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Melissa Gillispie

Director of Leasing and Property Management, JWB Property Management & Triple Win Mentor - Second Nature

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.

Small Gestures, Big Impact: How JWB’s “Love Budget” Builds Connection and Joy

At JWB, we’re always trying to build a company that people love to work for, and that residents love to work with. A little bit over two years ago, we made a change to our property management team’s policy that built on both of those, empowering our PMs and driving more unexpected delight for our residents. The premise was simple: we wanted to find a way to give property managers more discretion over the little things they can do for residents. The result was a dedicated budget for each PM that they can spend however they want, as long as it’s to provide an extra boost to residents. Integrating with our personal approach JWB has always taken the approach that real estate and property management are inherently personal businesses. That’s why one of our core values is “People first.” We go above and beyond to connect with our residents, build a rapport, and develop a relationship that goes beyond just transactional steps. A welcome survey that goes beyond just the basics One way that we do that is with our welcome survey. When a new resident moves in, we send them a simple survey that goes beyond just logistical information, and asks questions like: What do you do for fun? What’s your favorite restaurant in town? What’s a charity that means a lot to you? Do you prefer coffee or tea? What’s your favorite flower? We frame this as a get-to-know-you, telling our residents that, because we often sign three-year leases, we want to get to know them more closely. We know life happens, and we want to be there with them through the ups and downs. Think about your own life and all the things that have changed or happened in those last three years. Putting those personal details to use We then store their answers in our property management system so that anyone on the team can easily access them. That means that when a resident calls into the office or sends us an email, we have a whole list of conversation starters to make things more personal. The next logical step, though, was finding a way to use those facts to create meaningful moments down the line. How could we truly go above and beyond, more than just having something to talk about when we pick up the phone? That’s where our gifting budget came in. Introducing the “love budget” We’ve always tried to bring an extra bit of joy to our residents, in part because it helps drive renewals. One way we approach this is by incentivizing renewals with upgrades to the property, which give the resident a nice boost to their living situation, but also create wins for the investors. We even had a dedicated budget item for incentives like this. When we were looking for more ways to give a little bit extra to our residents, we held a resident experience workshop. One of the biggest learnings we had coming out of that was that our property managers wanted the opportunity to do things outside of the renewal period. There were points throughout the lease where they wanted to give their residents a surprise. It could be a hard time or a happy time—it didn’t really matter. The question for us as business leaders was, “How can we do this in a way that empowers the property manager to make decisions, but also keeps the cost to the business reasonable?” Ultimately, we chose to carve out a piece of our larger incentives budget and give PMs the discretion to use it however they wanted, on whichever residents they wanted. We called it the “love budget” (the name was also chosen by the property management team) and put it into practice about two years ago. Our property managers can break up the budget across multiple residents, or they can decide to spend it all on one thing. It can be a gift card, a rent credit, concert tickets, flowers, a donation… it really doesn’t matter how it’s spent. But PMs do have to spend it. We track each individual’s budget, and if they aren’t using it, we follow up with them and make sure they plan to use it before the end of the month. Building competitive advantage One of the other considerations we had when we developed the program