Chris Gillespie | July 29, 2024

Why are people so unclear at work? I’m sure you’ve seen it. Passages like the following are as common as they are mystifying.

Yikes. Stir that conjunctive cocktail. Doesn’t ever settle, does it? And if you’re curious if it’s just you because you don’t have context, it’s not. I asked friends in said niche to unpack it and received mostly laughs and sighs.

If taken at those words—their work words—most people appear crazed. But that’s also unfair because it’s not the whole story. Drop that same person into an email thread about a weekend away with friends and they’re clear as day:

Same individual. Two modes. What the heck is that about? Why can’t they bring that to work? What is it about the work environment that encourages such metaphorical mixology? Ferments such a wretched brew of buzzwords and cliché?

Whatever the answer, the default is that people seem to choose their words poorly at work. They hold forth at great length but little communication occurs. Whenever someone says “we’ll optimize that later,” they delay the real work because optimize for what? And how? And if they ask someone to “move the needle,” they draw no closer to any such movement because they have not agreed on what it measures. In desk-worker parlance, they “toss it over the fence,” and hope it all works out.

Which makes me sad. For we have over a million glorious English words but use just 20,000; and at work, we scramble their meaning and invent noxious new concoctions that leave everyone else guessing. We make a mess and rely on the interpretive generosity of strangers.

For those of us for who communication is our art—whose pay depends on flinging exact ideas into others’ minds and helping others do the same—that won’t do. But it’s where most of us start. In a stupor.

I should know. That’s how I communicated my whole life until a chance opportunity.

Change only happens in a mirror

I always was a wretched writer and to remind myself of this journey, I pored through the weepy, feckless travel diaries I kept in my early twenties. The words meandered—awkward, artless, as lost as their author. Below, a passage.

If it sets the scene, I’d also recently gotten a tattoo and felt it important others know I liked cigars. Yeesh. Nobody ever communicated less plot in more words than young me. What astounds me is that I nevertheless suspected myself a great writer despite abundant evidence to the contrary. I held my dream of literary stardom tight—any feedback would have shattered me—so my writing never improved.

Yet I would frequently offer to write. Below is a passage from a manual I wrote for a search-and-rescue unit I volunteered with. It was received with, shall we say, no fanfare—just stares.

It continues like this for 70 pages. I later served on the governing board of our student center while at San Francisco State University. Here too, the business writing muse rose within me. I wrote manuals on managing vendors and other topics I knew little about. That team politely nodded and filed my work away for very safe keeping.

And that’s just how it was with me for decades.

The thing about feedback is that I fear it most when I actually need it. And I was delicate. So I found excuses. I built elaborate mental fortifications and preferred defending my fragile, fictive sense of literary genius to any glimpse of reality. Occasionally I’d get up the courage. I took one creative writing class in college. But when I received heavy redlines on a paper, I panicked and dropped the course.

I was, for this whole portion of my life, entirely hardened to feedback. My mind was set and no wisdom could penetrate.

Then I made it about business

Strange events led me to work in tech as a software salesperson. I’d been lured by the charming delusion that I, being clever, could put in a few years of selling software then retire and figure out what I really wanted to do. Let me be clear. This is not how compensation plans are designed or how any of this works. But I was young and such was my belief so I found myself wearing a patagonia vest and dialing numbers with a headset on.

Let me summarize the sales culture at this company: People were not fired but rather “disappeared” in the Orwellian sense. We’d return from lunch to find a coworker’s things gone, their coffee still steaming. If asked, managers told us not to talk about it.

At this company, the head of sales would stalk the office with a bow-legged gait howling about needing “butts in seats.” My manager would spin in his chair with a baseball bat and recount the “chicks” he’d “crushed on” the night prior. The women who succeeded in this wasteland were wrought of iron. It was an emotional pressure cooker with no valve.

Some months in, my friend and I were nearly broken people and so launched a series of petty rebellions. One day we hauled camping gear up to our floor’s balcony to make pancakes for everyone. My boss was outraged but silent. He glared, arms crossed, through the plexiglass.

My friend and I also quietly interviewed with other teams around the office. We were grasping for a ripcord. I found mine in an opportunity, once again, to write.

Despite my despair, I had a good sales year. My boss thought me effective, so I was given choice territories. In plying New York, I’d realized the companies there knew less about software and needed more convincing. I’d hustle down to the fourth floor and ask the marketing people for help—could they give me something to reassure finicky financial services companies that we could aid them? And those busy marketers replied, “Why don’t you write it?”

And there was the offer. Once again, the business writing muse stirred within me. Once again, I wrote. The marketing team replied to my submission with—to my elation—“This is great.”

Then the hammer—“We have edits.”

And for the first time there was no panic. I accepted the changes, left comments, and sent it back. After, I sat, puzzled. What happened to all my defenses? But in reflection, it was clear I’d been receiving writing feedback the whole time I’d been in sales. All the emails. All the calls. All the presentations. To work in sales is to endure a living state of perpetual critique—everything you do is scrutinized. If you don’t devise the exact right phrase, tone, or axiom to earn a response from a stranger, you fail—and can’t pay rent.

Without realizing it, I had become well-versed in clipping excess words and parentheticals and conducting tone checks. I’d grown used to my manager literally breathing in my ear telling me to adjust my speech. The writing feedback had skirted my defenses because it had come in through the side door—the office door.

