Leaders List interview: 60 seconds with Margaret O’Sullivan

Date: 28 Feb 2024

Ashleigh John

This week’s 60-second piece is dedicated to Margaret O’Sullivan, Managing Partner of O’Sullivan Estate Lawyers.

Tell Citywealth readers a bit about your role.

I am the Managing Partner of O’Sullivan Estate Lawyers LLP, a Toronto-based boutique trust and estate law firm I founded over 25 years ago. I have a full legal practice but also executive oversight of the firm’s administration and strategic objectives working with our business manager and the admin team.

What does a typical day look like for you?

A typical day is full of multitasking. Dealing with an endless flow of emails, interspersed with video calls, telephone calls and in-person meetings and juggling a lot of different priorities, including the general running of the firm. It is often a long day, but never boring and always something new!

Tell us about some recent, interesting client instructions.

Many of the matters I deal with have a cross-border or multi-jurisdictional slant to them. A recent estate planning matter involved several jurisdictions in which the client had assets in Ontario, the U.K., Italy, an U.A.R., Spain and a Cayman trust. There was a lot of complexity and interesting legal issues in navigating through all of the issues and dealing with the various family members.

What challenges do your clients face and how are you helping your clients to overcome them?

Some of the challenges my clients are facing are more and more tax compliance, changing rules which often are not carefully drafted resulting in reporting obligations which capture too broad a group of taxpayers, not just the ones who are the target of the new rules. It is increasingly harder for clients to keep on top because their professional advisers are also struggling to do so as well so they can properly advise them, often in too short time frames and without adequate guidance from tax authorities.

What is your proudest professional achievement?

It is hard to identify my one proudest professional achievement, but being nominated for [Outstanding Individual of the Year – Powerwomen Awards] is one of them, but in general terms, I am proud to have so many great clients and the honour and satisfaction of being a person they rely on and look to guide and advise them on many important and sensitive issues.

What do you consider to be the most important attributes for a leader?

The most important attribute for a leader is being humble. Being humble keeps you in touch and flexible so you can lead from the ground up with strength. Keeping calm and measured is important, in assessing a difficult situation, then deciding on a course of action. Having confidence is key to being able to be effective and obtain good solutions.

Who do you most admire and why?

I admire many people, including my wonderful husband because he always has great insight, knows what is truly most important in life and is very principled. In terms of famous people, I have to hand it to Winston Churchill. When I think of how he led his country and the world to great victory under such adversity, I always get a lump in my throat.

Where was the last place you travelled to for work or pleasure?

My last trip was to our condo in the Florida Keys over the holidays where we enjoyed lots of good family times, sunshine, the ocean and generally just chilling.

If you weren’t in this industry, what else might you be doing?

If not a lawyer, I have always thought being a discretionary investment advisor would be challenging and interesting and would put you in the center of understanding the macro geopolitical and economic events and their impact on markets, but as well the micro side of dealing with many interesting private clients and having long-term relationships, which I also enjoy in my law practice.

How do you relax after a long day?

After a long day, I like a good dinner, some nice conversation with family and a couple of times a week my personal training. After that I am completely relaxed, come Friday night, I look forward to coming home and sharing a nice glass of red wine with my BF husband.

You can view Margaret’s profile on the Leaders List here.