“The best way to find out if you can trust somebody is to trust them.”
Ernest Hemingway
“Annoying” is such a convenient little word.
I throw it around the way people complain about bad coffee or rainy Mondays. It makes something sound harmless, temporary—here one second, gone the next.
But annoyance has a way of sticking, doesn’t it?
Sometimes it’s not the thing itself that lingers, but what it points to.
A clue.
A breadcrumb trail leading to something deeper: frustration, misalignment, even a quiet erosion of trust.
The question that followed me home
It began over hotel coffee and stale pastries at an industry conference—the kind with harsh lighting, polite conversations, and a food table more symbolic than satisfying.
That’s where a former client—we’ll call him Chuck—cornered me.
We exchanged pleasantries, each dutifully feigning genuine excitement about the other’s recent professional accomplishments.
But small talk quickly faded, replaced by familiar comfort food: shared workplace complaints.
Chuck described a recent project his team had wrapped up—one I might’ve been involved in days of yore. Between lukewarm sips of hotel coffee, he shared his frustrations, subtly hinting at how much smoother things might’ve gone had I still been around.
It felt oddly flattering—like being indirectly praised for my absence.
Then, without warning, Chuck stopped mid-sentence and asked, awkwardly earnest, “Was I annoying to work with?”
The question landed abruptly—like someone handing me a mirror at precisely the wrong angle. I laughed nervously, buying myself time before answering diplomatically, “Hmm… well, yes…sometimes.”
We both chuckled, letting the awkwardness dissolve into safer topics like mutual acquaintances and industry gossip.
But long after the conference ended, Chuck’s question lingered. Because the honest answer was far less diplomatic and far more emphatic: yes, he was annoying. Gold-medal-in-the-annoying-olympics annoying.
But why, exactly?
What specific brand of irritating had he perfected so thoroughly?
And more importantly, was there a deeper lesson hiding beneath all that carefully cultivated annoyance, just waiting patiently for me to finally recognize it?
The high price of annoying leadership
That question nudged me to think about annoyance more closely. In some ways, it wasn’t even a question—it was a confession. Chuck suspected, deep down, that his way of working didn’t always bring out the best in people.
And that’s where leadership gets tricky.
Because finding faults is easy. We do it on the freeway, at the grocery store, in staff meetings that could’ve been emails. But leadership isn’t about spotting what’s wrong—it’s about deciding what to do with it.
Awareness is cheap.
Turning awareness into practice, and practice into trust—that’s expensive.
Chuck was living proof of how expensive it can get. He wasn’t annoying in the casual way—like someone who hums in the office or replies “Thanks!” to every email. His was a high-grade, industrial-strength kind of annoying.
Systematic. Predictable. The kind that seeps into the work itself.
With Chuck, projects that should’ve been sprints turned into marathons. Conversations spiraled into circles. Edits multiplied like rabbits. His brand of annoying followed you home, pulled up a chair at the dinner table, and whispered on Sunday night: “Don’t get too comfortable, Monday is coming.”
And yet—Chuck wasn’t mean or incompetent. Quite the opposite. He was smart, capable, even likable.
Which almost made it worse.
Because here’s the thing: Chuck hadn’t hired me to be his stenographer. He’d hired me to bring expertise his team didn’t have. That was the expensive part. But instead of cashing in on it, he kept grabbing for the cheap stuff—injecting himself into copy, strategy, design. Edits on top of edits, decisions that weren’t his to make, fingerprints on things he’d hired me to handle.
Emails stretched into endless volleys—“one more tiny thing” lobbed back and forth until progress became performance art. Eventually, I stopped trying to win the rallies. I pre-edited my work to match what I thought Chuck would approve, even when it meant shelving better ideas.
And here’s the funny part (funny in hindsight, anyway): it wasn’t the edits that wore me down. It was realizing I’d become his psychic assistant, filtering every decision through the question: “What would Chuck change?”
It was easier, frankly, to just surrender up front.
Looking back, that’s what stung. Not the difference in taste—I’ve worked happily with people whose preferences were miles from mine. What broke me was the message buried under every “tiny” change: “I don’t trust your judgment.”
Awareness is cheap. Trust is expensive. And Chuck was a masterclass in what happens when you keep paying for the wrong thing.
