Roll For Insight

Author: Ash Blackwater

  • 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.

  • You Can’t Coach Effort, But You Can Sure Kill It

    You Can’t Coach Effort, But You Can Sure Kill It

    One of the biggest lies people tell in leadership is that you “can’t teach work ethic.”

    And sure, effort isn’t something you can program into someone. You can’t flip a switch and make someone care, but what most people miss is this.

    You can kill effort.

    You can take someone who shows up motivated, who wants to do a good job, who takes pride in their work, and you can snuff that fire out with the right combination of disregard and betrayal.

    I once worked a job for a company that said they ran their business like “one big family.” The job was pitched as “just like running your own business.” They made it sound entrepreneurial. Empowering.

    Spoiler alert. It was not. 

    I was running a route, managing deliveries, and dealing with customers. One day, I got a call from a client who ran a grimy little bar-and-grill in a small town. The kind of place where the floor is sticky before it opens and the menu is mostly deep-fried regret. He was furious about a bathroom supply listed on his invoice. It was something that was billed weekly but only replaced monthly. Standard stuff. But this guy lost it. 

    I was nowhere near his town that day, but I explained that I’d make it right the next time I was out there. That wasn’t enough. He wanted immediate resolution, even though there was no actual problem beyond his inability to read a billing cycle. 

    What did the company do? 

    They sent someone out immediately. Not because it made sense. Not because it solved a real issue. But because the guy yelled loud enough. Just like that, my plan, not to mention my credibility, got tossed out the window. 

    By the time I showed up the next week, the guy was emboldened. He treated me like I owed him something beyond the service I already promised to deliver. I do work for my customers. That’s always been my mindset. But I also expect to be treated like a human being. What he expected was submission.

    I drew a line. I told him that whatever game he was playing with other vendors wasn’t going to fly with me. I called my manager and said I was done with the stop. The customer was harassing me, and I wasn’t going to tolerate it. 

    At first, they said all the right things. “We’ve got your back.”
    Then a few days later, my manager wanted to “talk it out.”
    Then came the plan. We’d all meet together.
    I siad fine, but the guy needed to apologize to my face. That was my line. 

    Cue to the next week. I show up at the stop. No manager. I call him.

    “Oh, we handled it already,” he says. “Everything’s good.”

    Everything wasn’t good.

    I was standing outside a business where I’d been treated like garbage, expecting support, expecting a boundary to be honored. Instead, I got, “We talked it out without you.”

    That was the moment the job broke for me. 

    I kept working there for a while, but the switch had flipped. I stopped going above and beyond. I stopped trusting leadership. They’d proven that a customer’s comfort mattered more than my dignity. And no amount of company slogans or empty praise could put that fire back in me. 

    That’s what people forget about effort.
    It’s not a resource you extract.
    It’s a gift people give. Until they realize you’re not worth giving it to.

    So yeah, you can coach effort. But if you’re careless, you can absolutely kill it. And when you do, don’t act surprised when your best people start looking for the door.

  • What My Worst D&D Session Ever Taught Me About Psychological Safety

    What My Worst D&D Session Ever Taught Me About Psychological Safety

    You can learn a lot about leadership by watching what happens when it’s done badly, especially at a D&D table.

    Years ago, I joined a campaign run by a GM who pitched it as gritty, dark fantasy. Think Game of Thrones but with dice. We all nodded eagerly. Sure, dark fantasy. Why not?

    But then things got weird. Fast.

    It wasn’t long before “gritty” turned into “gratuitous.”  The GM introduced a villain who wasn’t just evil, he was deeply, awkwardly inappropriate. Every interaction was loaded with uncomfortable innuendo, forced humor, and themes that didn’t just cross lines, but pole-vaulted over them

    The first few sessions, the table laughed nervously. It felt safer than speaking up. We thought it was just a misstep. Surely it would get better. But it didn’t. Instead, session after session, we sank deeper into discomfort. People stopped making eye contact. Jokes dried up. Roleplaying felt awkward, like navigating a social minefield. 