“Nobody should be allowed to create general advertising until he has served his apprenticeship in direct-response,” David Ogilvy wrote in On Advertising. And for this time, I now feel grateful. When you live a perpetual cycle of rejection, you gain one of the most crucial skills in writing: theory of mind. And you also gain another: a finely-tuned nonsense meter.

In sales, you’re constantly weighing the truth of other people’s arguments to discern when they have no idea what they’re talking about, but cannot admit it. They often retreat behind vague, circular pronouncements. For example:

Sales work teaches you to drain that wretched, office-specific brew of buzzwords and cliché from copy to say what you actually mean. You learn to interrogate analogies like “a crazy blender of creepy crawlies” and ask, is that right? Do I mean it literally? Could I be clearer?

I found I could read reports from big analysts like Forrester and Gartner and tell that they were using many words to say essentially nothing. And I could intuit the motive: They’re paid for their reviews, which creates a conflict of interest. They can’t say one vendor is better than another because both vendors are paying them. So they offer only empty hand waving.

And so, I simultaneously lost my fear of being edited and gained the power to edit myself. When my company launched a program to get more employees writing for the blog, I seized the opportunity. The prize for writing twenty articles was a MacBook. My ambition was ascendant. If I had an Apple laptop, I’d be a creative. I might make writing my vocation.

From then on, I wrote. My boss would walk by and I’d whip up my work software and pretend to update contacts, then he’d pass and I’d resume. I’d use my articles as a forum to opine about sales management and how to improve it. Some mornings the marketing team would publish one of my articles and I’d get stares from sales peers across the open floor plan. My critiques were landing a little close to home. I’d also stalled—there was only so much I could figure out on my own.

Finally, one Friday, I knew I could not go on and resigned. I asked my manager out onto the corner balcony. He knew it was coming.  Almost shaking, I asked when I’d be whisked out. He laughed, surprised, “Oh, we don’t do that to people we like.”

I quietly waited out the rest of the day, burning with my secret. I told the team. I said my goodbyes. I was free. At home, I settled into reading—elated—I was now a writer. Without any of the training. Without any qualifications. Without any degree. Without any prospect of work. The more I sat on it, the wider the chasm yawned, and my mood plummeted.

Can a business writing course for professionals really help you? I bet it can

Fast forward three years and I’m looking over Times Square on a sweltering night on break from a business writing course at the vocational school Gotham Writers. My companions are reporters and novelists. I am the lone actual business writer, by which I mean, a person writing for and within companies. Everyone else started in the creative world, and I’m painfully aware of their advantage.

Specifically, we’ve just discussed Gay Talese's “Frank Sinatra Has a Cold,” the most famous profile in the history of profiles, and we’re all awestruck, but none more so than me. The story is at once easy and grand, sweeping and specific. I feel inadequate.

Yet this is the moment when things changed for me. This is when I finally drew from that deep historic well of journalistic and essayist wisdom—and yeah, felt regret. Why did I labor so long alone? Why didn’t I find a guide sooner? Why didn’t I declare my ambition earlier, and begin that necessary cycle of feedback and growth? Why didn’t I think to find a course where I could learn everything everyone else already knew?

For example,

Everything I learned in this course was invaluable. It was also incomplete. Rather than reporting on businesses, I was reporting from within, as a content marketer, which is not what this course was set up to teach. Things I’d learned in sales gave me a different, in some ways, more detailed understanding. So I began customizing those frameworks for my line of work.

I tried to describe what I call the novely-newspaper introduction. Reporters write top down, most important facts first to last. Novelists bury the facts to create tension and plot. At work you need both. You can achieve that in an introduction where you give away the facts, but imply there’s more to the story. Look at any good work article and it follows this format.

Or the fact that at work, people tend to use subtitles. I feel they’re best when they’re packed with opinion, and you load the whole story in there. So instead of “Conclusion,” which is an empty signpost, say, “You should hire us” and go on to explain why.

I had a handicap in some ways, and in others, a great advantage. I wanted to share that. Which is why, tucked below my papers in that class is an outline for the story you’re currently reading. I started it back then but realized I wasn’t yet its match. I would set it aside. But now, after ten years of writing, I’m ready.

I’ve just helped create the first online business writing course for our creative studio, Fenwick, and that feels like the completion of this arc. It imparts all the hard-won knowledge of ten years of writing at work—of parsing the jargon and nixing the buzzwords and merging these two worlds—compacted into three breezy weeks.

When someone asks who the new writing course is for, I tend to reply, “Me.”

It’s for the Chris who hid. Who suspected himself of writing greatness but was too shy to use the title “writer” until several years into that work. Who suffered in silence and later, nearly died inside when an editor laughed at him for not knowing what an “em dash” was. Who remained in a stupor for needlessly long. Who didn’t read Joseph Campbell’s The Hero with a Thousand Faces with an eye to applying it to writing until far, far too late.

If that Chris read Campbell’s book sooner, he might have noticed this passage. And realized that though the hero has the power to heed or refuse the call, he cannot complete the cycle without assistance.

Maybe, if you’ve seen yourself in any of this story, this article is me here to get you. And the magical item I have to offer is this course.