Keith Serry / Consultant and social entrepreneur

Keith Serry likes to introduce himself as, in order of importance, a father, husband, lawyer, communicator and entrepreneur.  After a few years as a litigator and general counsel for a charity, Keith returned to his career in consulting in 2014.  His company, Conseil Keith Serry Inc., supports innovators in both for and not-for profit sectors who are trying to improve their bottom lines and get their messages heard.  In addition to his own company, Keith has founded/co-founded several NGOs, including CJAM (the Montreal Artists' Legal Clinic) and, most recently, The Fact Project. 

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Let’s start with the basics. Did you always imagine yourself going to law school?

In a word, nope.

I guess part of going to law school at 36 (or changing careers that “late” in life) adds plenty of unexpected to the mix. I was really fortunate to get the opportunity to go to McGill at a point in my life where a transition was necessary. I had just moved to Montreal to be with my then girlfriend (now my wife) and was faced with the challenge of “what’s next”. To move from Ottawa to Montreal I had shut down my business (I was a public relations and corporate communications consultant) and try to restart in a new city, in a new language and – given that PR is often a business based on your contacts  – with an empty rolodex. 

To a certain extent, I had always thought about a legal education, but it never would have happened had this transitional opportunity not presented itself. (Oh, and I seriously considered doing a PhD in music cognition in Daniel Levitin’s lab instead, but I guess that’s a anecdote for another interview)

What makes your career lawfully uncommon?

My career is lawfully uncommon because I’m lucky enough to get to pick my spots. My consulting company (Conseil Keith Serry Inc. where I do government relations/regulatory/sundry strategic consulting) has sufficient revenue that I’m able to chose my legal clients and pro-bono engagements on a “do I care about this?” basis instead of a “do I need this to pay the rent?”  basis. I also have a partner with a good career which allows our family the financial security for me to take risks.  Anyone who doesn’t acknowledge the role good fortune played in their success is not to be trusted.

At what moment did you realize that you wanted to switch gears?/At what moment did you realize that you wanted to do law your own way?

There are two answers to this question. The first is “within 24 hours of starting as a summer student at my first law firm”. The second is more subtle.

Like many law students I spent a lot of time and energy in the course au stages process, suspicious that big law life might not be for me but not wanting to “knock it until I tried it”. At my first day walking into my downtown office, I was hit with a “this isn’t you” feeling. It wasn’t a knock on anyone there, just that elusive “fit” problem.

I ended up doing my stage and my first few years of practice at a smaller firm. At IMK I was surrounded by some of the smartest, friendliest, most professional lawyers in the business. I felt fortunate to work there and was still bummed that it wasn’t a great fit: I didn’t see enough of my family, the work was intellectually stimulating but not necessarily socially rewarding and I had a tough time adjusting to litigation culture.

I moved on to a GC role in a non-profit for a year and ended up (nearly 10 years after I’d left consulting) back, in some ways where I started and in many ways where I belong.

What got your juices flowing or tickled your fancy while at law school?

I am a social animal to a fault. Law school was fantastic because I was surrounded by dozens of smart, socially-engaged, articulate people. Interacting with them, learning from them and being inspired by them was a treasure.

Some of the profs were pretty good, too. Oh, and law firms that brought Schwatz’s to Coffeehouse.

What made your blood boil or made you snooze while at law school?

My blood doesn’t boil very easily, but, I think people should be reminded of how fortunate they are. I grew up with very little and, in my 20s, wouldn’t have conceived of a law school education as a possibility. Ambition is learned and taught. If you’re the typical law school student, you’re there in large part not only because of the work you put in, but also as the product of everyone who helped you get there; everyone who contributed financially or socially to your ability to conceive of yourself as talented/smart/hard working enough to go to and complete that education. When you go on to whatever your legal education grants you, spare some thought for that good fortune and act/live/spend accordingly.

Do you still see law all around you?

I’m tempted to pour one out for Mary Tyler Moore here.

