PEGGY HILLER
Empowering Boards and Leaders to Get Leadership Transition Right the First Time.
Leadership transition is the most vulnerable—and most powerful—moment in an organization’s life. When it’s handled wrong, it costs $250K+ in disruption and cultural damage. When it’s handled right, it becomes a catalyst for transformation.
PEGGY HILLER
Empowering Boards and Leaders to Get Leadership Transition Right the First Time.
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Leadership transition is the most vulnerable—and most powerful—moment in an organization’s life. When it’s handled wrong, it costs $250K+ in disruption and cultural damage. When it’s handled right, it becomes a catalyst for transformation.
About Me
Why I Know This Work:
I am a Product of an Unsuccessful Leadership Transition
In August 2024, I was asked to resign as CEO after 19 months.
Not for poor performance—I was fired without cause and given a severance package. Not for lack of effort—I’d worked non-stop since day one. Not for lack of capability—I’d spent 25 years as a top executive and gone through an extensive search process to win this role.
I was fired because the leadership transition was set up to fail from the start.
Here’s what was missing:
No transition plan. I was accountable to the board, but they never defined expectations beyond the hiring process. I navigated using my own judgment and relied on a team I’d just inherited to show me the way. The organization gave me no roadmap for success—and the only formal feedback I received was being let go.
No clarity on purpose. The board was fractured on the organization’s mission. They couldn’t tell me what problem we existed to solve—because they didn’t agree themselves.
No transparency about organizational friction. The board knew about long-standing issues—structural problems, internal organizational politics, cultural tensions—but never disclosed them. I was left to discover friction points on my own, months into the role, when I should have been addressing them from day one.
No feedback infrastructure. I received zero performance evaluations in 19 months. When concerns existed, they festered in silence until it was too late.
By the time the board asked me to resign, the damage was done—to them, to me, to the organization we were supposed to be leading together.
The cost was devastating:
The organization lost 30+ months of progress—my hiring process, my short tenure, then rehiring again. They paid for a failed search, my severance, and interim leadership. The staff endured months of limbo, confusion, and a leadership vacuum during a time of both opportunity and challenge.
And I lost my confidence and hard-fought career reputation.
What I learned in 12 months of recovery:
This wasn’t about me. It wasn’t about the board. It was a systems failure.
Key leader transistions fail when organizations assume clarity instead of creating it.
That’s the work I do now.
I help orginizations navigate the most vulnerable moment in an organization’s life—lkey eadership transitions— whethers it;s a CEO, GM, Executive Director, or any critical leadership role, so the transition becomes a catalyst for transformation rather than a wound that takes years to heal.
I know this work because I’ve failed at it personally.
Now I help organizations get it right the first time.
A Leadership Transition is not a Pause in the work.
It Is the Work.
MY EXPERIENCE:
- 25+ Years Operational Leadership and Organizational Development
- VP Operations, Arapahoe Basin – multi-millon dollar operational oversight and Culture Guru
- CEO, PSIA-AASI – nationwide 35,000 members, 8 regions
- SPHR Certified
- Personal Experience with Leadeship Transition Failure
- Let go as CEO when transition infrastructure was missing
- Developed System for Successful Leadership Transition from public failure
- Modern Leadership & Technology
- Post-grad certificate Aritificial Intelligence from UT Austin
- Help Leaders use AI to support (not complicate) transition
- Deep Commitment to Ski Industry
- 30+ years ski and outdoor recreation
- Methodology applies to resorts, hospitality, non-profits, membership organizations, and broader service industry.
When To Call Me
Before a Leadership Transition If:
- You’re planning a CEO/senior leadership change in the next 6-12 months
- You’re not sure if your board and current leader agree on organizational purpose
- You’ve had leadership turnover in the past that didn’t go well
- You want this transition to strengthen your organization and launch your next successful era without the typical 18-month performance dip.
During a Leadership Transition If:
- You’re in the first 90 days and clarity feels elusive before positions harden and trust erodes.
- The new leader and board/ownership don’t seem aligned
- Old habits are resurfacing despite new leadership
- Feedback isn’t flowing or trust isn’t forming
After a Leadership Transition If:
- You’re 6-12 months in and momentum hasn’t returned and you need to know if this is fixable.
- Performance is fine but trust is fragile
- You’re not sure if you have a transition problem or a leader problem
WHAT I DO
- I work with boards and leaders new to their position to navigate the leadership transition – the most vulnerable moment in an organization’s life.
- My focus is on the system, not just the person:
- Organizational purpose clarification before Day One
- Board-Leader alignment on expectations, authority, communication and existing friction points
- Feedback infrastructure that surfaces problems early
- Organizational Structural assessment during transition
- Support for the new leader and board through first 12 months when trust is forming
- The goal: Turn transition into transformation, not trauma.
I approach key leadership transition systematically,
ensuring the time, money and effort to bring on a new leader pays big dividends in organizational performance.
HOW WE WORK TOGETHER
Pre-Transition Strategic Partner
- Timeline: 3-6 months before leadership transition
- Deliverables: Purpose clarification, structure review, transition plan
- Format: Monthly board sessions + leader prep
Pre-Transition Through Transition Strategic Partner
- Timeline: 3-6 months before leadership transition + first 6 months of new leadership
- Deliverables: Organizational Purpose Clarification, Structure Review, Transition Plan, Success Metrics Defined, Roles for Board/ Ownership Defined, Onboarding Plan for New Leader, Coaching New Leader, 90 day, 6 month, 12 month check-in Planning
- Format: Monthly board sessions + leader prep
Transition Embedded Support
- Timeline: First 12 months of new leadership
- Deliverables: 90-day feedback design, 6/12-month check-ins, board-leader alignment
- Format: Bi-weekly leader coaching + quarterly board sessions
Transition Recovery
- Timeline: When transtion has stalled or failed
- Deliverables: Diagnostic, trust rebuilding, structural repair
- Format: Intensive 90-day Intervention