When micromanagement creeps in
What I saw in Chuck wasn’t unique. That brand of annoying has another name—micromanagement.
That’s the tricky part: it rarely introduces itself as micromanagement. It shows up dressed as “helpful guidance” or “friendly advice,” but underneath it whispers, on repeat: “Trust me, I know better than you.”
It’s irritating enough when someone else does it.
Worse, I’ve caught myself doing it too—slipping into the same habits I used to loathe, as if annoyance were contagious.
Which is probably why Chuck’s question lingered. Annoyance was never really the issue. The issue was trust—and how quickly it erodes when we reach for control instead of letting people do the work we asked them to do.
When bold ideas turn beige
The worst thing about micromanagement isn’t just that it frustrates people—though it certainly does. It’s that it quietly rewires an entire team. Like an invasive houseplant, it starts small—a leaf here, a subtle vine there—and before long, it’s taken over the whole culture.
Suddenly, people don’t show up to meetings with their best ideas. They show up with safe ones.
They stop brainstorming and start guessing—watching for the eyebrow raise, the approving nod, the subtle cues that say, yes, that’s what the boss wants.
Before long, the team looks less like collaborators and more like nervous contestants on a game show called “Will They Like It?”
And that’s the heart of it: micromanagement trains us to stop trusting ourselves. Bold ideas feel risky, because risky means edits, and edits mean more work. So we adapt. We compromise. We sand down the edges of our creativity until we’re left with the safest middle ground—the beige paint of workplace collaboration.
And while beige is perfectly fine for a living room wall, nobody dreams of building a career around it.
The sneaky irony is that, as leaders, beige feels good at first.
Everyone seems to be doing exactly what we want. But what we gain in predictability, we lose tenfold in creativity, passion, and originality. Instead of a team empowered to innovate, we end up with talented people carefully tiptoeing around our preferences, treating their jobs like a frustrating version of Simon Says.
The leadership multiplier
The truth is, micromanagement is deeply myopic.
It keeps the spotlight fixed on the leader—our preferences, our control, our fingerprints on every project. But leadership isn’t supposed to be about us. The point isn’t to create work that reflects our tastes—it’s to build teams that create work none of us could pull off alone.
When trust is missing, people play it safe.
But when trust is present—when it’s practiced and reinforced—something remarkable happens. People stop trying to guess what the boss wants and start bringing their best, boldest ideas. They work with more joy, more pride, more creativity. They create things they actually want to sign their names to.
And here’s the part we often forget: trust multiplies. The more you extend it, the more you earn it back. Give people space to decide, to own, to lead—and they repay you with commitment, creativity, and accountability.
Why trust breaks the math
Leadership, at its best, isn’t about making sure things get done. It’s about making sure the right things get done—in the right way—by people who feel trusted enough to actually own them.
That’s where the math changes.
With micromanagement, the output is capped at what one person is capable of. At best, 1+1=2.
But with trust, the numbers stop behaving.
Teams build on each other’s ideas, spark new solutions, and generate momentum that feels almost impossible to explain. 1+1 doesn’t equal 2 anymore—it equals 11.
Of course, trust isn’t easy.
It takes discipline to resist the itch to control, and practice to give people space to surprise us. But that’s the difference between a team that’s simply completing tasks and a team that’s doing its best work—work that is bigger, bolder, and more meaningful than any one of us could pull off alone.
The question behind the question
Chuck’s question—“Was I annoying to work with?”—still makes me smile. In the moment, I laughed and dodged with diplomacy. But looking back, I see it differently.
It wasn’t just a self-conscious question. It was a human one. A quiet confession. He wanted to know if the way he showed up left room for others to do their best work—or if it got in the way.
And that’s the question I keep returning to myself. Not because I want to flagellate over every edit or suggestion, but because I’ve seen how easily the impulse to control sneaks in.
Even with the best intentions.
Even when I know better.
But I’ve also seen what’s possible when trust takes its place. Teams that stop hedging. People who bring their boldest, proudest ideas. Work that carries joy, ownership, and surprise—the kind you’d never have imagined if you’d clung to control.
Because in the end, the measure of leadership isn’t how much the work reflects us. It’s how much the team feels empowered to create what none of us could have done alone.
That’s the difference between beige compromise and bold creativity. And honestly, beige walls chip easier anyway.
