Chaotic Commits | Software, AI, and Uncomfortable Truths

Joanne Skiles

The podcast that says the thing everyone in the room is thinking but nobody puts in the post-mortem. Chaotic Commits covers software engineering, AI, cloud architecture, and engineering leadership (not that sanitized LinkedIn version, the real one). Architecture decisions that almost broke everything. Management lessons learned the hard way. The bigger questions about who gets to build the future and what that actually means. New episodes every week. Hosted by Dr. Joanne Skiles, AWS Community Builder, engineering leader, and speaker at AWS re:Invent, AWS Summits, GHC, and more.

Episodes

  1. chore: you are no longer an individual contributor

    May 8

    chore: you are no longer an individual contributor

    What nobody tells you before you become a manager: the skills that got you promoted are the exact skills that will trip you up in the new job. Writing the code is no longer the job. The team is the job. And learning that takes longer than it should. I learned it during a User service migration that should have gone cleanly. I had the blueprint. I ran the same migration myself, textbook perfect, six months earlier. I gave my team every step. But I didn't give them the reasoning behind the steps. The migration failed. And when I had to reflect on whose fault it was, the answer was uncomfortable. In this episode: the identity shift that comes with leaving IC work and the grief nobody names, why there is no single right management template and how to find yours, the accountability inversion (what it actually means when your wins belong to your team and your failures belong to you), and what it looks like inside organizations where managers never learned this. This episode is for engineers making the move into management and wondering why it feels wrong even when they're trying hard, technical managers who are still writing code their teams should be writing, and anyone who has ever handed someone a process without handing them the reasoning. Topics covered: engineering management, IC to manager transition, technical leadership, new manager advice, engineering team accountability, software engineer career growth, managing software engineers, management mindset shift, engineering leadership podcast, microservice migration lessons, developer career advice, first-time manager. If you've given someone the blueprint and watched them fail, and had to sit with why, this one is for you.

    20 min
  2. feat: I let an AI run a D&D campaign and it tried to kill everyone

    May 1

    feat: I let an AI run a D&D campaign and it tried to kill everyone

    I built a serverless AI dungeon master on AWS. Within twenty minutes, a player had broken it completely. Within forty minutes, a dragon had killed everyone at the table. Including the people who hadn't done anything wrong. This is the story of building a real AI agent system using Amazon Bedrock Agents, AWS Lambda, API Gateway, and DynamoDB, and then watching what real users actually do with it. We go deep on the architecture: how Bedrock Agents handles tool orchestration and game state, why a three-second Lambda timeout will absolutely kill your AI inference workload, and what happens when an LLM gets an API contract that even AWS can't implement consistently. But the technical failures aren't the point. The point is what a Dungeons and Dragons campaign reveals about production AI systems: the gap between what you designed for and what users actually do. Hallucinations, tool misuse, unconstrained autonomous behavior, and the cost of building AI systems you can't observe. The same failure modes that made my friend's halfling rogue get eaten by a dragon show up in clinical decision support tools, customer service bots, and production AI agents. The sandbox is just where you can afford to find them first. If you're building agentic AI systems, or thinking about it, this one's for you. Dev.to Article: https://dev.to/aws-builders/building-a-serverless-dungeon-master-agent-on-aws-3j7k Topics: AWS Bedrock, serverless AI, agentic AI architecture, LLM tool use, prompt engineering, AI observability, AWS Lambda, API Gateway, DynamoDB, production AI failures, responsible AI design

    22 min

About

The podcast that says the thing everyone in the room is thinking but nobody puts in the post-mortem. Chaotic Commits covers software engineering, AI, cloud architecture, and engineering leadership (not that sanitized LinkedIn version, the real one). Architecture decisions that almost broke everything. Management lessons learned the hard way. The bigger questions about who gets to build the future and what that actually means. New episodes every week. Hosted by Dr. Joanne Skiles, AWS Community Builder, engineering leader, and speaker at AWS re:Invent, AWS Summits, GHC, and more.