish. Influence isn’t what you say. It’s the energy field you create. Your Challenge This Week Before your next high-stakes meeting, pause outside the door. Take one deep breath and ask yourself: What energy does this room need from me right now? Then bring only that. Nothing more. You’ll be amazed how fast everything slows down when you do. Final Word Charisma captures attention. Composure builds trust. One is about how loudly you shine; the other is about how steadily you glow. The leader who can stay centered when everyone else is spinning doesn’t just have influence — they are the influence. And that’s the kind of power that never burns out.
The Badge of Busyness If there were an Olympic event for back-to-back meetings, most executives I know would medal. They wear it proudly — the calendar that looks like a Tetris board, the 11:30 p.m. emails, the constant refrain of “crazy week.” Busyness has become our favorite drug. It keeps us numb, important, and conveniently distracted from the one question we don’t want to face: What am I actually doing that matters? I’m not judging; I’ve lived this. Years ago, I was “that guy” — sprinting through 14-hour days while telling myself reflection was for monks or consultants between clients. Then one day, after a particularly pointless meeting, I realized something embarrassing: I couldn’t remember the last time I’d had a single original thought. Why Thinking Feels Unproductive Here’s the irony: most leaders know they need to think more. They just can’t stand how useless it feels. Sitting in silence doesn’t produce slides or metrics. There’s no dopamine hit, no “good meeting” to log. But thinking time is like compound interest. It looks small in the moment and enormous over time. When you actually stop, patterns appear. You notice which fires you keep putting out, which meetings could’ve been emails, and which goals you’re chasing that don’t even belong to you anymore. A Simple Truth Busyness is a form of self-defense. If you never stop moving, you never have to confront the uncomfortable truths that surface when you do. That’s why reflection feels awkward at first — it threatens your illusion of momentum. But momentum without direction is just noise. A Founder’s Story One founder I coached had the classic startup badge of honor: chaos. His day started at 5:30 a.m., ended around midnight, and he bragged about being “in the weeds” with every decision. I asked, “When do you think?” He said, “All the time.” I said, “No — I mean deliberately.” He stared at me like I’d asked if he did yoga with dolphins. We scheduled two hours of thinking time a week. The first few sessions drove him nuts. He kept checking email, pacing, making lists. Then, around week four, he sent a note: “I finally realized half my problems were the result of not thinking before saying yes.” That’s the power of reflection — it turns self-inflicted chaos into clarity. The Science Behind Stillness Here’s the biology of it: when you’re rushing, your brain lives in survival mode — flooded with cortisol, locked on what’s urgent. When you slow down, another network kicks in — the one responsible for creativity, empathy, and pattern recognition. That’s why your best ideas show up in the shower or on long drives. The brain finally has enough quiet to connect dots. You don’t need more input. You need more oxygen. Why Leaders Avoid It Two reasons. It’s vulnerable. Reflection forces you to notice things you’ve been ignoring — the conversation you keep postponing, the hire you know isn’t working, the ambition that’s turned into exhaustion. It’s inefficient… at first. There’s no immediate ROI. But over time, reflection prevents the expensive rework that comes from impulsive decisions. As one client told me, “I used to say I didn’t have time to think. Turns out, not thinking was costing me time.” How to Reclaim Thinking Time (Without Quitting Your Job) Schedule “white space” like a meeting. Literally block it on the calendar. Call it “Strategy,” “Clarity,” or even “Meeting with Myself” if you’re worried someone will book over it. Change environments. Go walk, drive, sit somewhere with natural light. Different settings unlock different neural pathways. Ask bigger questions. Instead of “What needs to get done?” ask “What actually matters now?” or “What am I pretending not to know?” Capture patterns, not notes. Don’t transcribe thoughts — notice themes. What keeps repeating? That’s your mind begging for attention. End reflection with one action. Otherwise, it turns into rumination. Decide one thing to start, stop, or say no to. The Humor in It I once told an overworked exec, “Block 90 minutes a week just to think.” He said, “What should I do during that time?” That’s the problem in one sentence. Thinking is doing — it’s just quieter. What Happens When You Build the Habit At first, reflection feels indulgent. Then it feels useful. Then it becomes addictive — in a good way. Your decisions get cleaner. Your conversations sharper. Your stress lower. You stop reacting and start designing. Because clarity saves more time than hustle ever will. Your Challenge This Week Find one 60-minute window. No phone, no laptop, no music, no distractions. Just a notebook and a question: “What’s one thing I keep doing that no longer deserves my energy?” Don’t overthink it — just listen for what surfaces. That hour will tell you more about your leadership than a dozen status meetings ever could. Final Word In a world obsessed with movement, stillness is rebellion. But it’s also intelligence. The best leaders aren’t the busiest. They’re the ones who’ve learned that reflection isn’t retreat — it’s refinement. The next breakthrough won’t come from another meeting. It’ll come from the silence you’ve been avoiding.
