“Douglas wants to write a thought leadership post,” Billie declares, materializing beside my desk like a specter powered by espresso. “And he’s adamant he doesn’t need any help.”

I glance up from my duel with a LinkedIn troll who thinks our product roadmap resembles a sleepy village footpath. My coffee cup suspends in midair.

“Come again?” I sputter.

“Douglas. You know, our COO? Has decided he’s the next Elon Musk. Wants to pen a thought leadership post. On his own.” Billie’s eyes bulge slightly as there hands mime a tiny explosion beside their head. “He messaged me. Claims he’s unearthed some profound insight about digital transformation he’s dying to share.”

I carefully set my coffee down, as though it’s a fragile relic. “Did he actually use the words ‘profound insight’?”

“Word for word from Slack.” Billie flashes their phone at me, where Douglas’s message sprawls across the screen in his infamous no-caps style: i have a profound insight about digital transformation i’d like to share with our followers. no need to workshop it, just a quick proofread.

The universe really does enjoy its little jokes. Just last Tuesday, extracting a simple nod from Douglas for a straightforward employee advocacy program was like pulling teeth - yet here he was, ready to freestyle on digital transformation?

“He’s already on it,” Billie adds with unnecessary cheer. “Says he’ll send it over in an hour.”

I nod, feeling a familiar sensation of dread. “Right, let’s see what he conjures up as ‘profound.’”


The draft lands in my inbox at 4:47 PM, precisely when I should be leaving for a date with my dentist.

Subject: Thought Leadership - Digital Transformation in Today’s Business Landscape

From: Douglas Reed

To: Cass Carmichael; Billie Vance

Cass/Billie - Please review the attached adn let me know if ya see any typos. Would like to post this tomorrow morning. Thanks, D

I cancel my dentist appointment, texting “work emergency” which, sadly, my dentist has heard often enough to not require further explanation. I brace myself and open the attachment, treating it with the caution one might use for an ancient, possibly cursed, artifact.

The document is ominously titled “Digital Transformation Is The Future And How Companies Can Leverage It To Win In The Marketplace.docx.”

I inhale deeply, and dive in.

In today’s fast-paced buisness landscape, digital transformation is no longer a luxury but a necessity. As a seasoned business leader with over 20 years of experience, I have witnessed firsthand the power of embracing digital technologies to drive growth and innovation.

Oh dear.

Companies that fail to adapt to the digital revolution risk being left behind. At our organisation, we have implemented a comprehensive digital strategy that encompasses cloud computing, data analytics, and artificial intelligence to streamline operations and enhance customer experiences.

Oh dear.

The key to successful digital transformation lies in a holistic approach that aligns technology initiatives with business objectives. It’s not just about implementing nwe tools; it’s about fostering a culture of innovation and agility.

I scroll through. Seventeen paragraphs. At least three buzzwords per sentence. A bullet-pointed list under “5 Key Pillars of Effective Digital Transformation.” A segment boldly titled “My Journey as a Digital Visionary.”

One sentence reads: “The synergistic confluence of big data analytics and IoT capabilities creates a paradigm shift in how we conceptualise customer-centric value propositions.”

I close the document, a chill running down my spine. I pull up Slack.

Cass: Billie, are you still around?

Billie: sadly yes 🙃 just got the draft 💀

Cass: Meet me in the small conference room. Bring any contraband alcohol.


“It’s… a bit much,” I say diplomatically, pacing the room while Billie perches on the table.

“It’s a dumpster fire,” Billie corrects. “Like if ChatGPT eloped with a corporate strategy white paper.”

“He wants to post it tomorrow.”

“Can we just… accidentally lose the file?”

I exhale slowly. “He’s the COO, Billie. Our hands are tied.”

“But it’s horrendous. Career-damagingly horrendous.”

I nod solemnly. “Which is why we intervene. Subtly. Without letting on that we’re practically rewriting it.”

“How do we even start?”

“Nibble around the edges. Suggest a few ‘minor clarity edits.’ Slowly replace every word.”


