Sherry Waddingham MBA, PCC
I work with experienced leaders navigating moments where something is shifting.
A new role. Increased expectations. Organizational pressure.
Or the quieter realization that the way they have always led no longer quite fits what is now required.
Leadership can look confident from the outside.
Inside, it is often more complex.
I make sense of what is happening beneath the surface of leadership.
Background
Before this work, I spent more than a decade in senior leadership roles inside complex organizations.
I led teams, managed high-stakes client relationships, and worked in environments where expectations were high and the pace was fast. Decisions carried weight. The pressure to perform was constant.
That experience shaped how I understand leadership.
Not just what it looks like from the outside, but what it actually feels like to carry it.
The responsibility.
The ambiguity.
The internal pressure to remain steady while everything around you is moving.
That perspective continues to inform how I work today.
The Work
Over time, I became increasingly interested in something I was seeing repeatedly in my own leadership and in others.
Capable, experienced people encountering moments where things no longer worked the way they used to.
Situations that should have been manageable becoming unexpectedly difficult.
Patterns repeating, even when the leader knew better.
Transitions that looked straightforward on paper, but felt far more complex in practice.
That curiosity became a body of work.
It led me into deeper study of psychology, human behaviour, and leadership development. More importantly, it shaped how I began to understand what is actually happening in those moments.
Most leadership challenges at this level are not about knowledge or capability.
They are about the internal adjustments that real change requires, and the patterns that make those adjustments harder to see.
How I Work
The leaders I work with are experienced, thoughtful, and capable.
They are often navigating a gap. Not in skill, but between how they have led successfully in the past and what the situation in front of them now requires.
Our work creates space to make sense of that.
We look closely at what is happening beneath the surface of the situations they are dealing with. The patterns shaping their responses. The assumptions influencing their decisions. The dynamics that may be holding things in place.
From there, different ways of seeing, and leading, become available.
The goal is not to fix the leader.
It is to help them lead with clarity, steadiness, and a stronger sense of their own judgment in environments that are often anything but clear.
Approach
My work sits at the intersection of leadership experience and psychological insight.
That combination allows conversations to move beyond surface-level advice into the patterns that often shape how leaders think, decide, and respond under pressure.
The work is warm, but not soft.
What leaders often find most useful is not reassurance. It is clarity.
Credentials
Professional Certified Coach (PCC)
Member, International Coaching Federation
MBA, Queen’s University
Psychology Certificate, Toronto Metropolitan University
Advanced Training in Depth Psychology & Therapeutic Coaching, Alex Howard Group
The Judy Project for Executive Women, University of Toronto
Additional training includes trauma-informed approaches, conflict facilitation, and personality frameworks that deepen my understanding of how people lead and navigate complex environments.
Client Reflection
“When I began working with Sherry, I was facing a very difficult situation in my leadership role and had started to question my value as a contributor.
Sherry helped me rebuild confidence in my own judgement and gave me practical tools to navigate difficult situations.
What stood out most was her ability to create a space where I felt understood and seen, while also being direct about what is really happening. The work had a lasting impact on how I approach leadership and difficult conversations. I still find myself asking, ‘what would Sherry do?’ ”
Head of Operations, Marketing & Communication Services
Final Thought
Leadership transitions are rarely just about new responsibilities.
They involve shifts in how someone sees their role, their decisions, and themselves.
Supporting leaders through those moments, when something is changing but not yet fully clear, is the work I care most about.