Roll For Insight

Category: Leadership Lessons

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

    The Rules Changed, But We Just Forgot to Tell You

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

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

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

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

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

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

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

    References:

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    So here’s how we do it better.

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

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

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

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

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

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

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

    Citations:

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

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

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

  • Why Emotional Intelligence Is Basically the GM Screen of Real Life

    Why Emotional Intelligence Is Basically the GM Screen of Real Life

    Back when I first started GMing tabletop games, I thought the little cardboard screen was mostly there to hide my dice rolls when I fudged the numbers to keep the rogue from dying in a sewer. And yes, it did that job just fine. But over time, I realized the real power of that screen wasn’t secrecy—it was stability. The GM screen lets me manage perception. It let me project confidence even when I had absolutely no idea what I was doing. When the bard decided to barter with a dragon mid-combat and the plan somehow worked, the screen let me scramble silently while saying, “Interesting choice. Give me just a moment to calculate how that would work.” Behind the cardboard? Full panic. In front of it? Implacable dungeon master. That, my friends, is Emotional Intelligence.

    If you’ve ever been in charge of anything—whether it’s coordinating a crew of overcaffeinated delivery drivers or guiding your friends through a dungeon full of murder skeletons—you already know what it’s like to look serene on the outside while your brain is breakdancing through a five-alarm crisis. Emotional Intelligence, or EQ if you’re trying to sound fancy in a meeting, isn’t about shutting off your emotions like some kind of sociopathic vending machine. It’s about mastering the subtle art of emotional stagecraft: knowing which feelings to air out, which ones to fold up and tuck behind your metaphorical GM screen, and when to pull yourself together just long enough to keep the whole table from flipping over. Because let’s be honest—if you’re leading without Emotional Intelligence, it’s not a game anymore. It’s just trauma with dice.

    aniel Goleman—the guy who basically turned Emotional Intelligence into a bestselling brand—divides it into five domains: self-awareness, self-regulation, motivation, empathy, and social skills. Sounds tidy enough to fit on a poster in a corporate hallway next to a stock photo of people high-fiving in a wheat field. But here’s what most leadership books don’t tell you: nobody can see you doing any of this. There’s no glittery badge that lights up when you regulate your emotions or empathize correctly in a staff meeting. These skills operate in stealth mode. They live in the five-second pause after someone screws up and you’re deciding whether to guide them through the wreckage or launch into a “what the hell is wrong with you” monologue. Emotional Intelligence is like a hidden dice roll behind the GM screen—no one at the table sees the number, but they all feel whether you rolled a nat 20 or a critical fail based on what happens next.

    One of the coolest things Emotional Intelligence gives you is the ability to pause the movie before your brain hits the “yell and break things” button. It lets you choose your reaction instead of letting it choose you like some rage-filled claw machine. Back when I was still new to management and clinging to my systems like they were ancient scrolls of forbidden knowledge, one of my team members absolutely annihilated a process I’d spent weeks building. Not out of spite—just out of panic, pressure, and possibly a complete misunderstanding of how calendars work. The whole thing imploded and we lost an entire day’s worth of work. My gut reaction was the usual greatest hits: jaw clench, pulse spike, and a deep internal scream that translated to, “How?! Why?! What is wrong with you?!”

    But this is where EQ stepped in like the friend who quietly takes your drink away before you do something you’ll regret. I took a walk, breathed like a Buddhist monk who just sat on a Lego, and reminded myself that throwing a tantrum wouldn’t magically fix the inventory or make the team smarter. So I came back and said—calmly, somehow—“Walk me through this. I want to make sure we set you up better next time so this doesn’t feel like your only option.” That moment of controlled response didn’t just fix the process. It built trust. It said, “Yeah, you screwed up—but I’m not gonna throw you into the volcano for it.” And that quiet, invisible choice right there? That’s the kind of leadership that keeps the party from turning on each other and flipping the whole damn table.

    Now, some people hear “Emotional Intelligence” and think it’s just a fancy word for not showing weakness. The toxic version of that idea turns into the blank-faced, corporate manager archetype who says things like “Let’s circle back” and “Appreciate your candor” while privately fantasizing about rage-punching the break room fridge. But EQ isn’t about bottling everything up and sealing it with a smile. It’s about using emotion with intention. If someone drops the ball and you don’t feel even a flicker of frustration, congratulations—you’ve officially detached from reality. But the moment you let that frustration blast out like a busted fire hydrant, you’re not leading anymore. It’s not cathartic. It’s damaging. And once your players—sorry, I mean employees—realize your screen has holes, they start making decisions based on your volatility rather than your vision.

    This is the fork in the road where Emotional Intelligence separates actual leaders from people who just have the bigger desk. Because here’s the thing, your team isn’t a set of problems to be fixed—they’re a party of weird, unpredictable adventurers, each hauling around their own unique stats and baggage. You don’t get loyalty by being louder or squeezing harder. You don’t get trust by demanding it like a toddler screaming for snacks. You have to earn those things the hard way—by listening when it’s inconvenient, by managing your own emotional mess before cleaning up someone else’s, and by realizing that just because you feel something doesn’t mean it gets to grab the wheel. Feelings are passengers. You’re the one supposed to be steering.

    I once had a player who treated failure like a personal insult from the universe. If a plan fell apart, he’d slump in his chair, glare at the dice like they owed him money, and spend the next hour passive-aggressively dismantling the vibe. I had every excuse to boot him from the table or call him out in front of the group, but that would’ve been leadership in the same way a fire extinguisher is interior design. Instead, I remembered something from a leadership book that actually stuck: Emotional Intelligence lets you guide people without turning everything into a power struggle. So I pulled him aside and said, “Look, the dice aren’t out to get you. They’re just throwing curveballs. This is improv, not a performance review. Let’s figure out how to make the twist part of the story.” He didn’t suddenly become a model player, but he did start seeing the GM screen as a boundary—not a battleground. That’s the job. Leadership isn’t about proving how right you are. It’s about steering the ship through the storm without convincing the crew they’re all going to drown.

    And make no mistake: your plan will fall apart. Leadership is improv. It’s crisis management. It’s trying to guide a group of people toward a shared goal when everyone has a different idea of what that goal should look like—and someone keeps trying to seduce the dragon. Emotional Intelligence doesn’t make you immune to stress, it just keeps you from turning that stress into shrapnel.

    So if you’re in charge and find yourself saying, “I’m just being real,” or “They need to toughen up,” take a second and ask: who’s actually behind the screen right now—the leader who sees the group’s needs and responds accordingly or the panicked goblin in your head that’s slapping at the controls, trying not to lose control? 

    Because the screen isn’t there to block out your humanity—it’s there to keep you from flinging it around like a live grenade.

  • 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.

  • 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.

  • 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.