Cricket Oles
Meet Cricket
Cricket Oles is a Partner at McChrystal Group, where she focuses on organizational transformation and leadership team effectiveness. She joined in 2014 and was elevated to Partner in 2023.
Cricket works with organizations across industries but with a particular emphasis on helping large organizations navigate operating model changes and executive leadership team dynamics. Most recently, she led a project helping build a digital health and personalized medicine business with one of the world's largest pharmaceutical companies. As well, she is leading a project with a federal financial institution, designing a new leadership development program aimed at driving culture change.
From 2020 – 2022, Cricket served as the Chief of Staff to the President of McChrystal Group, Chris Fussell. In this role, she supported key strategic initiatives, including the development of new client relationships and driving internal strategic priorities. She is passionate about the Chief of Staff role and leads McChrystal Group’s Chief of Staff Network, a series of retreats and trainings focused on developing the Chief of Staff role inside organizations.
Cricket joined McChrystal Group in 2014 after receiving a Bachelor of Arts in Economics and International Relations from the University of Southern California. While in school, she interned for the International Committee of the Red Cross in Geneva, Switzerland, and completed field research in Cuba.
B.A. University of Southern California
Written Articles/ Materials
Chief of Staff Resource
The Chief of Staff Playbook: A Proven Framework for Excellence
The 2024 Chief of Staff Playbook is your essential guide to mastering complexity, aligning teams, and driving impactful leadership. Featuring proven frameworks, actionable tools, and real-world insights from McChrystal Group’s leadership experts, this updated resource is designed to help Chiefs of Staff excel in their unique, dynamic roles.
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.
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.
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.
Playbook
The Chief of Staff Playbook: A Proven Framework for Excellence
The 2024 Chief of Staff Playbook is your essential guide to mastering complexity, aligning teams, and driving impactful leadership. Featuring proven frameworks, actionable tools, and real-world insights from McChrystal Group’s leadership experts, this updated resource is designed to help Chiefs of Staff excel in their unique, dynamic roles.