Workshop Series: Governing the Family Business Across Generations

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From Taxi Lines to Boardrooms: Leading Through Disruption, Innovation, and Uncertainty

📅 Date: Thursday, November 26, 2026 🕓 Time: 11:30am - 2:00pm

📍Location: Conestoga College - Waterloo Campus

Markets change. Technology evolves. Leadership priorities shift. The challenge is knowing when to adapt and how to move forward with confidence.

Join Sheldon McCormick, former Uber Canada executive, entrepreneur, and family business investor, as he shares practical lessons from navigating rapid growth, disruption, and transformation. Drawing on experiences in technology, entrepreneurship, and family business, Sheldon will explore how leaders can recognize change early, make better decisions, and position their organizations for long-term success.

What You'll Take Away

• Recognize when strategy needs to evolve

• Balance stability, growth, and innovation

• Navigate AI, digital transformation, and succession

• Make confident decisions amid uncertainty

• Build resilience for long-term success

Sheldon McCormick

CEO - Communitech

Supported by

📅 Date: Wednesday, November 18, 2026 🕓 Time: 12:00pm - 1:30pm

📍Location: Caldwell Group - 120 Victoria Street South, Suite 301, Kitchener, Ontario, N2G 0E1

Participants will explore:

• Understanding the family's overall financial position, including the business, real estate, investments, and debt.

• Balancing the business's capital needs with the family's retirement income, financial security, and plans for the next generation.

• Assessing whether succession plans are realistic, including how they can be funded and how to provide fairly for children both inside and outside the business.

• Coordinating the work of the family's financial, accounting, and legal advisors.

Subsequent sessions led by McCarter Grespan will build on these discussions by exploring the legal and governance considerations that support effective decision-making and successful transitions. Planned topics include wills, estate and tax planning, shareholder and other key agreements, and structures that support both ownership and leadership succession. Discussions will examine how early planning, clearly defined responsibilities, and shared expectations can help families navigate change, preserve relationships, and reduce the potential for conflict.

Throughout the series, participants will be encouraged to bring perspectives from across generations and consider how the concepts and strategies discussed apply to their own family and business circumstances.

Family Wealth and Business Decisions (Workshop 1)

This interactive workshop, led by The Caldwell Group, explores how families make financial decisions when the needs of the business, current owners, and the next generation overlap. The discussion will consider competing priorities, whether succession plans are financially workable, and how the family's advisors can support coordinated decision-making.

Members Only Event

AI Toolkit for the Modern Manager

Workshop

Leadership focused on human AI orchestration, responsible AI use and team enablement. All levels in this first workshop.

More details to come.

📅 Date: Friday December 4, 2026 🕓 Time: 8:30am - 12:30pm

📍Location: TBD

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Holiday Social

📅 Date: TBD 🕓 Time: TBD

📍Location: TBD

Social Event

Presented by the CFFB Programming and Events Committee.

More details to come.

Members Only Event

The future is always changing, and few people explain it better than Larry Smith.

Join us for our first gathering of 2027 as Larry returns to share his perspectives on where we've been, where we are today, and what may lie ahead. Combining economic insight, practical observations, and his trademark humour, Larry delivers presentations that are both informative and entertaining.

Larry Smith

University of Waterloo Economics Professor

Making Sense of What Comes Next

📅 Date: Thursday, January 21, 2027 🕓 Time: 11:30am - 2:00pm

📍Location: Conestoga College - Waterloo Campus

Sponsored by

The Importance of Having Wills and Estate and Tax Planning for Family Members in Corporate Governance

📅 Date: Thursday, February 11, 2027 🕓 Time: TBD

📍Location: McCarter Grespan Lawyers - 539 Riverbend Dr, Kitchener, ON

Workshop

More details to come.

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Virtual Event TBA

📅 Date: Thursday, February 25, 2027 🕓 Time: TBD

📍Location: Virtual

📅 Date: Wednesday, March 24, 2027 🕓 Time:TBD

📍Location: TBD

Special Guest Speaker to be Announced

Supported by

More details to come.

Sponsored by

More details to come.

Shareholder Agreements and Other Key Agreements to Support Succession and Leadership

📅 Date: Tuesday, April 6, 2027 🕓 Time: TBD

📍Location: McCarter Grespan Lawyers - 539 Riverbend Dr, Kitchener, ON

Workshop

More details to come.

Lead by

Multi-Generational Panel:

Sharing Perspectives Across Generations

📅 Date: Thursday, April 22, 2027 🕓 Time: TBD

📍Location: TBD

More details to come.

Sponsored by

Sabrina Fitzgerald

Moderator

CFFB Milestones Gala

📅 Date: Thursday, May 27, 2027 🕓 Time: TBD

📍Location: TBD

Celebrating 30 Years!!

More details to come.

Summer Social

📅 Date: TBD 🕓 Time: TBD

📍Location: TBD

Social Event

Presented by the CFFB Programming and Events Committee.

More details to come.

Lead Change with a Strategic Plan that Actually Works

Neil Thornton

Founder - The Thornton Group

📅 Date: Friday, September 25, 2026 🕓 Time: 11:30am – 2:00pm

📍Location: Conestoga College – Waterloo Campus

Director's Crisis Playbook

📅 Date: Wednesday, October 21, 2026 🕓 Time: 4:00pm – 6:00pm

📍Location: Westmount Golf & Country Club

Jaime Watt

Author

Past 2026-2027 Events

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