Best Leaders Research
By Rich Hagberg
•
November 28, 2025
The Nicest Boss in the World He was adored. He remembered birthdays, checked in on people’s families, and stayed late helping fix slides no one asked him to touch. His team called him “the best boss we’ve ever had.” He was also running on fumes. Behind the warm smile was a leader quietly burning out — drowning in everyone else’s problems, too empathetic for his own good. If you’re a leader who prides yourself on caring deeply, this might sting a little: empathy, taken too far, becomes control in disguise. Empathy’s Secret Shadow Empathy is essential for leadership. It builds loyalty, safety, and trust. But the same trait that makes people feel seen can also make them dependent. When you can’t tolerate someone else’s discomfort, you start protecting them from it. You step in to fix, to soothe, to rescue. It looks noble. It feels generous. But it quietly steals agency — theirs and yours. Your team stops growing because you’re doing their emotional labor. You stop leading because you’re managing feelings instead of outcomes. That’s the hidden cost of care. The Emotional Guilt Loop Over-empathetic leaders live in a constant tug-of-war between compassion and guilt. They think: “They’re already stretched — I can’t pile more on.” “If I push harder, I’ll seem uncaring.” “I’ll just do it myself; it’s easier.” Sound familiar? That’s not empathy anymore. That’s guilt masquerading as kindness. And guilt makes terrible business decisions. Because guilt doesn’t guide you toward what’s right. It just steers you away from what feels uncomfortable. A Founder’s Story One founder I coached, let’s call her Lina, led with heart. She built her company around “people first.” And she meant it. But somewhere along the way, “people first” turned into “me last.” She couldn’t say no. She kept saving underperformers, approving vacations during crunch time, rewriting others’ work to spare them stress. Her team adored her — until they didn’t. Because beneath her helpfulness was quiet resentment. And resentment always leaks. The breakthrough came when she realized something simple but hard: “I was protecting people from learning the hard parts of growth.” That’s when she started leading again instead of parenting. When Caring Becomes Control Here’s the paradox: the more you care, the more you risk over-controlling. You jump in to fix not because you don’t trust them, but because you feel for them. It’s empathy turned inward — I can’t stand watching them struggle. But leadership isn’t about eliminating discomfort. It’s about using it wisely. People grow by stretching, not by being spared. When you save someone from every failure, you’re also saving them from competence. The Biology of Burnout Chronic empathy triggers chronic stress. When you absorb other people’s emotions all day, your nervous system never gets a break. You start mirroring everyone’s anxiety like an emotional amplifier. Your brain thinks you’re in crisis — even when you’re not. That’s why over-caring leaders are often the first to burn out. Their compassion becomes constant cortisol. The irony? The leaders who want to create safety for others end up unsafe themselves. How to Care Without Carrying Feel, then filter. It’s okay to feel someone’s frustration. Just don’t keep it. Ask: “Is this mine to hold?” Help through accountability. Say, “I know this is tough, and I also need you to take ownership.” The and matters. Let discomfort be developmental. When a team member struggles, resist rescuing. Stay present, not protective. Coach before you comfort. Instead of “Don’t worry,” try, “What do you think your next move is?” Reframe empathy as empowerment. Caring isn’t about absorbing pain; it’s about believing people can handle it. Funny but True One exec I worked with told me, “Every time I stop helping, I feel like a jerk.” I said, “No — you feel like a leader. It just takes a while to tell the difference.” He laughed and said, “So… you’re telling me leadership feels bad at first?” I said, “Exactly. Growth always does.” The Cultural Ripple Effect When leaders overfunction, teams underfunction. When leaders hold space instead of taking space, teams rise. Empathy should expand others, not consume you. The healthiest cultures balance care and candor — support and stretch. They normalize struggle as part of the process instead of something to be hidden or rescued. That’s what real compassion looks like in motion. The Maturity of Tough Empathy Empathy without boundaries is exhaustion. Empathy with boundaries is wisdom. The mature version of empathy doesn’t say, “I’ll protect you.” It says, “I believe you can handle this — and I’ll walk beside you while you do.” That’s not cold. That’s developmental. Your Challenge This Week Notice where you’re rescuing someone instead of coaching them. Pause before you step in. Ask yourself, Am I helping because they need it — or because I need to feel helpful? Then take one small risk: let them handle it. They’ll probably surprise you. And you’ll feel lighter than you have in months. Final Word Caring is beautiful. It’s what makes you human. But unchecked empathy turns leaders into emotional pack mules — carrying what was never theirs to bear. Real leadership is still full of heart. It just remembers that compassion without accountability isn’t love. It’s fear. And the moment you stop rescuing everyone, you finally start freeing them — and yourself.
