Ryan Flynn

Meet Ryan
Ryan Flynn is a Partner at McChrystal Group where he advises leaders on major organizational transformation initiatives. His clients have included members of the Fortune 100 and the FTSE 350, and have spanned industries including Financial Services, Professional Services, Manufacturing, and Technology.
From 2020-2021 he led a McChrystal Group team engaged with a national, nonpartisan network of US State and Federal leaders in their response to COVID-19. This work included routine engagement with the White House and other critical leadership groups on time-sensitive decision-making for COVID-19 response.
Prior to joining McChrystal Group in 2014, Ryan worked for Alvarez & Marsal where he provided financial and operational management consulting services to state and local governments. During his MBA Ryan held roles with CrossBoundary, an emerging markets investment firm, Biohaven Pharmaceuticals, a clinical- and commercial-stage pharmaceutical company, and the Office of the Governor of Connecticut.
Ryan received his MBA from the Yale School of Management and his BA from Trinity College, CT. He has lived and worked in Europe, the Middle East, and Africa and currently resides in Philadelphia, PA.
B.A. Trinity College CT
M.B.A. Yale School of Management
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
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.
Rethinking Leader Development: Lessons from the Closure of General Electric’s Crotonville
The closure of GE's Crotonville serves as a wake-up call, and with companies such as 3M and Boeing also in the midst of selling leadership campuses, it further highlights the inadequacies of 20th-century conventional leadership development methods. The trend underscores the pressing need for a shift in approach to leader development. We posit that the answer lies in embracing a digitally enabled and highly targeted approach to leader development. This approach leverages technology to deliver personalized learning experiences tailored to individual needs and specific business objectives.
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.