Caitlin Milligan Sheaffer

Caitlin Milligan Sheaffer is a digital project manager at Simple.  She’s passionate about exploring and developing systems of feedback that help people learn from each other. She’s channeled this work at Simple by digging into incident management and postmortem processes.

She came to digital project management after spending almost a decade in stage management for live theater. When she’s not at work, Caitlin enjoys practicing capoeira and adventuring in the Pacific Northwest.


Learning From Failure: Getting More From Your Postmortems

October 13th | 3:00 PM

Does your company “do postmortems” but never actually schedule them? Do you have great learning conversations and then struggle with follow-through? Do you have lots of enthusiastic individual contributors but no buy-in from management? Postmortems can be a great tool for learning, but it can be hard to extract full value from the process.

In this interactive, conversation-based session, we’ll discuss what works for your postmortems and what doesn’t. Come ready to share your experiences — if you use some successful strategies in your organization, we’d love to hear about them! We’ll also touch on how and why company-wide support can boost your postmortem work to the next level.

You’ll leave this session with:

  • Strategies for engaging management in your postmortem program
  • Ideas about how to move your great conversations into solid action
  • A template for kickstarting postmortems at your organization