By Rich Hagberg
•
November 28, 2025
The Smart Leader’s Blind Spot It’s strange how often the smartest people make the worst decisions under pressure. They don’t lose IQ. They lose perspective. I’ve seen this happen more times than I can count. A sharp, decisive executive starts second-guessing every move. They overanalyze, overwork, and overcontrol — all in the name of being “thorough.” They think they’re being rational. But underneath the spreadsheets and meetings is something far less logical. It’s fear. The Fear That Doesn’t Look Like Fear We think of fear as panic — sweating, shaking, obvious. But most leadership fear hides behind competence. It shows up as perfectionism, busyness, overcommitment, indecision. It sounds like, “Let’s get more data.” “Let’s not rush this.” “Let’s keep this one close.” That’s not analysis. That’s avoidance with a better vocabulary. When fear runs the show, the goal subtly shifts from making the right decision to avoiding the wrong one. And those two things are worlds apart. The Cost of Fear-Based Leadership When leaders operate from fear, everything tightens. They stop listening. They rush to defend. They play small when the company needs boldness. They keep people who are loyal over people who are competent — because loyalty feels safer. And here’s the real tragedy: the team starts copying the fear. They become cautious, compliant, quiet. Pretty soon, no one’s leading anymore. They’re all managing risk — mostly emotional risk. A CEO’s Moment of Truth One CEO I coached — brilliant, confident, deeply human — was terrified of being wrong in front of his board. He masked it well. On the outside: decisive. Inside: a constant hum of anxiety. After a tough quarter, he admitted, “I realized half my decisions weren’t based on strategy — they were based on protecting my image.” That moment of honesty was the start of his maturity curve. Once he could name the fear, it stopped running his show. He didn’t become fearless. He became aware. And awareness is what turns reaction into wisdom. Why Fear Feels Safer Than Clarity Fear has a strange way of convincing us it’s caution. Caution whispers, “Slow down and look.” Fear screams, “Don’t move.” The first sharpens judgment. The second paralyzes it. And the more we listen to fear, the more it disguises itself as prudence. That’s why emotional maturity isn’t about suppressing fear. It’s about being able to say, “Ah, that’s fear talking — not fact.” How Fear Distorts the Mind Here’s what happens when fear hijacks leadership: Tunnel vision: You fixate on the immediate threat and forget the big picture. Confirmation bias: You start looking for data that validates your anxiety. Short-termism: You make safe decisions that feel good now and cause pain later. Blame shifting: You protect your ego by pushing ownership outward. The mind gets smaller. The leader gets reactive. The company gets stuck. The Maturity Shift Emotional maturity isn’t about being unshakable. It’s about staying curious in the presence of fear. Mature leaders don’t pretend they’re fearless. They just don’t let fear make the decisions. They pause, breathe, and ask, “What part of this is data, and what part is my insecurity talking?” That single question can change everything. A Founder’s Story A founder I worked with once said, “I’m not afraid — I just have high standards.” But as we unpacked it, he realized those “high standards” were actually a way to control outcomes. He feared disappointment — his own and others’. When he finally stopped trying to protect his reputation and started protecting his clarity, his decisions got faster and cleaner. The business didn’t just grow — it started breathing again. Because when you stop trying to look right, you finally have room to be right. Funny, But True I once asked a CEO what he’d do differently if he weren’t afraid of failing. He said, “Probably the same things I’m doing now — just with less Advil.” That’s the thing: most leaders already know what to do. Fear just makes it hurt more. How to Lead Without Fear (Even When It’s There) Name it early. The sooner you recognize fear, the less power it has. Ask yourself, “What’s the story fear’s telling me right now?” Reframe mistakes as tuition. You’ll still pay for errors — might as well learn something from them. Separate identity from outcome. A bad decision doesn’t mean a bad leader. It means a leader who’s still learning — like everyone else. Keep one truth-teller nearby. Someone who loves you enough to tell you when you’re acting from ego. Practice micro-bravery. Tell one hard truth a day. Say “I don’t know” once a week. Let discomfort become strength training. The Paradox of Fear Fear doesn’t make you weak. It means you care. But if you never face it, it becomes your compass — and it always points backward. Courage, maturity, clarity — they’re not opposites of fear. They’re what happen when you stop running from it. Your Challenge This Week Next time you feel that knot in your stomach — before a board meeting, a tough conversation, a high-stakes call — pause. Ask yourself: What am I afraid might happen? Then ask: What might happen if I act from clarity instead of fear? That’s not therapy. That’s leadership hygiene. Final Word The mark of maturity isn’t fearlessness. It’s self-awareness. You can’t control your fear. But you can choose whether it sits in the driver’s seat or the passenger’s. Great leaders don’t wait for fear to disappear. They lead with it beside them — quietly, respectfully — but never in charge.
