Interviews
John DiMichele: The Change Agent
April 25, 2025
By Arianna Marino
The Toronto Regional Real Estate Board (TRREB) is Canada’s largest real estate board, serving over 70,000 REALTOR® members across the Greater Toronto Area (GTA) and beyond. TRREB is a not-for-profit corporation founded in 1920 by a small group of real estate practitioners, with the vision to provide an inclusive, supportive, and connected organizational community that anticipates Member needs and expectations for years to come. The board also actively engages in government relations and housing policy advocacy, working to promote sustainable homeownership and fair real estate practices. At the helm of this organization sits CEO John DiMichele, bringing over two decades of industry experience and technology expertise to the role.
DiMichele’s career began as a real estate broker and manager before joining TRREB as Chief Information Officer in 2002, where he led major technology advancements. Since becoming CEO, he has championed initiatives to protect MLS® data, enhance privacy, and modernize real estate infrastructure. He launched TRREB’s Market Year in Review & Outlook Report, driving key conversations on housing supply, affordability, and economic growth. He is also the visionary behind PropTx Innovations Inc., TRREB’s technology subsidiary, and a leader in the Future Facing MLS® initiative. In our conversation, DiMichele shares his candid thoughts on the industry and what the future holds for MLSs, as well as his approach to leading TRREB to create meaningful impact.
A Tech-Driven Journey
How did you get involved with the MLS-PropTech industry?
I’ve been passionate about technology since my university days, as the school had a world-renowned computer program. I realized that business was not keeping up with new tech, so I started improvising and applying what I knew with what was available. I bought a laptop as soon as they were available and realized how powerful these new tools could be for business. For example, there was no remote access to the computer system at the Real Estate Board, so I adapted existing technology and created remote access for myself.
What inspired you to pursue a career in this industry?
It was more circumstance than inspiration. As a Broker, I used technology as a tool to help usher in a new era in this business. I was the first Broker (that I know of) to drop Cat5 cables at all REALTORS®’ desks, forced salespeople to buy laptops, and got rid of all but one shared computer.
Our market share went from being in the 20s to number 4 in our market area in less than 8 months. Shortly after that, I was recruited for the CIO role at TRREB and was charged to bring in a new MLS system. While in that role, I also spent 12 years as a member of the national MLS and Technology Council that was responsible for realtor.ca
How have your previous experiences shaped your approach to your role as CEO?
TRREB leadership provided me with the confidence and support that allowed me to bring in new tech solutions to solve age-old problems—and we were successful. For example, strong authentication and the CONNECT system (I created the architecture for an advanced data-share type platform) that required no data transfer. This would prove to be effective, efficient, and exciting (The cost per user was .36 cents per member per year!)
Who or what has been the most significant influence on your career, and why?
TRREB’s former CEO Don Richardson. He was truly a brilliant and genuinely good person. He was a great thinker and could see things most people could not. Don was incredibly supportive and a calming influence and would always offer sage advice while allowing me to be creative and take calculated risks.
What personal traits or skills have been most instrumental in your career progression?
Creativity, flexibility, and always listening to those I work with—as they are all much smarter than me.
Can you discuss a recent project or innovation that you're particularly proud of?
The founding of PropTx Innovations Inc. In the last 10 months, we have added 14 associations to our PropTx MLS platform. This was an unprecedented project and it was not an easy lift. The work continues.
Leaders Have to Lead
What is your leadership style, and how has it evolved?
I try to lead by example and work to be supportive of my team. It has evolved into a more motivational position. When someone comes to me with an idea, and they believe in it, I make sure they have every opportunity to be successful.
What role does mentorship play in your leadership, and how do you mentor others?
That’s a daily thing. I do not force it, but leaders have to lead. Leaders also have to be visible so I will go to them. I try to foster an environment of collaboration and open conversation and know that I’m available to them for any reason or discussion.
How do you approach decision-making and strategy as CEO?
Depending on the matter to be decided, I gather and have at hand all the information available and then discuss with the team and a selection of those that would be impacted. Once we’ve had the opportunity to consider all aspects, we will decide accordingly. Sometimes it does come down to my decision alone; however, I believe that the difference between success and failure is in making informed decisions and adjusting accordingly. My mantra is “evidence-based decision-making; NO guessing.”
What do you believe is key to maintaining a productive and happy team?
Allow them the ability to express themselves in all ways. Encourage them to be creative. Listen to them. Help them grow. Allow for work/life balance. Ask them if there’s anything they need, and if there is, do whatever you can to accommodate (within reason).
What strategies do you use to build and lead successful teams?
Empower the team lead, as they are the ones that do the heaviest lifting—so they can surround themselves with the right people.
How do you ensure diversity of thought and perspective within your team?
They have the opportunity to be creative and take the initiative. In other words, there is no such thing as a bad idea.
What advice do you have for emerging leaders in the industry?
If you have a vision or a thought about this industry as a whole, talk about it with your peers no matter what it is. This is how great things begin. Never be afraid to bring forward a new idea or decommission something. Be a change agent.
Looking Ahead
What do you think are the biggest challenges facing the MLS industry today?
Government intervention. Specifically, the fact that the incredible value of the local MLS is taken for granted and that it is not understood or respected. We all need to work hard to change that in the minds of all participants, the consumers, and those that govern.
What is a common misconception about the MLS industry that you’d like to clarify?
The MLS is taken for granted and it is undervalued. It is the engine that allows the industry to provide accurate, timely, complete, current data to the trusted professional so they can advise their clients and help them make a confident decision—whether they are buying or selling property.
One other element is critical; the MLS is accessible. The real estate market never closes and the MLS system has to be there.
What's your prediction for the next big disruption in MLS or real estate technology?
I still believe we will see blockchain in the industry.
How do you approach adapting to changes and disruptions in the business landscape?
I’ve been described as a “change agent.” Depending on the disruption (if there is any aspect of a controlled response) it's always better to try to see a glimmer of positivity. You can build on that positive and you’d be surprised as to what could evolve.
What’s one outdated practice in the real estate industry that you’d like to see change?
There are so many. Generally, I believe professionalism is undervalued and bad actors should not be allowed to trade.
If you could reimagine one aspect of the real estate industry from scratch, what would it be?
The lack of respect, protection, and control of the data. This consumer information is private and confidential and it should be treated as such.
One of the most under-discussed challenges right now is data security and protection. The protection of IP and copyright is one of the highest expenses in our shop. We could all be doing better in that area.
In your opinion, what is the most underrated tool or technology in real estate right now?
The MLS itself is taken for granted. Turn it off for a day or two and let’s see what happens.
Beyond the Boardroom
What's the best piece of professional advice you've ever received? “You can’t do everything.”
How do you balance work and personal life in such a demanding industry? I don’t.
Do you wish to share anything about your family?
They are extremely patient!
What do you do to unwind or relax after a busy week?
I work out and play music as much as possible.
If you could spend a day with any historical figure, who would it be and why?
There are a few; however, I’ll say Winston Churchill, because in the face of the greatest threat he still made difficult decisions.
Can you share a surprising fact about yourself that not many people know?
I was a pretty good varsity level athlete. Also a squash pro!
What’s a skill or hobby you’ve developed outside of work that has positively influenced your professional life?
I play the guitar and sing. It's the best distraction as it takes me into a completely different mind space. Freeing your mind from daily concerns for a short while helps to relieve the angst and welcomes fresh thoughts.
What motivates you to keep pushing boundaries in your career?
All the people around me and the opportunity to make a real difference.