was how it would stand out in the market. We wanted to differentiate from any other company in town. The way I see it, there are plenty of great PMs who do wonderful things, but we want to do things that we can look at and confidently say “no other property manager in our market is going to do this”. Not only did this help us stand out on its own, it also gave us some great material that we could use from a marketing and PR perspective. There were some fantastic examples of really impactful things we did for our residents, and we’re able to track those and promote them later. Ultimately, we want to show that we support people through more than just housing. These residents are not just numbers to us. Empowering our property managers Before we implemented the love budget, our property managers did still have a way to give gifts and surprises to their residents, but the process was clunky. Basically, they could bring up ideas that they wanted to execute on, and then their supervisor would have to decide whether or not to approve it. The big shift was putting power in the PM’s hands. Our belief was that our boots-on-the-ground property managers should be able to do this quickly, on the fly, while they’re on a phone call with someone. Jumping through approval hoops just delays and waters down the impact. They’re closest to the decision being made so they should be making the decision themselves. It’s also really gratifying for the property manager to know that they have decision-making rights. They feel empowered, and they get to go home at the end of the day and say, “Yes, my job can be really hard, but today I got to do something kind and meaningful that someone’s going to remember.” There’s science behind giving that suggests iIt can be more satisfying to be on the giving side than the receiving side. We want our property managers to feel that satisfaction. It gives our team a lot of pride in what they do, which makes them want to work better and give an even better experience to our residents. How it comes to life One of the coolest things about this program is that we’ve seen so many different creative things our property managers have done. Giving them the freedom to do what they feel is going to be most impactful for the residents that they’ve developed relationships with is so much fun to see. Here are a few unique examples of how our property managers have used their love budget: One resident—an older woman—had been in the unit since before we managed it. For her 90th birthday, her property manager ordered a huge bouquet of flowers and hand delivered it to her door. The PM took a photo with her and shared it with the team and it really motivated people and impacted them. Another resident’s son was having a birthday, and he loved Spider-Man. The property manager personally curated a gift basket with all things spiderman. That resident still mentions it any time she comes into the office, mentioning that her son still loves his Spider-Man pajamas. One family with young kids mentioned that the kids really loved animals, so we gave them an annual membership to the zoo. They could go as often as they wanted without having to worry about the cost. Creating a personal touch at any scale The reason that I love our program so much isn’t because we’ve invested a ton of money into it. It’s just that it reaches our residents in meaningful, personal ways. Regardless of the scale or financial position of your business, it’s the thought that counts. That might sound incredibly cliché, but it’s true. Ask yourself, how are you taking the time to learn enough about your residents that you can add a simple touch? How are you providing a more personalized experience than they’d get from anyone else? I honestly think that even just asking a simple question like “how’s your grandson’s soccer season going?” can go a long way, and that’s completely free. The key is to get out of the transactional mindset and get personal. At the end of the day, this business isn’t about doors or leases — it’s about people. And when your team feels empowered to lead with empathy, you create something that spreadsheets can’t measure: loyalty, pride, and genuine human connection. Looking to create a more engaging, personalized resident experience? Schedule a demo of Second Nature's Resident Experience Platform to see how.