By Rich Hagberg
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November 21, 2025
The Overworked Hero Syndrome You can spot this one a mile away. They’re running at 120%, inbox exploding, calendar packed like a game of Tetris. They tell themselves it’s noble — “The team’s counting on me.” But deep down, it’s addiction. I know this pattern because I’ve lived it. That little rush you get when someone says, “We couldn’t do this without you”? That’s the dopamine hit of leadership ego. Feels good. Until it doesn’t. Because being indispensable isn’t a compliment. It’s a warning. Why Smart People Struggle to Let Go Most leaders don’t hoard work because they’re bad at delegation. They hoard because delegation threatens their identity. If your sense of worth comes from being the fixer, the doer, the one who “always delivers,” letting go feels like erasure. Who are you if you’re not in every meeting? Who are you if things go fine without you? That’s the emotional root of overwork — not competence, but fear of irrelevance. Control in Disguise Delegation looks like an operational skill, but it’s really emotional work. Leaders tell me all the time: “I can’t delegate — my team’s not ready.” What they mean is: “I can’t delegate — I’m not ready.” The truth is, your people won’t become ready until you give them the chance. That’s the brutal math of leadership: you can have control, or you can have scale. You don’t get both. A Founder’s Story A founder I coached — let’s call her Sara — ran her company like a benevolent tornado. She did everything: strategy, hiring, investor calls, even reviewing design files “just to make sure the tone was right.” When she came to me, she was working 80-hour weeks and quietly resenting everyone she was “helping.” I asked, “What would happen if you stopped fixing things for people?” She said, “They’d drop the ball.” Six months later, she tested it. She handed off a project completely — no shadow-managing, no emergency check-ins. Her team nailed it. She said, “I didn’t realize they were this capable.” I said, “They didn’t realize you were this controlling.” We both laughed — but she got the point. The Real Meaning of Delegation Delegation isn’t a time-management trick. It’s a transfer of trust. It says, “I believe you can handle this — even if you don’t do it exactly my way.” It’s also a developmental gift. When you delegate fully, you don’t just lighten your load — you level someone up. Delegation is how leaders stop being the engine and start being the architect. The Fear Behind “It’s Easier If I Just Do It” That sentence might as well be carved on the tombstone of burned-out executives everywhere. Sure, doing it yourself feels faster. But every time you do, you quietly train the organization to need you. You build a culture of dependence — and then complain that people don’t take initiative. Delegation feels risky because it is. You will lose control of how something gets done. But you gain something far more valuable: time to lead, not just manage. Funny but True I once told a CEO, “If you died tomorrow, who could run your company?” He said, “That’s morbid.” I said, “No — that’s planning.” He got the message. A few months later, he’d built a real leadership team for the first time. He told me, “It’s weird — I’m working less, and everything’s better.” That’s not weird. That’s delegation done right. How to Build the Trust Muscle Start small, but mean it. Hand off one real decision — not a token task. Resist the urge to check back in “just to see how it’s going.” Define success, not the path. Set the destination clearly, then step back. They’ll probably surprise you with how differently — and often better — they get there. Coach after, not during. Let people own outcomes before you give feedback. Growth requires a little space to fail safely. Reward initiative, not imitation. If you only praise people for doing things your way, you’ll never build leaders — only clones. Say thank you — and mean it. Appreciation is the emotional contract that makes delegation sustainable. The Emotional Reframe Delegation isn’t about trust in others. It’s about trust in yourself — in the system you’ve built, in your ability to recover from other people’s mistakes, and in your willingness to be unnecessary. That last one’s the hardest. But when you finally stop trying to be irreplaceable, your company starts becoming unstoppable. Your Challenge This Week Write down everything on your plate. Circle three things that drain you but could teach someone else something valuable. Pick one and delegate it — completely. Then, when the urge to “check in” hits, take a walk instead. Let them own it. When it works — and it will — tell them. Celebrate it. Because that’s how trust compounds. Final Word Letting go doesn’t make you weaker. It proves you’re strong enough to lead without needing to control. Every founder eventually faces the same test: can you stop being the engine and start being the ecosystem? The day you say yes, you stop leading through force and start leading through faith. That’s not surrender. That’s courage.
