Mastering Real Estate Team Management

In the bustling world of real estate, success often hinges not only on individual prowess but also on effective team management. As the industry evolves, so do the strategies for building and leading high-performing teams.
Recently, in a webinar hosted by Aaron Billings from Royal LePage professional development department, Matthew Regan, CEO of The Regan team shared invaluable insights into team management, gleaned from his extensive experience.
Whether you are a seasoned agent considering forming a team or a team leader seeking to optimize performance, the insights shared here offer invaluable guidance for navigating the complexities of real estate team management.
Transition from Agent to Business Owner
Matthew Regan’s career trajectory in real estate embodies a transformative journey from a youthful agent chasing deals to a seasoned business owner cultivating sustainable growth. With 21 years in the industry, Matthew openly acknowledges the myriad mistakes and burnout he experienced in his pursuit of success. However, a pivotal decision to relocate and shift his focus towards building a business marked a significant turning point.
By embracing a strategic approach and relinquishing his role as a frontline agent in 2017, Matthew embarked on a path of deliberate growth and transformation. His journey underscores the importance of treating real estate as a business, not just a relentless pursuit of transactions.
Navigating the Choice
For new Realtors® in the competitive real estate market, the choice between joining a team or striking out solo, presents a significant dilemma. Drawing from the wealth of experience, Matthew Regan provides insightful guidance tailored to each individual’s unique circumstances.
While acknowledging the merits of team collaboration, Matthew stresses the importance of meticulous research and self-assessment before reaching a decision. He advises aspiring Realtors® to carefully evaluate the strengths, objectives, and available resources. For those inclined towards independence, Matthew suggests harnessing the training and assistance provided by brokerage companies such as Royal LePage.
Conversely, individuals craving guidance and structure may find solace and support within a well-established team environment. He underscores the necessity of comprehending the team’s operational model, the leader’s availability for mentorship, and the level of autonomy accorded to team members.
Ultimately, the decision hinges on personal inclinations, aspirations, and alignment with the team’s values.
Evolving Real Estate Team Dynamics
Matthew provides insights into the changing business models of teams, highlighting the entrepreneurial essence and support structures for agents. He emphasizes the crucial role of culture in team dynamics, echoing sentiments from industry leader like Netflix’s co-founder. Matthew underscores the appeal of teams for agents seeking structure, guidance, and a sense of community in today’s dynamic work environment.
Whether an agent opts to join a team or remain independent, understanding the nuances of team dynamics and culture is essential for a successful and fulfilling career in the real estate market.
Crafting the Ideal Team
Building a successful real estate team goes beyond simply growing numbers. It is all about cultivating a culture and assembling a team with the right character and skill sets.
Matthew shares a personal story highlighting the importance of cultural fit over sheer productivity. He emphasizes the significance of hiring individuals who align with the team’s values and ethos, stressing the importance of trustworthiness and professionalism in client interactions. Matthew underscores the complexity of the hiring process and advises both recruiters and potential team members to be transparent and realistic about expectations.
Ultimately, fostering a cohesive and harmonious team environment is a paramount for long-term success in the Canadian real estate industry.
Navigating Lead Distribution with Precision
Controlling the outcome of the game is crucial, particularly when it comes to lead distribution within a real estate team. Matthew Regan advises Realtors® to communicate their expertise and specialization in specific geographic areas to their team leaders. By showcasing the knowledge and track record, the real estate agents can instil confidence in their ability to effectively handle leads within their niche.
Noticeably, Matthew cautions against overly focusing on lead distribution during initial interviews, as this may negatively impact the perception of the candidate. Instead, he encourages the agents to prioritize demonstrating their skills, professionalism, and cultural fit with the team. Ultimately, effective communication and a clear understanding of one’s strengths are essential for success in lead distribution within real estate teams.
Understanding Fees and Splits
Delving into the economics of real estate, Matthew offers some valuable insights into the fee structures and percentage breakdowns that agents can expect when joining a team. He elucidates the distinction between costs and splits, emphasizing that while splits denote the division of income between the agent and the team leader, costs encompass both fixed and variable expenses incurred in the business.
With fixed expenses like personnel and office space, and variable expenses associated with listings, the overall cost of sale for a team can range from 40 to 45%. Matthew underscores the challenge of maintaining a profitable margin, particularly for independent agents striving to scale their businesses. He highlights the formidable task of achieving a 50% profit margin, underscoring the value proposition that teams offer in alleviating the financial burdens and providing essential resources for Realtors® to thrive.
Cultivating a Book of Business
Mentorship and Growth Opportunities
The journey of building a book of business within a real estate team is multifaceted, with varying approaches depending on individual circumstances. Matthew Regan offers nuanced perspectives on the expectations surrounding a prospective agent’s existing clientele and their potential for growth within the team. While having a pre-existing book of business is advantageous, particularly if well-organized and utilized effectively, there is also ample room for mentorship and support from the team leader and fellow agents.
