Maryann Kerr

When you trust your intuition and feed your curiosity you open your soul to learning that will help you soar.


According to positive psychology researcher Michelle McQuaid, lost productivity at work, as a result of “bad bosses” costs the U.S. economy alone $360B a year. Maryann Kerr is on a mission to create well led, kinder, collaborative, inclusive and diverse workplaces where productivity is high, and turnover is low. With a focus on B-corps and the philanthropic sector, the Medalist Group will position your organization to attract and retain the very best talent.

Over 34 years in the philanthropic sector Maryann served multi-faceted local, provincial and national organizations in executive leadership and senior philanthropic positions. Over the course of her career Maryann has worked with outstanding teams of volunteers and staff to raise almost $100 million. Her greatest accomplishment is the community of amazing social change fundraisers she mentors and coaches on a voluntary basis.

Today, Maryann is CEO and Chief Happiness Officer of the Medalist Group a boutique organizational health and philanthropy firm founded in 2006. The Medalist Group conducts all service offerings using an appreciative enquiry approach to assess culture, employee engagement and productivity.

Maryann currently sits as Past-Chair of the Board of Directors, Gilda’s Club Greater Toronto. Member, Board of Directors Next Gen Men. Previous Board experience includes Big Sisters of Toronto, the Toronto Zoo Foundation and AFP Golden Horseshoe Chapter.

Where did the idea for your company come from?

I’ve worked in the social profit sector for 34 years.  The first 25 years of my career were just this wonderful trajectory of what we commonly define as successful:  more responsibility, greater fundraising targets, bigger titles, larger teams and compensation packages and more complex work.

Over the course of the last nine years, I’ve been fired three times.   Ouch. During the same time, I completed a master’s degree in Leadership and I continued to do contract work through my consulting business.  You know with each firing, but most certainly by the third, you have to say to yourself, what is wrong with me?  You spend a lot of time in reflection and with coaches and mentors reliving the minutiae of the experience and trying to put yourself in the shoes of the person who made the decision to let you go.

Part of what you learn when you study leadership is that you must look inwards and figure out what you could have done differently.  You take responsibility for both the way you acted and reacted in an organization as well as the way others acted and reacted in relation to you.  There really is no use saying well if only that boss of mine had done X or Y.  So, I did a lot of thinking and reading and soul searching.

And then a good friend said you know maybe it’s not you.  What?  Maybe it’s not me?  I started to apply what I knew, what I observed and what I experienced in terms of great organizations and ones that were mediocre or toxic.  I saw that there was a very strong link between workplaces with poor leadership and lack of attention to organizational health and culture and the epidemic of turnover in the social profit sector.  I asked myself, my colleagues, my clients: What can we do to make a difference in the sector, address the issue of high turnover and create more human workplaces?  My practice is now firmly focused on the co-creation of kind, collaborative, productive workplaces

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

What I love about what I’m doing is that a typical day is eclectic, energetic and filled with work that is relational.  I spend a lot of time asking questions and listening.  I read a lot.  I connect with my community of practice on Linked In.  I mentor and coach.  I’m driven by what my clients help to identify as their challenges and learning opportunities.  I’m inspired by people who want to change the places they lead to create kind, collaborative and as a result highly productive workplaces.

How do you bring ideas to life?

I believe that listening is an act of love. I do what I can to create environments where the wisdom in the room is given space to emerge. I think the answers we are looking for are usually right in front of us we just rarely have the creative space and time to allow them to surface. Ideas are the easy part. Execution – now that’s another story!

What’s one trend that excites you?

I’m fascinated by the concept of B-corps and the B-economy.  I think this idea that we can care about humanity, want a more humane workplace and redefine what it means to create inclusive organizations to address the worlds largest problems and at the same time turn a profit is fascinating.  It marries my entrepreneurial spirit with my desire to advance social change.

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

I feed my curiosity. I read a lot and expose myself to diverse perspectives and disciplines. I read about philanthropy or fundraising or leadership and organizational health, art, urban development, farming, feminism, economics whatever strikes a chord. I try to read alternative opinions to my own to make space for another point of view.

What advice would you give your younger self?

I would tell my younger self to finish school while you don’t have other huge responsibilities in life. I couldn’t afford to finish my schooling in my 20’s and got distracted in College in my role as President of the Student Union. And I’d tell my younger self that as much as I wish it were not the case, and we can list a ton of hugely successful entrepreneurs who never finished school, we still live in a world where the privileged can shut you out as an employee or as an entrepreneur if they don’t buy into who you are based on some really shallow measures like degrees.

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

I believe being able to manage conflict in a team is hugely important. I loathe confrontation but I deeply appreciate conflict. Many believe those two things are mutually inclusive. If you don’t have a great team where vulnerability-based trust is a basic currency, then it is true that conflict is only confrontational. If you have mechanisms in place, developed over time and with a lot of intentionality, to facilitate diverse points of view, you have an organization that is nimble, innovative and highly productive. Most people believe that conflict and confrontation are the same thing. I do not!

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

I trust my intuition and I listen to the universe. I don’t have a huge Linked In community but in the space of one month I went from 1500 connections to 3500. It happened organically because I started to reach out to people who I felt cared about the same things that I did. I started to post about the things I really believe in and suddenly discovered this community of people who were doing incredible work in the very area I was moving towards. That was completely driven by my intuition and by listening to others who could see something in what was happening in my life and offered signs of encouragement.

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

Connecting with competitors. If you work from a growth mindset instead of a sense of scarcity you recognize that there is more than enough work to go around.  Much of my initial success came as a result of referrals from my “competitors.”  Similarly, I want to understand my competitors so well that I know when a job makes more sense for them because I understand the nuanced differences between our businesses.

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

I don’t believe in failure. I believe if we learn something from challenges, then it wasn’t a failure at all. My biggest challenge is finding investment capital and I overcome it by trusting that when I invest in my business, I will ensure a return. I’ve stopped looking externally and plan my investments so that I can afford them personally. I don’t have a desire to scale my business into a huge organization. I want to stay small and local and change the world one client at a time.

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

I would love to see someone come up with a way to digitize and monetize the business of coaching and mentorship.  I’ve seen some attempts but don’t think anyone has really figured it out fully. You can get apps that do this in the fitness space, and you can get a bit of this in terms of daily business affirmations but deep coaching and mentorship which is a very personal journey is not there yet.

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

I upgraded my train ticket to Business Class so I could sleep for a few hours!!

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

I love SurveyMonkey. It allows me to check in with clients and potential clients and gather data that helps me make data driven decisions.

What is the one book that you recommend our community should read and why?

My favourite book is The Alchemist by Paulo Coehlo. I think everyone should read it because there are lessons on every page that apply to all aspects of our lives. And read it more than once. I think depending upon where you are in life – you get something different out of it every time.

What is your favorite quote?

“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” Maya Angelou

Key Learnings:

  • When you trust your intuition and feed your curiosity you open your soul to learning that will help you soar.
  • When you co-create kind, collaborative, respectful workplaces the result will be enormous engagement and productivity.
  • Read, read and then read some more and don’t focus on only one kind of book or one area of interest. There is no better way to open your mind to possibility.
  • Add The Alchemist to your reading list and relax into the idea that if you watch for the signs, the universe will conspire in favour of your dreams.