Sure, but not in the way I did in law school. When you’re studying you are intensively thinking about law – particularly written law – and the strands that it weaves into everything. My life and career are more frequently spent thinking about what I guess was called “legal pluralism” in law school: how rule-based social interactions are and how much or how little we can predict the behaviour of others based on those rules.

You are at a coffee house speaking to a first-year law student. What advice would you give them? Please provide your answer in a tweet. Yes, that means 140 characters and hashtags.

@keithserry Play it right and these will be some of the most rewarding years of your career, but don’t worry. No need 4 answers yet #trusttheprocess

What is the day in the life of Keith Serry look like?

Today’s a Monday and my schedule looks like this (it’s not typical, but few are):

  • 5:00 (ugh) get up
  • 5:10 Espresso
  • 5:30 Cab from home to train station
  • 6:10 Train departs for Ottawa
  • 6:10-8:20 On the train, review: drafts of correspondence from a client CEO regarding a funding proposal; power point deck that will be delivered by a client later that day to government officials; and, comments made by colleagues on a presentation I’ve developed for a new NGO (The Fact Project, an organization dedicated to the promotion and defense of fact-based public discourse); and reply to email regarding a talk about music publishing and royalties I gave on Saturday for CJAM (the Montreal Artists Legal Clinic) at Pop Montreal’s music business workshop.
  • 8:45 Hotel check in. Room is ready early (score!)
  • 9:00 Walk to first meeting of the day at the offices a government relations firm. Meet of one of my clients there (“A” is the Chief Commercial Officer of a biotechnology company) to prepare for the presentations A will give to government officials throughout the day.
  • 11:00 Meeting at the Ministry of Finance. A’s presentation goes swimmingly.
  • 12:00 Lunch at the Whalesbone. Great chowder.
  • 14:00 Meeting at the PMO. Run into Mathieu Bouchard (the Prime Minister’s chief QC lieutenant, and one of my former bosses at IMK) while waiting in the lobby.
  • 15:00 Meeting at the Ministry of Innovation Science and Economic Development.
  • 16:00 Back to the hotel. Reach out to members of the Fact Project’s Ottawa organizing committee (including McGill law alumni David Groves) about our upcoming Ottawa launch meeting. Make arrangements to have coffee with him tomorrow.
  • 17:30 Beers with A and the head of the Canadian Stem Cell Foundation.  I’m concentrating on the conversation despite the fact that the TSN ticker is announcing that my favourite hockey team (the Ottawa Senators) has traded a hot young prospect for one of my least favourite hockey players (Alex Burrows).
  • 18:30 Dinner with A at North and Navy. Debrief the day and plan tomorrow.
  • 20:30 Back to the hotel, watch the Sens get pounded by Tampa. Facetime tuck ins back home. Do physio (wrecked my shoulder in the gym last summer and the reduced physical activity has made me a little crazy). Try to read a few pages of Tim Wu’s The Attention Merchants before.
  • 23:00 Sleep. 
Photo of Keith from his law schools days. Group shot of his Laskin Moot team. Keith says his team mates are all super heroes, as they now include, from the left, Owen Ripley, now Chief of Staff to the Deputy Minister of Heritage, Stephanie Bachand, now Deputy Director of Human Rights and Indigenous Affairs Policy at Global Affairs Canada and Palma Paciocco, now an Assistant Professor at Osgoode Hall.

Photo of Keith from his law schools days. Group shot of his Laskin Moot team. Keith says his team mates are all super heroes, as they now include, from the left, Owen Ripley, now Chief of Staff to the Deputy Minister of Heritage, Stephanie Bachand, now Deputy Director of Human Rights and Indigenous Affairs Policy at Global Affairs Canada and Palma Paciocco, now an Assistant Professor at Osgoode Hall.

If you were given the blessing and curse of an extra hour every day to do whatever you wanted, what would it be?

If I was given the hour conditionally in exchange for a guarantee that I used it for physical fitness (yoga, gym work, bike riding) I would accept it gratefully.

Any regrets? (Yeah, we are retrospective like that).

That’s broad.

Career wise, not many. Situations I have regretted usually revolve around me taking the easy, obvious opportunity instead of working harder to demand/chase the thing I really want.