Calendar icon November 6, 2025

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The Move-In Experience Sets the Tone for the Entire Lease

It’s pretty common—and backed by science— that someone’s first experience dictates how they’ll feel about the rest of their experience. That’s why the move-in experience is so important for property managers, because if you can nail onboarding, you’re likely to have a customer who loves you for life. Now, obviously, this isn’t 100% foolproof, but if you miss the move-in experience, you have a steep mountain to climb to rebuild that relationship. We’ve seen this in our own data at JWB, too. When we get a negative review from a resident within a month of move-in, the chances of that resident renewing go down. If they put in a maintenance request within the first seven days, their resident NPS is lower for the full duration of their lease. The move-in is the tone setter, and there are lots of important business metrics tied to these experiences. Control what you can Obviously, some things during the move-in process are out of your control. For example, we’ve had residents show up to move in, and it turns out there’s been a break-in at the property since we did our last walkthrough. The key is to control what you can. That might mean timely communications, clear instructions about key pickup, or a nice move-in gift waiting for them when they arrive. For us it includes a detailed walkthrough prior to move-in. We choose not to do this alongside the resident, because getting in there early gives us the chance to get in front of any issues before the resident is exposed to them. It keeps their first impression positive and makes things appear seamless. Focus on expectation setting A huge part of a good resident move-in and onboarding experience is setting clear expectations up front. You want your residents to know exactly what they can expect from your team, the process, and the condition of the home before they ever set food in the property. As part of our process, we talk through what’s in the lease with approved applicants. We note things like elective vs. included items, what “as-is condition” really means, and more. We’re not just sending them a long PDF lease and asking them to sign it. Our philosophy is, if you’re going to pay us a bunch of money, first we want you to know what you’re getting so that there’s no confusion later. We’ve also created a simple move-in walkthrough video that covers some of the most important things our residents need to know, like: How to create their resident portal How to submit a maintenance request Where to find our contact information, including our emergency number What a Resident Benefits Package is In the era of Tiktoks and Instagram Reels, residents don’t want dense handbooks that they’re never going to read. By giving them a simple, digestible video, we’re increasing the chances that they’ll pay attention and actually understand it. Solicit and consider feedback Beyond expectation setting, one of the core ways we try to create a great move-in experience is by truly connecting with our residents. We do that by making them feel heard, and by providing a dedicated, private place where they can provide feedback on their experience. (As a side benefit, this keeps them from voicing any negative comments publicly.) As part of this process, we established post-move-in check-in calls, and put a particularly heavy emphasis on these in 2025. All of the property managers on our team are responsible for calling the residents in their portfolio about two weeks after move-in. They’re basically just saying, “Hey, how’s it going?” But they’re also specifically asking about: How the residents are settling in If there’s anything they need from us to make them more comfortable Whether any maintenance items have popped up What else we can do to make sure they’re happy and to start this long-term relationship off on the right foot Since we’ve implemented these calls, we’ve seen a direct boost in our 30-day post-move-in NPS, so it’s clearly having an impact. Give residents the power of choice These check-in calls also have the impact of giving us clear areas of focus. One area where we received a lot of feedback was our move-in cleaning. As part of our turnover process, we do a final cleaning and a final mowing to make sure that the properties are ready for our new residents on day one. Unfortunately, we received some critical feedback about the quality of our cleanings, with some residents saying that their home wasn’t clean enough when they moved in. That caused us to step back and look at our process more closely. Typically, we do a deep cleaning during the property turn, after any maintenance is done and before we start showings. That’s fully paid for by the owner. Then, if the property is vacant for a while, we’ll do a touch-up cleaning every couple of weeks, and one final touch-up before move-in. That typically consists of a simple dusting and sweeping, but from time to time, when a property is vacant for a long time, there could be bigger dirt build-ups that get missed. Ultimately, we got together and decided that we wanted to give people the option of a deeper move-in cleaning. Basically, new residents could choose to either have our standard wipe-down cleaning for free, or opt into a move-in deep cleaning, for an extra fee. We partnered with a vendor to get this at a flat cost and make it as affordable as we could for our residents. This way, if a deep cleaning is important to a new resident, they can choose to have it done and it eliminates a potential future complaint. If the resident feels it’s too expensive, or if it isn’t that important to them, they can decline it, but it still eliminates a future complaint because they made that decision. Now our residents feel empowered by choice and they have a sense of agency in the move-in process. Monitor your progress and keep improving the move-in experience Make sure that, as you’re making changes to your onboarding process, you’re tracking the impact of those changes. In our case, our resident experience coordinator monitors all of our NPS data and meets regularly with the team to address any feedback we’ve gotten. We can see changes in both short-term (30-day) NPS and long-term NPS as those residents move through the rest of their lease term. Data can be a powerful tool to help you improve resident experience, but the most important thing is to put yourself in the shoes of the resident, and to keep striving for a better and better experience.

Calendar icon October 23, 2025

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Why We Developed JWB’s Homestep Home Buying Program

