BONUS How AI Took the Boring Out of Agile Coaching With Michael Dougherty

BONUS: How AI Took the Boring Out of Agile Coaching—Where Scrum Masters Should Actually Start, With Michael Dougherty

Today we speak with Michael Dougherty — "Agile Mike" — about how a 30-year veteran of solution development and product leadership made AI a working part of his Agile coaching practice. Michael walks us through the journey from early ChatGPT curiosity, to documentation as the first real win, to the personal-passion project that built his comfort with the tools, and finally to where every Scrum Master should start: the retrospective.

From Curiosity to Toolbox: A Slow Burn That Started With User Stories

"I tried, and I thought it sucked at that. I'd rather write this by hand."

 

Michael's AI journey started in late 2022 with ChatGPT — like most coaches, he tried to make it write user stories and acceptance criteria. It didn't work. The output wasn't usable, and he went back to writing them by hand. What looks like a failure was actually the first lesson: not every coaching task is a good fit for AI, and the way to find out is to try. He kept experimenting in the background through 2023 and 2024 — Claude, Grok, Perplexity — while keeping personal use and business use cleanly separated. The real shift came at the Department of Homeland Security, where he sat alongside ex-Googlers, ex-OpenAI people, and an Anthropic alumnus on the team building DHS's internal chatbot. Watching what AI could do inside a heavily-protected enterprise environment changed his frame: this wasn't a productivity hack anymore, it was infrastructure.

The Boring, Tedious, Now Quicker: Documentation as the First Real Win

"AI has taken all those boring, tedious tasks and made them quicker, more valuable, and more fun to boot."

 

The first AI practice that stuck was documentation — the part of Agile coaching nobody enjoys but every client demands. Michael had spent years writing SDLC docs from blank pages, and his co-author on Shift: From Product to People used to look at empty docs and ask for help getting started. AI removed that blank-page problem. He'd give the model the team context, the client's documentation requirements, and a template — and get a draft to edit. He stayed in the loop as the human, bringing context, judgment, and final shape, but he no longer started from zero. The same shift happened with presentations: instead of fighting PowerPoint spacing, he tells the AI to drop content into a template and gets back a formatted deck. Small tasks, but multiplied across a coaching week, they bought back real time.

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