The Unfortunate Story of the Leader and the Staplers: A diary of regret, poor decisions, and why I should have got a coach years ago

So, there I was, 28 years old, accepting my first proper ‘big’ leadership role with the kind of unshakeable confidence that can only come from having absolutely no idea what I was doing. I’d read the books, watched the TED talks, and been to the excited conferences. I had resolute opinions about servant leadership, and the importance of having a growth mindset, and the unquestioned value of coaching. I was 100% ready for the role, the challenge, and my team!

I was not ready.

What I Expected:  

To finally implement all those brilliant ideas I’d been mentally collecting for years like some sort of management squirrel hoarding theoretically valuable acorns.

What I Got:  

Fourteen consecutive conversations about the thermostat, three passive-aggressive email chains about whose turn it was to buy milk, and the dawning realization that my “brilliant ideas” looked considerably less brilliant when they had to survive contact with actual humans who had, inconveniently, also brought their own brilliant ideas to work.

The thing nobody tells you (and I do mean nobody, possibly because they’re all too traumatized to speak of it) is that leadership is often less about “inspiring visionary on a mountaintop” and more about “bewildered camp counselor trying to get everyone to the same destination while half the group insists the map is upside down and the other half has wandered off to look at a particularly riveting tree.”

The Vision Thing 

Before becoming a leader, I had what I can only describe as cinematic expectations. I would cast my irresistible vision of teamwork, and togetherness, and collaborative effort. People would lean forward in meetings, eyes practically glistening with the excited lure of endless possibility. We would march proudly toward a shared future, unified and purposeful with square chins and unrelenting steely gazes.

The reality? I spent the first three months trying to explain a perfectly straightforward strategy while my team nodded politely and then continued doing exactly what they’d been doing before, which (and here’s the kicker) was often better than what I’d suggested anyway.

Turns out “casting vision” in practice means repeating yourself so many times you start to question whether you’ve actually said anything at all, or whether you’ve been miming this entire time and everyone’s been too polite to mention it.

The Decision-Making Fantasy 

Here’s what I thought happened: Leader identifies problem, weighs options with Solomon-like wisdom, makes decision, everyone gratefully implements it. Clean. Efficient. Vaguely heroic – but not so much as to make me blush in public.

Here’s what actually happens: Leader identifies problem, discovers it’s actually seven different problems wearing a trench coat pretending to be one problem, spends two weeks gathering input from people who all want completely different things, makes a decision, immediately second-guesses that decision, lies awake at 3am wondering if they should reverse the decision, doesn’t reverse it, then six months later someone casually mentions they solved the whole thing differently anyway and it worked fine.

I once spent an entire afternoon agonizing over whether to change our project management software. I made spreadsheets. I ran a trial period. I surveyed the team. We switched. Three people used it. Everyone else continued using a shared Google Doc that someone had apparently created years ago and never mentioned to me.

Democracy dies in darkness, but apparently so does project management.

Ooooh, I really wish I’d gotten a coach.

The Feedback Delusion 

Before: “I’ll create a culture of radical candor where we all help each other grow through honest feedback. High challenge. High support. Marvelous.”

After: Spending 45 minutes crafting an email that essentially says “please stop doing that thing that I told you to stop doing” but in 12 paragraphs of such carefully calibrated language that by the end, I’m no longer certain I haven’t actually thanked them for doing the thing that I think I told them not to do.

The feedback sandwich (you know, compliment, criticism, compliment) seemed so sensible in theory. In practice, people remember only the bread. I once told someone “You’re doing great work, but we need to discuss your timekeeping, and your presentations are excellent!”

Three months later, in their self-evaluation: “As you noted, my presentations are excellent.”

The timekeeping? Still catastrophic. But those presentations? Chef’s kiss.

Why, oh why didn’t I get a coach? Why?

The Meeting Revelation 

I was so smug about meetings before I had to run them. All those terrible meetings I’d sat through? Not on my watch, mister. My meetings would be dynamic, purposeful, finishing early with action items so crisp and clear and tightly tucked in you could practically bounce a quarter off them.

Then I discovered that meetings are where logic sometimes goes to die and time moves like treacle …with the flu. Someone will derail a 30-minute discussion about Q3 goals to tell a seven-minute story about their nephew’s piano recital. Another person will say “quick question” and then ask something that requires a doctorate in philosophy to answer. Someone will definitely say “let’s take this offline” about something we are literally, currently, online to discuss.

And you, the leader, will sit there trying to steer this ship while also wondering whether you left the oven on, and whether it’s too late in your career to retrain as a lighthouse keeper.

Lighthouse keepers don’t have meetings.

The Conflict Management Surprise 

Books about leadership made conflict sound like an opportunity. A chance for growth! A healthy tension that sparks innovation!

What they meant: You will become an emotional hostage negotiator, except everyone’s already taken themselves hostage and you’re trying to convince them to release themselves while they insist everything’s fine, they’re fine, why are you even here, they’re FINE.

I once spent a week mediating between two colleagues who were, and I’m not exaggerating, arguing about the correct way to format bullet points in shared documents. Not whether to use them. Not what to put in them. The formatting. Sentence case versus title case. There were camps, and factions, and sides to take.

We’re talking about fully grown adults with mortgages and opinions about monetary policy, locked in mortal combat over capitalization.

