Cricket Oles
Meet Cricket
Cricket Oles is a Partner at McChrystal Group where she serves as the Chief of Staff to the President. In this role, she supports key strategic initiatives, including the development of new client relationships and driving internal strategic priorities.
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
B.A. University of Southern California
Written Articles/ Materials
Case Study
Driving Alignment within a Shared Services Organization
Economic and political pressures on the healthcare industry present challenges to established companies whose traditional operating models are no longer driving desired performance. With shifting consumer expectations and increasing competition from younger, more agile companies, well-established companies need to evaluate which processes and systems are still fit-for-purpose and which need to be radically transformed.
Insights
What Is a Chief of Staff?
A Chief of Staff can be a multifaceted and indispensable position in modern organizations. Cricket Oles answers some of the most common questions we get about Chief of Staff responsibilities, important skills, and relationship within the broader organization.
Chief of Staff Framework
The McChrystal Group Chief of Staff framework is broken into four quadrants along the lines of what a Chief is expected to accomplish as they develop in the role to support the success of a task-saturated senior executive. Learn how Chiefs can leverage the framework as they progress in their role.
Weekly Whiteboard
Chief of Staff Framework
The McChrystal Group Chief of Staff framework is broken into four quadrants along the lines of what a Chief is expected to accomplish as they develop in the role to support the success of a task-saturated senior executive. Learn how Chiefs can leverage the framework as they progress in their role.
