Roll For Insight

Tag: leadership

  • 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.

  • Radical Honesty Sounds Great Until You Actually Try It

    Radical Honesty Sounds Great Until You Actually Try It

    You’ve probably seen the phrase “radical honesty” floating around in TED Talks, thought leader newsletters, or stitched onto decorative pillows sold by entrepreneurs who post five-minute clips of themselves walking through their neighborhoods at 6 a.m. It sounds brave. Disruptive. Empowering. 

    But here’s the thing. Radical honesty feels great when you’re the one saying it. It’s a lot less fun when you have to live with it. 

    Because honesty isn’t just about blurting out whatever you think. That’s not honesty. That’s social arson. Leadership honesty–the kind that actually works–is about being accountable to the truth, even when it’s inconvenient, even when it costs you something, and even when you really want to dodge it with a little strategic word salad. 

    When I Ran a Bike Shop, Honesty Wasn’t a Brand. It Was a Liability.

    Back when I owned a bike shop, I couldn’t bring myself to lie to a customer. Not about the quality of a product, not about how much they needed something, not even about their cracked carbon frame that definitely wasn’t “just like that when I got it.”

    This wasn’t because I’m especially noble. It was just because I’d rather lose a sale than lose sleep over it. I turned down commissions. I steered people toward cheaper items that worked just as well. I never pushed brands I didn’t believe in, even when reps dangled incentives in front of me like a meatball sub in front of a hungry dog. 

    That got me a reputation for being “honest but blunt,” a few angry internet reviews from people who didn’t like hearing the truth, and a lot of customers who kept coming back because they knew I wasn’t full of it. 

    There’s research backing this up. A University of Chicago Booth School of Business study found that individuals consistently underestimated how positively others respond to honesty, especially when delivering truths that are hard to hear. Across experiments, asking participants to speak honestly for a few days or give blunt feedback, the findings showed that honesty was far more pleasant and socially connective than people had predicted. 

    That doesn’t mean that honesty always feels good in the moment. But it does build trust. 

    What It Looks Like in Leadership–and In RPGs

    Let’s take a break from the workplace for a second and talk about tabletop roleplaying games. If you’ve ever been a Game Master, you already understand leadership in its purest, least compensated form. You are the final authority on what’s true in that world. 

    When your players ask, “Does the guard look nervous?” they aren’t just testing your improvisational skills–they’re testing whether the world reacts in a way that feels real. If everything always breaks in their favor, they’ll know the fix is in. If nothing ever does, they’ll stop trying.

    Good GMs–and good leaders–understand that the job isn’t about making things easy. It’s about making things clear. Clarity creates trust. Consistency builds momentum. Honesty creates a space where people can actually do something useful instead of wasting all their energy trying to decode your mixed signals. 

    That applies whether you’re managing three warehouse employees who treat the breakroom microwave like a performance art piece or running a team of elven rogues and bard college dropouts. 

    Honesty Isn’t a Hammer–It’s a Compass

    One of the most common misuses of honesty in leadership is treating it like a hammer. “I’m just being honest,” says the manager as they whack a team member with a barely filtered complaint. That’s not honesty. That’s emotional outsourcing. 

    Real honesty is a compass. It keeps you oriented, even when the terrain sucks. 

    It’s saying, “I missed something during planning, and that’s why we’re behind schedule,” instead of, “We’ve had to make some pivots to align with evolving priorities.” It’s acknowledging when someone’s right, even if you feel insecure. It’s telling someone they’re falling short and offering them a path to improvement, dropping that truth bomb and moonwalking out the door. 

    This is the principle behind Kim Scott’s concept of Radical Candor, which encourages leaders to “care personally while challenging directly.” It’s a balance between honesty and empathy–between clarity and cruelty. 

    And it works because it’s sustainable. People can tell the difference between a leader who’s being transparent to avoid manipulation and one who’s just looking for an excuse to say whatever’s on their mind without consequences. 

    Honesty Means Letting the Bad News Be Real

    One of the hardest parts about being honest as a leader is accepting that sometimes, the bad news just sucks. There’s no silver lining, no spin, no nifty metaphor that’s going to make the metrics look better or the budget any less wrecked. 

    And in those moments, people don’t need you to inspire them. They need you to acknowledge reality. They need to see you take responsibility.