    And nobody said anything. 

    After one particularly uncomfortable session, a player quietly texted me, “I don’t know if I want to come back.” Neither did I.

    The problem wasn’t that the GM was trying to push boundaries.. Plenty of great stories explore dark or mature themes thoughtfully. The real issue was that he never checked in. He assumed we were fine with the tone he’d chosen because we hadn’t explicitly said otherwise. Silence, he thought, was consent. But silence was just confusion and discomfort wearing a polite mask.

    This happens in workplaces, too. Leaders set a tone, sometimes unintentionally, through the jokes they tell, the way they handle conflict, or how they respond (or don’t respond) when someone crosses a line. And employees, like players, pick up on cues fast. If speaking up feels risky, most people won’t. They’ll just quietly check out, waiting for the campaign (or the job) to end. 

    Psychological safety isn’t about protecting feelings. It’s about creating an environment where people feel safe enough to speak up when something feels wrong or off or uncomfortable. Great GMs and great leaders both understand this. They watch the table carefully. They notice body language, hesitations, awkward silences. And instead of pushing blindly forward, they pause. They ask. They adjust. 

    That campaign ended abruptly. Players drifted away until there was nothing left but a few awkward goodbyes in the group chat. And while I wish we’d said something sooner, the truth is the responsibility to create safety always lies first with the person in charge. 

    So here’s the hard-won wisdom. 

    If you’re running the table (or the team) your job isn’t just to tell the story or set the direction. It’s to make sure the people in front of you feel safe enough to tell you when the story isn’t working. 

    Otherwise, you risk losing more than a few sessions. You risk losing trust entirely. And once that’s gone, the game’s over, whether you’re ready or not.

  • Your Team Isn’t “Difficult.” You Just Haven’t Actually Led Them Yet.

    Your Team Isn’t “Difficult.” You Just Haven’t Actually Led Them Yet.

    I’ve worked for people who thought leadership was about standing at the front of the room and being the loudest voice. People who believed that if someone didn’t fall in line, it was because they were lazy, disrespectful, or “not a good fit for the culture.”

    They didn’t see any of it as a reflection of their leadership.
    Because in their mind, they weren’t the variable.
    They were the constant. The standard. The boss. 

    Here’s the truth. 

    If you think your team is difficult, but you’ve never take time to learn wat matters to them, what motivates them, what stresses them out, what they actually need from you, then they’re not the problem.

    You are. 

    I’ve seen it more than once. A new program gets introduced. A new role is added. The person in charge resists it from day one. Not because it’s a bad idea, but because it wasn’t their idea. They don’t want to learn what it does, why it’s needed, or how it fits into the bigger picture. And when the person in that role doesn’t thrive immediately, because, surprise, they’re getting zero support, the response is, “See? Told you it wouldn’t work.”

    That’s not leadership. That’s sabotage with a name badge.

    But here’s the kicker. Those people? When they finally get a leader who gets it, someone who pays attention, listens without judgement, and adapts their approach, they become unstoppable. 

    The “difficult” ones are often the most loyal, the most effective, and the most creative members of the team once they feel seen and trusted. But they don’t respond to positional authority. They respond to earned respect. 

    If your go-to move is to write people off because they don’t immediately jump when you say jump, you’re not leading. You’re just managing compliance and calling it culture. Leadership is not a personality contest. It’s a relationship. And relationships take work. So the next time you catch yourself muttering that your team is difficult, stop and ask:

    Have I actually tried to understand them?

    Have I given them the support I expect them to give me?

    Have I adjusted my style to match the needs of the people I’m supposed to be guiding?

    If the answer is no, then you haven’t led them yet. 

    You’ve just been standing near them while stuff happens.

  • Rebuilding Sucks, But So Did Being Out of Shape

    Rebuilding Sucks, But So Did Being Out of Shape

    There’s no poetic way to say this. Coming back to the bike after a long time off sucks. 

