Gary Simonsen’s Enduring Legacy: A Retrospective on Leadership and the Evolving Canadian Real Estate Landscape

As the final chapter of a distinguished career at the helm of the Canadian Real Estate Association (CREA) closes, Gary Simonsen, alongside his wife Kathy, embarks on a well-deserved two-month journey through the enchanting Far East. Days after formally stepping down as CREA’s esteemed CEO, the couple traded the demanding pace of industry leadership for the serenity of sun-drenched beaches in Thailand and the vibrant cityscape of Singapore, marking a significant transition into retirement.

Simonsen, known for his forward-thinking approach, emphasizes the importance of a clear break when transitioning from such a pivotal role. “I think it’s important that when you make a change, you don’t just go home and say, ‘I’ll have a coffee and read the newspaper.’ That is going to last for a very short period,” he wisely notes. This sentiment encapsulates a career defined by decisive action and strategic vision, qualities that propelled CREA and the Canadian real estate sector forward for decades.

A Journey Through Canadian Real Estate: From Winnipeg to CREA’s Apex

Gary Simonsen’s journey through the intricate world of organized real estate commenced in 1984, laying the groundwork for what would become an influential career. His early days were spent contributing to the Winnipeg Real Estate Board, where he honed his understanding of the industry’s foundational elements and the critical role of local associations. This initial experience provided him with invaluable insights into the daily operations and challenges faced by real estate professionals.

In 1997, Simonsen’s expertise and leadership potential brought him to Ottawa, where he joined the Canadian Real Estate Association. Over the next decade and a half, he steadily climbed the ranks, demonstrating an unwavering commitment to the association’s mission and its members. His dedication culminated in 2011 when he was appointed CEO of CREA, a role he embraced with strategic fervor and a profound sense of responsibility. As CEO, Simonsen was tasked with navigating a rapidly evolving industry, advocating for Canadian Realtors, and ensuring the association remained a vital resource for its growing membership.

Weeks prior to handing over the reins to his successor, Michael Bourque, Simonsen took the time to reflect on his transformative tenure with REM editor Jim Adair. Their conversation delved deep into the monumental shifts he witnessed and spearheaded within organized real estate (ORE) and the broader Canadian real estate industry. His reflections offer a unique historical perspective, revealing the challenges overcome and the innovations embraced under his leadership.

Navigating the Evolving Landscape of Organized Real Estate

Simonsen’s time at CREA coincided with an era of unprecedented change within the real estate sector. He keenly observed a fundamental transformation in how brokers operate, moving away from a largely uniform approach to a rich tapestry of diverse business models. “When I started, the manner in which brokers conducted business was kind of similar – now there is a real diversity of business models,” he explains. This shift presented a complex challenge for associations like CREA, whose mandate is to serve all members effectively. The complexity amplified as ORE evolved beyond a typical professional association to a critical provider of significant, indispensable business services that members rely upon daily for their livelihood.

The Dual-Edged Sword of Technological Advancement

Technology, Simonsen notes, has been a principal driver of change, profoundly impacting both the role of the Realtor and how ORE itself leverages digital tools. The advent and proliferation of social media, in particular, presented a paradox. On one hand, it offered an unprecedented ability to connect with individuals and disseminate information far more efficiently than ever before. “The ability to reach folks who were difficult to reach before” became a significant advantage, fostering greater community and connectivity within the industry.

However, this enhanced connectivity came with a challenging downside. Social media’s open nature also created avenues for misinformation, allowing “somebody who’s got a crazy wild idea to simply provide misinformation about something.” This often led to “unnecessary churn,” as associations found themselves constantly correcting inaccuracies and managing the fallout from poorly informed debates. Simonsen laments how social platforms, despite their potential, sometimes undermined intelligent discussion, replacing thoughtful, written exchanges with terse, often overly simplistic communications. “Now, people don’t want two written pages, they say just give me a tweet. And that is supposed to capture what can be a pretty complex issue,” he observes, highlighting the struggle to convey nuance in a soundbite-driven world.

The Rise of Adversarial Dynamics and Regulatory Burdens

Beyond technology, Simonsen pinpointed another significant shift: the increasing adversarial nature of real estate transactions. With the evolution of agency, where agents on opposing sides of a transaction represent distinct fiduciary responsibilities, a more contentious environment emerged. This shift impacted not only individual transactions but also, at times, the dynamics within associations, creating a more challenging landscape for collaboration and consensus.

Compounding these internal shifts was a dramatic increase in government regulations across all levels – federal, provincial, and municipal. This regulatory proliferation created new tensions and significant compliance burdens for the industry. Simonsen recites a lengthy list of areas now subject to stringent oversight: “So, from mortgage rules, FINTRAC rules, privacy rules, anti-spam rules, to the regulation of education, dual agency…to a whole bunch of simple things like the signage brokers can use in their community, municipal bylaws – all of a sudden, there are a plethora of regulations.” This explosion of rules meant that real estate professionals and their governing bodies had to navigate an increasingly complex legal and operational framework, demanding constant adaptation and meticulous adherence.

