Roll For Insight

Tag: Workplace Culture

  • Cecil Stedman: The Adaptive Bureaucrat Nobody Wants to Be (But Somebody Has To)

    When I was writing about Omni-Man, I kept circling back to Cecil Stedman, the director of the Global Defense Agency. If Omni-Man is the worst-case scenario of charisma without ethics—the guy who can make mass murder sound like a pep talk—then Cecil is the polar opposite. He doesn’t inspire anyone. Nobody’s getting a Cecil tattoo. He looks perpetually hungover, like a guidance counselor who gave up on wearing ties sometime in the early 90s. But when the world is coming apart, he’s the one you actually want making the calls.

    Because Cecil isn’t about vision or inspiration. He’s about survival. He embodies what Ronald Heifetz and Marty Linsky call adaptive leadership—stepping into situations where there is no playbook, no technical fix, no “right answer” that saves the day. Omni-Man flexes, and cities crumble. Cecil grimaces, makes a decision that guarantees everyone will hate him, and then pours another drink. That’s actually the more realistic version of leadership.

    You can see it in how he operates: sending rookies into fights he knows they’ll lose, lying to Mark about how bad things really are until he absolutely has to tell him, constantly calculating which disaster leaves fewer bodies on the floor. He doesn’t pretend there’s a win waiting at the end. He just picks the path where the damage is survivable. That’s the entire premise of adaptive leadership—there’s no fixing the storm, only steering through it.

    This is why I can’t shake Cecil as the real counterpoint to Omni-Man. Charisma makes you believe in someone before you know what they stand for. Cecil makes you distrust him immediately, and yet, through sheer blunt honesty, he earns something more durable than admiration: grudging trust. He never tells you it’ll be fine. He tells you it’s going to be terrible, but here’s how we’ll get through it anyway. That’s a very different kind of authority than Omni-Man wielding his mustache like a badge of destiny.

    It also makes Cecil a pretty good metaphor for what happens once you’ve been leading people long enough to lose your illusions. Anyone who’s ever managed a warehouse crew, or run a hospital shift, or tried to GM a tabletop campaign knows what this feels like. You start bright-eyed, promising people big visions and meaningful work. Then reality sets in. The order backlog is impossible, the patients keep piling in, the party has just set fire to the only inn in town because someone thought a bar brawl would be “character-driven roleplay.” Suddenly, you’re not the inspirational Omni-Man figure anymore. You’re Cecil, making exhausted calculations about which choice leaves the fewest scars.

    That’s the unglamorous reality of adaptive leadership. Heifetz and Linsky talk about it as “living in the disequilibrium.” You can’t let things get so calm that people won’t adapt, but you also can’t let them get so chaotic that people panic or break. It’s this awful tightrope of tension management. Cecil lives on that rope. He knows if he underplays a threat, people die. If he overplays it, people revolt. So he does what real leaders do: he accepts that everyone will be angry with him, and then he does it anyway.

    Of course, there’s a cost. Cecil always looks one bad day away from collapsing into his whiskey glass. Adaptive leadership isn’t the kind of thing that makes you a beloved icon. It burns you out, leaves you scarred, and makes your victories invisible. No one celebrates the catastrophe you prevented. They only complain about the compromises you made. That’s why so many real-life leaders retreat into the comfort of technical fixes—new checklists, new policies—because at least those come with the illusion of control.

    But when you’re really in it—when you’re leading people through situations with no clean answers—charisma won’t save you. Vision won’t save you. The only thing that keeps people moving is knowing you’re willing to stand there with them in the middle of the wreckage, taking the heat and making the call. That’s Cecil. He doesn’t inspire. He endures. And in the long run, that’s what makes him the most honest kind of leader.

    Omni-Man showed us the dangers of charisma unmoored from ethics. Cecil shows us the price of leadership rooted in pragmatism. Between the two, Cecil’s the one you can actually trust to keep the world spinning, even if you hate him for how he does it. And if you’ve ever found yourself in a role where every option looked terrible but someone had to choose, congratulations: you’ve already had your own Cecil moment. You probably didn’t look good doing it. You definitely didn’t get applause. But you kept things alive long enough to fight another day. And that, grim as it sounds, is leadership.

    References

    • Heifetz, R. A., & Linsky, M. (2002). Leadership on the Line: Staying Alive Through the Dangers of Leading. Harvard Business Review Press.
    • Northouse, P. G. (2021). Leadership: Theory and Practice (8th ed.). Sage Publications.

