In real estate, success often hinges on performance, resilience, and relationships; yet few leaders regularly ask their people how they’re really doing.
Between vendor meetings, listing presentations, and endless open homes, it’s easy to overlook the wellbeing and motivation of the very team that drives results.
But ignoring it can be costly: disengaged employees are less productive, less loyal, and more likely to impact client experience.
As in many industries, real estate professionals are showing signs of strain.
According to Gallup, global employee engagement fell from 23% to 21% in 2024, marking only the second drop in over a decade, and leading to an estimated US$438 billion in lost productivity.
Engagement among managers declined more sharply, dropping from 30% to 27%. with younger and female managers seeing the biggest decreases.
Meanwhile, employee wellbeing also dipped for the second year in a row.
Gallup warns that if workplaces were fully engaged, the world’s economy could gain nearly US $9.6 trillion in added productivity, which is equivalent to about 9% of global GDP.
“Make sure your employees feel comfortable and safe with you,” Emma Seppälä, a Yale School of Management faculty member told the Harvard Business Review.
“If they don’t feel they can trust you or that you care, they won’t be open to talking to you.”
So how can principals, sales managers, or team leaders get beyond surface-level check-ins?
Here are six questions that can help uncover how your team members are truly doing, and what you can do to keep them motivated and engaged.
1. On a scale of 1–10, how are you showing up today?
Skip the small talk. A quick rating helps agents pause and reflect on their mindset. A “4” might signal burnout after a difficult vendor meeting or pressure from stalled listings.
Follow up gently: “What’s behind that number today?” You’ll often learn more than you would from weeks of casual chat.
2. What’s something outside of work that’s exciting you right now?
Selling property is all-consuming, but agents are people first. Asking about life outside work builds connection and helps you understand what fuels them.
Maybe it’s a fitness goal, travel plan, or family milestone. When you show interest in what matters to them, they’re more likely to trust you with what’s not working professionally.
3. Does your work feel meaningful to you at the moment?
Even in high-energy offices, some agents can feel adrif, particularly if deals have slowed or personal targets feel unreachable. Ask what aspects of the job they enjoy most and what drains them.
Then explore how to help them spend more time on the tasks that energise them, whether that’s prospecting, negotiation, or mentoring younger agents.
4. What could make this job more rewarding in the long run?
Retention is one of the biggest challenges in real estate. Understanding what keeps each team member engaged is key; whether it’s flexibility, recognition, training, or career progression.
Be honest about what’s possible, but keep the door open for creative solutions. Sometimes small adjustment, like shifting roles or sharing leads differently, can make a lasting difference.
5. What’s draining your energy right now, and how can I help?
Real estate can be relentless: long hours, emotional clients, and unpredictable outcomes. This question helps uncover what’s really weighing people down – be it admin overload, unrealistic expectations, or friction within the team.
Your role as a leader is to remove roadblocks where you can, and show empathy where you can’t.
6. Where do you see yourself in one, three, or five years — and how can I support that?
Too many real estate leaders focus on short-term KPIs and ignore long-term growth. Ask about their ambitions, inside and outside your business.
Do they want to become a lead agent, start a team, or branch into property management? When people see that you’re genuinely invested in their trajectory, loyalty and performance naturally rise.
There’s no one-size-fits-all script for these conversations. What matters most is your sincerity and consistency.
Whether you run a boutique agency or a large franchise team, taking time to check in personally, not just professionally, creates trust, resilience, and better results.
As leadership expert Steven Rogelberg told HBR: “Getting to know your team members as people with lives outside of work takes time and trust. But building this foundation is worthwhile because it makes it easier for people to talk about concerns later on.”
