Leadership Coaching

Leadership Coaching For Transitions

When you’re navigating a significant leadership transition, strategy alone isn’t enough.

I help leaders work with both:

  • the conscious decisions they need to make, and

  • the unconscious patterns blocking their progress

— so change actually sticks.


Who This Is For

This coaching is for leaders who are:

  • Stepping into new roles that require leading differently

  • Navigating organizational change while maintaining clarity

  • Outgrowing outdated definitions of success or leadership identity

  • Knowing what they should do but unable to move forward

  • Hitting the same patterns in different situations

  • Ready for depth work, not surface fixes


What We Work On

Leadership identity shifts

Understanding who you’re becoming as a leader — not just the role you’re stepping into.

Unconscious patterns that keep you stuck

Seeing the protective mechanisms, old beliefs, and identity attachments that shape resistance.

Decision-making from clarity

Distinguishing fear-based reactions from genuine knowing so choices align with the leader you’re becoming.

Working with resistance

Understanding what your resistant parts are protecting, rather than forcing through them.

Sustainable change

Building transformation that lasts because it addresses root causes, not symptoms.


The Approach

We work on two interconnected layers:

1. The Conscious Layer

Your decisions, strategies, goals, and practical next steps.

2. The Unconscious Layer

The patterns, beliefs, and identity structures driving your resistance.

Most leadership coaching focuses only on the first layer.
Real, lasting change requires working with both.

This is not skills training or performance coaching.
It’s depth work integrating leadership strategy with psychology.


Coaching Packages

3-Month Engagement

6 sessions (biweekly)
For leaders navigating a specific transition.
We identify key patterns, clarify decisions, and build strategies for moving forward.

6-Month Engagement

12 sessions (biweekly)
For leaders ready for sustained depth work.
We address root patterns, work through identity shifts, and create lasting change that extends beyond the immediate transition.

Most clients choose the 6-month engagement for deeper transformation. The 3-month package works best for leaders with a specific, time-bound decision to make.

All sessions are 60 minutes via Zoom, confidential, direct, and grounded in both psychological insight and practical strategy.

Investment begins at $2,500 CAD for individual coaching packages.

Organizational leadership development programs are customized based on scope and needs.

Let’s discuss which approach is right for your situation on a complimentary discovery call.

 

Next Steps

Ready to Start?

Schedule a complimentary 30-minute conversation to discuss:

  • The transition you’re navigating

  • What’s keeping you stuck

  • Whether this approach is the right fit

Not Sure Yet?

Subscribe to my newsletter where I explore the conscious and unconscious dimensions of leadership, transition, and lasting change. 

Get In Touch

Book Your Free Discovery Call Now

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Email

info@sherrywaddingham.ca

Location

Toronto, Canada