Sherry Waddingham

I have always been curious about people.

Why we do what we do. Why we repeat patterns we know are not working. Why one person can leave us feeling grounded while another has us questioning our sanity before lunch.

Curiosity has shaped my work as a senior leader, coach, facilitator, writer, and observer of human behaviour.

Over time, I became less interested in generic advice and more interested in what is really happening underneath the problem.

What are we reacting to?

What pattern keeps repeating?

What are we not seeing?

What happens when two people’s habits, fears, expectations, and blind spots collide?

I am direct, warm, curious, and not especially interested in pretence.

I like clear thinking, honest conversations, sharp observations, and enough humour to keep difficult subjects human. Sometimes the fastest way to understand a complicated dynamic is to compare it to canned tuna pretending to be sushi.

Before moving into coaching and writing, I spent more than a decade in senior leadership roles inside complex organizations. Since then, I have spent nearly two decades working with people through coaching, facilitation, leadership development, psychology, and therapeutic coaching.

What I believe is simple:

Patterns have a reason.

Understanding is not the same as excusing.

Compassion does not require self-abandonment.

Boundaries are not cruelty.

And sometimes the healthiest response is to stop trying harder and start seeing more clearly.