Jennifer Mathers McHenry is the Managing Partner of Mathers McHenry & Co.

Jennifer obtained her LL.B. from the University of Windsor in 2003 and her LL.M. from the University of Toronto in 2004.  She has since practiced in the areas of employment and commercial litigation at two premier litigation firms in Toronto. She founded Mathers McHenry & Co., a boutique firm focused on executive employment and workplace law, in 2019.

Jennifer regularly advises both executive and other senior employees and employers about employment law and with respect to all aspects of the employee/employer relationship, including: offers of employment, human rights obligations, changes of control, mergers and acquisitions, executive compensation, resignations, termination of employment, constructive dismissals, and post-employment fiduciary and contractual obligations.  Jennifer also frequently helps senior executives navigate investigations and interpersonal and other complexities that regularly present themselves in the context of the employment relationship, all with an eye on their legal rights and options.  Her litigation practice encompasses a wide range of complex employment and workplace-related commercial and appellate litigation, including actions involving wrongful and constructive dismissal, breaches of human rights legislation, breach of contract, professional negligence, breach of confidence, unfair competition, negligent misrepresentation, partnership disputes, and shareholder disputes.

Jennifer was a founding member of the Advocate’s Society’s Employment and Labour Law Practice Group, and is a regular speaker in schools, for continuing education programs, and in the media on matters pertaining to employment and executive employment law. This winter term Jennifer will be teaching as an Adjunct Professor at the University of Toronto Faculty of Law in its “Law of Leadership” LLM program. 

1. How did you get involved in your current area of practice? 

I didn’t quite fall into employment/workplace law, but I didn’t set out to do it either. I started out as a commercial litigator and I loved it, but didn’t love the fact it is very hard to build a self-sustaining practice in that area of law.  So when I started looking for a new role I wanted something that would be just as engaging but would let me be a bit more entrepreneurial and take the lead both on practice building and on files a lot earlier in my career.  Employment law with an executive focus ticked all those boxes. 

2. What qualities and/or skills are important for leaders?  

First, real leaders are not abusive. As a profession I think we let powerful rainmakers get away with a lot and that needs to stop. Once we get past that very low threshold, I think a good leader provides not only support but sponsorship designed to make those she works with not just profit centers but future leaders themselves; she will let those around her shine and help them do it; and she will give credit to those under her who earn their success (we all had help getting started, whether it was a referral of clients or hours of factum editing, and it is important to remember that).

3. What qualities and/or skills do you look for in a junior? 

Smart is the entry level criteria so that almost goes without saying, but it is too important not to say. I also look for people who I want to spend time around. That doesn’t mean they need to be someone I’d be friends with outside the office (though obviously that’s nice), but does mean they have to be someone I like, trust, and know has values about the profession and practice that are not in conflict with mine. I want to work with people who are successful because they care deeply about the work they do and the clients we serve such that they will insist on excellence from themselves, who practice with integrity, and who are frank and direct, both with me and in their communication with clients and other counsel. I also want someone who more often than not makes my life easier instead of harder.

4. What advice would you give a young woman starting her practice? 

1) Learn as much as you can and remember that no one knows what they are doing when they first start out. 2) Don’t be afraid to ask questions but only ask questions you can’t answer yourself. 3) Network and more importantly remember the world is small but our profession is a whole lot smaller. The person on the other side of a file may be someone you encounter repeatedly, or he or she may be someone from whom you someday get a reference or a referral. Advocate for your clients and beat the other side, yes, but don’t do it by being sharp or even needlessly difficult. I truly don’t believe that serves the clients well and it definitely doesn’t serve you well in the long term. 4) As a junior your role is to treat the partners or your bosses as your clients – the easier you make their lives the more indispensable you become as a colleague (as it happens, this also applies to judges – make their life easier by colour coding, being organized, thinking ahead about what they need to have in front of them, etc).

5. What advice would you give a mid-level junior looking to advance her career? 

1) Be strategic and pro-active about where your career is going and what skills and other assets you need to get where you want to go and to have options available to you. Don’t be passive about getting what and where you need to be and carve out the time to figure out what those things are! 2) Find sponsors and mentors. This profession can be tough but it is filled with fantastic people who are willing to help each other out. Access that. 3) Remember that there are always options. You are never truly stuck.

6. What can we do to address the continued attrition of women in law?  

First, we can ensure people recognize that their options are not binary. I think many people look at it as stay in a firm I’m unhappy in or leave law (private practice, especially), stay in a model I’m unhappy in or leave law, stay in abusive environment or leave law, stay in the status quo or leave the area of practice, stay and work 90+ hour weeks or accept less interesting work, stay on Bay or leave the area you work in. I no longer think that is our reality. Lots of firms are out there doing things differently. Lawyers often negotiate for a living yet when it comes to negotiating a structure for themselves feel hemmed in by the “way it’s done”. Lawyers, toss that thinking (and firms, let them!). 

Second, and I don’t mean to imply this is pervasive or the key reason we’re losing women, but we as a profession can stop tolerating terrible behaviour and that will help – personally I will not seek to work with or refer work to anyone I know to be abusive to those he or she works with. That should not be revolutionary, but if it were the norm I think law firms would become better places to work because the rainmakers who are abusive (and we all know they exist) only have power while they make rain.  

7. If you could give yourself one piece of advice when you were starting out in law, what would it be? 

This may sound arrogant but honestly I’m happy with my trajectory so I would not suggest I do anything differently. I think I would tell my younger self to relax a bit when things were not going as planned – I really do believe there are many paths to a successful and satisfying career. In another life I’d have been a very happy M&A lawyer or gone into business.  Leaning into the idea there is no one way to be happy in law is freeing.

8. Is there anything else (advice, an interesting experience, tips, etc.) that you would like to share with our members? 

Succeed with positivity. Lift people up. Do it every opportunity you have.  Help students behind you. Send referrals to colleagues you know are good.  Tell the reporter who calls you that you can’t answer their question but give them someone who can. Decline work you are not able to do well and give it to someone who can. Give your colleagues credit for their wins and their contributions to yours. Appreciate the people who work with and for you and make sure they know it.  As Lizzo says “If I’m shinin’, everybody gonna shine.” I love that and consider it my unofficial firm motto.

This post is part of YWL's Managing Partner Series. This series features Q&A-style blog posts where women managing partners from small, mid-sized and large law firms answer questions about their path to success and share their advice for young women in law.