Upscale was a large scale agile transformation at a 50 team software company. Brent and I were on the leadership team. The aim of Upscale was to address the gridlock problem with cross-team projects. Jade brought in James Shore, author of The Art of Agile Development, and he led us through a massive amount of change. Upscale was extremely successful, but there were missteps and challenges. We retrospect on Upscale, and talk through cross-team dependencies, and especially into the massive self-selection event, where most of the people in engineering got to choose which team they wanted to be a part of. The episode covers a lot of topics in organizational design, team autonomy, and change management.