Every brokerage promises coaching as part of its value proposition. It’s one of the biggest recruiting differentiators in the industry.
However, as teams and brokerages grow, or when they’re belt-tightening amid a tough market, one-on-one coaching often becomes the first casualty. In-house sales managers can’t conduct meaningful weekly coaching sessions for dozens, or even hundreds, of agents, and outsourcing becomes too expensive.
It’s that scalability problem that companies like Shilo are trying to solve with tech. I recently talked to CEO and founder Justin Benson as the company rolls out its 1:1 AI coaching program and asked how it’s trying to solve this persistent pain point for clients.
Coaching doesn’t scale like recruiting does
A successful recruiting push can leave your brokerage lopsided, since recruiting scales much faster than leadership capacity. That could leave you with one sales manager overseeing dozens of agents.
For the agents recruited, the weekly coaching calls they were promised often dwindle down to monthly check-ins — or they disappear entirely. That’s not necessarily caused by poor leadership, but a combination of sales managers stretched too thin and simple economic reality.
“There are not enough days and there’s not enough profit that gets made inside of a real estate organization to hire a fleet of sales managers,” Benson said. That’s why “the best teams don’t even have lead problems. They have a training problem.”
That training problem has a dollars-and-cents impact at the brokerage level. Since most established teams already have significant lead flow, conversion, not lead volume, becomes the limiting factor when it comes to growth.
Better conversions create better outcomes, and improving existing agents often delivers greater ROI than buying more leads. But training up those agents to make them better at conversion takes time, money and personnel.
Why AI isn’t replacing coaches
According to Benson, the idea that AI will replace humans is the wrong framing. Instead, AI should handle the repetitive coaching work humans struggle to sustain consistently, “replacing the part of the job that never scales.”
A solid AI coaching program can include:
- Weekly accountability
- Personalized role play
- Practice between meetings
- Progress tracking
- Surfacing issues leaders should address personally
“People listen to the feedback from Shilo because the AI doesn’t have an opinion about them,” Benson said.
While AI notices patterns, people build relationships. Brokerage leadership remains responsible for culture, celebration, empathy and intervention, while AI takes charge of the repetition behind successful coaching. That means humans have the bandwidth to reach out when:
- An employee is struggling
- A family is in crisis
- An agent is celebrating a win
- Recognizing agent and organizational milestones
“A human still needs to build culture in an organization,” Benson said, “and we can’t replace that.”
Questions every brokerage leader should be asking
For brokers determining whether or not to add AI coaching to their training program, these questions can help guide your thinking.
Where is the real bottleneck in your business?
Is it lead generation? Or is it helping the agents you already have convert more of the opportunities they’re getting?
Can every agent on your team realistically receive meaningful coaching every week?
Not a group training or sales meeting but individual feedback based on their actual conversations. If the answer is no, where are the gaps showing up in your results?
What percentage of your managers’ time is spent coaching versus preparing to coach?
Reviewing calls, gathering data, scheduling meetings and tracking follow-up all consume valuable hours. How much time is left for the actual coaching?
Are you measuring activity or improvement?
KPIs like dials and appointments matter, but are you tracking whether agents are actually becoming better communicators? How do you know whether or not coaching is working?
Is your coaching personalized or one-size-fits-all?
Do new agents, seasoned producers and different personality types all receive the same advice, or are managers adapting their coaching to the needs of each individual?
If your best sales manager left tomorrow, would your coaching program survive?
Strong coaching systems shouldn’t depend entirely on one exceptional leader. How much institutional knowledge lives in one person’s head, and how can you surface it effectively?
Do your agents receive feedback only when something goes wrong?
Consistent coaching creates momentum. Reactive coaching often creates defensiveness. Which experience are your agents getting?
Are you investing as much in developing agents as you are in recruiting them?
Most brokerages spend significant time and money attracting talent. Once agents join, does your investment in their development match your investment in bringing them through the door?
What work can only a human leader do?
If technology can surface trends, organize feedback and reinforce habits, how should your managers spend the time they get back? Coaching? Mentoring? Culture? Recruiting? Strategic planning?
If every agent improved just one critical skill over the next 90 days, what would have the biggest impact on your business?
Benson points to one clear answer: helping agents consistently define the next step in every client conversation.
“If you can increase your ability to communicate, you’ll have better conversations,” he said. “If you have better conversations, your life is going to change as a result.”
Troy Palmquist is the founder and principal at HomeCode Advisors. Connect with him on LinkedIn.
