Replacing the spreadsheet that ran the planning process
Working with a program management leader at a large tech company to replace the spreadsheet planning process their executives reviewed monthly, with a tool they built, deployed, and extended themselves.
A program management leader ran a planning and reporting process that senior leadership reviewed every month. It lived in a spreadsheet touched by dozens of teams, held together by hand-pasted updates and constant shepherding. Migrating to a real tool had been “next quarter” for over a year, stuck behind budget and tool-consolidation debates.
Before
After
They came in trying to get AI to do the task. The turning point came early: stop automating the spreadsheet and build its replacement. We started by proving the foundation: that they could stand up and share a working application inside their company at all, before investing in any real functionality. With that settled, a long spoken interview became the spec. I asked how the process actually worked and what good would look like, played my understanding back to them, and we shaped that conversation into a plan we reviewed and refined together.
From there they built in phases, their hands on the keyboard the whole time. Each phase ended the same way: try it, react to it, fold the feedback into the plan, checkpoint, and move on. When a path was painful the first time through, we distilled it into a reusable skill so it never had to be painful again. Between sessions they shipped improvements on their own, and my role shifted to the moments that benefit from experience: catching a wrong turn early, structuring context, and weighing in on the few decisions worth being opinionated about.
Within ten days of the first session they had a working tool they were showing colleagues and preparing to bring to leadership as the replacement for the process, including answering an executive's wish to simply ask an AI assistant for a team's status update. In their own words, the shift was simple: they stopped asking AI to do the task and started asking it to build the tool that does it.
An update they sent after the sessions ended: “Thanks to you, I launched my app to production and migrated and provisioned my own standalone service, despite Claude and at least three different engineers telling me I wasn't going to be able to do it solo.”