Matthew also stresses the importance of organizational tools like CRM in maximizing the potential of one’s network and emphasizes the high return on investment associated with leveraging personal connections. Whether through structured mentorship programs or individual initiatives, agents are encouraged to proactively cultivate their networks and capitalize on the relationships they have built over time.
This holistic approach underscores the team’s commitment to nurturing talent and fostering long-term success for all the members of the company.
Harnessing Technology for Team Success
In navigating the complexities of the real estate industry, leveraging technology emerges as a cornerstone of The Regan Team’s approach to success. Matthew sheds light on the proprietary platform, honed over nine years to streamline operations and empower agents. With built-in AI capabilities, the platform offers innovative solutions for lead generation, communication, and workflow optimization.
Matthew also underscores the importance of simplicity and clarity in tech adoption, emphasizing the need to cut through the noise of the industry. Tracking business metrics, such as top sources of leads, becomes instrumental in driving informed decision-making and learning from past mistakes. While there is always a plethora of tech options available, the focus remains on practicality and effectiveness in achieving the team’s goals.
Optimizing Tech for Enhanced Performance
Delving deeper into the realm of technology, Matthew Regan underscores the importance of selecting tools that align with the team’s objectives while minimizing distractions. Whether it is a leveraging voice messaging to connect with clients or utilizing email marketing platforms, the focus remains on scalability and efficiency.
Moreover, tools like SEMrush offer a glimpse into the website performance, highlighting the significance of generating traffic and optimizing online presence. As the team continues to evolve, the emphasis lies not only on functionality but also on strategic utilization of any technology to drive results.
Maximizing Efficiency with basl.ai
The Regan team gets the aid of Basil, a robust tech stack designed to streamline operations and enhance productivity. Basl.ai encompasses a suite of tools tailored to meet the diverse needs of every real estate professional. From AI-powered algorithms that expedite letter writing tasks to comprehensive training resources, Basl provides a holistic solution for agents.
This tech stack prioritizes functionality and user-friendliness, allowing team members to focus on the core responsibilities without being bogged down by cumbersome processes.
Leveraging the Strengths
In highly competitive market like Clarkson, where multiple top teams compete for dominance, finding your competitive edge requires strategic alignment with your strengths and values.
- Focus on RelationshipsRecognizing that not every agent is inherently relationship-oriented, The Regan Team encourages every agent to excel in their natural strengths. Whether it is a transactional expertise or exceptional customer service, agents are encouraged to cultivate the unique approach to client interactions.
- Marketing and BrandingSome agents may choose to invest in marketing and branding efforts such as bus shelter ads or billboards to enhance their visibility in the local market. While this can be effective, it requires a significant financial commitment and long-term dedication to yield results.
- Client Touchpoints
Implementing a robust client touchpoint system, ensures consistent engagement and communication with clients throughout the year. Whether it is through emails, phone calls, or client events, maintaining regular contact fosters strong relationships and keeps the team top of mind. - Team CollaborationSurrounding oneself with a supportive team that complements individual strengths and fills in any gaps is crucial for success. Whether it is hiring an administrator to handle client-facing interactions or partnering with colleagues who excel in different areas, teamwork enhances overall competitiveness.
Ultimately, finding success in a competitive market requires a combination of self-awareness, strategic planning, and collaboration.
Measuring Success
Matthew Regan’s perspective on success challenges conventional notions, emphasizing the need for individuals to define their own version of success. Success, he argues, is not a one-size-fits-all concept but rather evolves with time and personal circumstances.
Balancing Priorities
Regan highlights the importance of balance, stressing that success should not come at the expense of well-being or relationships. Balancing monetary goals with personal aspirations, such as travel or family time, is crucial for long-term fulfilment and sustainability.
Guarding Against Comparison
Moreover, Regan warns against the pitfalls of comparison, especially in today’s age of social media. The curated images of success portrayed online often do not reflect reality, leading to unnecessary pressure and anxiety. It is essential to filter out the noise and focus on defining success on your own terms.
In conclusion, mastering the real estate team management is an ongoing journey of growth and adaptation, rooted in trust, professionalism, and collaboration. By embracing strategic thinking, fostering a cohesive team culture, and leveraging technology effectively, Canadian real estate professionals can navigate the complexities of the industry and achieve sustainable success in today’s dynamic market landscape.
Related Posts

August 2025 GTA Real Estate Market Update | Regan Irish
The August 2025 GTA Real Estate Market Update reflects renewed momentum and affordability in Toronto, Oakville, Mississauga, Burlington, and Muskoka. Thanks to steady interest rates and appealing home prices, July proved surprisingly dynamic. Let’s dig into the numbers and what they mean for you.
Interest Rates Remain Stable — Affordability Fueling Activity
In July 2025, the Bank of Canada maintained its key rate at 2.75%, its third consecutive pause. With lower borrowing costs now more accessible, affordability is encouraging a wave of renewed buyer activity.