You’ve Met This Leader — Maybe You’ve Been This Leader They’re in every company. The one who rewrites your email “just to tighten it up,” sits in on meetings they don’t need to, and then complains that no one takes ownership. If you’re smiling, you probably recognize them. If you’re wincing, you probably are them. I’ve been that person. Control looks like competence until you realize it’s just fear in a tailored suit. Control Feels Smart — It’s Actually Emotional Self-Defense On the surface, micromanagement looks like high standards. Underneath, it’s self-protection. When things feel uncertain — a shaky market, an unpredictable teammate, a decision you’re not sure about — your brain hits the panic button: Grab the wheel. Fix it yourself. And for about five minutes, it works. You feel calm again. Order restored. Then the cycle restarts: relief, exhaustion, resentment. The pattern isn’t strategic; it’s chemical. The Biology of “Let Me Handle It” Neuroscientists could tell you it’s your amygdala firing, but you don’t need a lab to recognize it. It’s that pulse in your neck when someone questions you. The twitch in your fingers when you see an email thread veering off course. Your body thinks it’s protecting you from danger. It’s really protecting you from discomfort. The Fallout Nobody Talks About When leaders grip too tightly, a few predictable things happen: Initiative dies. People stop taking risks because they know you’ll redo their work. Speed tanks. Every decision bottlenecks at the top. Your best people leave quietly for air. You end up tired, irritable, and muttering that “no one has good judgment anymore.” That’s not leadership. That’s adult babysitting. Why We Keep Doing It Because control gives a quick hit of safety. For a brief moment, you feel indispensable again. But dependency feels like loyalty until it’s not. You train your team to need you, then resent them for it. That’s the hidden cost: you create the very helplessness you complain about. A Founder’s Wake-Up Call One founder I coached — let’s call him Mark — was in every meeting, approving every pixel, every sentence. He told me, “I can’t delegate; they’re not ready.” I said, “Are they not ready — or untrained because you won’t let them try?” He laughed, then sighed. Six months later he’d handed off half his decisions. The company was running smoother. He said, “Turns out they didn’t need me in every room. I just needed to feel needed.” Exactly. The Opposite of Control Isn’t Chaos It’s clarity. When expectations, priorities, and values are clear, you don’t need to hover. People move with confidence because the direction is obvious. Control fills the gap where clarity is missing. Get clearer, and the need to control starts dissolving on its own. Five Ways to Loosen the Grip Name the fear. Is it fear of failure, of being judged, of becoming irrelevant? Labeling shrinks it. Define “good enough.” Perfectionism keeps you chained. “Done” is usually 80 percent. Delegate one layer deeper than feels safe. You’ll twitch. Let it happen. That’s growth, not danger. Ask for alignment, not detail. “Are we still headed in the same direction?” beats “Show me the draft.” Celebrate the decisions you didn’t make. Each one is proof the system’s working. Your Team Feels What You Feel Teams mirror their leader’s nervous system. If yours hums with anxiety, theirs buzzes with it. If yours is steady, they breathe again. One exec told me, “I realized my panic was contagious. So I started practicing calm.” Within weeks, meetings got shorter, people more decisive. Emotions scale faster than strategy. Funny But True I once asked a CEO why he personally approved every expense report. He said, “To stay close to the details.” I said, “No — to stay close to control.” He laughed, deleted himself from the workflow, and called it his “first act of liberation.” The Inner Work Beneath Letting Go Control isn’t a systems problem. It’s a self-trust problem. When you trust that your worth isn’t tied to omnipresence, delegation stops feeling like loss. You stop needing to prove usefulness and start multiplying it through others. That’s the real transition from doer to leader. Your Challenge This Week Pick one thing you’ve been white-knuckling — a project, a client, a decision. Hand it off completely. Tell the person, “I trust you.” Then walk away. You’ll feel the urge to peek. Don’t. Let them carry it. Let yourself breathe. You’ll both grow faster than you think. Final Word Control looks like strength. But real strength is staying steady when you’re not in control. Because leadership isn’t about gripping tighter; it’s about building clarity, trust, and calm so others can steer too. Let go. The road’s wider than you think.