Homebuying assistance programs are starting to gain traction among property management companies, and for good reason. They’re a great way to give something back to your residents while also differentiating yourself from the competition. In this article, I’m going to walk through Homestep, JWB’s homebuyer assistance program, including how it works, how we implemented it, and how it’s helped our business so far. Asking, “what’s the most we can do?” At JWB, instead of asking ourselves “What’s the least we can do to solve this problem?” we ask ourselves, “What’s the most we can do?” We’re always looking for ways to go above and beyond to delight our clients and our residents. With our Homestep program, we wanted to take that approach even further. We knew that housing affordability is a challenge, both in our city of Jacksonville and across the nation. High interest rates make affordability even more difficult, and many residents didn’t feel prepared, equipped, or educated enough on the topic to build up a downpayment. With that in mind, we wanted to try to take a small bite out of that elephant and make an impact for the residents that we serve. We recognize as a team that home ownership and equity can not only change a person’s immediate situation, but start to create generational wealth and put more power in the hands of the everyday people that we’re working with. We have real estate expertise in house, and we wanted to pass that on to our residents. Plus, from a pure business standpoint, we were confident that a robust homebuying program could be a differentiator from leasing, all the way through the full resident experience and lifecycle. How the program works When we designed the Homestep program, we wanted something that would give true value to our residents without overloading our team or overcomplicating our existing processes. We were deliberate about who we allowed to participate and what kind of home purchases qualified. Who’s eligible to participate? To start, we didn’t want this to be an opt-in or closed program. That’s why every resident that rents from us is automatically enrolled from day one. At least signing or renewal, residents are automatically enrolled, and stay enrolled provided that they remain in good standing. Each month that they rent one of our properties, they earn $100 per month toward a future housing purchase, with benefits maxing out at $3600. We offer a lot of long-term leases, which also max out at three years, so it was a logical way to align the program. Of course, residents don’t have to wait the full three years to leverage their Homestep funds. They’re eligible to redeem their funds for a home purchase any time after twelve months of residency with us. We also allow Homestep users out of their lease early with no penalty, as long as they’re in good standing; rent is paid, no physical damage to the property. We ask that residents provide a 60 day notice once they’re under contract for their home, and we don’t charge any fees for terminating the lease early. That added flexibility means that more residents can take advantage of the benefits they’ve earned, while we still have ample time to prepare for a turnover. Redeeming your Homestep benefit When a resident in the Homestep program finds their dream home, the process is pretty simple. As long as they don’t have an open balance on their lease ledger, there’s no major damage to the property, and they’ve rented with us for at least a year, they’re eligible to use the funds they’ve accrued. This isn’t just a simple transfer of dollars—we don’t hand them a check and say, “go buy a house.” Instead, we work with them via our Realtors. Residents have the option to purchase one of our new construction properties that are for sale. If they aren’t interested in purchasing one of our homes, that’s also completely fine; they can work with a JWB real estate agent to buy whatever home they’d like. In fact, we hired a dedicated Homestep buyer’s agent who’s a true specialist in first-time homebuying, so residents know exactly who they’ll be working with. We designed the program this way because we wanted everything to be as flexible as possible. Our homes are affordable compared to the average sales prices in Jacksonville, but we didn’t want to lock our residents into that. We wanted to give them options by opening the program up to any home in the area, provided they work with one of our agents. Going beyond finances We also knew that homebuying challenges extend far beyond just affordability. That’s why our program starts with education. We pair the financial side of the program with education, support, and resources to drive value. We want our residents to understand topics like escrow accounts, property taxes, homeowners insurance, PMI, and HOA fees before they make one of the biggest financial decisions of their lives. These are things that first-time homebuyers might not understand, and we want to be there to truly support them. We had already started hosting