GTA Market Overview: Sales Surge, Prices Slightly Dip
- Home Sales: 6,100+ transactions region-wide, marking a 10.9% increase YoY and the strongest July since 2021.
- Month-over-Month: Seasonally adjusted sales rose 13% from June to approximately 5,744 units, the biggest monthly gain in nine months.
- New Listings: Up 5.7% YoY, totaling 17,613 new offers.
- Price Trends:
- The MLS® Home Price Index (HPI) Composite Benchmark fell 5.4% YoY.
- The average GTA selling price dropped 5.5% YoY to around $1,051,719.
- Word on the street indicates the HPI drifted slightly lower—about $979,000, down 0.2% from June.
What It Adds Up To: Buyers are back in force—sales are outpacing new listings while prices softened, creating renewed market opportunities.
City Highlights
Toronto
A more balanced landscape—but some segments remain soft. Condos and detached homes see inventory rising; semis are steadier.
Oakville, Mississauga, Burlington & Muskoka
While TRREB doesn’t break down by city in these reports, regional trends suggest:
- Mississauga & Burlington: Strong rise in listings and dipping average prices give buyers leverage.
- Oakville: Stability in demand for luxury keeps discounts modest.
- Muskoka: Continued strong interest in sub-$2M waterfront properties should benefit from broader GTA momentum.
What This Means for You
- For Buyers:
Renewed affordability, rising inventory, and favorable interest rates make August a prime time to move. - For Sellers:
A more balanced market—strategic pricing and quick response will be key to success. - For Investors & Cottage Buyers:
Strong July sales in the GTA point to increasing investor interest; Muskoka remains a high-value lifestyle and investment destination.
Work With the GTA Real Estate Experts
Whether you’re planning to buy a Muskoka cottage, invest in a luxurious Oakville property, or explore options across Toronto, Mississauga, or Burlington, now is the time to act.
Regan Irish & Associates specializes in luxury, resale, and investment properties across the GTA and Muskoka. Our market insight and negotiation skills help you get the best results—whether buying, selling, or investing.
1320 Cornwall Rd Unit 103, Oakville, ON L6J 7W5
905.842.7677
Visit reganirish.com
Let’s make today’s market your opportunity—contact us today!

Alex Irish & Associates and The Regan Team Announce Strategic Merger
Two of the most respected names in real estate, Alex Irish & Associates and The Regan Team, are excited to announce a strategic merger that will combine their expertise, resources, and market reach. This partnership of Regan Irish & Associates brings together the strengths of both firms, offering an enhanced real estate experience for clients across Southern Ontario, including expanding into new regions like Collingwood and Muskoka. The merger reflects both brokerages’ long-standing commitment to providing high-quality, relationship-focused service while leveraging new technologies and business strategies to ensure their clients receive unparalleled support.
“Alex is the consummate professional,” said Matthew Regan, CEO of The Regan Team. “She embodies the qualities of a person I would trust with my own home sale, and I am excited to partner with her to combine the best of both our brokerages. Our goal is to create a work culture that allows our agents to thrive, while being confident and equipped to provide the service our clients deserve. Our clients are going to benefit immensely with a wider and deeper net of potential buyers and an even further reach in marketing and advertising.”
Alex Irish, Founder of Alex Irish & Associates, emphasized that this partnership is the next natural step for her business. “By combining our resources and efforts we knew we’d be able to create a better real estate experience for our clients, our agents and business partners.” she explained. “This merger allows me to focus more on client relationships while also mentoring our agents who can continue to offer that same high level of service. Matthew has built a business model that aligns with my long-term vision, allowing us to scale while still maintaining the personal touch. Simply put, we are better together.”
Alex has built her brand over decades, particularly in the Oakville area, where her name is synonymous with excellence in real estate. Her personal approach, based on referrals and repeat business, has earned her a loyal clientele. Matthew has focused on recruiting top agents and scaling his business, growing The Regan Team to one of the top brokerages in Canada. This merger offers an exciting opportunity to grow into new territories. Together, the merged brokerage will have 15 offices spanning from Niagara to Toronto to Muskoka. This expanded presence means more resources for clients, from enhanced marketing capabilities to a wider net of potential buyers.
The merger will officially take effect on October 31, 2024, and the new branding and operations will be rolled out in the coming months.
About Alex Irish & Associates
Alex Irish & Associates, led by Alex Irish, is a highly respected name in Oakville, known for its personalized, referral-based business model and long-standing relationships with clients. Alex has built her brand on trust, excellence, and attention to detail, qualities that will remain at the forefront of the merged firm.
About The Regan Team
The Regan Team has a long-standing reputation for innovation, process-driven operations, and a focus on agent recruitment and development to provide the highest level of service for their clients. Under Matthew’s leadership, the brokerage has expanded its presence across Ontario, providing agents with the tools and support needed to succeed in a competitive market. For more information on this exciting merger, please contact Matthew Regan.