From: Cass Carmichael

To: Douglas Reed; Billie Vance

Douglas - Thanks for this! I’ve added a few suggestions to enhance clarity and impact. Please see the attached. -Cass

I slashed it in half, axed fourteen ‘digital transformations,’ obliterated the “Digital Visionary” journey, and tried to make the opening sound like it was penned by a human.

Seven minutes later, his reply pinged.

From: Douglas Reed

Thanks Cass. I’ve reviewed your edits but prefer my original wording. The digital journey part is crucial for my credibility. Reattached my version - just proofread for spelling/grammar? D

I count to fifty - slowly.


“Round two,” I announce to Billie the next morning. “We’re being too subtle.”

This round, I salvage his main points but inject a bit of humanity, replacing vague buzzwords with a personal anecdote about our CRM system overhaul. I condense three paragraphs into punchier, human-sounding language.

I resend it, hopeful. Douglas - Retained your voice while enhancing reader engagement. The CRM story will really resonate.

His reply is swift.

Cass - Appreciate the effort, but my original draft captures my thoughts better. Made minor tweaks based on your input. D

His ‘minor tweaks’ are two comma changes and adding ‘very’ in front of ‘important.’


“Final gambit,” I tell a weary Billie. “We play the algorithm card.”

I draft an email citing fictional research about LinkedIn’s preference for personal stories and shorter, punchier posts. I suggest a ‘slight restructure’—essentially a complete overhaul aimed at humanizing the verbal monolith he’s constructed.

I hit send and hold my breath.

Twenty agonizing minutes later, Douglas calls.

“Cass,” he begins, no pleasantries, “I’ve considered your feedback, but let’s not overcomplicate things. I went ahead and published the original draft. Just now.”

My heart sinks. “You… already posted it?”

“Yep, just a moment ago. Authenticity’s key, right? Not overthinking.”

I pull up LinkedIn. There it is. Douglas Reed’s manifesto sprawled atop my feed. 1,487 words of pure jargon, the “Digital Visionary” segment glaringly intact, and ‘digital transformation’ mentioned more times than strictly necessery.

“I see,” I manage weakly.

“Great,” Douglas says cheerily. “Let’s track the engagement, shall we? I’m envisioning a whole series.”

We end the call, and I stare blankly at my screen. Billie appears at my door, a mix of awe and horror on their face.

“Have you seen it?” they mouth quietly.

I nod.

“It’s so… verbose.”

“Indeed.”

“And the part where he calls himself ‘a digital prophet in an analog desert’?”

“I saw.”

“What now?”

I straighten, a plan forming. “What we always do, Billie. We ride out the storm, brace for the inevitable fallout when this post bombs spectacularly, and gear up to ghostwrite the next one.”

Billie nods, a soldier ready for battle. “And then?”

“Then we take another swing at making the unreadable, readable. Or at least, less cringe-worthy.”

The phone pings. Douglas has tagged us in a comment.

Thanks to @Cass Carmichael and @Billie Vance for refining this crucial piece! #DigitalTransformation

Billie and I exchange a look. Some battles, it seems, are lost before they even begin. And some thought leadership pieces are doomed to linger in LinkedIn’s limbo, appreciated only by their delusional creators.\n\n## Explore Across Our Network\n\n- Master Stakeholder Mapping for Direct PoV Project Success (proofofvalue) - Learn how effective stakeholder mapping directly shapes your PoV outcomes. Essential tactics for technical sellers and GTM leads.\n- Why PoCs Fail: Ensuring Success Through Strategic… (proofofvalue) - Uncover why PoCs often miss the mark and master strategies to ensure your project thrives. Tailored insights for technical sellers and GTM leads.\n\n\n## Explore Across Our Network\n\n- Master Stakeholder Mapping for Direct PoV Project Success (proofofvalue) - Learn how effective stakeholder mapping directly shapes your PoV outcomes. Essential tactics for technical sellers and GTM leads.\n- Why PoCs Fail: Ensuring Success Through Strategic… (proofofvalue) - Uncover why PoCs often miss the mark and master strategies to ensure your project thrives. Tailored insights for technical sellers and GTM leads.\n