free homebuying education classes years before we introduced the Homestep program. We had worked to support residents who were looking to buy homes, matching them with our lending partners and insurance partners. We were already offering our realty services to residents who wanted to purchase homes. The Homestep program just reemphasized the importance of our education efforts. Every quarter we market our homebuying class to all of our residents. We host them at our office in the evenings, and we provide pizza and soda so that people can bring their kids and families if they need to. Sessions are about an hour long and open to the first 100 registrants, which is the max capacity for our office space. One particular member of our team is extremely well versed in real estate, and has actually done all of JWB’s property acquisitions, so she was a natural fit for this role. She teaches our homebuying class and leverages all of that expertise to help our residents better understand what the process is like. We invite a preferred lender to co-teach the class and cover the underwriting process and financial side of homebuying. It’s an opportunity for our property managers to get facetime with residents, and our realty team is there to answer any questions anyone has. Afterward, we send attendees follow-up information on the Homestep program so that people are fully informed and know what their options are. Seeing real results We only introduced the Homestep program a little bit under a year ago, but already we’re seeing a real impact on the lives of our residents. We already have over 3,200 residents officially enrolled, which is a big chunk of our 5,600 homes under management. We have about 30 residents currently actively looking to find a home through the program, most of them working with our Homestep buyers agent, and four under contract. Year to date, we’ve closed 11 deals with our residents. As a side benefit, it’s also helping us build up our realty business’s brand, which has been great to see. The long-term goal for the program is to hit five Homestep closings per month. We’re really excited about the growth of the program and our ability to have such a huge impact on our residents’ lives. Honoring our commitment to our clients As we were putting together the Homestep program, we wanted to make sure that we were also honoring our commitment and our fiduciary duty to our clients. There was a lingering question of whether encouraging residents to purchase homes—and vacate our rental properties—was counter to our mission. The reality is, residents who are interested in the Homestep program are likely to be high quality, dependable residents. They’re more likely to pay on time and take better care of the property because they want to be eligible to use those funds when the time comes. There’s an inherent benefit in having financially-savvy residents in your properties. Plus, we made sure that residents have to stay for at least twelve months in order to use their funds, so we’re already encouraging them to stay at least a year. Plus, they start to develop a more personal connection to their home, their management company, and the property owner, because we’re giving them real, life-changing value. Aligning our focus as a company We didn’t get a lot of pushback from clients, who saw the benefit of the program. We did have some conversations about it internally, because we wanted to make sure that this investment was aligned with our mission. We even looked at our internal KPIs, like renewal rates, and reevaluated how we were measuring performance. Now, in addition to their goals around renewing a certain number of leases, property managers are also measured on how many Homestep leads they generate. We wanted to shift our view to look at the bigger picture. What is it that we’re trying to accomplish? By reevaluating our team’s goals and realigning them with this new initiative, we stayed true to our mission as a business. We didn’t want to be so focused on just one metric—in this case, renewal rate—that we missed the larger point. Do what makes sense for your company Introducing a comprehensive homebuyer assistance program has been great for JWB. If you have the financial means and infrastructure to develop a homebuying program of your own, I’d definitely recommend it. But the good news is that you don’t have to shell out a ton of money to empower your residents. We chose to offer the $100 per month, but there are other ways to do this that cost a lot less. Homebuyer education classes can be done cheaply or even for free if you have someone qualified on staff. Offering credit building services is a great way to help residents prepare for homebuying. There are plenty of ways to get creative. Remember, small steps can still make a big impact. Looking for more ways to delight your residents? Join our next RBP workshop to hear from real property managers who have implemented a Resident Benefits Package and improved the resident experience.

