Malcolm MacKillop

Build relationships; always tell people the type of work you do and only spend time with those clients who you enjoy being with. Your time is valuable.


Malcolm MacKillop is a founding partner of Shields O’Donnell MacKillop LLP, which is a boutique labor and employment firm based in Toronto, Canada. He specializes in employment law, and has built a strong background in a variety of legal areas throughout his career. Over the last 30 years, Malcolm has had the opportunity to work as a successful trial lawyer, professional speaker, professor of law, and has worked as an author of several law texts. His most notable texts include Employment Law Solutions, Creative Solutions, and Damage Control.

Malcolm MacKillop earned his law degree from the University of New Brunswick Law School, graduating in 1983, before being called to the Newfoundland and Labrador Bar in 1984. He would go on to work as a columnist for the St John’s Evening Telegram, where he was able to discuss relevant issues on employment law. In 1986, Malcolm passed the Ontario Bar and was able to gain invaluable experience as a trial lawyer in employment and labor law after accepting a position at a large Bay Street law firm.

Malcolm MacKillop’s experience in law has provided him with a wealth of knowledge across a variety of topics. Malcolm’s expertise allows him to provide employers with strategic employment-related advice and to litigating disputes including just cause, wrongful dismissal, constructive dismissal, human rights, occupational therapy health and safety, employment standards, and fiduciary litigation. He has been included as a guest speaker on several television and radio programs, including The Fifth Estate; W5; CBC – The National; CBC – The Journal; Pamela Wallin Live; CBC Radio; and 680 News. Malcolm’s wealth of knowledge and extensive experience make him a trusted source in employment law in Canada.

Malcolm MacKillop has built a strong reputation for himself through his work at Shields O’Donnell MacKillop LLP. He has been named as one of the Top 500 Lawyers in Canada by Lexpert since 2008 and was listed as a leading employment law practitioner in the Guide to Best Lawyers in Canada in 2012. In 2016, Malcolm was awarded the coveted Randall Echlin Mentorship Award for his continued work and advocacy.

In addition to his work in employment law, Malcolm MacKillop is also committed to philanthropy and has had a profound impact on those in need. He is one of the co-founders for the Lawyers International Food Enterprise (LIFE), which helps to raise awareness of child poverty across Africa. In 2011, LIFE was awarded the Zenith Award, which recognizes philanthropy efforts that have an international impact. The LIFE organization has not only helped thousands of children living in Africa, but they have raised over $600,000.00.

In addition to his work with LIFE, Malcolm MacKillop is also an active member of the “Feed the Hungry” program, which is run by The Law Society of Upper Canada. He provides financial support and serves weekly meals to homeless individuals. In the past, he has served on the board of the National Ballet of Canada, the Toronto Human Resources Professional Association, and the National Club.

Where did the idea for Shields O’Donnell MacKillop LLP come from?

My partners and I realized an opportunity to create a small dynamic management-side employment and labour boutique where service and quality of work were our two main objectives.

What does your typical day look like and how do you make it productive?

I start every day with an exercise where I can plan out my day before I arrive at the office. When I arrive I create an urgent to-do list so that I can ensure urgent client needs are met as soon as possible.

How do you bring ideas to life?

I encourage all of my team members to come up with new ideas and to propose any ideas for discussion.

What’s one trend that excites you?

The legal profession and delivery of services are rapidly changing. As a small, highly effective professional service firm it is very exciting to be at the forefront of these changes.

What is one habit of yours that makes you more productive as an entrepreneur?

I try to get at least several hours every day of quiet, uninterrupted time and I schedule my calls with clients.

What advice would you give your younger self?

Have a vision of where you want to be – 5 years; 10 years and 15 years – and think about what to do to get there and set reasonable yearly goals.

It’s not a race; it’s a journey.

Tell us something that’s true that almost nobody agrees with you on.

People can change.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Build relationships; always tell people the type of work you do and only spend time with those clients who you enjoy being with. Your time is valuable.

What is one strategy that has helped you grow your business?

Keep in contact with clients once they have career changes. When the client secures another job, they’ll remember the relationship they had with you.

What is one failure you had as an entrepreneur, and how did you overcome it?

Not understanding how people would respond to my opinions; putting yourself in the shoes of the other person is important.

What is the best $100 you recently spent? What and why?

As a firm, we support Feed the Hungry. There is nothing more powerful then serving 400 meals to homeless people. The meals cost more than $100, but the satisfaction it provides is worth every penny.

What is one piece of software or a web service that helps you be productive?

An eclipse is an e-discovery tool that helps us manage document-intensive litigation.

What is your favorite quote?

You miss 100% of the shots you don’t take. Wayne Gretzky