    For another take on why avoiding clarity isn’t kindness, check out this Forbes piece, “Why Leaders Are Ditching the ‘Nice Boss’ Approach,” which argues that stepping away from vague reassurance toward honest communication actually builds stronger, more engaged teams. 

    Here’s the Real Trick: They’ll Start Doing It Too

    Once people see you modeling this kind of honesty–not performative honesty, but the kind that actually costs you something–they start to feel safe doing it, too. They admit when they’re confused. They speak up sooner. They stop hiding behind half-truths and start engaging like they’re actually on the same team. 

    That’s how culture changes. Not through posters in the hallway or all-hands pep talks. Through consistent, exhausting, thankless moments of being honest when it would be so much easier not to be. 

    You don’t need to tell everyone everything all the time. But if you’re not telling the truth, they’ll know. And once that trust is gone, it doesn’t come back with a company picnic.

    Whether you’re rolling dice behind a screen or making calls on the warehouse floor, honesty isn’t a luxury. It’s your north star. And following it isn’t always comfortable. But it’s the only way anyone gets anywhere worth going.

  • “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.

  • Sorry, We’re All Out of Suckers to Promote

    Sorry, We’re All Out of Suckers to Promote

    There’s a quiet panic in a lot of middle management circles right now, and it’s not about job security–it’s about succession. Business Insider recently ran a piece titled “Gen Z doesn’t want to be the boss, and it’s creating a succession crisis,” and the headline alone tells you everything you need to know. Managers across industries are looking around and realizing the next wave of workers isn’t lining up to be promoted–and for once, it isn’t being blamed on laziness. It’s clarity. 

    Gen Z watched the previous generation get sold a bill of goods. “Put in your time, go the extra mile, and you’ll climb the ladder!” was the pitch. But what did they actually see? Their parents and mentors burned out, underpaid, micromanaged, and tossed aside the moment they became “too expensive.” In a world where salary data is public and people share horror stories about middle managers crying in their cars during lunch breaks, you can’t sell a promotion as a reward anymore. It’s just…more work for a little more money and a whole lot more stress. 

    As someone who’s held leadership roles across multiple blue-collar environments–warehouses, delivery hubs, bike shops, you name it–I’ve lived that exact transition. That moment when you’re no longer “part of the team”  but not really upper management either. You’re stuck in the awkward middle, trying to protect your people from decisions you had no say in, while getting scolded from above for not “driving results.” I once had a boss who called me into his office to say I wasn’t “being inspirational enough.” I was running on five hours of sleep, conducting a bunch of new-hire training, covering a sick call-out, and rebuilding a spreadsheet that someone decided to delete while I was gone over the weekend. But sure, let me whip up a TED Talk real quick to inspire the team. 

    So yeah, Gen Z is opting out And that’s not a sign of laziness–it’s a sign of intelligence. They’re demanding clearer boundaries, more support, and actual authority to make decisions if they’re going to be held accountable for outcomes. They want leadership with teeth, not just titles. 

    What many companies are experiencing now isn’t a leadership vacuum. It’s a backlash. A generation is finally asking, “Why would I take on the stress of management when you’ve made it clear you don’t value the people doing that work?” If you want to fill the leadership pipeline, you don’t need to offer more free pizza or cute job titles. You need to rebuild trust. And that starts with listening. 

    Because here’s the secret no one wants to say out loud: You can’t guilt people into being passionate about a broken system. Not anymore. 

    And that’s not a crisis. That’s an opportunity. 

    It’s an opportunity to redefine what leadership actually is. To stop treating it like a punishment for doing well at your job. To make mentorship part of the job instead of an unpaid side hustle. To give new leaders room to breathe, grow, and–this is important–fail safely. It’s a chance to let go of the myth that the loudest of busiest person in the room is the best candidate and start rewarding people for emotional intelligence, clarity of vision, and actual people skills. 

    In other words, if no one wants to be the kind of boss we’ve had, maybe it’s time to create the kind of bosses we’ve always needed. 

    Let Gen Z say “no thanks” to the old system. Then build a new one that’s actually worth saying yes to.

  • Most People Don’t Quit Because of the Work. They Quit Because of the Bullshit.

