Roll For Insight

Category: Workplace Real Talk

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.