I suggested we simply pick one and move on.

They looked at me like I’d suggested we all start wearing capes and brandished canes and top hats.

The Empowerment Paradox 

“Empower your team,” they said. “Trust them to make decisions,” they said. “Get out of their way,” they said.

So I did. I stepped back. I empowered. I trusted.

Then someone bought 400 staplers because they were “on offer” and we’re a team of 12, and another person decided to completely restructure our filing system at 4pm on a Friday without telling anyone, and a third person took “make it your own” as permission to redesign our entire client proposal template in a font that can only be described as “ransom note chic.”

Now I’m somehow both a micromanager (because I’d quite like to know before we acquire a lifetime supply of office supplies) and too hands-off (because apparently “use your judgment” doesn’t automatically calibrate everyone’s judgment to sensible levels).

There’s a sweet spot between “controlling overlord” and “absent landlord” but I’ll be damned if I can find it. It moves. Daily. Hourly, sometimes.

I REALLY should have got a coach. Like, genuinely. This is not a drill.

The Performance Review Horror 

I thought performance reviews would be really clear, and candid and straightforward. We’d look at someone’s work, discuss it like adults, agree on development areas, everyone leaves feeling motivated and clear.

Instead, I’ve learned that performance reviews are elaborate theater where both parties pretend the last 12 months went differently than they actually did. I’ll bring up areas for improvement I’ve mentioned monthly since February. They’ll act surprised, as though I’ve produced this feedback from thin air like some sort of criticism magician.

Or worse, they’ll bring a list of everything they’ve ever done, including “maintained positive attitude during fire drill” and “learned to use new coffee machine,” and expect equal credit for both. And possibly a raise for one of them.

I once had someone list “showing up” as an achievement. Not showing up on time. Not showing up despite difficulties. Simply showing up. As though we were all surprised they’d remained corporeal throughout the quarter.

A coach. I needed a coach. Past tense. Fifteen years ago. Someone please invent time travel so I can go back and get a coach.

The Terrible Truth 

Here’s what nobody tells you when you’re reaching for that leadership role, ruddy of face and full of bright-eyed optimism: sometimes leadership is just trying to keep reasonably intelligent people from making batsh*t decisions while somehow convincing them it was their idea to be reasonable in the first place.

You will have the same conversation so many times you’ll start to wonder if you’re stuck in a time loop. You will make decisions that literally nobody asked for and everyone will have opinions about. You will try to solve problems only to discover you’ve created three new problems – like trying to get an octopus into a string bag…you get another leg in and another one pops out.

And yet.

(There’s always an “and yet” in these things, isn’t there?)

There are moments. Brief, fleeting moments where something actually works. Where the team pulls together and does something genuinely good. Where someone says “thanks for backing me on that” and you realize that maybe, possibly, occasionally, you’re not completely terrible at this.

These moments last approximately 4.5 seconds before someone emails you about the thermostat again and has anybody seen their stapler.

But they’re there.

What I’ve Actually Learned 

You know what I did eventually do?

I got a coach.

I know, I know. Groundbreaking stuff. Only took me five years, two nervous breakdowns, and a minor stapler-related trauma to figure it out.

And here’s the thing that makes me want to laugh and cry simultaneously: it helped. Immediately. Annoyingly so. Turned out having someone to talk to who’d seen all this nonsense before, who could say “yes, the thermostat thing is normal, here’s why it’s happening and here’s what you can actually do about it” was, and I cannot stress this enough, TRANSFORMATIVE.

All those conversations I’d been having with myself at 3am about whether I was doing everything wrong? Turns out they’re more productive when you have them with another human during daylight hours. Revolutionary concept.

My coach didn’t have all the answers (because nobody does, and anyone who says otherwise is selling something). But they had MUCH better questions. They had perspective. They had the magical ability to say “so what I’m hearing is…” and somehow translate my incoherent rambling into actual clarity.

They also laughed. A lot. Particularly at the stapler incident.

Could I have muddled through without one? Sure. Was I muddling through without one? Demonstrably, yes. But was it efficient, or pleasant, or remotely sustainable?

Absolutely not.

Leadership isn’t what I expected. It’s better and worse and weirder than anything I could have imagined. It’s less about having all the answers and more about knowing who to ask when you don’t. It’s less about grand gestures and more about showing up when things are messy and unclear (which, inconveniently, is most of the time). It’s about not being too big to dig.

And sometimes, it’s about admitting you need help before you’re buried under 400 staplers and the accumulated weight of your own stubbornness.

So here’s what I wish someone had told me on day one, ideally before the thermostat wars began:

Get a coach!

Not because you’re failing. Not because you’re inadequate. But because trying to figure out leadership alone is like trying to cut your own hair while blindfolded – technically possible, but why would you do that to yourself?

Sound good?

Right then. I’m off to my coaching session where we’re going to discuss why I apparently can’t say no to purchasing requests.

Progress, people. Slow, expensive, progress. I think I’ll call my coach before signing this requisition for, let’s see…. Oh, more staplers.

Written by Antonio Garrido. Have you read?
Best Books. Countries with the Most Billionaires.
Most overlooked humanitarian crises. Best Countries for Retirement.
Best countries for hiring freelancers. World’s Best Public Relations Agencies (Top PR Firms).