PEGGY HILLER
Hiring the right CEO is the beginning, not the end.
A new CEO and their board are essentially strangers who just committed to leading an organization together. What happens in that first year — between the new leader, their board, and the organization — determines whether the hire succeeds or becomes a very expensive mistake.
That is the problem I solve.
The search finds the right person. I make sure they succeed — and the board succeeds with them.
I work with boards of mission-driven, board-governed organizations in the gap between finding the right person and having a successful one. When it’s handled wrong, it costs $250,000 or more in disruption, severance, 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 let go without cause and given a severance package. Not for lack of effort — I had worked without stop since day one. Not for lack of capability — I had spent 25 years as a senior executive and gone through an extensive search process to win this role.
I was let go because the leadership transition was set up to fail from the start..
Here is 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 had 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 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 signicant:
The organization lost more than 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 uncertainty 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 transitions fail when organizations assume clarity instead of creating it.
That’s the work I do now.
I help mission-driven, board-governed organizations navigate the most vulnerable moment in an organization’s life—the CEO transition— so it becomes a catalyst for transformation rather than a wound that takes years to heal.
I know this work because I lived it from the CEO’s chair.
Now I help organizations get it right.
A leadership transition is not a pause in the work.
It is the work.
My Experience:
- I spent 17 years as Vice President of Operations at Arapahoe Basin, overseeing multi-million dollar operations across one of Colorado’s most storied mountain resorts. I then served as CEO of PSIA-AASI, a nationwide membership organization with 35,000 members across eight regions. That CEO tenure ended after 19 months — not because of failure in the role, but because the transition lacked the infrastructure to succeed.
- I spent the following year reverse-engineering what went wrong. The result is my three-phase Leadership Transition Architecture System, built from that experience and now the foundation of my consulting practice.
- I hold an SPHR certification and have spent more than 30 years working in and around mission-driven, board-governed organizations.
When to Call Me:
Before a Leadership Transition If:
- You are planning a CEO leadership change in the next 6 to 12 months
- You are not sure if your board and current leader agree on organzational purpose
- You have had leadership turnover in the past that did not go as planned
- You want this transition to strengthen your organization and launch your next era without the typical 18-month performance dip
During a Leadership Transition If:
- You are 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 is not flowing or trust is not forming
After a Leadership Transition If:
- You are 6 to 12 months in and momentum has not returned
- Performance is acceptable but trust is fragile
- You are not sure if you have a transition problem or a leader problem
What I Do:
- I work with mission-driven, board-governed organizations to navigate leadership transition – the most vulnerable moment in an organization’s life.
- My focus is on the system, not only 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, before they become failures
- Organizational structural assessment during the transition window
- Support for the new leader and board through first 12 months, when trust is still forming
- The goal: Turn transition into transformation, not trauma
How to Work with Me:
I approach every engagement systematically, ensuring the time, money and effort your organization invests in bringing on a new leader pays dividends in organizational performance and board confidence
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 board and leadership roles, new leader onboarding plan, coaching and 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- and12-month check-ins, board-leader alignment
- Format: Bi-weekly leader coaching + quarterly board sessions
Transition Recovery
- Timeline: When transition has stalled or failed
- Deliverables: Diagnostic assessment, trust rebuilding, structural repair
- Format: Intensive 90-day Intervention

