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
Chief of Staff Resource
Navigating Complexity: Leadership Learnings from Chiefs of Staff
Discover key leadership lessons from McChrystal Group's Fall 2024 Chief of Staff Retreat. Learn how to navigate ambiguity, build high-performing teams, and balance strategic priorities for greater organizational impact.
The Power of the "5 Whys"
Discover how McChrystal Group's Chief of Staff, Cricket Oles, uses the Five Whys technique to identify root causes and solve organizational challenges effectively. Learn how to apply this method to drive lasting change.
Insights
Navigating Complexity: Leadership Learnings from Chiefs of Staff
Discover key leadership lessons from McChrystal Group's Fall 2024 Chief of Staff Retreat. Learn how to navigate ambiguity, build high-performing teams, and balance strategic priorities for greater organizational impact.
Chief of Staff Framework: A Strategic Approach
McChrystal Group's Chief of Staff Framework is a strategic approach designed to enhance the effectiveness of Chiefs of Staff by aligning their role with the needs of both the principal and the aligning their role with the needs of both the principal and the organization. Learn how to navigate this critical leadership position with precision.
Weekly Whiteboard
The Power of the "5 Whys"
Discover how McChrystal Group's Chief of Staff, Cricket Oles, uses the Five Whys technique to identify root causes and solve organizational challenges effectively. Learn how to apply this method to drive lasting change.
Chief of Staff Framework: A Strategic Approach
McChrystal Group's Chief of Staff Framework is a strategic approach designed to enhance the effectiveness of Chiefs of Staff by aligning their role with the needs of both the principal and the aligning their role with the needs of both the principal and the organization. Learn how to navigate this critical leadership position with precision.
