Cricket Oles
Meet Cricket
Cricket Oles is a Senior Principal 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
Connecting a Matrixed Organization
McChrystal Group partnered for 15 months with a UK-based global engineering and design company to accelerate the cultural shift necessary to enable leaders to leverage the company’s diverse set of technical capabilities and expertise across its full range of customers.
Chief of Staff Resource
Do you need a Chief of Staff?
Even before the COVID-19 crisis, executives within Fortune 500 companies were dealing with too much complexity to succeed without a strong support staff. Chris Fussell discusses strategic lessons learned during his career on the staff of a 3-star general, and current business partner Stan McChrystal, and how these tactics transcend the role of many corporate Chiefs of Staff.
Playbook
Do you need a Chief of Staff?
Even before the COVID-19 crisis, executives within Fortune 500 companies were dealing with too much complexity to succeed without a strong support staff. Chris Fussell discusses strategic lessons learned during his career on the staff of a 3-star general, and current business partner Stan McChrystal, and how these tactics transcend the role of many corporate Chiefs of Staff.
Way to Work in 2022 Playbook
Slow Is Smooth, Smooth Is Fast Playbook: This playbook provides practical tips and insights on how you and your teams should be thinking about leading with intentionality, shaping resilient culture, and forging deeper connections to tailor your environment to the challenges ahead. In each of the playbook’s sections, we will focus on how your teams can operationalize these concepts in your People, in your Processes, and in your Technology.
