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Triple Win Property Management Blog

Leading Means Truly Connecting with your Team

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. About two years ago, I had a big shift in my professional life. I was promoted into a director position, and, for the first time in my career, I was a layer removed from most of the individual contributors on my team. As someone who cares deeply about coaching, knowing my team, and forming relationships, it was jarring. I felt disconnected, and it was a tough adjustment. Shortly after, I was in a leadership class when one of the instructors asked a simple question: “How much time do you spend with the people who are doing the work?” It was pretty eye-opening for me, in part because I’ve always felt that JWB is a social workplace where we all want to get to know each other. But the truth was, I wasn’t spending that much time with my team, and it was having a negative effect. I wanted to make sure that members of my team knew where I was coming from when I communicated things to them; that I had their best interest at heart, and that I wanted to be a coach, not a dictator. So the next logical question was, “how can I build up these relationships to foster more connection and trust?” How to build relationships with your team Once I started thinking deliberately about how to form closer relationships with the “doers” on my team, it actually came pretty naturally. The challenge wasn’t in coming up with the ideas, but in actually executing them. In a business as busy as property management, it’s not easy to make time for team building. It tends to be one of the first things to fall off the priority list when other things pop up. The most important part of setting up any kind of team building program is to commit to it and see it through. With that said, here are some of the different ideas that I’ve either done myself, seen done well at JWB, or heard positive reviews of from people in my network. 1:1 coffee and lunches This was the first large-scale, deliberate plan that I put in place when I realized that I needed to form stronger relationships with my team. I committed to taking a different member of my team out for coffee or lunch each week. I set no agenda and I had no ulterior motives; it was purely to get to know each other. I tried to minimize how much we talked shop, and instead learn what kinds of things each person enjoys, how they communicate, and what they’re passionate about. This wasn’t a small undertaking for me, because the teams I managed totalled over 50 people, but it was well worth it. I connected with people that I had otherwise never even met. Notes of gratitude Another approach I took was to write a couple of notes of gratitude to teammates each week. They were delivered privately, and were just intended to let that person know that I saw how hard they were working and what they were achieving. If you have a performance management or HR tool, take a look and see whether it includes a feature that will let you do this virtually. You can even set a calendar reminder each week to sit down and write a nice note to a couple of teammates. They don’t have to be long. The point is just to make the recipient feel seen. Team appreciation events While an office pizza party may get a bad rap, in-office team building can still be impactful. We recently celebrated team appreciation week, and we made a big deal of it! We didn’t announce the full scope of what we were going to do, so it was a nice surprise for most of the team. We had a team lunch, but we also gave out awards and hosted free raffles for our employees to win fun prizes. Just making the time was important in itself. Desk rotations Another tactic we use from time to time is switching up where people are sitting. Not only does it offer a literal fresh perspective, but it also helps break down silos across teams. People make friends with the people physically closest to them, and for leaders and managers, sitting with different groups can help build relationships and trust with them, too. Setting expectations I am a huge proponent of setting expectations, especially when onboarding new employees. I think one of the most important things you can do as the leader of a team is set non-negotiables for how people behave and how they treat each other. Not only does this keep people in check, it also gets everybody on the same page about how their teammates and managers are going to communicate. If you set the expectation up front that you’re going to provide weekly feedback in order to help everyone grow, your employees won’t be caught off guard when they receive constructive criticism. Far-reaching impacts Of course we all want to get along well with our colleagues, and we want to like the people we work with. But at the end of the day, what do we really get out of fostering these relationships? In my experience, the impacts are pretty significant. Fostering better work: When people feel seen, heard, and appreciated, they’re much more motivated to show up to work as their best selves. They’re going to perform better and go above and beyond, because they know that effort will be recognized. Increasing team retention: Again, no one wants to be at a workplace where they feel undervalued. When people have more trust in their team, they’re likely to stick around longer. Creating a safe space for hard conversations: People are more likely to open up about tough topics when they don’t feel like they’re going to be judged, especially when they’re talking to their managers. By creating a safety net for difficult conversations, you allow your employees to be more honest and resolve challenges more quickly. Increasing receptivity: Employees who take feedback well are invaluable, and one of the best ways to help them do that is by making sure they trust you to give honest, effective evaluations. When they know you’re coming from a place of genuine helpfulness, as opposed to tearing them down, they’re less afraid and more receptive. Building accountability: Team members are also more likely to hold each other accountable when there is a closeness and trust factor. When they know their feedback will be taken in a positive light, they feel more confident providing it in the first place. All of this makes people more comfortable, more productive, and more likely to approach their work with a positive attitude. True at any size One thing I want to make sure to emphasize is that this isn’t just something you need to focus on at a larger company like JWB. While smaller teams often know each other well just by the nature of their work, that isn’t always true. For example, a small team may have remote workers who only get a chance to connect with in-office staff a couple of times per week. Or you may have maintenance coordinators, leasing agents, or inspection staff who spend most of their time out of the office, visiting properties. They may not have the same opportunities to forge close relationships with their teammates, and may feel disconnected. Just because there isn’t a layer of management between you and the rest of the team doesn’t mean you don’t need to invest time and energy to form connections. In fact, if you have to ask the question at all, it’s probably worth it to put some 1:1 meetings on the calendar and get a pulse check from your team. It can’t hurt to get the ball rolling. Final thoughts When you’re a busy property management leader, it can be tough to find the time and energy to focus on team building. But you have to do the work so that the people who work for and with you understand who you are, where you’re coming from, and why you care.

