The Sunday Funnies • January 19, 2026
Don't Blame the AI — Episode 1
The Vague Request
“Which Johnson? What report? EOD in which timezone?”
Welcome to “Don't Blame the AI” — an 8-part series exploring why AI implementations really fail. Spoiler: it's not the AI's fault. Read Freedom '26 for the vision.
“I'll just guess and hope I don't get fired.”
The Point
Every knowledge worker has lived this moment. You get a message with just enough information to be dangerous:“Need the Johnson report updated by EOD.”
Which Johnson? There are four in the CRM. What report? The Q3 analysis or the vendor comparison? Updated how? New data? Different format? EOD in which timezone? Your manager is in London this week.
You have two choices: ask clarifying questions (and risk looking incompetent) or make your best guess and hope you don't get fired. Most of us guess. We fill in the gaps with assumptions. We deliver something that's 60% right and spend the next day on revisions.
This is exactly how AI agents work too. When you give them incomplete context, they fill in gaps. They make assumptions. They deliver something that might be 60% right.
The difference? When you guess wrong, it's “a misunderstanding.” When an AI guesses wrong, it's “AI isn't ready for enterprise.”
The Human Version
“The dirty secret of knowledge work: most deliverables are educated guesses wrapped in confident formatting. We've just gotten good at hiding it.”
Want the full context? Read the companion blog post.
Read Freedom '26