  • The Rules Changed, But We Just Forgot to Tell You

    The Rules Changed, But We Just Forgot to Tell You

    Nothing makes people question your leadership faster than realizing the finish line they’ve been running toward just got picked up and moved. This is the organizational version of telling a kid they can have dessert if they finish their vegetables, then halfway through the broccoli deciding they also need to clean the garage and mow the lawn first. The dessert was never the point. The goal was to keep them occupied until you could figure out how to get out of your own chores.

    In corporate life, this usually shows up when leadership makes a promise they didn’t fully think through. The intent might have even been noble at first — “Hey, we’ll make sure everyone gets a fair shot at promotion.” But when the sign-up sheet fills faster than expected and the people who actually have to conduct those evaluations start sweating about their workload, suddenly there’s a brand-new hoop to jump through. A leadership assessment. A timed test. An extra round of manager sign-off. And here’s the kicker: fail that extra hoop and you don’t just miss your shot — you don’t even get told what you did wrong, so you can fix it next time.

    From the outside, this reads less like “streamlining the process” and more like “we realized how much work this would be for us, so we invented a filter to thin the herd.” There’s no transparency, no feedback, and no sense that the people in charge remember they promised you something in the first place. Which brings us to the real damage: it’s not the inconvenience that kills morale. It’s the unspoken message that your leadership’s word is provisional. Conditional. Entirely dependent on whether it still suits them to keep it.

    If you’ve ever run a game of D&D, you know exactly how this plays out. You tell your group that if they defeat the Big Bad Evil Guy, they’ll hit Level 10. This is the campaign’s driving goal. Every plan, every detour, every questionable alliance with shady NPCs is about gearing up for that final fight. Then, right before the big showdown, you say, “Actually, before you can fight him, you’ll need to pass this riddle challenge. Fail, and you can’t try again until next year. Oh, and I won’t tell you what answers you got wrong.” At best, the players feel blindsided. At worst, they start suspecting you never really wanted them to succeed in the first place. And once players stop trusting their GM, the game stops being fun. They’ll still show up — sunk-cost fallacy is a hell of a drug — but the spark’s gone.

    And here’s where leadership theory has been screaming warnings for decades. In transformational leadership, one of the core jobs of a leader is to inspire people toward a shared vision through consistency, trust, and integrity (Bass, 1990). If the vision changes, you bring your team along for the why, the how, and the what’s-next. But if you just quietly rewrite the playbook mid-season without telling anyone, you’ve broken what Rousseau (1995) calls the psychological contract — that unspoken agreement between leader and team about what each side owes the other. Once that’s broken, even the most committed, high-performing people start conserving their energy. Not out of spite, but out of survival. They’ve learned the rules can change without warning, so why go all-in?

    There’s a way to fix this without torching morale, but it requires humility and a little bit of courage. If you truly can’t honor the original path you laid out — whether because of volume, budget, or your own failure to anticipate demand — transparency is your only way out. Spell out what’s changing, why it’s changing, and how people can still succeed under the new system. Give feedback, even if it’s just “You scored lower on decision-making under time pressure — here’s where to practice.” If you have to thin the candidate pool, do it in a way that still respects the original promise, even if it means spreading things out over a longer timeline. Otherwise, you’re just selecting for the people most willing to tolerate frustration, which is not the same as selecting for the people most capable of leading.

    The rules can change — life’s unpredictable, and leadership is about adapting. But if you want your people to keep showing up with full effort, the one rule that can’t change is this: when you say something matters, it has to keep mattering, even when it’s inconvenient for you.

    References:

    Bass, B. M. (1990). From transactional to transformational leadership: Learning to share the vision. Organizational Dynamics, 18(3), 19–31.

    Rousseau, D. M. (1995). Psychological contracts in organizations: Understanding written and unwritten agreements. Sage Publications.

  • The Feedback That Was Actually a Trap: Weaponized Coaching and the Illusion of Development

    The Feedback That Was Actually a Trap: Weaponized Coaching and the Illusion of Development

    There’s a moment in bad D&D campaigns when the GM grins too much. You know the look. The party just triggered something, maybe opened a door they weren’t supposed to, or used a clever workaround to bypass some elaborate puzzle, and the GM, instead of rolling with it, tilts their head and says, “Interesting.” That’s the moment you realize you’ve made a mistake. Not in the game. In trusting the GM. Because that smile? That’s the “this is going in the kill box” smile. And the only reason your character’s still breathing is because the plot isn’t done punishing you yet.