One of the biggest dilemmas that founders face knowing when and why to bring in a Chief Operating Officer (COO) . Too early, and you risk creating bureaucracy before the business finds its footing. Too late, and the founder becomes a bottleneck, throttling growth and burning out teams. Get the wrong type of COO, and you’ll spark culture clashes or stifle innovation. I have had 4 COOs over my career. Their styles and capabilities were very different and the role I needed them to play differed dramatically based on the stage of the company. Some of them worked out beautifully and were the perfect complement to my founder tendencies and limitations. Some were a disaster. Here is what I learned. The COO is the most variable role in the C-suite. Some founders never hire one. Others go through three or four before finding the right fit. In many cases, the question isn’t if you need a COO—it’s what type of COO your company and your leadership style demand at this stage of growth. Let’s break this down. Why COOs Matter Founders are visionaries. They are idea machines, market spotters, and force-of-nature storytellers who rally talent and investors around a dream. But those same strengths often come paired with weaknesses: disorganization, impatience, lack of systems, and difficulty letting go of control. A strong COO is the counterweight. They turn vision into execution. They stabilize culture. They keep promises made to customers and investors. And, at the right time, they free the founder to do what only the founder can do—set direction, evangelize the mission, and keep the spark alive. But “COO” isn’t one job. It’s a category. And picking the wrong type is like forcing a square peg into a round hole. The Seven Archetypes of COOs 1. The Executor The backbone of day-to-day operations. They build systems, enforce discipline, and make the trains run on time. Best fit: Visionary founders who thrive on ideas but leave chaos in their wake. Stage: Early scaling, when the business needs process without killing momentum. Examples: Sheryl Sandberg at Facebook (balancing Zuckerberg’s vision), Gwynne Shotwell at SpaceX (stabilizing Musk’s whirlwind). 2. The Change Agent The fixer. Brought in when transformation is urgent—scaling fast, restructuring, or pulling out of crisis. Best fit: Founders who know the business has outgrown their own operational grip. Stage: Scaling into hypergrowth, or turnaround scenarios. Examples: Daniel Alegre at Activision Blizzard, leading cultural and operational overhaul. 3. The Mentor/Partner The grown-up in the room. A seasoned leader who steadies a first-time or young founder, often more coach than operator. Best fit: Visionary but inexperienced founders, often in the earliest stages of institutional growth. Stage: Transition from startup scrappiness to formal organization. Examples: Eric Schmidt at Google—while not COO by title, he played this role for Page and Brin. 4. The Heir Apparent The COO as CEO-in-waiting. They take on broad P&L responsibility, often shadowing the founder before succession. Best fit: Companies preparing for leadership transition. Stage: Later scaling into maturit Examples: Tim Cook at Apple before succeeding Steve Jobs. 5. The MVP Functionalist The specialist. A COO with deep expertise in one critical area—finance, product, supply chain, or sales. Best fit: Founders strong in vision but weak in a single domain essential to scaling. Stage: Startup to early scale. Examples: Prabir Adarkar at DoorDash, covering finance and operations. 6. The Complement to the CEO’s Gaps A tailor-made role. If the founder is a disorganized visionary, the COO is structured and disciplined. If the founder is technical but introverted, the COO is outward-facing and people-savvy. Best fit: Any founder aware enough to know their own blind spots. Stage: Anywhere, but especially scaling. Examples: Sandberg balancing Zuckerberg’s lack of operational rigor; Shotwell countering Musk’s volatility. 7. The Integrator/Hybrid The most complex type. They unify strategy, execution, culture, and talent at once—bridging across multiple functions. Best fit: Complex, multi-line businesses with global teams. Stage: Scaling into maturity. Examples: Angela Ahrendts at Burberry, integrating brand, culture, and operations before moving to Apple. Why Founder–COO Relationships Fail So Often If the COO role is so valuable, why do so many founder–COO relationships crash and burn? Boards are often gun-shy about hiring COOs because they’ve seen these partnerships implode. The reasons fall into several predictable buckets. 1. Lack of Role Clarity The fastest way to sabotage the relationship is leaving the COO’s job undefined. Who owns what decisions? Where does accountability lie? If the COO’s role overlaps with the founder’s, or isn’t communicated to the rest of the team, the COO quickly becomes either a glorified project manager or a powerless deputy. Both end badly. 