Taxing Tax Issues for the Sole and Small Firm Lawyer: Part 1 - Family, Employment

Taxing Tax Issues for the Sole and Small Firm Lawyer: Part 1 - Family, Employment

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CPD Accredited Credits
Professionalism: 0.75
Mark DeGroot
Kara Denny
Tannis Waugh
Toronto Lawyers Association (TLA)
40 minutes
$89.00 plus tax
Includes Handouts

Tax issues are what keep the sole and small firm lawyer up at night.  Issues that have crossover application into different areas are the most challenging.  This program will address tax topics that commonly intersect in family, estates, real estate, and employment law.

Mark DeGroot, DeGroot Family Law

  • As far as professionalism is concerned: I can address the sham issues with CRA that we discussed. Much of my discussions of the points also concern competence – as it will be information about what to watch out for in addressing common practices.
  • As it concerns Estates: I will discuss estate freezes and how they are treated for equalization purposes. If you are not careful, the estate freeze can be found to be a sham and set-aside for equalization purposes. Steps can be taken to avoid this from happening.
  • As it concerns Business: I will discuss how incorporating a business can be used for effective tax deferral purposes, however, care needs to be taken when incorporating and running the business. There may be a need to ensure a constructive or resulting trust in the business cannot be made out by a spouse. Further, how retained earnings in a corporation are treated in family law when addressing support.
  • Estates/Real Estate: a common practice by parents is to name their children as joint tenants on cottage properties to avoid probate. This tax planning can have unintended impacts on the child’s equalization obligations if precautions are not taken, such as marriage contracts – specifically, if the property is found to be a matrimonial home, the child must include it for EP purposes and cannot claim an exclusion (large financial impact) – further, there are certain rights that arise to the ex-spouse as it concerns matrimonial properties.
  • With that in mind the description of my section could be described as: Discussing basic tax principles in family law and the unintended impact tax planning in estates and business can have in family law as it concerns support and equalization.

 Kara Denny, Rapley and Company

  • Advising clients in precarious, short-term contracts of their rights and/or obligations
  • Advising business/corporate clients and individuals of their income tax obligations should the relationship be re-characterized (i.e. retroactive payment of Employment Insurance, CPP, and/or repayment of ineligible deductions, etc.)
  • Identifying the “true nature” of the relationship (employee/independent contractor/dependent contractor) by looking beyond the contract (Competence)
  • In the current economic climate retaining independent contractors, rather than hiring full-time employees, is an attractive option for companies.  Tax law plays a principal role in determining whether an individual is an employee, an independent contractor or something in between. While the relationship may be “re-characterized” at any point, the true nature of the relationship may become particularly meaningful upon its termination. This presentation will briefly examine the potential tax implications associated with mischaracterizing the relationship, with a focus on litigating issues of reasonable notice and wrongful dismissal. It will include a review of the relationship hallmarks lawyers should look for when assisting clients embroiled in employment disputes and provide an overview of the income tax considerations they should be aware of and advise their clients of when negotiating settlements. 


Barrister and Solicitor Mark DeGroot

Mark practices as a sole practitioner exclusively in family law.  He began his career at a large, national law firm where he worked primarily on family law matters. He subsequently joined a boutique family law firm in downtown Toronto where he gained extensive experience in both simple and complex family law cases. This experience ranged from amicable separation agreements to high-conflict divorces, which required hearings at all levels of court in Ontario, including the Ontario Court of Justice, Ontario Superior Court of Justice, and the Court of Appeal for Ontario. 

Kara Denny

Kara is a civil litigator with Rapley & Company and is experienced in the trial, defence and prosecution of medical malpractice, professional negligence, motor vehicle, personal injury, occupier’s liability, breach of contract and product liability claims. She has appeared at every level of Ontario Court, in a number of administrative tribunals, and in hundreds of mediations.

Kara earned a Bachelor of Science (Hons.) in psychology at the University of Toronto and worked as a social worker for several years before attending Osgoode Hall Law School and obtaining her Bachelor of Laws in 2008. While at law school Kara worked as a research assistant and for Legal Aid Ontario and has previously worked at the Ministry of Finance as a senior tax advisory specialist prior to Rapley & Company.

Tannis Waugh

Tannis WaughTannis was called to the bar in 2003 and practices in the areas of real estate, corporate/commercial, and estate planning. She practiced in a boutique firm in Toronto for three years before becoming a sole practitioner.

As a former Trustee for the Toronto Lawyers Association, Tannis has been involved in advocacy and education initiatives, most notably the moderator and presenter of continuing education programmes and writer of articles for the TLA journal.

She is also a member of the Condominium Sub-documents Committee of the Working Group on Lawyers and Real Estate which is responsible for producing province-wide precedent materials for condominium transactions.

Tannis is a frequent presenter for continuing legal education programmes and, in the past, has spoken on the issue of real estate, estates and ethics for the Canadian Bar Association, Ontario Bar Association, Law Society of Upper Canada, and the Toronto Lawyers Association.

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