Family Business Succession
–
Balance complex relationships, tax implications, and financial needs.
Michael Cadesky and Hugh Woolley break down effective tax planning strategies for family business succession including estate freezes, redemption programs, and intergenerational transfer rules.

- Why Pass Family Business to Children: Motivations and Considerations
- Complex Relationships: Owner, Employee, and Family Dynamics
- Purchase Price Approaches: Gifts, Freezes, Soft Terms, and Arm's Length Sales
- Valuation Considerations for Different Types of Family Businesses
- Identifying and Managing Potential Conflicts of Interest
- Capital Gains Exemption Planning for Business Transitions
- Estate Freeze and Redemption Strategies
- Separating Operating Business from Real Estate Assets
- Butterfly Reorganizations for Tax-Efficient Transitions
- Valuation Discounts and Their Impact on Succession Planning
- Overview of New Intergenerational Transfer Rules
- Immediate vs. Gradual Transfer Options and Requirements
- Substantive Conditions for Qualifying Transfers
- Joint Election Requirements and Liability Considerations
- Extenuating Circumstances and Exceptions
- Peter, Paul and Mary Case Study: Transitioning to Active vs. Non-Active Children
- Analyzing Different Business Types and Values (F1, F2, F3 Companies)
- Implementing Redemption Programs and Payment Structures
- Calculating Time Horizons for Complete Transitions
- Refinements to Basic Succession Strategies
- Potential Pitfalls in Intergenerational Transfers
- Use of Trusts in Succession Planning: Limitations and Opportunities
- Reversible Freeze Strategies for Flexibility
- Family Law Considerations in Business Succession
- Protecting Parents from Retroactive Tax Consequences
Seminar Snapshot
This course provides guidance on transitioning family businesses to the next generation. You'll learn how to evaluate different succession approaches, implement tax-efficient strategies, and navigate the new intergenerational transfer rules. Through real-world examples, you'll develop the skills to structure transitions that balance family dynamics with optimal tax outcomes.
This course is for you if you are responsible for:
- Advising business owners on succession and transition planning
- Structuring tax-efficient transfers of family businesses
- Implementing estate freezes and corporate reorganizations
- Navigating complex family dynamics in business transitions
- Ensuring compliance with new intergenerational transfer rules
Meet Your Presenters

Michael Cadesky
Michael Cadesky is the managing partner at Cadesky Tax and a committed contributor to the tax and accounting professions since 1980, earning the title of Fellow from CPA Ontario. He is a past governor of the Canadian Tax Foundation, past chair of STEP Canada and STEP Worldwide, and past chair of the CPA Canada Tax Committee for Small and Medium-Sized Enterprises. Michael is also the co-author of 11 books on tax subjects and the author or co-author of numerous papers and articles on Canadian and international taxation.

Hugh Woolley
Hugh Woolley is an independent tax consultant who has taught income tax for over 30 years for a number of different professional organizations. Hugh has written courses for CPA Canada and over 10 papers for the B.C. Tax Conference as well as papers for the CTF's National Tax Conference and STEP Canada's National Conference. From 1990–1992 he worked at the CRA's Rulings Directorate in Ottawa writing "butterfly" tax rulings. Hugh is a past Governor of the Canadian Tax Foundation.
Trusted by CPAs and Tax Professionals across Canada
This is a first time for me as well. Your firm was recommended to by one of my friends. Great source of information.
Thank you Mike, Hugh and team! I enjoyed the practical and realistic solutions to various tax issues.
Thank you ALL for such high quality courses and answering the questions in detail! So glad I found you guys!
Thank you very much for the seminars. They are very informative and helpful.
Thank you for the wonderful presentation, materials, and handling of queries as always.
This is my first time taking the Cadesky Tax Seminars. I am learning a lot and watching archived courses too. You have done a great job. Thank you so much!
I really enjoy your seminar series. Your presentations are extremely thorough and you explain complex tax issues very clearly.
The presentations are relevant. The material is easy to follow. Worked examples are excellent. It is a great value.
Be First to Know About New CPD Courses
Stay ahead on Canadian tax developments with timely course updates, expert insights, and early access to new CPD programs.