Sherry Waddingham MBA, PCC

About Sherry Waddingham

I work with experienced leaders navigating moments of significant transition. Promotions. New roles. Organizational change. Or the quiet realization that the way you have always led no longer quite fits the demands in front of you.

Leadership can look confident from the outside. Inside, it is often more complex.

My Background

Before becoming a coach, I spent more than a decade working in senior leadership roles inside complex organizations.

I led teams, managed complex client relationships, and worked inside organizations where expectations were high and the pace was fast. Decisions mattered. The pressure to perform was constant.

Those experiences gave me a deep appreciation for the realities of leadership that are rarely discussed openly. The responsibility leaders carry. The uncertainty they often navigate alone. The internal pressure to remain steady while everything around them is changing.

That experience, combined with formal training in coaching, psychology, and human behaviour shapes how I work with leaders today.

What Drew Me to This Work

Like many leaders, I reached a point in my own career where success on paper did not fully answer the deeper questions.

I had achieved the milestones that were supposed to signal progress. Yet I found myself increasingly curious about the forces that shape how we lead.

Why capable people sometimes second guess themselves.
Why certain patterns repeat even when we know better.
Why transitions in leadership roles can feel unexpectedly destabilizing.

That curiosity became a body of work.  The patterns I kept encountering in my own leadership and in the leaders around me, became the foundation for how I think about transition, identity, and change.

It led me into deeper study of psychology, leadership development, and coaching. And it became clear over time that many of the struggles leaders face are not about knowledge or capability.  They are about the internal adjustments that accompany real change.

For nearly two decades, I’ve worked as a coach and facilitator with leaders navigating complex change. 

How I Work With Leaders

The leaders I work with are typically experienced professionals navigating significant moments in their careers.  They may be stepping into a larger role, leading through organizational change, reconsidering what success means for them, or simply feeling the pressure that comes when expectations increase but clarity does not.

Most are not lacking knowledge or capability.  What they are navigating is the gap between who they have been as a leader and what the situation in front of them now requires.

Our work creates space to think clearly about what is really happening beneath the surface.  We examine patterns shaping how you respond under pressure, the assumptions quietly influencing your decisions, and the dynamics that may be holding the situation in place, until you can them clearly enough to lead differently.  

The goal is not to fix the leader.  It is to help them lead with greater clarity, steadiness, and self-trust as the environment around them evolves.

My 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 deeper patterns that often drive leadership challenges.

The conversations are warm but not soft.  Leaders often find that what is most useful is not reassurance, it is clarity.

Clients often describe the work as thoughtful, grounding, and deeply practical. Conversations that create the space to think clearly in environments that rarely slow down.

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 change.

Client Reflections

“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 are about the internal adjustments that allow someone to step into a new level of leadership with confidence and clarity.

Supporting leaders through those moments is the work I care most about.