    That’s what fake coaching feels like in the workplace.

    It starts off warm. Encouraging. Your boss says they’re “invested in your development” and want to “help you grow.” It’s like they just pulled you aside in the tavern and offered you a side quest. You feel chosen. Important. Maybe this is it—your chance to level up, to finally get out of the hell that is middle-tier oblivion where your talents are wasted and your coffee goes cold before you remember where you left it. But instead of getting a magic item, you get assigned a “stretch project” with no guidance, no resources, and no context. And somewhere around hour fourteen of trying to decode the office spreadsheet equivalent of ancient dwarven runes, you realize: this wasn’t a gift. This was a test. And you are not supposed to pass it.

    This is what I call development theater—the illusion of mentorship with none of the substance. It’s the kind of thing that looks amazing in a quarterly report. “We’re committed to employee growth,” they’ll say, while quietly tossing people into career quicksand and blaming them for not building a ladder. And the worst part? You can’t even prove it. Because technically, they did coach you. They gave you feedback. They offered you opportunity. They gave you rope—just enough to hang yourself artistically, in the break room, next to a printout of last year’s mission statement.

    The TTRPG version of this is the GM who swears they’re “collaborative,” then turns every piece of your backstory into a trap. You tell them your character once abandoned a sibling in a burning village? Great. Now the final boss is the sibling, and no, you don’t get a redemption arc, you get stabbed with a flaming pitchfork while the GM does a bad voice and says, “This is what you deserve.” You thought you were building a narrative. Turns out, you were providing raw materials for a vengeance fantasy they’ve been workshopping since their sophomore year creative writing class.

    But let’s go back to the office. Because this isn’t just bad management—it’s a strategy. It’s called plausible deniability leadership. It’s what happens when someone wants you gone, but doesn’t want to look like the bad guy. So instead, they offer you “growth.” They suggest “areas for improvement.” They ask you to “stretch beyond your comfort zone,” while quietly collecting screenshots and calendar invites like evidence for a crime they’re planning to report after the fact. You’re not being coached. You’re being turned into a cautionary tale.

    And you start to notice it, too late. You start wondering why your emails are getting ignored. Why projects get reassigned without explanation. Why every compliment you get sounds like it came from an AI that only read the first paragraph of your résumé. You start to feel like you’re being haunted by a ghost version of your reputation. Like someone filed a secret report that says you’re “difficult to work with,” and now everyone’s treating you like a cursed item—technically useful, but risky to equip.

    Leadership theory actually has a name for the good version of this: Individualized Consideration, one of the pillars of Transformational Leadership (Bass & Riggio, 2006). That’s when leaders offer feedback and development tailored to each person’s goals, strengths, and needs. But there’s a dark mirror to this: Pseudo-Transformational Leadership (Bass & Steidlmeier, 1999), where the tools of mentorship get twisted into performance theater. It’s the difference between helping someone grow and using the language of growth to justify pushing them out. The difference between a GM saying, “Let’s explore your character’s fears,” and a GM saying, “Hey, I noticed your character’s afraid of drowning, so I made all the dungeons water now.”

    And no, it’s not just one bad boss or one bad GM. This happens in systems where psychological safety—the foundation of trust and learning on any team—is treated like a luxury add-on (Edmondson, 1999). The moment people start to feel like feedback is a setup, they stop trying. They shut down. They play it safe. They stop asking questions, stop offering ideas, stop rolling with disadvantage unless absolutely necessary. And then leadership turns around and says, “Why don’t we have more innovation around here?”

    Here’s the wild part: most of the time, the people doing this think they’re being kind. They think that by softening the truth, or sugarcoating the failure, they’re protecting you. They don’t realize that fake feedback is worse than silence. That pretending to help while secretly preparing your exit is like handing someone a parachute made of spaghetti. You’re not saving anyone. You’re just putting on a show before the impact.

    So here’s how we do it better.

    If you’re in charge of people—at a table, on a loading dock, in a customer service team in a crumbling office park built entirely out of sadness and reused drywall—then ask yourself: Is this feedback meant to help this person? Or is it meant to protect me from looking like the bad guy later? Because that’s the line. That’s the moment when you decide whether you’re going to lead with integrity or script a fake redemption arc just to cover your own plot holes.