Calendar icon April 22, 2025

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Creating a Coaching Culture at your Property Management Company

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. What is coaching? 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: Supervision is the process of managing tasks, quality control, and day-to-day work. Management is a bit broader, and includes setting a vision and developing a process. 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?” What is a coaching culture? 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: What are the standards they set for themselves? What are their personal core values? What are their goals? 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. Allowing room to fail forward 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 coaching is important in property management 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. Planning a career in property management 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. Bringing coaching into reviews 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?” Coaching doesn’t just happen downward 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. Watch now

Calendar icon April 8, 2025

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Onboarding: Getting the Most from your New Property Management Staff

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. Training your property management staff can be a lengthy, difficult process. Once you’ve found and made an investment in the right people, you need to set them up for success as quickly and effectively as you can. How can you make sure you’re onboarding new employees in a way that helps them and the business be successful? In this article, I’ll walk you through our approach to training and onboarding at JWB Property Management, and give actionable tips on how you can set your staff up to win. Our onboarding approach The specifics of onboarding staff varies a bit based on the needs of the role and the structure of the company, but we have a pretty rigid schedule for the first three to four weeks, which includes: Expectation setting Role-specific training Crosstraining Each step is vital to setting up your team for success, so let’s walk through them one by one. Expectation setting Expectation setting is one of the most important parts of onboarding employees, and most companies completely overlook it. My philosophy is, people don’t know how to be successful until you tell them. You can’t just assume that they’ll know what’s expected of them. The better you can set clear expectations upfront, the more likely everyone is to be successful. A lot of managers think that being direct with expectations is somehow mean, wrong, or micromanaging. I couldn’t disagree more. In my experience, avoiding these kinds of conversations sets everyone up to fail. “Clear is Kind” - Brené Brown Being direct with your employees about what you expect from them gives them the best tools to be successful. That’s why we spend up to three hours in the first week just on expectation setting. I ask new employees what their goals are, what they expect from the role, and what their own standards for themselves are. Then I walk through what my expectations are, and we make sure we’re aligned. That sets them off on the path to success from their very first day. The best thing I can do as a leader is develop people to be better than I am, as quickly as possible, and setting expectations kicks off that development. Role-specific training Role-specific training is the process of training new employees in the actual day-to-day work they’ll be doing. We take a hear/read/see/do approach, meaning that people with different learning styles can still be successful. Our training materials include: Existing documents like leases and policies Videos Readings Hands-on activities New hires work closely alongside their new teammates to gradually take on daily tasks and get first-hand experience. That’s when we start getting them on the job and actually handling their routine responsibilities, while still providing someone to answer questions along the way. Crosstraining Every new hire also does extensive crosstraining with every other department. For example, a new property manager will spend time with accounting, construction, and legal. This time is focused on making sure that everyone understands the way that their work affects other people. It builds company culture and teamwork, but also helps give new team members a sense of purpose and meaning, knowing the larger impact of their work. Basically, we don’t want people going through the motions in a silo. We want them to know their coworkers on other teams, and to see the value that they bring to the organization. This is also where our mentorship program comes in. At JWB, mentors are well established employees who can help take someone from day one to day 90. They’re typically not from the same team as the new hire, and they provide a safe place to ask the silly questions that people are uncomfortable asking their bosses, or the unwritten rules of the company culture. Sticking to a timeline In property management, everything can feel like it has to happen immediately. But training takes time. That’s just the nature of it. We try to pace our new hires, while also pushing them to grow quickly and get up to speed. That pace is set by the hiring manager, and the new hire is expected to flag any issues if they arise. (Of course, that expectation is outlined clearly in the expectation-setting stage!) Here’s an example of the timeline we’d typically hold a new property manager to. Week one focuses on: Expectation setting Introductions to the team Intro to rent collection Week two transitions into: Executing rent collection alongside another teammate Learning how to manage renewals By week 2 they’re assigned a portfolio of about 100 properties, which they’re managing with the help of their manager. By week 4 they have 250-300 properties and are starting to get more comfortable working independently. By day 45, a new hire should have the same portfolio size as any other property manager. Of course they’ll still have questions, and that’s normal and expected, but they’ve reached competency. By day 90 they’re fully self-sufficient and doing the same work as a property manager who’s been there for a while. They don’t need someone looking over their shoulder or keeping tabs on them. At this point, we hold a 90 day check-in, which is mostly an evaluation of skills competency. It helps us make sure that the employee is feeling comfortable and is capable of doing the work. And if they aren’t, it provides us an opportunity to catch things early and make the necessary corrections. Final thoughts Onboarding is absolutely crucial to getting your team up to speed and working together well. It’s your opportunity to really give people a workplace that they can feel proud of, and to build a thriving business in the industry that we all feel so passionate about. Put in the work to get onboarding right, and help everyone succeed. Want to learn more about how to grow your business strategically? Join me and Tony Cline for a Triple Win Live on setting and optimizing KPIs for your property management company. Register now