Championing Good Governance: A Pillar of Stability

Amidst these challenges, Simonsen proudly points to one of the most positive internal changes within ORE: a heightened awareness and appreciation for the importance of robust governance. He emphasizes the critical role of “having directors who are well trained, who understand their roles and responsibilities, who can hold folks like me to account, but do so in an appropriate way.” This focus on ethical and effective leadership ensured that CREA remained accountable, transparent, and resilient in a rapidly changing environment, providing a stable foundation for its expansive operations and advocacy efforts.

CREA’s Growth and its Indispensable National Mandate

Simonsen’s tenure at CREA also saw a remarkable expansion in its membership. When he first joined the association, it served approximately 65,000 members. By the time of his retirement, that number had almost doubled to 124,000, and it continues to grow, though the association anticipates a stabilization in the coming year. This significant growth underscores the increasing professionalization of the real estate sector and CREA’s vital role in supporting its members nationwide.

Looking two decades into the future, Simonsen firmly believes that advocating for the industry will remain CREA’s fundamental “raison d’être.” “There is nobody else who can play that role on a national basis,” he asserts, highlighting the unique position and responsibility of the association to represent the collective interests of Canadian Realtors on a national stage, influencing policy and shaping the industry’s future.

The Future of Real Estate Technology: The MLS Evolution

On the technology front, Simonsen acknowledges that evolution is constant and unpredictable. He playfully references a long-standing industry question: “There has always been concern that, wow, does CREA have plans for a national MLS?” He muses, “Who knows, it may evolve to that at some point. Is that going to be in my lifetime?” he says, laughing. “Probably not! But there will continue to be changes to technology.” This lighthearted acknowledgment points to the perpetual innovation within real estate technology, from data analytics and AI to virtual tours and blockchain, all of which continue to reshape how properties are listed, marketed, and sold. The question of a unified national MLS, while perhaps still distant, remains a testament to the industry’s ongoing quest for efficiency and comprehensive data sharing.

Reflecting on a Rewarding Career: Pride, People, and Purpose

Despite the demanding nature of his role, Simonsen cherishes the many rewarding aspects of his career. One of the greatest privileges, he recalls, was the “unique opportunity to see the country one end to the other and lots of places in between.” Estimating around 70 plane rides per year, including transfers, this extensive travel allowed him to connect directly with members in every corner of Canada. These interactions fostered a profound sense of pride in being Canadian and representing ORE. He emphasizes the distinct advantage of Canada’s real estate ecosystem: “The fact that we own the MLS trademark and the Realtor trademark, and how we are structured and organized here…we are the envy of countries around the world,” he proudly states, underscoring the strength and recognition of the Canadian model.

Simonsen’s admiration extends to the people he worked with. He describes the volunteer members and peers as an “outstanding group of individuals…people who are committed and care.” Similarly, he praises the CREA staff as a “wonderful team,” highlighting their “care, compassion and dedication,” exemplified by their heartwarming sponsorship of a Syrian family settling in Canada. These relationships, built on mutual respect and shared purpose, were clearly a cornerstone of his professional satisfaction.

The Road Not Missed: A Look at the Challenges of Leadership

While his reflections are overwhelmingly positive, Simonsen is candid about aspects of the job he will gladly leave behind. With a wry smile, he invokes Spiro Agnew’s famous phrase: “I won’t miss the negative nabobs – the naysayers, the doomsayers.” This sentiment reflects the constant pressure and occasional negativity that often accompany high-profile leadership roles, where criticism, both constructive and unfounded, is an inevitable part of the landscape.

Beyond the emotional toll, there were significant logistical demands. “I won’t miss spending a lot of time in airports,” he admits, acknowledging the relentless travel schedule. Most profoundly, he reveals the all-encompassing nature of the CEO role: “And the nature of this job, and it’s partly self-imposed, but it’s 24/7. You are on call and dealing with stuff seven days a week.” This demanding schedule often meant significant personal sacrifice. He and Kathy own a home 90 minutes from Ottawa, a distance that often felt much greater due to his inability to be there frequently. “I’m looking forward to having one place to hunker down,” he says, expressing a simple yet profound desire for domestic stability.

A New Chapter: Consulting and Continued Contribution to the Realtor Community

As one chapter closes, another begins. Upon returning from his well-deserved vacation, Simonsen will embark on a new professional journey, joining the consulting firm TNG. His focus will be on working with associations and not-for-profit organizations, with a specific aspiration to continue engaging with clients within the real estate realm. His extensive experience and strategic acumen will be applied to critical areas such as strategic planning, facilitation, and governance reviews, offering invaluable guidance to organizations navigating their own evolutions.

Gary Simonsen leaves CREA with “nothing but positive feelings,” carrying with him a deep sense of accomplishment and gratitude. He expresses a heartfelt hope that in his new consulting role, he will discover ways to “continue to contribute to the Realtor community.” His legacy at CREA is one of visionary leadership, resilience in the face of change, and an unwavering commitment to the Canadian real estate industry and its professionals. His contributions have undoubtedly shaped the landscape of organized real estate in Canada, leaving an indelible mark for generations to come.