How to build a productive, long-lasting real estate team


Planning to grow your team this year? Don’t jump in headfirst. The more time you spend honing your strategy now, the less time you’ll lose to organizational or retention issues down the line.

In a session called, “Lessons Only Experienced Entrepreneurs Can Teach” from a recent Side conference, four leaders of top-producing teams had the following advice for agents looking to build a durable and successful real estate team.

Know why you want to grow and structure your team accordingly

Brett Jennings

“Don’t grow for growth’s sake,” said Brett Jennings, founder of Real Estate Experts in San Jose, CA. “Get clear on what’s motivating you.”

Chances are, if you’re looking to increase your team’s headcount, what you’re actually chasing is something broader like higher income or better work/life balance. And just adding more team members, without strategic processes and systems in place, won’t get you to those goals.

Chris Kappmeyer learned this lesson firsthand. In the ‘90s he built up a large company that he eventually sold to a national franchise, in part because he didn’t enjoy the day-to-day aspects of overseeing so many agents. “It took way too much time,” he explained.

Chris Kappmeyer

Now he is using a model at All Hands Real Estate in Austin, TX that allows him to increase production while playing to his strengths. He’s the rainmaker on his team, with several assistants working under him who handle things like showing houses and implementing his unique listing process. When a home goes under contract, he takes over and handles negotiations.

In contrast, Brett realized his motivation was helping more agents change their lives through real estate. So he designed his company, Real Estate Experts, such that he has his own small team of five — the Brett Jennings Group — plus another 50 agents spread across additional groups. Together, they transacted over $1 billion in 2021.

“This way, when we bring in agents and coach them up to the point where they’re making great money, we have a path for them to grow even further as the leader of their own team,” Brett explained.

Understand your culture and hire to it

If you want to build a lasting, successful team, you need to get crystal clear on what you’re looking for in new hires.

Kelli Griggs

Kelli Griggs’s Navigate Realty in El Dorado, CA is the number one boutique brokerage in her market — which she credits in no small part to her firm’s strength of culture. “We know exactly who we are,” Kelli said. “We treat everyone with respect, but we also debate and speak our minds. And we think about that when we interview new agents. We are very selective of who we invite into our office; we strive to keep a healthy balance of happy, encouraging, and thoughtful agents.”

Helen Chong similarly has strict culture conventions she adheres to when hiring for the HAYLEN Group in San Jose, CA. “I always ask them, ‘Why do you want to be in real estate?’ And I don’t want the people whose answer is just: ‘To make money.’”

Helen Chong

Helen moved to the U.S. from Hong Kong alone with little to no money. She entered into real estate because she learned there were safe ways to achieve financial security through real estate analysis. Her primary aim is to help her clients do the same, and she prioritizes that ethos when looking for new hires to her team.

“All of my agents came in with absolutely no experience,” she said. “But they all have one thing in common: passion. For me to bring someone on, I have to understand their motivations.”

Find your support system and learn from it

Figuring out how to structure and grow your team can be daunting. That’s why it’s so important to surround yourself with people who’ve already been there. As Side partners, Chris, Brett, Kelli, and Helen have access to a business manager, a dedicated recruiting team, and a collaborative, nationwide network of the world’s best agents.

“As an indie broker, I didn’t have anyone to talk to about this stuff,” said Chris. “Now that I’ve partnered with Side, I can strategize with my business manager and learn from what other Side partners have done. I’m more comfortable taking risks and trying new things.”


About Side

Side is a behind-the-scenes brokerage platform that exclusively partners with top-performing agents, teams and independent brokerages to create and grow their own boutique brands without the cost, time or risk of operating a brokerage. Side’s proprietary technology platform and premier support solutions empower its agent partners to be more productive, grow their business and focus on serving their clients.





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