Calendar icon March 27, 2025

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Hiring in Property Management: How to Build a Thriving Team

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. Hiring is one of the most important decisions that you can make in property management, but it’s often rushed or overlooked. While it can be challenging, it’s absolutely worth the extra time and effort to find people who will thrive at your company. How can you make sure you’re choosing the right people, not only for the open role, but also for your company culture? In this article, I’ll share how we approach hiring at JWB Property Management, including how we conduct interviews and make sure we’re aligned with candidates. Hiring for values before skill I had no experience in property management when I started at JWB as a trainer and administrator. Instead of being hired for my experience, I was selected for my values and belief systems, which meshed well with the rest of the company. One of the best things about hiring in property management is that many roles are extremely teachable. You don’t need a ton of experience in the same role in order to be successful. There are certainly exceptions—like accounting or construction—that need specific hard skills. But most job responsibilities can be taught. That provides a huge opportunity to really dig into a candidate’s values and evaluate whether they’ll be a good addition to the team, rather than looking just at their resume and work experience. In industries where roles are highly technical, you may not have that luxury. But in property management, especially because it’s such a service-focused industry, hiring for values is essential. Evaluating your candidates In the spirit of hiring for values, we focus a lot of our interview process on our company’s core values. We aim to hire people who will help our organization continue to grow, innovate, and push forward, regardless of their previous experience. Considering applications Our initial application only has one question beyond basic information: “What makes you an A-player?” We don’t even ask for a resume up front, because, again, we’re more interested in soft skills and values than specific work experience. From there, we use an assessment tool to better understand people’s drive, motivation, and working style. Each job has different targets for different strengths, so the assessment helps us align applicants with the right positions. Once we think someone may be a good fit, that’s the stage where we ask for a resume. We’re looking for things like attention to detail, communication style, and how they present themselves, not specific hard skills. Interviewing top prospects We’re very intentional about making our interview process thorough. We don’t want it to be overly simple or easy, because we want people who are motivated. Our application process provides natural steps where applicants who aren’t as driven will weed themselves out. Evaluating skills, not experience Once a candidate moves into the interview stage, we shift some of our focus to the job itself, and the skills that we want to see for that role. In the first interview, they meet with a member of our leadership team, along with the hiring manager, to talk about the skills needed. Again, this is not about their experience in a similar role. For example, someone applying to be a property manager needs customer service, organizational, and communication skills. They may have those from a past job outside of property management, and we welcome that. Finding values alignment Our second interview is focused specifically on core values. We want to know who you’re going to be when you show up to work everyday. We have a set list of questions that we try to ask during this stage, and they’re fully based on our particular core values. Your company’s values will vary, so you should construct your interview questions accordingly. Seeing them in action Finally, we conduct what we call a shadow interview. If we think someone is a good fit and we want to hire them, we have them come in for a day and actually be in the office with us. They might take phone calls, go on site visits, submit work orders, or help show a vacant unit. This is all intended to see body language, attitude, and other behavior that we might not see in a couple of short interviews. We typically try to align shadow interviews with our company all-hands, because that’s a huge display of our culture. The idea here is that a shadow interview should be mutually beneficial; the candidate should get a sense of our culture and make sure it’s the right situation for them, just as much as we want to make sure they’re the right person for the role. Final thoughts Hiring employees can seem like a daunting task. In fact, that’s why so many small companies tend to wait too long to hire. They’re so focused on trying to complete the day-to-day that they don’t prepare for hiring ahead of time, and then wind up putting it off. One of my biggest pieces of advice for growing companies is to take the time to figure out how you want to hire before you need to hire. You don’t want to wait until a crisis is happening to decide how you’ll respond to a crisis. A lot of companies only start thinking about growing when they’re reaching a breaking point. They’re under a ton of pressure. If you have a plan in place ahead of time, you don’t have to make emotional decisions. You can approach it logically and calmly, and make better decisions. When you plan ahead and hire deliberately, you can create and sustain great teams to elevate our industry, and provide value and purpose-driven cultures. Interested in learning more about structuring and expanding your business? Download Second Nature's property management business template. Download now

Calendar icon March 25, 2025

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