Sean O'Connor (Datadog)

Episode 78 · January 6th, 2022 · 46 mins 57 secs

About this Episode

In this episode, rachel, Kendall, and Sean talk about:

  • The genesis of this podcast, and who we have to thank
  • How taking the traditional path of CS to engineering leadership is the rare case
  • Getting into guiding and mentoring at a small company named Huge (lol)
  • Being glad for having done the deathmarch type work when you were younger
  • Learning many important lessons via a failed startup
  • Why consulting is often not appealing
  • Finally getting into bonafide engineering management, with no training
  • A free podcast idea: Awkward Silences
  • The blessing and curse of being a problemsolver
  • The idea that listening is an action
  • Not being able to let go of puns
  • Timing complexity when trying to promote internally
  • How high trust environments must exist across a given company to work well, and how this makes hiring a much higher stakes proposition
  • Intent to 3D print and make things out of wood

You can find Sean at

Special thanks to Mel Stanley for our theme music <3