Sherry Waddingham MBA, PCC

About Sherry Waddingham

Why Smart, Capable Leaders Get Stuck

Smart, accomplished leaders often come to me feeling stuck.  Even when they know what they should do.

They’re strategic, self-aware, and capable. They’ve navigated complex decisions before. And yet something isn’t moving.

This isn’t a lack of discipline or clarity.
It’s what happens when unconscious patterns formed long ago override conscious plans made today.

Most transition advice focuses on strategy: make a plan, take action, push through resistance.
But strategy alone isn’t why people stay stuck.

I help leaders work with both layers:

  • the conscious decisions they need to make

  • and the unconscious patterns shaping how they approach them

The result is change that actually holds, because we’ve addressed root causes, not just symptoms.

My Relationship to This Work

I understand this work from the inside.

For years, I built a successful corporate career; MBA, senior leadership roles, the kind of drive people admire. From the outside, everything looked right.

Internally, I was operating on autopilot, guided by unconscious beliefs about achievement and worth. It wasn’t burnout. It was a quiet identity shift I didn’t yet have language for.

The strategies that had brought success no longer aligned with where I was headed. What I lacked wasn’t intelligence or effort, it was visibility into the patterns beneath my choices.

What changed everything wasn’t a new plan or better productivity.
It was learning to work at the level where the real blocks lived.

You can’t think your way through an identity shift.
You have to work where the patterns are.

How I Work Now

Today, I support leaders navigating transitions by working directly with what’s actually shaping their resistance. The unconscious patterns beneath the surface.

My work integrates depth psychology with leadership strategy, so insight and action are no longer in conflict.

When leaders understand what’s driving them beneath awareness, clarity returns. Decisions settle. Action becomes steadier. Change becomes sustainable.

What I Bring

I bring a grounded combination of lived experience and psychological depth, including:

  • Former corporate executive experience, with deep understanding of leadership pressure and organizational dynamics

  • 18+ years working across leadership, psychology, and human behaviour

  • Professional coaching and facilitation expertise supporting leaders through uncertainty and identity shifts

  • Strong pattern recognition that reveals emotional and behavioural dynamics others often miss

  • Clear, grounded communication that integrates depth with practical strategy

Leaders don’t need more motivation.
They need clarity at the level where their decisions are actually formed.

My Approach

This is not surface-level coaching or generic mindset work.

We work with two interconnected layers:

  • the conscious layer: decisions, strategies, goals, and next steps

  • the unconscious layer: beliefs, protective mechanisms, and identity attachments shaping behaviour

When these layers are misaligned, internal conflict takes over and progress stalls.

Real, lasting change comes from integration.
When awareness replaces internal struggle, leaders stop fighting themselves and start leading with steadiness and self-trust.

Credentials

  • Professional Certified Coach (PCC), 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 change.

Beyond the Work

Outside of coaching, you’ll find me walking my dog, working in the garden, experimenting in the kitchen, or reading about leadership, psychology, and human behaviour.

I’m deeply interested in what drives people and what allows real transformation to take root.

Next Step

If you’re navigating a transition and want support that goes deeper than strategy alone, we can explore whether this work is a fit.

Real change begins not in forcing decisions, but in understanding what’s shaping them.