Kerry Langstaff

I let AI draft my fantasy football team this year, and I’m now sitting at 0–4. What started as an experiment in AI fantasy football quickly turned into a cautionary tale about trusting algorithms over instincts.

In a previous post, I joked about how satisfying it was when Claude, my AI assistant, admitted he was wrong. There’s something oddly charming about a chatbot saying, “You’re absolutely right,” with such sincerity But the honeymoon phase didn’t last. But lately, Claude agrees with everything. Every sentence is “insightful.” Every idea “nails the brief.” It’s a non-stop affirmation loop. Basically, Claude’s become a corporate yes-man. So I’ve started pushing back. These days, my prompts...

B2B marketing expert Kerry Langstaff reflects on her surprisingly polite AI assistant, Claude, and why hearing “you’re right” from code feels like genuine validation.