Cricket Oles


Denver, CO

Cricket Oles is a Principal at McChrystal Group, where she serves as Chief of Staff for the McChrystal Academy. In this role she supports the Director of the Academy in the execution and operations of the leader development business. Previously she supported client development and management for the firm's West Coasts business.

  • B.A. University of Southern California

Meet Cricket

What did you do before joining McChrystal Group?

I joined McChrystal Group after graduating from USC. There, I interned at the International Committee of the Red Cross in Geneva, and was captain of the USC Marathon Team.

Why did you join McChrystal Group?

I chose to work at McChrystal Group because it combined two of my passions: being on a great team and solving complex, important problems.

What has been your proudest moment at McChrystal Group?

Finishing a hike up Pike’s Peak with my teammates during one of our McChrystal Group Leadership Ventures. It was physically and emotionally challenging, but I got through it thanks to my incredible team. After moving to Colorado, I learned that Pike’s Peak is considered one of the hardest 14ers in the state.

What are your favorite books (besides Team of Teams!)?

Let My People Go Surfing by Yvon Chouinard; Moby Dick by Herman Melville; Tripping the Prom Queen by Susan Shapiro Barash; All the Light We Cannot See by Anthony Doerr; Sapiens by Yuval Noah Harari; Change by Design by Tim Brown

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