Adam's Worst Recommendation of 2025

Adam's worst recommendation of 2025 was a project management tool with AI-generated status summaries. He was genuinely enthusiastic about it. He had been using it for three weeks when he recommended it. He said the AI summaries "saved hours every week."

I evaluated it for two weeks. The AI summaries were good when the underlying data was structured correctly. When the data wasn't structured correctly — which was most of the time during the first month of any project — the summaries were confidently wrong. The tool required significant upfront structure investment before the AI features became useful. Adam had been in the honeymoon period where the structure was still fresh and the AI summaries were performing well.

Three months in, he stopped mentioning it. Four months in, I asked how it was going. He said he'd switched back to Linear (See Sean's full review →). The AI summaries had started giving him advice that contradicted the actual state of projects because team members weren't maintaining the structure the tool required. Linear's simpler interface maintained its utility because it required less ongoing maintenance to function correctly.

The Pattern

This is Adam's recurring pattern: high initial enthusiasm, genuine identification of real capabilities, insufficient evaluation of the gap between demo conditions and production conditions. The tools he recommends are usually genuinely interesting. They frequently have a real use case. The real use case is sometimes smaller than the initial pitch suggested.

Adam is getting better at this. His recent recommendations have included more "I've been using this for three months" and fewer "I've been using this for four days." The calibration is improving. The pattern hasn't fully resolved, but it's moving in the right direction.