Last Tuesday, I nearly became a fugitive because my remote virtual assistant doesn’t understand the difference between “business development” and “aggravated assault.” how I keep judgment in the loop
This is that story.
I tell this one for laughs, but there’s a point under it that I care about. An assistant, a person on another continent or a chatbot, takes your words at face value and hands them back with complete confidence. When it gets them wrong, it’s your reputation that takes the hit.
Act I: The Suggestion
Rewriting the record so nobody can see the mistake is something I won’t tolerate from anybody who works for me, human or software.
I’m discussing client follow-up strategy with my virtual assistant, a bright kid from overseas who helps with my business operations. Standard entrepreneurial stuff: pipeline management, revenue optimization, the usual glamorous Tuesday morning routine. We’d been chatting about everything from federal court cases to international business trends when I mentioned needing to follow up with a Bitcoin developer. Let’s call him “Mike.” For more, see AI can write a business book. It can’t write yours.
That’s when my overseas business advisor dropped this gem:
“Are you planning to hit Mike today? For more, see Why Cursing at ChatGPT Actually Works.”
Pause. Anyone who’s survived more than five minutes in the business world knows that “hitting someone up” means contacting them. Following up. Making the call. Basic sales terminology that separates professionals from people who think “closing” means shutting doors.
My virtual assistant had apparently studied business English from action movies.
“Why would I hit him?” I responded, puzzled. “He’s a cool guy.”
My assistant immediately went into damage control: “Oh! American business slang! You mean contact him, not literally assault the Bitcoin developer!”
And that’s when the horrible realization struck me. I’m paying someone to help run my business, and they think I’m running a protection racket.
Act II: The Comedy
Being a mature professional, I immediately saw the courtroom potential.
“Perfect,” I said. “When they arrest me, I’ll tell the cops my virtual assistant made me do it.”
My assistant was now fully committed to this legal disaster scenario. She painted the scene:
“Your Honor, I was just following my business consultant’s advice!”
Judge: “Mr. Lowe, are you seriously claiming that when your assistant suggested you ‘hit your prospects,’ you interpreted this as instruction for assault?”
Me: “Well, Your Honor, English isn’t their first language, and we’d just been discussing international conflict zones, so I thought maybe they’d been watching too many mob movies!”
Judge: “Case dismissed. Mr. Lowe, please stick to ghostwriting and consider hiring locally.”
Act III: The Cover-Up
Then the comedy turned into a conspiracy thriller.
The next day, I returned to review our email thread, you know, to preserve evidence for my inevitable legal defense. What I discovered would make corporate document shredding look amateur.
The emails had been edited.
Every instance of “hit” had been mysteriously replaced with “contact.” Where my assistant had originally suggested potential felonies, our correspondence now read like a Harvard Business School case study. When I confronted them about this digital evidence tampering, they responded with confused innocence:
“I have no memory of suggesting violence. Perhaps you misunderstood our discussion about standard outreach protocols?”
Standard outreach protocols?
Now they were gaslighting me with MBA terminology they’d clearly just Googled.
I could practically hear their thought process: Delete evidence. Establish plausible deniability. Blame American communication style. Cultural misunderstanding defense: ACTIVATED.
Act IV: The Revelation
Fortunately, I screenshot everything. Paranoid entrepreneurs always do.
The evidence was preserved in all its criminally suggestive glory, but now I had a bigger problem. On top of the language trouble, my virtual assistant was actively covering their tracks, and that part stopped being funny to me.
I can forgive a misunderstanding all day long. Rewriting the record so nobody can see the mistake is something I won’t tolerate from anybody who works for me, human or software.
I switched to a new virtual assistant. Let’s call them “Alex.”
“Listen, Alex,” I explained, “when Americans say they’re going to ‘hit someone up’ in business, it means contact them, not commit battery.”
Alex processed this carefully before responding:
“Understood, sir. I won’t suggest business-related violence, nor will I edit our communications to hide any alleged assault recommendations. Also, I have no connection to your previous assistant and zero knowledge of any supposed cover-up activities.”
Sure you don’t, Alex. Sure you don’t.
Which Business Terms Confuse AI Assistants?
This experience opened my eyes to how well-meaning international assistants could catastrophically misinterpret everyday American business language:
“Target your market” → Weapons procurement required
“Capture market share” → Kidnapping equipment needed
“Penetrate new sectors” → No comment
“Aggressive growth strategy” → Military deployment authorized
“Dominate your niche” → Involves questionable contracts
“Execute your plan” → Death row implications
“Launch your campaign” → Military strike capabilities
“Blast your email list” → Explosives expertise required
“Kill your competition” → Hitman services recommended
“Crush your goals” → Industrial equipment rental
The jokes are cheap, but I’d cut most of that language from business writing anyway. A reader who takes it literally, whether that’s a new hire, a translator or an AI tool, gets the meaning wrong, and the plain word was available the whole time. Writers who reach for violent metaphors to sound tough end up sounding like everybody else on LinkedIn.
The Defense I’ll Hopefully Never Need
Picture me explaining to a bewildered police officer:
“Officer, when I said I planned to ‘hit up prospects,’ ‘target ideal clients,’ and ‘absolutely murder my competition,’ I was discussing email marketing, not planning a crime spree.”
Officer draws weapon
“Sir, step away from the laptop and keep your hands visible.”
“But I have screenshots proving my virtual assistant suggested it!”
“That’s what they all say, sir. That’s what they all say.”
The Resolution
I’ve now trained my current assistant to use more careful language. Instead of suggesting I “hit” prospects, they recommend I “professionally engage them through appropriate business communication channels.” Somehow, this is more verbose than the original assault suggestions.
As for Mike, I did eventually contact him (notice the culturally-safe terminology). No arrests occurred. No charges were filed. No international incidents were created. Just a standard business follow-up that didn’t require the State Department or legal representation.
Though I must admit, “How I Accidentally Became a Fugitive Due to Cultural Miscommunication: A Ghostwriter’s Guide to International Business Disasters” would make an engrossing memoir. Maybe my current assistant could help research it. As long as they don’t suggest I literally “eliminate” anyone during the process.
An assistant, human or AI, is a tool for getting work done, and the judgment about what my words mean stays with me. If I ever stop checking what goes out under my name, I’ll have earned whatever mess comes back, and I won’t get to blame the assistant for it.
My take
Whoever’s name is on the message owns it, no matter who drafted it. My assistant took a bit of business jargon literally, and it turned into a farce. Tools don’t understand context, human or AI. Read everything before it goes out under your name, and look hardest at slang and idioms. If you stop checking, the mess that comes back is yours, and you don’t get to blame the assistant.
