Stephen Gleave


Stephen Gleave, a Hamilton-based lawyer, has become a recognized expert in Canadian employment law. He has practiced law since 1990, litigating many of the country’ most important employment cases.

After many years working at law firm Hicks Morley, Gleave joined DLA Piper (Canada) LLP in 2019, where he’s currently a partner. Gleave’s clients have included organizations in commercial and employment disputes, of which he has handled hundreds of arbitrations. His experience also includes 50 labour and civil injunctions, as well as 50 trials spanning his long career in law.

A member of the Law Society of Ontario and the Canadian Bar Association, Gleave has been repeatedly recognized for his work. That includes a listing in the Best Lawyers in Canada guide, the Best Lawyers Global Business list, and the Canadian Legal Lexpert® Directory for Labour and Employment.

Several of Gleave’s most interesting cases have been covered by news media. As a result, he regularly provides commentary on Canadian employment law cases.

After relocating his practice from Toronto to Hamilton, Gleave now lives with his family on a farm in historic Ancaster. There, Gleave has several outdoorsy pastimes, including raising Highland cattle and farming fruits from the orchard. The rest of the time, he pursues his other interests of agriculture, running and fly fishing.

Where did the idea for your career come from?

It may not sound immediately interesting to many people, but it’s actually a fast-changing section of law to be involved with. Every year, Canada passes new laws that change or add to the existing rules on employment, so that means you have to stay active and up to date, which isn’t true with many other areas of law. More importantly, you’re dealing with a variety of stakeholders in cases like this, and often entire companies instead of just two individuals in a civil case, for example. It requires a lot of research and a lot of in-person arbitration skills. I find it a very stimulating career to be involved with.

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

I love to run, and like many other working professionals I know, it’s become really important for maintaining my productivity from day to day. So I make sure to hit the road with my trail shoes as often as possible.
Aside from that, I rely on the wonderful technology we now have at our fingertips each and every day for scheduling and keeping track of my cases and clients. It’s never been easier to be available, and leveraging that has made life as a lawyer much easier than it often was in the analog days.

What’s one trend that excites you?

Working on my land at home in Ancaster has become a passion project of mine, and I’ve been happily surprised to find out that many people are interested in the work I’m doing with my trees, orchards and bees, for example. More and more people, I think not only in Canada, want to spend more time in nature or more time gardening and cultivating. The planet needs us to do more, and the fact that so many people want to get their hands in the dirt is really motivating.

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

I keep a pretty tight agenda and track everything I do, on a daily, weekly, and monthly basis. Juggling my position as a partner at a law firm with my agriculture work isn’t always easy, so I need to make sure that I’m scheduling my time intelligently to accomplish all the things I need and want to do.

What advice would you give your younger self?

I think many young professionals, myself included, start their careers thinking they need to focus on one thing at the exclusion of everything else in order to get ahead. I’ve since learned that balance has some serious advantages. Spending more time outside in nature, for example, gives my brain a break, and I often find myself processing complex cases at the same time that I’m gardening or completing other tasks on the farm. I would tell my younger self it’s okay to branch out more. You have the time: you just need to manage it.

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

Lots of people in the industrial agriculture industry believe that the trend of at-home gardening and the DIY food movement is just a fad. I believe it’s the beginning of a cultural shift that will continue to spread and grow (pun intended).

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

Learn something new. It can be something small, or it can be something that requires hours of your time, but always be learning something new. It doesn’t have to be related to your job or a way of making money. I think entrepreneurs need a steady supply of new material to keep their brains running fast, and focusing on diverse interests has certainly helped me.

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

Ask for referrals. It’s the simplest, oldest and still the most important thing for finding new clients. Most of the time, when you’ve done a good job for a client, they’re more than willing to help you out. However, you still need to ask. You need to ask them, “Hey, could you recommend me to someone?” Or also, “Hey, would you mind telling me if you know a person or business in need of a similar service?” The vast majority of the time, I get something helpful from exchanges like those, especially when I ask in person. Doing it over the phone or online or in a text just doesn’t have the same success rate.

What is one business idea that you’re willing to give away to our readers?

Pay attention to trends and extrapolate what’s likely to succeed. The best ideas come from research tied to reflection. There needs to be some evidence or basis for why you think a certain product or service is likely to succeed. At the same time, you need an angle that seems obvious in hindsight, but which no one else has thought about or at least executed.

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

I’ll go with the personal example on this one. Every time I spend $100 on my farm, I consider it money well-spent. And I’ve spent a lot more than $100 to improve my trees, orchards, livestock and bees. When you spend money on something that actually makes your land more livable and beautiful for you and your family, it’s impossible to articulate how much that’s actually worth.

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

I’m not sure I have a specific piece of software I can recommend, but I can say that I continue to feel amazed at the ease of finding answers online. Whatever you want to do or learn, there’s seemingly a way to find the information online, usually without paying a dime. There’s probably people out there with much better knowledge of specific technology than me, so I’ll just say that if you want to learn something, don’t wait around for a class or pay a local professional. Learn to do it yourself from one of the thousands if not millions of people handing out knowledge for free, on YouTube or elsewhere.

What is your favorite quote?

“Live in each season as it passes; breathe the air, drink the drink, taste the fruit, and resign yourself to the influence of the earth.” — Henry David Thoreau

Key Learnings:

  • Pursue a diversity of interests and don’t worry so much about specialization.
  • The world is full of free knowledge, from the internet to the public library. Take advantage of it.
  • Always be learning something new.
  • Running works! Find a way to keep moving forward and your career will follow.