    Most People Don’t Quit Because of the Work. They Quit Because of the Bullshit.

    There’s this idea some managers have that if someone quits, it’s because they “couldn’t handle the job.”

    Nah. 

    Most people don’t leave because the job is hard. 

    They leave because it’s unnecessarily hard.

    The work is fine. The bullshit is what breaks them. 

    It’s the unclear expectations.

    The last-minute policy changes.

    The meetings that accomplish nothing except making you late for the part of your job that matters. 

    It’s watching your boss walk past the overflowing trash can for the third time like it’s invisible. 

    It’s being praised for going “above and beyond” instead of just being given the time and resources to do the job right the first time. 

    It’s when the most difficult person on the team gets babied because “that’s just how they are.” 

    It’s when you ask a question and get treated like you committed treason. 

    People will lift boxes, sweat through 12-hour shifts, drive across the country, or sit through soul-crushing spreadsheets for years–if they feel like someone has their back. 

    But if you make them feel stupid, replaceable, or ignored?

    Then they’re gone. Even if their body is still clocking in. 

    Nobody’s quitting because they had to work hard. 

    They’re quitting because every time they tried to make it better, they got shut down or shrugged off. 

    And eventually, they realize they’re not burned out from the work.They’re burned out from caring in a place that doesn’t care back.

  • Most TTRPG Groups Don’t Fail Because of Bad Rules. They Fail Because Nobody Talks About What They Want.

    Most TTRPG Groups Don’t Fail Because of Bad Rules. They Fail Because Nobody Talks About What They Want.

    If you’ve ever watched a tabletop RPG group implode halfway through a campaign, odds are it didn’t happen because the rogue broke the stealth rules or someone forgot how grappling works. 

    It happened because the group never agreed on what kind of story they were telling. 

    That’s the real killer. Not bad dice rolls, not min-maxing, not even a toxic player (although that’ll do it too.) It’s mismatched expectations. One player wants a deep, interesting story where their backstory matters. Another just wants to vibe and roll for soup. A third is out here trying to trigger every combat encounter because they thought it was going to be dungeon-crawl heavy. 

    Nobody’s wrong. 

    But when nobody talks about it ahead of time, the group ends up playing three different games on the same night. And resenting each other for it. 

    A while back, I ran a Star Wars campaign set aboard a derelict research vessel in deep space. The tone I was going for was budget Event Horizon but everyone’s tired and no one trusts each other. No heroes. No clean uniforms. Just scavengers trying not to get pulled apart by a haunted ship with bad wiring and worse intentions. 

    The first character to show up was perfect. A burned-out salvager with a busted EVA suit and a cybernetic eye that twitched when the humidity got too high. Total grunge vibes. Paranoia baked into the character sheet. We were locked in. 

    Then came the next player.

    They introduced a rogue Jedi who was–how do I put this?–absolutely unhinged. 

    Imagine if Charlie Day got knighted by accident and now he has a lightsaber and a working knowledge of Force Push. He talked a mile a minute, stole rations from NPCs for “training,” and once used his telekinesis to hurl a toilet at a hallway camera for reasons I still don’t understand. His entire backstory hinged on being kicked out of multiple Jedi temples for “philosophical differences.”

    Now, this wasn’t a bad character. It just didn’t belong in this game. 

    By the third session, the tone was wrecked. One moment we were crawling through vent shafts trying to avoid a sentient virus, the next he was trying to telepathically convince the ship’s AI to adopt him. The salvager’s player pulled me aside, asking if I could “get things back on track.” The Jedi’s player thought they were keeping things fun. 

    Neither of them was wrong.
    But we never had the conversation.
    And by the time we tried, the tone whiplash had already torn the party apart.

    The game died a couple of sessions later. 

    It’s the same in leadership, by the way. 

    Small teams don’t fall apart because the spreadsheet formatting was wrong. They fall apart because no one agreed on what success looked like. No one clarified how they wanted to work together. Everyone just assumed their way was the default. 

    You have to talk about it. 

    You have to talk about tone, pacing, player buy-in, safety tools, table culture–all the boring stuff that keeps your game from catching fire three weeks in. It’s not exciting, but it’s essential. 

    Same goes for coaching.
    Same goes for management.
    Same goes for any environment where human beings are expected to collaborate and make something together. 