    It sucks when your lungs start burning during a warm-up.
    It sucks when you used to crush climbs and now you’re watching your heart rate spike just trying to hold an endurance pace. 
    It sucks when your body feels like a stranger. 

    For a long time, I told myself I was just busy. I had work, school, family. I was getting things done. But the truth is, I’d burned out. Hard. And once I stopped riding, it was easy to stay stopped. The idea of coming back felt overwhelming. I wasn’t just worried about losing fitness. I was worried about what it would feel like to face that loss head-on. 

    I’ve always had a tendency to go all-in on things. It’s part of who I am. Focused to the point of obsession, until the fuel runs out. Then I crash. I’ve never had a diagnosis, but if you drew a Venn diagram of ADHD, burnout cycles, and perfectionist tendencies, I’d be standing right in the middle waving. 

    So when I finally decided to get back on the trainer and rebuild, I thought I knew what to expect. Soreness, sure. Loss of power, fine. But I wasn’t prepared for the identity crisis. 

    I couldn’t even think of myself as the same rider anymore. That guy? He was long gone. That guy had an FTP that didn’t want to make him cry. That guy did events. That guy had a training calendar full of colors. This new guy? He was struggling to get through a Zone 2 ride without negotiating with his legs like they were on a union strike. 

    You don’t just return to cycling after time off. You reframe yourself. You rebuild a relationship with a sport that used to define you. And sometimes, that means giving up the fantasy of being “back to normal” and deciding what your new normal is going to look like.

    I had to stop thinking in terms of comparison.
    No more “I used to…”
    No more chasing ghosts on the leaderboard. 
    No more measuring today against the version of me who didn’t have a kid, a degree, and a whole catalog of professional baggage. 

    Now, I ride to feel strong again. Not fast. Not competitive. Just strong. Grounded. Connected to myself. 

    It’s not heroic. It’s not inspirational. It’s just honest.

    And honestly? Rebuilding sucks. 
    But being out of shape sucked more. 

    So if you’re staring at your bike right now, trying to psyche yourself up for a comeback, do it. But don’t expect to become your old self again. 

    You’re building someone new.

    And that version of you?
    They might not ride the same. 

    But they’ll ride for better reasons.

  • Leadership would be a dream job if it weren’t for all the humans involved.

    Leadership would be a dream job if it weren’t for all the humans involved.

    I’m half-joking. But only half. Maybe a quarter. 

    You can read every leadership book. Build a color-coded calendar. Learn about accountability systems, emotional intelligence, conflict resolution, and process optimization. You can even implement all of it with care, clarity, and just the right balance of empathy and authority. 

    And still, someone will misinterpret a message, blow up a group chat, refuse to follow a simple instruction, show up late, get in a passive-aggressive turf war over pallet space or lose their mind because you rearranged the whiteboard. 

    Why? Because humans are unpredictable. Messy. Emotional. 

    And they don’t always act in their own best interest. 

    Which is a real buzzkill when you’re trying to hit your KPIs. 

    I’ve led in environments where the plans made sense. The systems were solid. The logic was airtight. And it all fell apart anyway, because someone woke up  in a bad mood and decided today was going to be the day they were going to die on the hill of “we’ve always done it this way.” 

    That’s the part leadership books don’t usually prep you for. 

    They’ll teach you how to create structure. 

    They won’t teach you how to explain the same thing for the fifth time without sounding like an asshole. 

    They’ll show you how to build a motivational framework. 

    They won’t tell you how to handle a team member who’s mad that their buddy got moved to a different shift and now they “just don’t feel like trying.”

    They’ll preach servant leadership, strategic thinking, and communication theory. 

    They won’t prepare you for the moment someone walks into your office unannounced and says, “Can we talk about something weird that happened two weeks ago that I haven’t stopped thinking about?

    Leadership isn’t hard because the systems are complicated. 

    It’s hard because people are people. And people bring everything with them, their stress, their insecurities, their childhood trauma, their bad lunch, their loud opinions, their calendar confusion, and the fact that someone looked at them wrong in the parking lot that morning. 

