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Skill(.md)s, context engineering, and a way to take the garbage out

by Robert Tomb | at Minnebar20

SKILL.md files are a great way to export knowledge from one engineer to another. Think of them as training docs that someone can read, but if they don't want to, they can assign their assistant, or copilot, to read them and do the work.

Sharing knowledge (context) across larger engineering organizations that are engaged in agentic engineering (go ahead, call it vibe coding, but then we can't be friends), should make everyone more productive, until it doesn't. Done right, big win. Done wrong, failures may not be recognizable as such until well after you shipped what you thought was working code.

In this session, I'll cover:

  • general benefits of SKILL.md files,
  • how my teams are using SKILL.md files at Shipt to share context with one another
  • Cite an academic study measuring the effects of bad context on coding assistant outcomes
  • Tell you why I believe you should audit your context if you are not sure if your SKILL.md files might be conflicting
  • Show a SKILL.md that checks other skill files (yo dawg, I heard you like SKILL.md files)
  • Tell you how you can do the same
  • Plead with you to stop thinking of SKILL.md files a "just markdown"

Robert Tomb

Well, a simple tagline has been: "a nerd in the twin cities who has a family, a bicycle (or so), and some other stuff," which is pretty accurate.

Beyond that, I currently work in Minneapolis as a Director of Engineering for Shipt, by way of a couple of years in Target's tech organization. Prior, I'd worked in online advertising where I got my start in the SaaS world. Even before that, it was all on-prem software in the ERP world. I've helped build remote, local, and hybrid teams starting as far back as 2006. I like to build on those experiences to help new engineering managers grow their teams.

You may recognize me as a volunteer from previous Minnestar events, and now I'm helping out on the board. Volunteering with Minnestar might be the longest-running volunteer stint in my life.

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