    If you’re leading a game–or a team–you are responsible for helping people articulate what they want. And then you’re responsible for guiding the group toward a shared direction that honors as much of that as possible. 

    Because if you don’t?

    You’ll end up with a group of well-meaning, creative, passionate people–who can’t stand playing together.

  • Your “Open-Door Policy” Isn’t Working

    Your “Open-Door Policy” Isn’t Working

    Every toxic workplace has at least one thing in common. Someone in charge who proudly says, “My door is always open.” 

    They love saying it.
    They say it to new hires, to seasoned employees, to anyone brave or naïve enough to raise a concern. 

    And on paper it sounds great. An open-door policy! Transparent! Supportive! Efficient!

    Except it’s not. 

    Becaus here’s what never gets said out loud:

    If the room is full of tension, no one wants to walk through the door. 

    I’ve worked in environments where the person saying “my door is always open” was the same person we all tried to avoid. Where people kept mental tallies of how many days they could go without speaking to upper management. Where the only think “open” about the door was how wide your ass would get handed to you if you walked through it with a complaint. 

    That’s not access. That’s a trap. 

    An open-door policy doesn’t work if the culture around it tells people

    • You’re soft for speaking up.
    • You’re disloyal for involving HR. 
    • You’d better fix your attitude before you bring anything to leadership.

    That’s not leadership. That’s control with a smiley face sticker on it. 

    If you want people to actually talk to you, if you want to be the kind of leader people trust, you have to earn it with more than a catchphrase. You need to create an environment where people believe they’ll be heard, not punished. Where they know the risk of speaking up won’t outweigh the benefit of staying quiet. 

    That starts small. 

    It starts with how you react the first time someone tells you something uncomfortable. 

    It starts with how you treat the person who brings you bad news. 

    It starts with who you listen to, and who you dismiss. 

    I’ve seen “open-door policies” weaponized by managers who just wanted to avoid union pressure. I’ve seen leaders say “come to me with anything” and then roll their eyes in the breakroom when someone actually does. And I’ve seen great ideas die in silence because nobody wanted to be the one who “made it weird.” 

    You don’t need a policy. You need a presence. 

    And if you’re not getting feedback, it’s not because everyone’s happy. It’s because the door may be open, but nobody feels safe walking through it.

  • You don’t Have to Be the Fastest Rider to Lead the Group

    You don’t Have to Be the Fastest Rider to Lead the Group

    When people picture a group ride, they usually imagine the leader pulling at the front. Setting the pace. Cutting the wind. Hammering away while everyone else hangs on for dear life. 

    But the longer you ride, and the longer you lead, you realize that’s not always where the real leadership is happening. 

    Some of the best ride leaders I’ve seen weren’t the fastest. They weren’t even at the front most of the time. They were mid-pack, floating. Or sweeping the back, making sure no one got dropped. Calling out potholes. Offering a spare tube. Saying, “You good?” when someone looked like they were about to blow.

    That’s leadership, too

    There’s a myth in both sport and work that the leader is supposed to be the strongest. The fastest. The most dominant force. And yeah, sure, sometimes the situation calls for someone to pull. But other times, leadership means watching the group and adjusting. Slowing down when someone’s hurting. Speaking up when someone’s too gassed to advocate for themselves. Setting a tone that says, “We’re doing this together.”

    I’ve ridden with people who could crush me without breaking a sweat, but they couldn’t lead a group to save their lives. No awareness. No communication. Just tunnel vision and watts. And I’ve led rides where I was out of shape, fighting just to stay on, but still managed to guide the group because I knew what people needed. 

    It’s not about being in front.
    It’s about being in tune.

    If you coach athletes, train workers, GM players, or even just try to keep your family calendar from collapsing under its own weight, you’ve felt this. Leadership isn’t about outperforming everyone. It’s about knowing when to push, when to wait, and when to say, “Let’s stop for a second and make sure we’re all still here.” 

    The best ride leaders know this.
    The best coaches live it.
    And the best leaders don’t always look like leaders from the outside. 

    But ask anyone who was on that ride, who didn’t get dropped, who found their rhythm, who felt like they belonged, and they’ll tell you who was really in charge.