    Be honest. Be clear. If someone’s not meeting expectations, tell them—with support, with context, with a plan. Don’t dress it up in “opportunities for growth” if what you really mean is “we’re already interviewing your replacement.” If you’re a GM and a player is being disruptive or needs to shift how they engage at the table, don’t write it into the story like some kind of Saw-style morality lesson. Talk to them. You are allowed to be direct. You are allowed to be kind without being vague. You are allowed to be uncomfortable if it means being real.

    Because people know. They always know. The party knows when the GM has it out for them. Employees know when they’ve been moved to the short bench. And when trust breaks—when the coaching turns out to be a trap, when the feedback was just foreshadowing—it doesn’t just ruin one person’s experience. It poisons the whole table. It tells everyone else that growth is conditional. That failure is fatal. That support is a trick.

    And once people believe that, you don’t get innovation. You don’t get loyalty. You get silence.

    You get a campaign where nobody tries anything bold. A job where nobody brings up new ideas. A team that’s still technically alive, but spiritually checked out, like NPCs waiting for the next cutscene.

    So if you’re going to be a leader, be one. Don’t hand people a torch just to light their fuse. Don’t offer them a side quest when you’ve already decided how the story ends. And don’t call it feedback if it’s really just foreshadowing.

    We already know the trap is coming. The only question is whether you’ll pretend it was part of our development plan all along.

    Citations:

    Bass, B. M., & Steidlmeier, P. (1999). Ethics, character, and authentic transformational leadership behavior. The Leadership Quarterly, 10(2), 181–217.

    Bass, B. M., & Riggio, R. E. (2006). Transformational Leadership (2nd ed.). Psychology Press.

    Edmondson, A. (1999). Psychological Safety and Learning Behavior in Work Teams. Administrative Science Quarterly, 44(2), 350–383.

  • You Can’t Lead by Sucking the Joy Out of the Room: A TTRPG Guide to Negative Leadership

    You Can’t Lead by Sucking the Joy Out of the Room: A TTRPG Guide to Negative Leadership

    There’s a particular kind of emotional exhaustion that settles in when your Game Master thinks being in charge means being right all the time. It starts slow–your character’s little backstory never gets acknowledged, your clever ideas get waved off with a smirk and a house rule, and pretty soon you’re just rolling dice and getting your turn over with as little friction as possible. You used to be excited to play. Now you’re mostly just tracking hit points and trying to survive the session. It’s not that you don’t like the game. It’s that the person running it has made the table feel like a minefield. 

    I’ve had day jobs that feel exactly like that. 

    What I call Negative Leadership shows up in real life the same way it shows up in bad tabletop campaigns. It’s not always loud or theatrical. It’s a mindset. A controlling, defensive, brittle approach to being in charge. It’s the manager who talks like a GM who’s memorized every line of the module but hasn’t noticed that half the players are disengaged. They think “leadership” means quoting the rulebook and punishing deviation. They treat innovation like it’s cheating and feedback like it’s a charisma check they can refuse. 

    I’ve worked across a bunch of different environments–logistics, operations, customer service–and while the industries changed, the vibe of a bad manager never did. You try to bring something to the table, and they act like you’re violating canon. I once stayed late to help a new hire finish up a shipment–just helping out. Next day, I get pulled aside for “disrupting the process.” In another job, a manager pinned dollar bills to his office wall from bets he won against his own staff, like we were all stuck in some sad, corporate version of Tomb of Horrors. Nobody said anything, but we all saw the message: this place runs on ego checks. 

    What makes it harder is that most of these leaders don’t see themselves as the problem. They think they’re enforcing standards. That they’re the only thing holding back the chaos. But treating your team like a bunch of unruly NPCs doesn’t build order–it builds resentment. Calling someone “not great with people” doesn’t begin to cover it. It’s more like they see empathy as a homebrew mechanic they don’t trust. 

    Frederick Herzberg’s Motivation-Hygiene Theory puts a fine point on it: the stuff that demotivates people isn’t the same stuff that inspires them. You can have health benefits, free snacks, and an end-of-week XP bonus, but if your boss treats you like a barely tolerated raccoon who wandered into the breakroom–something to be monitored and controlled–you’re not going to stay motivated. You’ll stick around, maybe, but your heart won’t be in it. It’s like showing up to a dungeon crawl where the GM never lets you explore. You’re not playing–you’re just rolling to comply.

