Doing the Actual Work
Alright, we’re flashing back again.
It’s like 2005, I think.
After two years as a cook and a butcher, my dad finally convinced me to use my finance degree and get into the “corporate world.”
So I got a job as a low-level accountant responsible for accounts payable at a publicly traded company (shout out Lennar).
I doubted this was the big-time gig he dreamed of, but hey — I had to start somewhere.
Just take a second to picture The Office – and that’s literally where I worked.
Single floor, warehouse-style, overhead fluorescents.
Modular cubicles, a few sad vending machines, a breakout room with coffee pots and a microwave that just barely functioned.
The space – and the work – was… mundane…redundant…boring.
But we kept in good spirits, and we had a crew:
Marcia, Brandon, Edrica, Denise, Brandy, Savannah, Jon. And our fearless boss, Amy.
The accrual report from H-E-L-L
Part of my job at the end of the month was to print out (yes, print) a 200-page report listing that month’s expenses—every debit and credit—organized by vendor, date, amount.
I had to go through it line by line, checking against paid invoices and flagging anything that needed to be accrued for a different month.
The entire process was a huge pain in the ass.
The challenges? In a nutshell:
- Timing issues with backdated invoices and late payments
- Missing documentation for delivered items
- Expenses under wrong GL codes or vendor names
- 200 pages of manual cross-checking prone to human error
The process was typically straightforward:
- Step 1: I prepared the massive report
- Step 2: Brandy (my supervisor) reviews it
- Step 3: Amy (the Controller and big boss) gives final approval
But this particular month, fate had other plans.
With Brandy out of office, I found myself at 6pm on the last day of the month, staring at a report I knew wasn’t perfect.
My heart sank as I realized I’d have to hand it directly to Amy – no buffer or safety net.
The boss who rolled up her sleeves
Amy was a force of nature – tall, imposing at nearly 5’10”, with a thick Southern draw that could charm or cut depending on her mood.
She had a ballbuster sense of humor, cursed like a sailor, drove a sleek Porsche, and smoked those razor-thin Capri menthols within reach.
Her long, painted nails clickety-clacked across calculator keys at superhuman speed, tallying numbers faster than most of us could think.
I walked into her office, report clutched to my chest, and nervous AF, asked for help.
Instead of dismissing me or offering vague advice, Amy waved me in to her corner office, cleared a space at her side of the desk, and was like, “Let’s do this shit.”
For the next two hours, she didn’t just correct my work – she taught me how to actually think about the problems.
Page by page, she shared insider tricks: the spreadsheet she’d created to track recurring costs, which vendors always backdated invoices, how to catch discrepancies most people missed.
This wasn’t just a boss fixing my rookie ass mistakes.
This was someone who knew the importance of being hands-on, the whole teach-a-man-to-fish metaphor that I can never actually remember lol.
As some early 20-something, I honestly don’t know if what struck me was that Amy still remembered how to do the grunt work, or that she just so willingly dove back into it with me.
As the freakin’ Controller, she could have just said, “Do your best” or “I’ll catch your mistakes” or even find someone else to delegate it to.
Instead, she just rolled up dem’ sleeves.
There were three things that made this moment one that I somehow remember 20 years later:
- First, Amy clearly still knew her shit. Not in a theoretical, “I once did this” way, but in a practical, hands-on way that commanded instant, mucho respect.
- Second, by treating me as a colleague rather than a subordinate – pulling my chair to her side of the desk, etc – she created camaraderie instead of hierarchy.
- Finally, by sacrificing her own evening to ensure I learned properly, she demonstrated that leadership isn’t about status – it’s about service, mentorship, bringing the crew along.
Leaders who do the work
There are a million corporate buzzwords for this…
“Lead by example” “Player-coach” “Servant leadership”
Whatever.
The point is: if you can’t do the work, you’re just a professional manager or someone with a fancy title.
I’ve seen people in the C-suite or VPs get exposed in real-time when they’ve been too disconnected from the mechanics of their team’s work.
They give terrible advice, set shitty expectations, and lose credibility fast.
Are you a CEO who can’t shred apart your P/L anymore b/c you’ve become too reliant on your CFO?
A Digital VP that can’t break down a competitor with a SimilarWeb login and 30 minutes of free time?
A CRO who can’t open a clean spready and build your own revenue model in a few hours flat?
Guess what? Your gonna lose everyone’s respect, fast.
The moment you stop being able to jump in and actually execute, you start relying on authority rather than expertise.
And that’s the beginning of the end.
This doesn’t mean you need to be the best practitioner on your team – you shouldn’t be.
You’ve hired people who should be better than you at specific skills.
But you need to maintain enough working knowledge to actually understand what “good” looks like, what “hard” means, and how long things should take.
My trenches approach
I’ve made staying close to the work a key part of my own style. Here are two practical ways I do this:
1. Write the Copy
When an inexperienced team member turns in weak copy for an email, memo, or brief, I don’t just say “make this better” – I show them what better looks like. I’ll:
- Give specific line-by-line feedback
- Completely rewrite it myself
- Walk them through why my version works better
This accomplishes three things at once: they get actionable feedback, see what quality looks like, and know their boss can actually do the work they’re being asked to do.
2. Performance Reviews
When managing young leaders at Hampton who had never conducted performance reviews before, I didn’t just hand them a corporate template and be like, ‘go get em’.
Instead I:
- Showed them anonymized examples of my own reviews
- Provided a detailed template with my exact expectations
- Coached them through delivery techniques and actual language to use
This teaches them the skill while showing I’ve mastered it myself.
Summing it up
Maybe it’s the operator in me – the dude that just enjoys the detail, the nitty-gritty, getting into the weeds of it all.
Maybe it’s founder mode or the knowledge that the larger the gap between you and your team, the less respect and inspiration you tend to generate..
And the further removed I am from the actual work, the less useful my “leadership” really is.
But I’ve never forgotten what Amy taught me: respect isn’t handed out with your title.
It’s earned when your team sees you doing the actual work.
The rest is just a lot of talk.
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