Behind the Firewall: Notes of a Punk CIO

This week I asked ChatGPT to “use just the first character of titles and all sentences capitalized.”

Simple, right? Wrong.

What I meant:

• Titles → only the first word starts with a capital (e.g. Field notes from the gym)
• Sentences → start with a capital letter, as usual

What the AI understood:

• “Only capitalize the first letter of everything.”
• Result: lowercase sentence starts, frustration, and me yelling “FUCK” into the void (or rather, into the chat window).

Lesson?
If your instructions leave any room for interpretation, people will interpret them. And not always the way you intended, in fact in most cases not the way you intended.

It’s a reminder for all of us:

• Be specific.
• Break it down.
• Don’t assume “they get it” — especially when you’re the only one who’s been living with the idea in your head for 3 days.

Bonus insight? If you can get an AI to understand you perfectly… there’s hope for your team too. 😄