2. Founder’s Inability to Let Go Many founders simply can’t let go. They want to approve every detail, revisit every decision, and undermine the very autonomy they hired the COO to exercise. A COO who feels second-guessed or constantly overruled either disengages or quits. 3. Misaligned Vision and Values Operational excellence isn’t enough if the COO doesn’t fully buy into the founder’s vision and cultural values. When the COO wants to optimize for stability while the founder is pushing disruption—or vice versa—the two end up pulling the company in opposite directions. 4. Trust and Emotional Reactivity Trust is fragile. If the founder is volatile under stress, or the COO isn’t skilled at navigating the founder’s personality, the relationship becomes brittle. Outbursts, defensiveness, or miscommunications erode psychological safety between them and ripple across the organization. 5. Succession Ambiguity and Power Tensions Is the COO being groomed as the future CEO—or not? Few questions create more tension. If expectations aren’t clarified up front, the COO may feel misled and the founder may feel threatened. Meanwhile, employees begin to compare the two and pick sides. Boards have seen this movie before, and it rarely ends well. 6. Unrealistic Expectations Founders and boards often expect the COO to “fix everything yesterday.” In reality, operational improvements take time—learning systems, culture, and people. When results don’t appear overnight, frustration builds. On the flip side, some COOs expect to make sweeping changes immediately, without respecting the founder’s legacy or the team’s tolerance for disruption. 7. Culture and Communication Breakdowns The founder and COO need structured ways to align—weekly check-ins, clear communication norms, and mechanisms to resolve disagreements. Without them, minor irritations accumulate into major grievances. Worse, the team sees open conflict at the top and begins to question who’s really in charge. 8. Identity and Ego Issues Let’s name the elephant in the room: many founders see hiring a COO as an admission of weakness. They sabotage the hire by bypassing the COO or contradicting them in front of the team. On the other side, ambitious COOs often chafe at being “Number Two.” If the relationship isn’t anchored in humility and respect, egos will clash. How Founders Can Prevent the Breakdown Knowing the pitfalls is only half the battle. Preventing them takes deliberate work: Define the COO’s mandate explicitly —what they own, what’s shared, and what stays with the CEO. Set up trust rituals early —regular one-on-one check-ins to surface tension before it festers. Align on vision and values —not just what you’re building, but how you’ll build it and why it matters. Clarify succession expectations —is this person a partner, a long-term No. 2, or a potential future CEO? Say it. Set realistic timelines —agree on milestones, but don’t expect magic overnight. Communicate clearly to the org —so employees understand who does what and aren’t caught in the crossfire. Hire for complementarity —choose a COO who fills your blind spots, not one who duplicates your strengths. The founder–COO relationship is like a marriage with the pressure of Wall Street, venture capital, and 200 employees watching. When it works, it’s transformative. When it doesn’t, it’s messy, public, and expensive. The Founder × Stage × COO Fit So how do you know when and which type of COO to bring in? Here’s the decision logic: Startup + Visionary Founder Needs an Executor or Mentor/Partner. Someone to turn chaos into motion without killing energy. Startup + Operator Founder May not need a COO yet. If they do, it’s usually a domain specialist (MVP Functionalist) to cover blind spots. Scaling + Visionary Founder Needs an Integrator or a Complement to gaps. Execution and people issues become bottlenecks. Scaling + Operator Founder May need a Change Agent or Heir Apparent. The role becomes about transformation or succession. Mature Company + Visionary CEO The COO role is succession-oriented (Heir Apparent) or complex integration (Hybrid). Mature Company + Operator CEO Sometimes no COO is needed; the CEO already runs operations. In other cases, the COO is simply the next CEO waiting in line. Takeaway Hiring a COO isn’t about “offloading work.” It’s about admitting what kind of company you’re really building, and what kind of leader you are. If you’re the spark but not the engine, you need an Executor. If you’re a force of change but leave wreckage behind, you need a Relationship-Builder complement. If you’re building for the long haul, sooner or later you need an Heir Apparent. The best founders aren’t the ones who try to do it all. They’re the ones who know when to step aside—just enough—to let someone else make the company stronger. Closing Thought In Founders Keepers, I often say: what got you here won’t get you there. The founder’s job is to create possibility. The COO’s job is to turn possibility into performance. The only real mistake is waiting until your company is already fraying before you decide which kind of COO you need. By then, the cost of waiting may be higher than you can afford.
