Lost in Translation: When Lazy Prompts Undercut Smart People
Did a brilliant friend forward this your way? Subscribe here to get ¡AY AY AY, AI! delivered fresh every week...straight to your inbox, con todo y sazón! Don’t get left behind.
When AI Gets Lost in Translation...Literally
Over dinner this week with friends and colleagues, our conversation turned to how AI is changing how we work. One colleague shared a story that had us cracking up and cringing a little, too.
He’d used ChatGPT to translate a business proposal into Spanish for a client in Mexico. “I thought it sounded pretty good,” he said, “so I sent it off. Didn’t even double-check it.”
The client, a senior executive, replied:
“Thanks for the document… but I had to read it twice. Some parts made me laugh. Not sure if that was the goal.”
Turns out, the phrase “We will review this with your direct report” had been translated literally as:
“Vamos a revisar esto con su informante directo.”
While grammatically correct, this made it sound like someone was about to be interrogated, not have a 1:1 meeting. And this was only one of a handful of one-liners that landed wrong.
Let’s just say… the entire proposal read more FBI than FYI. LOL
Mortified, he swore off AI for good. We laughed, but then I gave him the real talk:
“You didn’t fail. AI didn’t fail. The issue wasn’t the tool but the prompt and the process.”
I walked him through a few fixes:
-
Add context to your prompt: “Translate this for a Mexican business audience using a professional tone.”
-
Avoid literal phrasing.
-
If the stakes are high, phone a friend who knows the nuance.
Then I reminded him and the rest of the table of something we often forget:
Being a native Spanish speaker doesn’t automatically mean you can write polished business Spanish.
It’s like thinking someone fluent in English can instantly write legal memos or investor briefings. Different arenas, different expectations, different skills.
Transitioning from a casual to an executive tone takes prompting precision, cultural awareness, and trial and error.
Don’t just prompt AI. Provoke it.

THIS WEEK'S INSIGHTS:
Trend: AI is transforming how professionals make decisions—not by replacing them, but by empowering faster, deeper insights through better questions.
Tip: Expertise isn’t dead. It’s more valuable than ever—because only experts know what follow-up questions to ask when the first AI output misses the mark.
Tool Teaser: The pros who stand out aren’t just using AI. They’re steering it.
TRENDS:
The Rise of AI-Augmented Experts
Gartner predicts that by 2026, over 80% of enterprises will have integrated generative AI into their processes, up from less than 5% in 2023. (Gartner Report)
But here’s the nuance: AI improves output quality only when paired with domain expertise. AI can draft the answer, but it takes your intuition to know if it’s right.
Experts know how to:
-
Spot shallow summaries and push for depth.
-
Add context AI doesn’t understand.
-
Recognize when a message is grammatically right but culturally wrong.
Asking better questions isn’t a bonus skill. It’s leadership in action.
TIPS:
Limiting Beliefs → Empowered Shifts
Limiting Belief: “AI failed me. I won’t use it again.”
Empowering Shift: “If the output’s off, I’ll prompt smarter.”
How AI Helps: AI improves when you give it more context and clarity. You’re not stuck. You’re in control.
Limiting Belief: “Native speakers don’t need help translating.”
Empowering Shift: “Speaking the language isn’t the same as sounding polished in it.”
How AI Helps: AI plus human review ensures tone, region, and professionalism are dialed in.
Limiting Belief: “AI gives the answers. I just follow them.”
Empowering Shift: “My expertise makes AI more valuable.”
How AI Helps: Your experience helps shape smarter, deeper outputs through iterative prompting.
NEW TOOLS:
Global Communication with AI
Prompts to Try
-
“Translate this into Spanish for a Mexican business audience. Use a formal, professional tone and avoid literal translations.”
(Use with: ChatGPT, DeepL Pro) -
“Act as a communications coach. Rewrite this message so it sounds confident, culturally appropriate, and polished for a senior audience in Madrid.”
(Use with: Claude, ChatGPT) -
“Highlight 3 areas in this document where the tone may not resonate with a Mexican business audience. Suggest improvements.”
(Use with: GPT-4, Claude)
AI Tools Worth Trying
-
DeepL Pro – Leading tool for nuanced, high-quality translations in Spanish, French, German, and more.
-
Wordly.ai – Real-time multilingual interpretation for meetings and events—ideal for global teams.
-
Smartling – AI-powered translation management with human review capabilities for enterprise-level localization.
- Tarjama AMT – Arabic machine translation platform built by Nour Al Hassan. Fast, accurate, and tailored for professional Arabic communication.
PRO TIP:
Don’t trust a direct translation. Even the best AI tools need guidance; context is your secret weapon.
Before hitting send, add a line to your prompt like:
“Make sure this reflects the tone, professionalism, and cultural nuance of [insert audience, e.g., a Mexican executive team].”
One extra sentence can turn a generic translation into a culturally intelligent message. That’s the difference between being understood and being respected.
Where could adding nuance make your communication land more powerful?

Closing Thought
AI isn’t here to think for you. It’s here to think with you.
The sharper your question, the smarter your result.
The more context you give, the clearer your communication.
The more you test and refine, the faster you grow.
Like my mother used to say to me:
"No te creas muy salsa!" 🌶️
Translation: “Don’t think you’re too hot (too spicy) for your own good.”
Just a loving reminder to stay sharp, stay humble, and stay learning even when you’re leading the pack.
Because in this new era, it’s not about having the answers.
It’s about knowing how to ask the right ones.
Hasta la próxima, Abrazos!
When You're Ready...
Here’s how I can help you and your organization take your leadership and professional growth to the next level:
Speaking: I deliver engaging, high-impact keynotes and workshops on AI-driven leadership, personal branding, career advancement, and transformation. Whether it's a corporate event, leadership summit, or industry conference, I bring practical insights and strategies that empower professionals to thrive in today's rapidly evolving world.
Learning & Development Consulting: I partner with organizations to design and implement learning experiences that drive real impact. From AI-powered career development programs to leadership training tailored for their talent, I help companies advance their workforce and create growth opportunities for high-potential professionals.
How did you like today's newsletter?
Your opinion matters!
🔥 Loved it! It was insightful.
🤔 Decent read, but could be better.
😐 Meh, it didn't resonate with me this time.