By Rich Hagberg
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November 21, 2025
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.
By Rich Hagberg
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October 28, 2025
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.
By Rich Hagberg
•
November 28, 2025
The Nicest Boss in the World He was adored. He remembered birthdays, checked in on people’s families, and stayed late helping fix slides no one asked him to touch. His team called him “the best boss we’ve ever had.” He was also running on fumes. Behind the warm smile was a leader quietly burning out — drowning in everyone else’s problems, too empathetic for his own good. If you’re a leader who prides yourself on caring deeply, this might sting a little: empathy, taken too far, becomes control in disguise. Empathy’s Secret Shadow Empathy is essential for leadership. It builds loyalty, safety, and trust. But the same trait that makes people feel seen can also make them dependent. When you can’t tolerate someone else’s discomfort, you start protecting them from it. You step in to fix, to soothe, to rescue. It looks noble. It feels generous. But it quietly steals agency — theirs and yours. Your team stops growing because you’re doing their emotional labor. You stop leading because you’re managing feelings instead of outcomes. That’s the hidden cost of care. The Emotional Guilt Loop Over-empathetic leaders live in a constant tug-of-war between compassion and guilt. They think: “They’re already stretched — I can’t pile more on.” “If I push harder, I’ll seem uncaring.” “I’ll just do it myself; it’s easier.” Sound familiar? That’s not empathy anymore. That’s guilt masquerading as kindness. And guilt makes terrible business decisions. Because guilt doesn’t guide you toward what’s right. It just steers you away from what feels uncomfortable. A Founder’s Story One founder I coached, let’s call her Lina, led with heart. She built her company around “people first.” And she meant it. But somewhere along the way, “people first” turned into “me last.” She couldn’t say no. She kept saving underperformers, approving vacations during crunch time, rewriting others’ work to spare them stress. Her team adored her — until they didn’t. Because beneath her helpfulness was quiet resentment. And resentment always leaks. The breakthrough came when she realized something simple but hard: “I was protecting people from learning the hard parts of growth.” That’s when she started leading again instead of parenting. When Caring Becomes Control Here’s the paradox: the more you care, the more you risk over-controlling. You jump in to fix not because you don’t trust them, but because you feel for them. It’s empathy turned inward — I can’t stand watching them struggle. But leadership isn’t about eliminating discomfort. It’s about using it wisely. People grow by stretching, not by being spared. When you save someone from every failure, you’re also saving them from competence. The Biology of Burnout Chronic empathy triggers chronic stress. When you absorb other people’s emotions all day, your nervous system never gets a break. You start mirroring everyone’s anxiety like an emotional amplifier. Your brain thinks you’re in crisis — even when you’re not. That’s why over-caring leaders are often the first to burn out. Their compassion becomes constant cortisol. The irony? The leaders who want to create safety for others end up unsafe themselves. How to Care Without Carrying Feel, then filter. It’s okay to feel someone’s frustration. Just don’t keep it. Ask: “Is this mine to hold?” Help through accountability. Say, “I know this is tough, and I also need you to take ownership.” The and matters. Let discomfort be developmental. When a team member struggles, resist rescuing. Stay present, not protective. Coach before you comfort. Instead of “Don’t worry,” try, “What do you think your next move is?” Reframe empathy as empowerment. Caring isn’t about absorbing pain; it’s about believing people can handle it. Funny but True One exec I worked with told me, “Every time I stop helping, I feel like a jerk.” I said, “No — you feel like a leader. It just takes a while to tell the difference.” He laughed and said, “So… you’re telling me leadership feels bad at first?” I said, “Exactly. Growth always does.” The Cultural Ripple Effect When leaders overfunction, teams underfunction. When leaders hold space instead of taking space, teams rise. Empathy should expand others, not consume you. The healthiest cultures balance care and candor — support and stretch. They normalize struggle as part of the process instead of something to be hidden or rescued. That’s what real compassion looks like in motion. The Maturity of Tough Empathy Empathy without boundaries is exhaustion. Empathy with boundaries is wisdom. The mature version of empathy doesn’t say, “I’ll protect you.” It says, “I believe you can handle this — and I’ll walk beside you while you do.” That’s not cold. That’s developmental. Your Challenge This Week Notice where you’re rescuing someone instead of coaching them. Pause before you step in. Ask yourself, Am I helping because they need it — or because I need to feel helpful? Then take one small risk: let them handle it. They’ll probably surprise you. And you’ll feel lighter than you have in months. Final Word Caring is beautiful. It’s what makes you human. But unchecked empathy turns leaders into emotional pack mules — carrying what was never theirs to bear. Real leadership is still full of heart. It just remembers that compassion without accountability isn’t love. It’s fear. And the moment you stop rescuing everyone, you finally start freeing them — and yourself.
