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The Leadership Community Behind Organizational Transformation

The Leadership Community Behind Organizational Transformation

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When the pace of change feels relentless and clarity seems out of reach, even the best leaders can lose their footing. Yet, the secret to leading through change isn’t found in structure—it’s found in people. 

In this episode of Lead the Future, Vince sits down with Michelle E. DiEmanuele, Secretary of the Cabinet for the Ontario Public Service, to explore how leaders can drive meaningful, sustainable business transformation by building strong leadership communities, leaning into purpose, and changing processes—not just structures. 

Michelle reflects on her leadership journey across the public, private, and healthcare sectors, sharing hard-earned lessons from guiding a 70,000-person organization through a pandemic. From navigating complexity like whitewater rafting to reigniting a sense of service in public institutions, her stories offer practical insights and powerful takeaways in resilience, accountability, and enterprise-wide leadership. 

"Community is citizenship. We all need to know who we are, why we’re here, and what we’re here to do — and we do it together."

Key Leadership Insights to Listen for: ​

  • How to lead large-scale transformation with belief, purpose, and values
  • Why building a community of leaders is critical in high-velocity change environments
  • The subtle power of frontline presence and using all your senses as a leader
  • What most leaders miss when they restructure — and how real change sticks through process 

Meet the Leader: Michelle E. DiEmanuele, Secretary of the Cabinet, Ontario Public Service

Secretary Michelle E. DiEmanuele has spent her career in the public, broader public, and private sectors leading large-scale service change and cultural transformation initiatives. She held leadership roles in several ministries, including Deputy Minister of Human Resources, Deputy Minister of Government and Consumer Services, Secretary to the Management Board, and Associate Secretary of the Cabinet. She is responsible for the introduction of the online birth certificate and other digital services to the public, and the first-ever “Money Back Guarantee” for government services in North America. 

Michelle returned to the OPS in 2021 to serve as Secretary of the Cabinet after more than a decade as President and CEO of Trillium Health Partners. During her tenure at the hospital, she established the Institute for Better Health, led the largest voluntary hospital merger in Canada between Credit Valley Hospital and Trillium Health Centre, created Partners Community Health, and stewarded the organization through a global pandemic. This was all while ensuring quality care and fiscal responsibility.  

Beyond her accomplishments in public service, Michelle has also served as Vice President of Branch and Small Business Banking, Retail Markets/Human Resources at CIBC, Vice President of Human Resources and Organizational Development at Brookfield Properties Ltd., and CEO of the Ontario Lottery and Gaming Corporation. 

She has been recognized with many awards, including being inducted into Canada’s Top 100 Most Powerful Women Hall of Fame and the Top 40 Under 40, which includes the most influential in the first decade of this award. She is also the recipient of Queen Elizabeth II’s Diamond Jubilee Medal and the Order of Ontario.  

Michelle holds an honorary Doctor of Laws (Hon. LL.D.) from the Faculty of Community Services at Toronto Metropolitan University and she is a Senior Fellow at the Munk School of Global Affairs and Public Policy in the University of Toronto. Michelle has also served on both public traded and private boards. 

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About Leadership Contract

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