  • Nobody Told Me Being a Manager Meant Having to Repeat Myself 400 Times

    Nobody Told Me Being a Manager Meant Having to Repeat Myself 400 Times

    When I started in my current role, no one warned me that 80% of the job would be repeating myself. 

    I thought it would be coaching. Teaching. Creating structure. And it is. On paper. But in practice? It’s standing in front of a different group of people every day, saying the same things in slightly different ways, hoping that this time it lands. 

    I train small groups. Sometimes just one person. Sometimes eight or nine. I walk them through the same material, safety standards, expectations, critical procedures. The content doesn’t change, but the people do. Which means every delivery has to adapt. 

    What clicked for the group yesterday won’t work today. 

    The guy in the back row who’s been a driver for 10 years and thinks he’s seen it all? He needs to hear things in a way that doesn’t make him feel talked down to.

    The nervous new hire who’s scared of reversing in a windowless van? They need clarity without pressure. 

    And the person who’s been half-listening because they think they’ve already passed everything? They’re the one that’s going to miss a critical detail and then say, “No one ever told me that.” 

    So you repeat yourself. 

    You find new metaphors. You switch up the tone. You test your own patience. And when someone asks a question you just answered, you don’t snap. You repeat it again, because your job isn’t to feel heard, it’s to be understood. 

    That’s the deal when you lead small groups. You’re not giving a TED Talk. You’re creating moments of clarity in a sea of distractions, nerves, and assumptions. That takes more than a slide deck. 

    It takes presence. Patience. And an understanding that you’re not failing when you have to repeat yourself. You’re doing the job right. 

    The day I really understood that was the day a trainee told me, “I don’t know why, but when you said it, it finally made sense.” 

    It wasn’t magic. It was iteration.

    And yeah, by that point, I’d said it 400 times.

  • Your Alignment Doesn’t Excuse Your Behavior

    Your Alignment Doesn’t Excuse Your Behavior

    If you’ve ever GM’d for more than five minutes, you’ve probably heard a player say, “Hey, it’s not me doing that, it’s just what my character would do.”

    And nine times out of ten, they say it right after doing something that completely derails the game. 

    It’s the alignment excuse. “I’m Chaotic Neutral.” “I’m Lawful Evil.” “I’m just playing my character.” Like putting it on a character sheet gives them permission to act like a tornado made of red flags and questionable decisions. 

    The same thing happens in the real world. 

    People use labels like personality types, star signs, Enneagram numbers, job titles, and even trauma to explain behavior they don’t want to be accountable for. “I’m just direct.” “I have no filter.” “I’m a disruptor.” “That’s just my leadership style.” As if naming the behavior makes it untouchable. 

    But here’s the thing.
    You don’t get to avoid responsibility just because your chaos is labeled. 

    I’ve seen players blow up a session and then shrug it off because “that’s what a Chaotic Good rogue would do.” I’ve seen people in meetings steamroll their coworkers because “they’re just super Type A.” At some point, it’s not about the label. It’s about the impact. 

    And let’s be honest. Alignment is supposed to be a guide, not a get-out-of-jail-free card. 

    Your character can be Chaotic Good and still care about how their actions affect the party. Your work personality can be “bold and assertive” without making your coworkers feel like they’re in a hostage negotiation. You can be a survivor of something awful and still be expected to grow, reflect, and not inflict that same chaos on others. 

    One table I played at, a character was labeled as evil, but what they really seemed to mean was that they didn’t operate with the same moral compas as the rest of the group. They weren’t villainous, just unpredictable. Not cruel, but hard to trust. It made for some interesting dynamics, but only because the rest of the group was constantly adjusting to avoid conflict. And over time, that gets exhausting. 

    Because it’s not just about how we behave. It’s about how we expect others to bend around our behavior. Some people hid behind “chaos” because it feels safer than vulnerability. Some people lean into a villain role because it’s easier than letting the group count on them. And some people avoid being called “good” because they associate that word with people who didn’t earn it. 

    But none of that erases impact. 

    Whether you’re at the table, in a workplace, or out in the world, you don’t get to throw your hands up and say, “Well, that’s just how I am.” Not if you’re playing with others. Not if you’re leading. Not if you’re showing up in a community with real people who are trying to make things better. 

    Alignment is just a compass.

    It’s not a defense strategy.