    And like any bad GM, the truly corrosive managers rarely blow up in obvious ways. It’s not all dramatic yelling or slamming doors. It’s a slow bleed: a joke that lands too hard, a change in protocol with no explanation, a public correction that wasn’t necessary. I once got called out for parking a training vehicle “the wrong way,” even though it was the safest available option. The response wasn’t, “Let’s talk through it.” It was, “Rules are rules.” No context, no conversation. Just pure authoritarian DM energy. 

    Douglas McGregor’s Theory X and Theory Y explains this kind of behavior. Theory X leaders believe that people are fundamentally lazy and need to be coerced into productivity. So they act like GMs who run every session like a power fantasy–one where players can’t be trusted to make good decisions, so every path is railroaded and every choice is an illusion. And when the team stops engaging, these managers see it as proof. “See? They only work when I’m watching.” Yes, because you’ve made watching feel like surveillance, not support. 

    The wild part is, I came into all those jobs wanting to contribute. I had ideas. I saw things that could be improved. I wanted to play the game well, not break it. But when your every move gets treated like a challenge to the GM’s authority, you eventually just stop rolling. Not because you don’t care, but because the consequences for trying feel too steep. 

    The worst leadership I’ve experienced didn’t look dramatic. It looked polite. Measured. Controlled. And deeply suffocating. You could ask questions, sure–but only once. And only if they were easy. The mood in the room said: Don’t make waves. It’s the difference between a campaign where the players feel powerful and one where they feel watched. Some leaders don’t know the difference. 

    What makes it worse is that these kinds of leaders often believe they’re respected. What they’re actually seeing is compliance dressed up as loyalty. It’s players nodding at the table because they’ve learned what happens if they don’t. Google’s Project Aristotle found that the most successful teams aren’t built on competence alone. They’re built on psychological safety–on people knowing they can speak up without getting wrecked by an attack of opportunity. Negative Leadership squashes that before the first session’s even over. 

    So what’s the fix? It’s not handing over the GM screen to chaos. It’s leading like someone who actually wants the party to succeed. Bernard Bass called this transformational leadership: building people up, not boxing them in. Sharing the story. Listening to the table. Trusting your team to be more than background flavor. 

    And here’s the kicker–any of us can drift into Negative Leadership if we’re not careful. All it takes is a little pressure, a little stress, and a little too much certainty. Suddenly, you’re making decisions to protect your own authority instead of supporting the people at the table. You’re no longer the GM guiding the story–you’re the final boss in someone else’s burnout narrative. 

    Leadership isn’t about being the smartest person in the room or holding the most lore. It’s about making the session better because you were there. If people feel freer, braver, and more creative when you’re gone, you’re not leading–you’re just running a game they can’t wait to finish. 

    And no one brags about surviving that campaign.

  • If You Think Leadership Is About Having All the Answers, You’re Probably the Problem

    If You Think Leadership Is About Having All the Answers, You’re Probably the Problem

    One of the first things I tell every new hire class is that they should ask as many questions as they want, and they should never feel weird about it. I explain that when they do, one of three things is going to happen. The first is that I’ll just give them the answer. I’ve been doing this long enough that sometimes I know the thing they’re asking about, and I’ll just give it to them straight. The second is that I’ll give them my best guess. I’ll say something like, In my experience, usually the best practice is this…” or “Here’s what most people in the industry do.” And the third is that I’ll tell them who else to talk to–because sometimes I’m not the right person to answer it. Maybe it’s a technical question with the app or some strange behavior with the hardware, in which case, a seasoned veteran out there actually doing the job in the wild is the best resource. But I’m never going to bluff or fake it. Not because I’m some sort of saint, but because I’ve worked under those kinds of people before. The ones who fake their way through every question, who have to be right all the time, who treat leadership like it’s just being the biggest brain in the room. And I’ve seen how much damage that mindset causes. 

    For some reason, a lot of us go into leadership thinking our job is to have all the answers. That’s the myth we’ve been sold. That the leader is the one who knows everything, who sees further than the rest of us, who walks into the meeting like a prophet and drops solutions on the table. It’s a comforting fantasy, especially when the stakes are high. But in practice, this kind of leader becomes a bottleneck. They kill collaboration. They build teams that are afraid to speak up, afraid to ask questions, and worst of all, afraid to think. The moment people on your team start believing that their value lies in saying nothing and deferring to the person in charge, you’ve lost. 