By Rich Hagberg
•
November 28, 2025
The Smart Leader’s Blind Spot It’s strange how often the smartest people make the worst decisions under pressure. They don’t lose IQ. They lose perspective. I’ve seen this happen more times than I can count. A sharp, decisive executive starts second-guessing every move. They overanalyze, overwork, and overcontrol — all in the name of being “thorough.” They think they’re being rational. But underneath the spreadsheets and meetings is something far less logical. It’s fear. The Fear That Doesn’t Look Like Fear We think of fear as panic — sweating, shaking, obvious. But most leadership fear hides behind competence. It shows up as perfectionism, busyness, overcommitment, indecision. It sounds like, “Let’s get more data.” “Let’s not rush this.” “Let’s keep this one close.” That’s not analysis. That’s avoidance with a better vocabulary. When fear runs the show, the goal subtly shifts from making the right decision to avoiding the wrong one. And those two things are worlds apart. The Cost of Fear-Based Leadership When leaders operate from fear, everything tightens. They stop listening. They rush to defend. They play small when the company needs boldness. They keep people who are loyal over people who are competent — because loyalty feels safer. And here’s the real tragedy: the team starts copying the fear. They become cautious, compliant, quiet. Pretty soon, no one’s leading anymore. They’re all managing risk — mostly emotional risk. A CEO’s Moment of Truth One CEO I coached — brilliant, confident, deeply human — was terrified of being wrong in front of his board. He masked it well. On the outside: decisive. Inside: a constant hum of anxiety. After a tough quarter, he admitted, “I realized half my decisions weren’t based on strategy — they were based on protecting my image.” That moment of honesty was the start of his maturity curve. Once he could name the fear, it stopped running his show. He didn’t become fearless. He became aware. And awareness is what turns reaction into wisdom. Why Fear Feels Safer Than Clarity Fear has a strange way of convincing us it’s caution. Caution whispers, “Slow down and look.” Fear screams, “Don’t move.” The first sharpens judgment. The second paralyzes it. And the more we listen to fear, the more it disguises itself as prudence. That’s why emotional maturity isn’t about suppressing fear. It’s about being able to say, “Ah, that’s fear talking — not fact.” How Fear Distorts the Mind Here’s what happens when fear hijacks leadership: Tunnel vision: You fixate on the immediate threat and forget the big picture. Confirmation bias: You start looking for data that validates your anxiety. Short-termism: You make safe decisions that feel good now and cause pain later. Blame shifting: You protect your ego by pushing ownership outward. The mind gets smaller. The leader gets reactive. The company gets stuck. The Maturity Shift Emotional maturity isn’t about being unshakable. It’s about staying curious in the presence of fear. Mature leaders don’t pretend they’re fearless. They just don’t let fear make the decisions. They pause, breathe, and ask, “What part of this is data, and what part is my insecurity talking?” That single question can change everything. A Founder’s Story A founder I worked with once said, “I’m not afraid — I just have high standards.” But as we unpacked it, he realized those “high standards” were actually a way to control outcomes. He feared disappointment — his own and others’. When he finally stopped trying to protect his reputation and started protecting his clarity, his decisions got faster and cleaner. The business didn’t just grow — it started breathing again. Because when you stop trying to look right, you finally have room to be right. Funny, But True I once asked a CEO what he’d do differently if he weren’t afraid of failing. He said, “Probably the same things I’m doing now — just with less Advil.” That’s the thing: most leaders already know what to do. Fear just makes it hurt more. How to Lead Without Fear (Even When It’s There) Name it early. The sooner you recognize fear, the less power it has. Ask yourself, “What’s the story fear’s telling me right now?” Reframe mistakes as tuition. You’ll still pay for errors — might as well learn something from them. Separate identity from outcome. A bad decision doesn’t mean a bad leader. It means a leader who’s still learning — like everyone else. Keep one truth-teller nearby. Someone who loves you enough to tell you when you’re acting from ego. Practice micro-bravery. Tell one hard truth a day. Say “I don’t know” once a week. Let discomfort become strength training. The Paradox of Fear Fear doesn’t make you weak. It means you care. But if you never face it, it becomes your compass — and it always points backward. Courage, maturity, clarity — they’re not opposites of fear. They’re what happen when you stop running from it. Your Challenge This Week Next time you feel that knot in your stomach — before a board meeting, a tough conversation, a high-stakes call — pause. Ask yourself: What am I afraid might happen? Then ask: What might happen if I act from clarity instead of fear? That’s not therapy. That’s leadership hygiene. Final Word The mark of maturity isn’t fearlessness. It’s self-awareness. You can’t control your fear. But you can choose whether it sits in the driver’s seat or the passenger’s. Great leaders don’t wait for fear to disappear. They lead with it beside them — quietly, respectfully — but never in charge.
