Melissa Gillispie is the Director of Leasing and Property Management at JWB Property Management, and the 2025 NARPM Jacksonville President. She has over 11 years of experience in property management and is currently a Second Nature Triple Win Mentor.
One of the biggest shifts I’ve felt in my time at JWB is leaning less into a culture of management, and more into a coaching culture. By focusing on the whole person, rather than just focusing on output, our team is built stronger for the long run.
Read on to learn more about what coaching is, why it’s so important in property management specifically, and what you can do to build a coaching culture of your own.
Coaching employees is the process of developing the whole person, rather than just trying to optimize how they achieve a specific business outcome.
Coaching is an evolution of supervision and management, and goes beyond either of those. Here’s how I differentiate:
Both supervision and management are focused on the organizational aspects, whereas coaching is about developing a person overall.
Yes, coaching also includes business needs, but it focuses on setting goals and achieving them on a personal growth level. Coaching includes understanding long-term drives, desires, goals, and intentions. It’s about asking the question, “How can I in this organization help you take a step closer to achieving those things?”
A coaching culture is an overall attitude throughout the organization that the whole team has each other’s personal and professional development in mind. First and foremost, a coaching culture starts with trust.
Employees need to know they can come to you honestly when something goes wrong. They need to know you’re not going to judge them for their long-term goals. They need to trust that you’re giving open and honest feedback to help them improve every day.
As a coach, what does that look like?
First, in order to build that trust, a good coach needs to be honest and give real, actionable feedback so that their employees can learn, develop, and become their best selves. That means setting the stage early.
In my first one-to-one with a new hire, I always ask a few questions to better understand what their non-negotiables are for themselves:
I also share these things about myself so that they have a better understanding of me as a person and of how we’ll work together. And, most importantly, sharing vulnerable information about myself also helps build that ever-important trust.
Part of creating a culture of honest feedback is also allowing room to fail. First of all, people shouldn’t be afraid to fail or make mistakes. Second, when they do make a mistake, they shouldn’t be afraid of coming to tell you about it.
Mistakes happen. The question should then be, “how do we learn from this, and hopefully prevent it from happening again?”
As a coach, your job is to be a safe place for failure. You can’t be reactive and harsh when someone makes a mistake. You need to turn mistakes into teachable moments and allow your team to fail forward, learn, and grow.
Why is coaching important in property management specifically? Well, for starters, no one really goes to school for property management. Most property management teams are made up of people like me, who started their careers elsewhere and found property management along the way. That means that there’s a lot of learning, which also means a lot of failure.
Plus, property managers carry such a large workload and such a long list of tasks that they’re bound to have something fall through the cracks. There’s just inherent human error. Failing forward is part of the job.
Property management also requires decision making at speed. You have to move from evaluation mode into decision-making mode so quickly that you need to be able to trust yourself, and to trust that you won’t get in trouble if you’re wrong. Too many people are held up by the fear of failure, so they don’t make quick decisions.
Because there isn’t a lot of formal education in property management, a lot of people in the industry also don’t have a great sense of the career trajectory. That’s where a coach can step in.
As a coach, you help shape an employee’s property management career path. Something I take a lot of pride in is my ability to understand someone’s strengths, identify what kinds of roles best suit them, and make that clear to them.
Coaching means providing growth plans for each role. If someone can do their job with their eyes closed, they probably aren’t being challenged, and they may start to lose interest. It’s your responsibility as a coach to keep leveling them up.
A good coach also provides the flexibility for employees to change trajectories. Your employees should feel comfortable coming to you with questions about their career in property management. Sometimes that means they may want to leave your team and transfer to another team in the organization. As much as it can be difficult to lose a good team member, part of being a good coach is helping them fulfill their maximum potential.
At JWB, we hold weekly one-to-ones with direct reports. Sometimes they’re very tactical and focused on ongoing projects, but we try to also work in time for long-term goal setting. As coaches, we’re constantly evaluating performance and making sure that team members are on track for what’s right for them. Doing this weekly helps prevent people from veering too far off track, then only hearing about it in an annual review.
Of course, we also hold annual reviews. In those meetings we make sure to establish long-term goals for the next year or two. These reviews also include the most important question a coach can ask: “How can I help you achieve this?”
It’s important to recognize that a coaching culture means coaching all of those around you, and being willing to be coached yourself. We’re all responsible to each other.
Making yourself coachable is half the battle. You need to listen to feedback and take it to heart. When I ask my employees how they best receive feedback, I also tell them how I best receive feedback myself. I make it abundantly clear that I’m not just open to feedback, I want feedback.
Coaching never stops. You never get to a point where you no longer need coaching. So keep coaching, keep being coachable, and keep building up better property managers who will push our industry forward.
Want to learn more about measuring performance, improving employee output, and growing your business? Watch the webinar that Tony Cline and I participated in, all about making your KPIs more actionable.