    I used to feel that pressure too, like my credibility depended on always having the one right answer locked and loaded at all times. But pretending to know everything doesn’t make you more credible. It makes you brittle. And brittle things tend to break when real pressure hits. Overconfidence in leadership, according to Entrepreneur, especially during crises, “can cross the line into the danger zone,” where authenticity gives way to ego and collaboration goes to die. 

    Over time, I’ve come to believe that one of the most important things a leader can say is, “I don’t know, but let’s find out.” Not as an escape hatch, but as an invitation. It tells the team that they’re allowed not to know either. It invites curiosity. It tells people that we’re here to learn together, and that finding the right answer is a shared responsibility, not a solo act for the boss. And weirdly enough, research backs this up. A recent meta-analysis found that when leaders express uncertainty instead of faking confidence, people actually trust them more and think they’re more competent. It’s one of those satisfying little paradoxes: the moment you stop pretending you’ve got it all figured out is the moment people start believing in you. 

    But if your default mode is always to have the answer, whether you actually do or not, you’re going to train your team into silence. And worse, you’re going to stop learning. One of the easiest traps to fall into is mistaking your authority for omniscience. But leadership isn’t about being the smartest person in the room. It’s about making sure the smartest ideas in the room have space to be heard. In my case, that often means handing the question off to someone who’s seen more edge cases, who’s driven more miles, who’s figured out a solution to that weird glitch I’ve never seen. I’d rather point someone to the best resource than try to impress them with some half-informed answer. That’s not humility for its own sake–it’s efficiency. 

    There’s a popular quote from Google’s Project Aristotle research that’s showing up in a lot of leadership seminars lately: the single most important factor in high-performing teams is psychological safety, which is the basic idea that people do their best work when they know they won’t be shut down, shamed, or penalized for speaking honestly, taking risks, or owning up to mistakes. And nothing destroys psychological safety faster than a leader who punishes questions, shuts down feedback, or reacts defensively to being challenged. Those leaders don’t build strong teams. They build echo chambers. And echo chambers can be quiet, not because everything’s working, but because no one’s talking anymore. 

    I’ve seen both kinds of leadership up close. I’ve had bosses who responded to every issue with a kind of rehearsed confidence. I even had one boss whose philosophy was, “Never let them see you sweat.” And I’ve had leaders who said, “That’s a great question. Let’s think through it.” The difference in team culture was night and day. One team was rigid and anxious, always waiting to be told what to do. The other was flexible, collaborative, and surprisingly resilient under pressure. The second team didn’t succeed because the leader had all the answers. We succeeded because the leader made space for us to ask the right questions. 

    That’s how I try to approach my own leadership now. I still prepare. I still try to be informed. But I don’t cling to the illusion that I’m supposed to know everything. I tell people what I know, I share what I’ve seen, and I point them to better experts when needed. I treat questions not as tests of my competence, but as chances to model how we figure things out. And when someone brings something to my attention that I hadn’t thought of? I thank them. Because that’s what we’re here to do–build something smarter than any one person could build on their own. 

    Leadership isn’t about having all the answers. It’s about guiding people through complexity without pretending the path is always obvious. It’s about saying “Let’s figure this out together” and meaning it. Because the moment you stop pretending to be the answer key is the moment your team finally gets permission to start solving problems with you.

  • “One Hop at a Time” Is a Leadership Strategy, Not Just a Survival Tactic

    “One Hop at a Time” Is a Leadership Strategy, Not Just a Survival Tactic

    As I’m working on a research project right now, I’m revisiting The Leadership Challenge by Kouzes and Posner, which is considered one of the staples in leadership literature. You know the type–corporate workshop bait, stuffed with stories meant to inspire you to “ignite the leader within.” And sure, some of it hits. A few of the ideas even spark something. But I also find myself grinding my teeth through some of the examples, especially the ones that seem to equate good leadership with getting your people to work late for free. 

    There’s a story in the book that really stood out, though, in a good way. It’s about a guy who climbed Mount Rainier as an amputee. Someone asked how he did it, and he said, “One hop at a time.” That’s it. That’s the whole strategy. One hop, then another, until he was on top of the mountain. 

