Rachel Freyman is Senior Litigation & Regulatory Counsel for a leading health system, where she advises executives and board members on the organization's most sensitive matters — government investigations, regulatory enforcement, and the decisions that shape culture and risk at scale.
She holds a J.D. from Northwestern University School of Law and serves as Vice-Chair of the American Health Law Association's Litigation and Liability Practice Group.
Rachel is also the creator of Choose Both™, the framework she developed from nearly two decades of watching high performers collapse under impossible choices. She speaks selectively on what she lives every day: the real drivers of retention, leadership, and career sustainability inside high-performance organizations.
The Three Keys: A Framework for Stuck Seasons. Rachel walks through the three behaviors that break high achievers out of either/or thinking — practical, repeatable, and usable the same day.
Sample question: Walk us through the Three Keys. What's the one most people get wrong first?
The Misdiagnosed Retention Crisis. 38 million people quit last year. 52% of that turnover was preventable. Rachel names what the workload diagnosis has been missing — and what actually keeps high performers engaged.
Sample question: If burnout isn't the real driver of turnover, what is?
The Either/Or Trap. Why the smartest, most capable people in your organization are making impossible tradeoffs in silence. And why engagement surveys don't catch it.
Sample question: How can a manager tell the difference between someone who's overloaded and someone who's stuck?
Why High Achievers Quit (and It’s Not Burnout). People don't quit because things are hard. They quit when they can't see a path that doesn't cost them something they're not willing to lose. Rachel unpacks the difference and what leaders are missing.
Sample question: What's the moment a high performer actually decides to leave — and why is it almost never the moment she gives notice?
What I've Learned Inside the Decisions Most Leaders Never See. From nearly two decades of senior counsel work advising executives and boards, Rachel shares what actually drives silent disengagement — and why the people best positioned to prevent it usually don't.
Sample question: What's the conversation happening in executive rooms about retention that isn't reaching the people it affects?.
International Performance Management Institute / American Health Law Association / Health Care Compliance Association / Tennessee Hospital Association / Hall Render
For speaking inquiries, podcast bookings, media requests, or press features, reach out below.