    And here’s the catch.

    You don’t get to opt out of that.

    You don’t get to say, “Let’s just stick to the work.”

     Because the work is the people. And the people are never just the job they do. 

    So yeah, leadership would be easier if people weren’t involved.
    But then it wouldn’t be leadership.

    It would be inventory management.

    If you’re in it for real, get used to the mess. 

    That’s where the good stuff happens anyway.

  • Well, That Meeting Could’ve Been an Email, and That Email Could’ve Been Nothing

    Well, That Meeting Could’ve Been an Email, and That Email Could’ve Been Nothing

    I’ve been in a lot of meetings. Most of them shouldn’t have happened. 

    I’m not talking about the rare, focused kind where problems get solved and decisions get made. I’m talking about the meetings that exist purely because someone, usually someone with a title, has it on their calendar every Tuesday at 9 a.m. and they don’t know what else to do with that slot. 

    The “check-in.”

    The “touch base.”

    The “round table” that isn’t round and doesn’t lead anywhere. 

    I once had a standing daily meeting where department heads were supposed to share updates about production flow. In theory, this was useful. In practice, it was a shouting match between people trying to deflect blame for missed numbers. Every day was a new version of “Your team is holding us up.” Followed by “Well maybe if your team didn’t hog all the resources…” It was like watching territorial raccoons fight over trash labeled “Process Improvement.” 

    Nothing got solved. But it kept happening every morning because “communication is important.”

    Sure. But bad communication isn’t neutral. It’s negative value. It doesn’t just waste time. It actively wears people down. 

    The worst part is that no one actually wants to be there. You can feel it in the room. People zoning out. Fake-laughing at unfunny jokes. Checking the time. Wondering if there’s a polite way to vanish. But they still show up, because that’s what we’ve all been trained to do. Keep showing up, even when the thing we’re doing has long since stopped being useful. 

    And then there are meetings where people show up just to complain about things no one in the room has the power to fix. 

    I’ve been in so many of those. Third-party contractors yelling about the same issues week after week, even though they’ve already been told a hundred times that the solution has to come from someone four pay grades above us. They know that. They keep bringing it up like we’re just going to break protocol and reprogram the entire logistics network out of spite. 

    That kind of meeting doesn’t just waste time. It creates conflict. It breeds resentment. People vent because they’re frustrated, but no one leaves feeling better. Nothing changes. It’s just a group therapy session run by someone with a clipboard and no authority. 

    Eventually, you realize the meeting isn’t about solving anything. 

    It’s about being seen having a meeting. 

    It’s about proving you care. Proving that you’re doing something. Proving to some invisible metric that you’re engaged. And that’s how you get a room full of adults sitting around a whiteboard every week pretending not to be actively dissociating. 

    Here’s what I’ve learned the hard way:

    If the meeting doesn’t have a purpose, cancel it. 

    If the meeting’s only purpose is to vent, call it what it is and bring snacks. 

    If people are just repeating the same complaints from last week, it’s time to figure out why they don’t just escalate it, or accept htat they just like the sound of their own outrage. 

    Most importantly, if you find yourself running one of these meetings, don’t take the silence as agreement. People aren’t quiet because they’re content. They’re quiet because they’re trying to disappear. 

    Sometimes, the best leadership move you can make is to say, “You know what? We don’t need to do this.”

    Then let everyone go back to doing something that actually matters.

  • So I Tried Being a Good Leader and Now Everyone’s Mad at Me

    So I Tried Being a Good Leader and Now Everyone’s Mad at Me

    At some point in your leadership journey, you will try to make things better. And people will hate you for it. 

    I learned that the hard way. I had just put the finishing touches on a new training process that had been causing problems for months. Packages were going missing. Damaged items weren’t getting documented properly. Everyone was stressed, and no one could tell me where things were breaking down. So I sat down and did the work. Rewrote the steps and double-checked everything against the actual day-to-day flow. 

    It wasn’t perfect, but it was better. 

    Then I rolled it out and the backlash was immediate. 