    Now I’ve never climbed a mountain–unless you’re talking about the kind made out of failed delivery metrics and climbs on a mountain bike trail that turn your quads into haunted meat–but the lesson rang true. Not because it was revolutionary, but because it confirmed something I already deeply knew from coaching, working and just generally trying to keep the wheels on the ground while moving forward. 

    There’s no magic—just movement.

    Every meaningful transformation comes from a thousand micro-decisions that add up over time. Or, as James Clear puts it, it’s about making tiny gains every day, compounding into something that looks impressive only once you zoom out far enough.

    As a cycling coach, one of the first things I learned was quadrant analysis. You basically take a piece of paper, draw a big plus sign splitting it into four sections. In one box you write where the athlete is now–their current fitness level, often including FTP (Functional Threshold Power), endurance capacity, maybe some recent performances. In another, you define the demands of the event they want to do–how long it is, what kind of terrain it’s on, what kind of energy system it’s going to tax. The third is the timeline–how much time do we have to prepare? And the fourth is the destination. What are their goals? Finishing on the podium? A personal record? What fitness level or skillset do they need to realistically develop to do it?

    That’s how you build the map. You don’t just hope for greatness. You break down the path between today and the event and you work backward from the finish line to structure the steps. Week by week. Ride by ride. It’s not flashy. It’s not magic. But it works.

    And I’ve found that model applies far beyond bikes. 

    Let’s say you’re managing a team of forklift drivers. Or DMing a group full of creative agents of chaos. Or trying to write a book while also raising a child, working full time, and keeping your sanity wired together with cold coffee and grim determination. The principle still holds. Big goals are built out of small, repeatable actions. You just need to know what to repeat. 

    The amputee climber didn’t conjure his way up the mountain. He didn’t pull out a TED Talk and inspire the snow into melting. He took one step, then another. He broke down the impossibility into micro-goals. From here to there. That’s it. 

    Same for the leader who wants to change a toxic work culture. You don’t fix the entire system in one keynote speech. But you might start by not rewarding the people who burn themselves out and punishing the ones who set healthy boundaries. You start by showing your team what matters through what you pay attention to. Then you do it again. Then you do it when nobody’s watching. Then you keep doing it even when you’re frustrated when it’s not moving fast enough. 

    The alternative is paralysis. 

    Too many people get stuck at the base of the mountain, looking at the summit the way a cat looks at a closed door–like something must be wrong with the universe if that’s where you’re supposed to go. I get it. I’ve stood there myself more times than I’d like to admit. Whether it was trying to build a business from scratch, dealing with toxic workplace nonsense, or trying to hold a half-shattered D&D group together after an emotional meltdown, it’s easy to feel like you’re supposed to fix everything or fix nothing. That’s the trap.

    So what does this mean for you as a leader, coach, or GM?

    It means you need to get comfortable with slow progress. You need to train yourself–and your team, or your players–to look for the landing spot for those hops. To recognize that mastery, growth, and even healing aren’t events. They’re practices. A good leader breaks down the mountain into legible steps. They don’t throw their team at the wall and see who sticks. 

    Here’s a quick framework you can actually use, whether you’re writing a campaign, leading a team, or building a new training plan:

    1. Define the summit – What’s the actual goal? Don’t say “be a better team.” Say “improve order accuracy by 20% in 90 days.” Or “get our bard to stop derailing every plotline with jokes about magical ass tattoos.”
    2. Evaluate your terrain – Where are we starting? What resources do we have? How much buy-in? What are the known obstacles?
    3. Estimate your hops – Break it down into manageable steps. Something you can do this week. Then next week. Then the one after that. Keep it visible.
    4. Adjust as needed – Don’t marry the plan. Marry the goal. Sometimes a hop turns out to be a skip or a backslide. That’s fine. Adjust. Keep moving. 

    Leadership isn’t about grandeur. It’s about momentum. And momentum comes from clarity and consistency. 

    And if you’re thinking, “Yeah, but my situation’s different,” you’re not wrong.

    Everyone thinks their mountain is the most unclimbable. Everyone thinks they’re the only one dealing with a team that’s checked out, a player who keeps trying to solo the boss fight, or a workplace that quietly celebrates burnout like it’s a personality trait. But the core strategy still applies. 

    You figure out what the next hop is. Then you take it. You stay honest about where you are, you respect the human limits involved, and you keep showing up. 

    That’s leadership. One hop at a time.