Some projects are paint-by-number endeavors with solid management support. Other times, what’s needed are radical transformations, a different architecture, or decommissioning a legacy system. Riddled with risk, communication challenges, and cross-team dependencies, these messy Staff+ projects are all around us.

This talk is about lessons learned over my career about executing challenging projects. The types of projects with politics, drama, tech debt, or past failed attempts. How do we know if the project is worth doing? Why has it failed before? Who’s blocking it? How do we know when to cut our losses and pause or cancel the project?

Staff+ engineers are often the only hope for an organization to overcome and deliver on these types of projects. Don't panic. I believe progress is possible and I'm here with tips.