    Suddenly I was “micromanaging.” People said I was “changing too much.”  One guy flat out told me I was making things harder on purpose. Never mind that we’d been talking about these exact issues in meetings for weeks. Never mind that I built the changes based on feedback they gave me. 

    They were mad. Because it was different. 

    That’s the thing no one tells you about trying to lead for real.

    When you challenge the way things have always been,  even with the best intentions, you don’t get applause. You get suspicion. Frustration. Eye rolls. People assume you have a hidden agenda, or that you’re trying to prove something, or that you’re just flexing. 

    I used to take it personally. 

    Now, I just see it as part of the job. 

    When you try to improve things, you’re sending a message, whether you mean to or not, that the old way wasn’t working. And if people built a sense of competence or pride around the old way? That feels like a threat.

    Even if you’re right.

    Especially if you’re right. 

    Good leadership will piss people off. Not because you’re cruel. Because you care enough to push through the part where everyone’s uncomfortable. You’re willing to stand in that storm, knowing the other side is a team that’s better prepared, more efficient, or less miserable. 

    But in the moment? It sucks. 

    You’ll be accused of things you didn’t do. You’ll be called controlling, arrogant, or out of touch. You’ll go home wondering if you screwed everything up. And then, slowly, the thing you changed will start to work. People will adapt. They’ll stop fighting it. They might even forget there was ever a time that it didn’t work that way. 

    And they won’t thank you.

    That’s fine. That’s not why you’re doing it. 

    So yeah, I tried being a good leader. I got yelled at. I got side-eyed. I got called things I won’t repeat here. 

    But the process worked. The problems got fixed. And eventually, the team stopped bleeding out time and energy on avoidable mistakes. 

    That’s leadership. It’s not pretty. But if you can handle the part where people get mad at you for caring, you might actually be onto something.

  • Coaching Isn’t Telling People What to Do. It’s Getting Them to Want to Do It.

    Coaching Isn’t Telling People What to Do. It’s Getting Them to Want to Do It.

    There’s a moment every coach hits, whether you’re working with a cyclist, a new trainee at the warehouse, or a kid learning to ride for the first time, where you realize that telling people what to do doesn’t actually work.

    You can write the perfect training play. You can explain the science. You can point to the numbers. But if they don’t want to do it, none of it matters. And if they do want to do it, half the time you could’ve said anything and they still would’ve figured it out. 

    Coaching isn’t about commands. It’s about buy-in. 

    I’ve seen it in cycling. I’ve worked with riders who had all the gear, all the tech, all the data, and none of the fire. They’d show up. They’d half-commit. They’d blame the plan, or the weather, or their FTP not climbing fast enough. And I’ve also coached riders who had old gear, chaotic schedules, and a million excuses not to try, but they wanted it. And they got better because they chose to. 

    I see the same thing at work.

    You can walk someone through the process a dozen times. You can demonstrate. Quiz them. Repeat yourself. But until they understand why it matters, and until they decide to care, you’re just noise in the background of their day. On the other hand, if you make them feel like their success is their own? Like they’re growing, not just following directions? They lean in. They start driving the process instead of being dragged by it. 

    Motivation doesn’t come from authority. It comes from belief.

    Belief in the task. Belief in the outcome. Belief in themselves. 

    That’s the difference between managing and coaching. 

    Managing is making sure boxes get checked. 

    Coaching is building the kind of mindset where people start looking for boxes you didn’t even ask about. 

    I’ve coached riders who hated intervals until they realized how strong it made them feel at the top of a climb. I’ve trained employees who didn’t care about safe loading procedures until it was tied to making sure they got home uninjured to their kids. You have to connect the task to something that matters. 

    Coaching isn’t “Do it because I said so.” 

    It’s “Do it because now you want to see how far you can go.”

    And sometimes that’s the most humbling part. Because when you coach well, they don’t need you forever. They get stronger. Smarter. More confident. And eventually, they start coaching someone else. 

    That’s not failure. That’s the goal.