Experience in business, law, and the business of law
Leanne Cherry
Leadership Advisor to Law Firms and Legal Leaders
Practical
Grounded in more than 30 years of experience in law, leadership, and talent development.
Collaborative
Creating a trusted space for thoughtful conversations, honest feedback, and meaningful growth.
Tailored
Supporting each leader's unique goals, challenges, and definition of success.
Thoughtful conversations are valuable. Turning them into action is what creates change.
I help clients identify practical next steps and provide the accountability to follow through.
Through executive coaching, leadership development, and strategic advisory services, I bring the perspective of someone who has experienced the legal profession from multiple vantage points—as a lawyer, senior talent leader, executive coach, and advisor. I believe leadership is learned and that thoughtful conversations can transform individuals, teams, and organizations.
I understand the legal profession from the inside.
Before becoming a coach and advisor, I practised law for almost 20 years and later served as Chief Talent Officer of one of Canada's largest law firms, leading its national talent strategy and working closely with senior leadership and its Board. My experience also includes executive leadership, governance, and Board service.
Over more than 30 years in the legal profession, I have developed a practical understanding of law firms, professional services, organizational dynamics, and the pressures that accompany demanding professional roles.
That experience shapes how I work. I understand context quickly, ask practical questions, challenge thinking when appropriate and offer perspective based on experience. Clients can bring the challenge as it is, talk it through candidly, and we work together to determine a practical way forward.
Clients seek my support when they are:
Transitioning into or preparing for leadership
Navigating difficult relationships
Seeking candid leadership feedback
Balancing competing priorities
Building their practice, influence, or leadership impact
Looking for a confidential sounding board
My approach is practical, collaborative and grounded in experience.
I work alongside leaders to help them think more clearly, navigate complexity, and make intentional decisions that strengthen both their leadership and their organizations.
Meaningful development begins with self-awareness. Together, we challenge assumptions, shift perspectives, and translate insight into practical action. The goal is meaningful, lasting change for both the individual and the organization.
Like many of my clients, I understand the realities of balancing a demanding career with the responsibilities of everyday life.
Raising a family while building my own career has given me a deep appreciation for the competing priorities leaders face.
As the proud mom of two amazing young men, I know that leadership extends well beyond the workplace. There is no perfect balance, but there is great value in creating a life and career that work together in a sustainable, meaningful way.
I believe the best leaders never stop learning.
My commitment to continuous professional development, including executive coaching, leadership assessment and graduate studies in counselling psychology, helps me bring current thinking, evidence-informed practice, and practical insight to every client engagement.
I also believe leadership is about the whole person. My own learning extends beyond professional development to include mental, physical, emotional and spiritual well-being. That holistic perspective shapes both my life and my advisory practice, helping clients build leadership that is not only effective, but sustainable.
Throughout my career, I have been fortunate to learn from exceptional mentors, coaches and leaders. Their wisdom continues to influence my work, and I strive to pass those lessons forward in every coaching and advisory relationship.
Let’s start a conversation
Whether you're investing in a leader, navigating organizational change, strengthening your leadership team, or looking for an experienced executive coach, I'd welcome the opportunity to learn about your goals and explore how I can help you achieve them.