Kris Bailey

Project

GrumpyDev

Giving AI agents the critical eye of a grumpy senior developer before they commit to a plan.

Current Status: Released

Visit grumpydev.ai

The problem

Why I made it

I kept running into the same problem: implementation plans created by agents looked complete at first, but were full of holes. I had to review them repeatedly, pointing out missed requirements, weak assumptions, and details that should have been resolved before any implementation began.

Then I noticed that I got much better results when I gave the agent a particular kind of prompt:

"A grumpy senior developer just looked at this plan, frowned, and told me to do better. What are the problems they were seeing?"

That framing made the agent stop defending its first answer and start looking for the flaws an experienced, skeptical reviewer would notice.

The project

What GrumpyDev is

GrumpyDev is a collection of skills and survey text files that set up the above mentioned framing, only a lot better. The files are designed to shape how an agent reviews its own plans and other work before presenting them as finished.

The goal is simple: make the agent less satisfied with its first pass. It should question its assumptions, find missing pieces, and produce an implementation plan that has already survived a more demanding internal review.

The outcome

Better plans before implementation

GrumpyDev does not replace human judgment. It gives the agent a stronger critical posture so the plan that reaches a human reviewer is more complete, more explicit, and less likely to hide expensive surprises.

(c) 2026 Kris Bailey