By Rich Hagberg
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November 21, 2025
The Overworked Hero Syndrome You can spot this one a mile away. They’re running at 120%, inbox exploding, calendar packed like a game of Tetris. They tell themselves it’s noble — “The team’s counting on me.” But deep down, it’s addiction. I know this pattern because I’ve lived it. That little rush you get when someone says, “We couldn’t do this without you”? That’s the dopamine hit of leadership ego. Feels good. Until it doesn’t. Because being indispensable isn’t a compliment. It’s a warning. Why Smart People Struggle to Let Go Most leaders don’t hoard work because they’re bad at delegation. They hoard because delegation threatens their identity. If your sense of worth comes from being the fixer, the doer, the one who “always delivers,” letting go feels like erasure. Who are you if you’re not in every meeting? Who are you if things go fine without you? That’s the emotional root of overwork — not competence, but fear of irrelevance. Control in Disguise Delegation looks like an operational skill, but it’s really emotional work. Leaders tell me all the time: “I can’t delegate — my team’s not ready.” What they mean is: “I can’t delegate — I’m not ready.” The truth is, your people won’t become ready until you give them the chance. That’s the brutal math of leadership: you can have control, or you can have scale. You don’t get both. A Founder’s Story A founder I coached — let’s call her Sara — ran her company like a benevolent tornado. She did everything: strategy, hiring, investor calls, even reviewing design files “just to make sure the tone was right.” When she came to me, she was working 80-hour weeks and quietly resenting everyone she was “helping.” I asked, “What would happen if you stopped fixing things for people?” She said, “They’d drop the ball.” Six months later, she tested it. She handed off a project completely — no shadow-managing, no emergency check-ins. Her team nailed it. She said, “I didn’t realize they were this capable.” I said, “They didn’t realize you were this controlling.” We both laughed — but she got the point. The Real Meaning of Delegation Delegation isn’t a time-management trick. It’s a transfer of trust. It says, “I believe you can handle this — even if you don’t do it exactly my way.” It’s also a developmental gift. When you delegate fully, you don’t just lighten your load — you level someone up. Delegation is how leaders stop being the engine and start being the architect. The Fear Behind “It’s Easier If I Just Do It” That sentence might as well be carved on the tombstone of burned-out executives everywhere. Sure, doing it yourself feels faster. But every time you do, you quietly train the organization to need you. You build a culture of dependence — and then complain that people don’t take initiative. Delegation feels risky because it is. You will lose control of how something gets done. But you gain something far more valuable: time to lead, not just manage. Funny but True I once told a CEO, “If you died tomorrow, who could run your company?” He said, “That’s morbid.” I said, “No — that’s planning.” He got the message. A few months later, he’d built a real leadership team for the first time. He told me, “It’s weird — I’m working less, and everything’s better.” That’s not weird. That’s delegation done right. How to Build the Trust Muscle Start small, but mean it. Hand off one real decision — not a token task. Resist the urge to check back in “just to see how it’s going.” Define success, not the path. Set the destination clearly, then step back. They’ll probably surprise you with how differently — and often better — they get there. Coach after, not during. Let people own outcomes before you give feedback. Growth requires a little space to fail safely. Reward initiative, not imitation. If you only praise people for doing things your way, you’ll never build leaders — only clones. Say thank you — and mean it. Appreciation is the emotional contract that makes delegation sustainable. The Emotional Reframe Delegation isn’t about trust in others. It’s about trust in yourself — in the system you’ve built, in your ability to recover from other people’s mistakes, and in your willingness to be unnecessary. That last one’s the hardest. But when you finally stop trying to be irreplaceable, your company starts becoming unstoppable. Your Challenge This Week Write down everything on your plate. Circle three things that drain you but could teach someone else something valuable. Pick one and delegate it — completely. Then, when the urge to “check in” hits, take a walk instead. Let them own it. When it works — and it will — tell them. Celebrate it. Because that’s how trust compounds. Final Word Letting go doesn’t make you weaker. It proves you’re strong enough to lead without needing to control. Every founder eventually faces the same test: can you stop being the engine and start being the ecosystem? The day you say yes, you stop leading through force and start leading through faith. That’s not surrender. That’s courage.
