Roll For Insight

Tag: Game Mastering

  • You Don’t Need to Know Everything—Just Stop Faking It

    There’s a particular kind of boss that’s worse than just a micromanager. It’s the kind who micromanages badly—hovering over tasks they don’t actually understand, second-guessing decisions with no context, inserting themselves into workflows like a toddler grabbing the steering wheel from the backseat. At least a competent micromanager might know what they’re interrupting. But this flavor of leader doesn’t know the work, won’t admit it, and compensates by managing through vague questions, performative stress, and ominous calendar invites titled “Touch Base.” If you’ve never had a boss like that, congratulations on your peaceful life. The rest of us are still flinching every time someone asks if we “have a minute.”

    I’ve worked under those managers, and—cards on the table—I’ve been one, too. Not in the mustache-twirling villain sense, but in the more common and less cinematic way: I got put in charge of something I didn’t totally understand, so I backed off too far because I didn’t want to come across like a dumbass. That’s the inverse version of the same mistake. Instead of meddling, I ghosted. I figured giving people space was the respectful thing to do, when what they actually needed was presence. Not command. Not control. Just the sense that I was there, paying attention, invested, and ready to help.

    Running a team without understanding their work is like Game Mastering a system you’ve never read. You might be able to fake it for a session or two. Maybe you’ve got the vibe down—narrating like Matt Mercer on half-speed, throwing in enough “roll for initiative” moments to keep everyone entertained. But sooner or later, your players are going to do something mechanical. They’ll try to shove a goblin off a bridge, or cast a spell that interacts with a system you didn’t prep, or—God help you—start asking about grappling rules. And now you’re scrambling through the Player’s Handbook like it’s a cursed tome, bluffing your way through it while everyone quietly starts texting under the table. Because nothing kills trust like a GM who pretends to know things they clearly don’t.

    Leadership theory has a name for this balancing act: Situational Leadership. Hersey and Blanchard laid it out in the late ’60s, but the idea still hits. It says your leadership style should adapt based on how competent and confident your team is at a given task. Some people need direction. Others need support. Some just need you to get out of the way and let them work. But the only way to figure that out is to actually know where they’re at. And that requires something micromanagers and absentee leaders alike tend to skip: asking questions and listening to the answers.

    Most micromanagers don’t think they’re micromanaging. They think they’re doing due diligence. Staying informed. “Driving results.” But what they’re actually doing is disrupting Self-Determination Theory—a cornerstone of motivation research that says people thrive when they feel autonomous, competent, and connected. Micromanaging undercuts autonomy. But if you also don’t know the work, it undercuts competence too—yours and theirs. You’re not just in the way; you’re actively creating friction, the same way a GM does when they override the bard’s plan just because they didn’t understand how Bardic Inspiration stacks.

    And on the flip side, disappearing because you don’t understand the work doesn’t help either. That just makes people feel unsupported, especially when things start going sideways. It’s the equivalent of a GM saying, “Well, that’s what your character would do,” and then zoning out on their phone while the players roleplay around them. Sure, you’re not interrupting, but you’re also not engaged. You’ve become the leadership version of ambient tavern music.

    So how do you do it better?

    You get curious. You name what you don’t know. You ask your team what they need from you today, not just what they needed when the project started. You ask, “What am I doing that’s helpful?” and brace yourself for the silence that might follow. You sit with it. Then you try again.

    You stop treating questions like traps and start using them like torches. You stop assuming that being “the boss” means you have to be the expert. And you realize that your credibility doesn’t come from having all the answers—it comes from helping the people who do their best work.

    If you’re running a campaign and you don’t know every mechanic, that’s fine. But don’t fake it. Bring in a co-GM, hand off to someone more familiar with the system, or prep more next time. In the moment, the best thing you can do is own it. Say, “I don’t actually know how this rule works—can you walk me through it?” And suddenly, you’ve transformed from an authority figure faking competence into a leader modeling collaboration.

    When you’re a leader and you don’t know the work, your job isn’t to disappear. And it’s not to overcorrect by smothering your team with bad advice. Your job is to learn just enough to be useful, to ask the right questions, and to create an environment where people feel like they can do their thing without you pretending to be the expert on everything. Because when people know you’ve got their back—not their keyboard—that’s when trust actually starts to build.

    And the next time you do have to give direction, it won’t sound like interference. It’ll sound like support.

    Citations:

    Deci, E.L., & Ryan, R.M. (2000). The “what” and “why” of goal pursuits: Human needs and the self-determination of behavior. Psychological Inquiry, 11(4), 227–268.

    Hersey, P., & Blanchard, K.H. (1969). Life cycle theory of leadership. Training & Development Journal, 23(5), 26–34.

  • “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.