By Rich Hagberg
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November 21, 2025
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.
By Rich Hagberg
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October 28, 2025
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.
October 25, 2025
It usually starts with a familiar scene. A founder at a whiteboard, marker in hand, speaking with the conviction of someone who can see the future before anyone else does. The team leans in. The idea feels inevitable. Confidence fills the room. That’s the moment when narcissism looks like leadership. For a while, it is. Until it isn’t. The Hidden Engine Behind Ambition Every founder carries a trace of narcissism. You need it to survive the impossible odds of building something from nothing. It’s the oxygen of early-stage ambition — the irrational belief that you can win when every signal says you can’t. But narcissism isn’t a single trait. It’s a spectrum — and the version that fuels creativity early on often morphs into the one that burns teams, investors, and reputations later. The Six Faces of Narcissism Psychologist Dr. Ramani Durvasula , whose research has shaped much of the modern understanding of narcissism, describes six primary subtypes. Each of them can be adaptive when balanced, or toxic when unregulated: Grandiose: The charismatic visionary. Inspires others when confident; crushes dissent when insecure. Vulnerable: The emotionally fragile version. Craves validation but fears rejection. Communal: The “good person” narcissist. Needs to be admired for being generous or kind. Malignant: Controlling, paranoid, and willing to harm others to protect ego. Neglectful: Detached, disengaged, treats people as instruments. Self-Righteous: Morally superior, rigid, convinced they are the only adult in the room. Most founders show traces of at least two of these. And in moderation, these traits help. They create drive, resilience, and belief — qualities that investors often mistake for charisma. The problem isn’t narcissism itself. It’s when ego outpaces emotional regulation . The Data Behind the Mirror Across our database of 122 startup founders , each assessed on 46 Personality & Leadership Profile (PLP) scales and 46 360-degree leadership competencies , narcissism emerges as both a predictor of greatness and a predictor of collapse . The 10× founders — those whose companies returned exponential value — were not humble saints. They were what I call disciplined narcissists: confident, ambitious, assertive, and driven by achievement — but tempered by empathy, patience, and ethical grounding . They scored high on Achievement, Autonomy, and Risk-Taking , but also maintained elevated scores on Patience, Optimism, and Model of Values . They didn’t fight their ego. They harnessed it. By contrast, founders whose companies failed — the unsuccessful group — were equally brilliant but emotionally unregulated. They scored significantly higher on Aggression, Defensiveness, and Impulsivity , and significantly lower on Trust, Empathy, and Consideration — roughly one standard deviation lower (10 T-score points) than their successful peers. Their leadership wasn’t powered by vision anymore — it was powered by reactivity. And that’s the moment when the very engine that got them to the starting line begins to tear the vehicle apart. When Narcissism Works Healthy narcissism gives founders gravity. It creates the magnetic field that pulls investors, employees, and customers into orbit. These founders are confident but not careless; assertive but not controlling. They operate from belief, not from fear. They’re the ones who use narcissism to build something enduring — not to prove something fleeting. In our data, they excelled in 360 ratings on Creating Buy-In, Delegation & Empowerment, and Adaptability — all behaviors that require trust and composure. They convert ego into execution. Their signature behaviors: Grandiose energy channeled into purpose. Malignant competitiveness transmuted into persistence. Vulnerability transformed into openness and reflection. Self-Righteous conviction turned into moral consistency. They’re still narcissists — but their narcissism serves the mission, not their self-image. When Narcissism Fails Then there are the others — the unregulated narcissists. At first, they look similar: bold, persuasive, unstoppable. But over time, their self-belief becomes brittle. Their aggression rises as trust falls. Their perfectionism becomes paranoia. Their autonomy becomes isolation. These founders scored roughly a full standard deviation lower (10 T-score points) than successful ones on 360 measures like Openness to Input, Relationship Building, Coaching, and Emotional Control . They don’t fail because they’re arrogant. They fail because they can’t tolerate limitation. Feedback feels like rejection. Delegation feels like loss of control. And the more power they get, the less self-awareness they have. They move fast, but the faster they go, the lonelier it gets — until the organization collapses under the weight of their unmet emotional needs. The Two Versions of the Same Founder Ego Regulation • Successful Founders: Confidence moderated by reflection and humility • Unsuccessful Founders: Volatility disguised as confidence Control vs. Trust • Successful Founders: Delegates, empowers, shares power • Unsuccessful Founders: Micromanages, distrusts, isolates Aggression Pattern • Successful Founders: Channeled into performance • Unsuccessful Founders: Expressed as conflict and coercion Recognition Need • Successful Founders: Purpose-driven validation • Unsuccessful Founders: Insecure approval-seeking Ethical Compass • Successful Founders: Consistent moral modeling • Unsuccessful Founders: Expedience and rationalization So the dividing line isn’t how much narcissism a founder has — it’s whether it’s anchored by self-awareness . The successful ones use ego as a tool. The unsuccessful ones use it as armor. The Spectrum of Founder Narcissism Grandiose • Healthy Expression: Charisma, conviction, inspiration • Unhealthy Expression: Arrogance, dominance, fragility Vulnerable • Healthy Expression: Self-reflective, emotionally transparent • Unhealthy Expression: Defensive, insecure, blaming Communal • Healthy Expression: Empathy without ego • Unhealthy Expression: Performative caring Malignant • Healthy Expression: Fierce but principled • Unhealthy Expression: Punitive, controlling, distrustful Neglectful • Healthy Expression: Independent but connected • Unhealthy Expression: Detached, emotionally absent Self-Righteous • Healthy Expression: Grounded in values • Unhealthy Expression: Rigid, moralizing, unyielding Every founder oscillates along this continuum. The goal isn’t to eliminate ego but to integrate it — to move from self-importance to self-awareness. The Psychological Root The most successful founders in our research share a quiet humility beneath their confidence. They’ve learned to hold two truths simultaneously: “I am extraordinary.” “I am not the whole story.” That paradox — ego with empathy, conviction with curiosity — is the hallmark of psychological maturity. It’s what allows a founder to hold power without being consumed by it. Their unsuccessful counterparts can’t hold that tension. They oscillate between superiority and shame — between “I’m brilliant” and “No one appreciates me.” That oscillation is the engine of the vulnerable-malignant loop , the psychological pattern that wrecks both cultures and companies. Coaching the Narcissist You can’t coach ego out of a founder. But you can coach ego regulation . The process usually unfolds in five stages: Recognition: Data first, not judgment. Use 360 feedback as an emotional mirror. Narcissists can argue with people; they can’t argue with their own data. Differentiation: Separate ambition from insecurity. Help them see what’s driving their overcontrol. Containment: Teach behavioral discipline — pausing before reacting, curiosity before correction. Connection: Reinforce trust-based leadership behaviors — active listening, recognition, and collaborative decision-making. Integration: Replace ego-defense with ego-service — using their confidence to develop others rather than dominate them. The shift doesn’t happen overnight. But when it does, the founder becomes more than a leader — they become a force multiplier. The Paradox in Plain Language Our forty years of data say something simple but profound: Every founder who builds something meaningful begins with narcissism. But only those who grow beyond it sustain success. Ego, when integrated, becomes conviction. Ego, when unintegrated, becomes compulsion. One builds. The other burns. Or, as I often tell founders: Narcissism builds the rocket. Empathy keeps it from burning up on re-entry. That isn’t metaphor. That’s psychology — and physics. Because unchecked ego obeys the same law as gravity: It always pulls you back down.
By Rich Hagberg
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October 21, 2025
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.
By Rich Hagberg
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October 14, 2025
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.
By Rich Hagberg
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September 28, 2025
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.