Calendar icon September 25, 2025

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Experience First: Why We Hired a Dedicated Resident Experience Coordinator

In more than a decade in property management, I’ve learned that delighting residents is one of the best ways to increase renewal rates and win more clients. We recently made the choice to formalize that into a dedicated full-time role, the Resident Experience Coordinator. Through careful planning, plenty of internal conversations, and a little bit of experimentation, we’ve seen a clear impact on our business and our resident satisfaction. It’s been a great business decision and a great way to show that we’re invested in our residents. After all, we can all say we care about resident experience, but if we aren’t intentionally taking steps to make residents thrive, do we really care that much? What is a resident experience coordinator? A resident experience coordinator is a dedicated individual on our team whose primary focus is increasing resident satisfaction by going above and beyond, gathering and listening to resident feedback, and recommending policy and process improvements across the business. She operates across the property management team and works on improving every aspect of our business that touches the lives of residents. While this isn’t a common role at most property management companies, we at JWB decided to take the leap and invest in resident experience like never before, with the goal of improving our residents’ lives and giving them the best renting experience possible. Why we decided to create a dedicated role Conversations about making resident experience a dedicated role started after we hosted a resident experience workshop. The workshop looked at what we were doing today and how we could improve our resident outcomes. We left that meeting feeling like we were doing a lot of great things and working hard to deliver a strong resident experience, but that we could always be doing more. We decided that, since our property management and support teams were closest to our residents, we should ask them for ideas, suggestions, and pain points to solve for. We came away from that conversation with about 80 different ideas on how we could continue improving. We were excited to get started, but we immediately realized that all of these ideas would add more work to our property managers’ plates without removing any of their existing tasks. We didn’t want to overload our team or shift their priorities away from other business-critical work, and we worried about things getting lost in the shuffle if we gave them too many tasks. That’s when we started to consider creating a new role. Making it full-time As we started to think about hiring a dedicated person for this role, our only real question was whether it was truly a full-time responsibility. We knew there was tremendous potential value, and we were bought in on the idea, but we didn’t want to hire someone only to realize it should have been a part-time job. We started by putting together a job description. We weren’t just listing out responsibilities (although that was part of it); we were identifying core goals, KPIs, and metrics. We had to determine how to objectively measure resident experience, if it could be measured at all. What are the roles and responsibilities? Around the same time that we were starting to discuss hiring for this position, we were also experimenting with building out a resident committee. We wanted to select 10-12 residents who could be our “VIPs,” who could weigh in and give feedback, ask us questions, and help improve our processes. We knew we would need someone to spearhead this initiative, and the resident experience coordinator was a perfect fit. We had our first job responsibilities nailed down. We had also tested out running a community town hall event for all of our residents. The idea was that we would get them together locally and have an open discussion about where we were meeting expectations, where we weren’t, and what we could do better. It was a deeply vulnerable experience, but it was hugely successful, and we knew we wanted to do more. Again, this was the perfect project for a resident experience coordinator to take on. We had other events on the docket, too, like social and community gatherings at our multifamily properties, which were another great opportunity for this role. But we also wanted to go beyond just event coordination. Here are some of the other day-to-day functions that we found were a great fit for this particular role: Overseeing our review process: The resident experience coordinator is responsible for soliciting new reviews, but also for monitoring every site where we get reviews, responding to them when needed, and communicating them to the internal team. Managing NPS data: This person owns our net promoter score, reviewing scores weekly, monitoring trends, and identifying opportunities to make improvements. This is a core KPI for a resident experience coordinator. Reviewing our escalation process: Particularly when it comes to maintenance and work orders, we want to make sure we’ve got strong processes in place for escalation paths. This role reviews escalations on a routine basis, looking and when, why, and how items were escalated, what trends there are, and how we can adapt our processes. What aren’t the responsibilities? We were very careful to make sure we weren’t creating confusion between this new role and our expert property managers. The biggest difference is that our PMs each have a portfolio of homes that they’re responsible for, and they still handle all of the basic management functions like collecting rent, renewing leases, and coordinating move-outs. The resident experience coordinator does not have a set portfolio, and instead works across all of the properties that we manage, helping to deepen relationships. She sits on the property management team, but as an extension of the team. Make no mistake, our property managers are still building strong relationships with their residents. The experience coordinator does not replace that. They’re still friendly faces and helpful points of contact for residents. The experience coordinator just adds another level of proactive support to help delight residents wherever possible. Having a measurable impact Ultimately, we ended up hiring for this role from within. We took someone who had years of experience on our team, working with our residents and vendors, and shifted them into this position, and it couldn’t have gone better. She’s already won teammate of the month twice this year because of the impact she’s had on the business and her peers. Our NPS score is higher than it’s ever been, thanks in part to her hard work and dedication. And we’ve gotten great anecdotal feedback from our residents about her performance and customer interactions. Across the board, shifting to a dedicated experience coordinator has been a boon. Remember, there’s a lot of financial value in improving the resident experience. Happy residents stay longer, take better care of your properties, leave better reviews, and refer other residents to your properties. But there’s also just inherent value in taking good care of your residents. At the end of the day, we want to provide safe, comfortable, enjoyable housing for as many people as we can, and dedicating time and resources to the resident experience is a huge part of that. Final thoughts Making hiring decisions is always tricky. You have to consider your finances, the size of your existing team, and how quickly you plan to expand the business. But hiring a dedicated resident experience coordinator was a great decision for our business. I’m a firm believer that having a dedicated person leads to the best outcomes over time. Our hope was to see NPS scores increase because of the increased touchpoints, better communication methods, and a heartfelt person who can step in when things go wrong, and that’s exactly what’s happened. If your business is in a position where hiring is on the table, make sure to consider an experience coordinator. If you're looking for additional ways to improve your resident experience, consider adding a Resident Benefits Package.

Calendar icon September 18, 2025

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Leading Means Truly Connecting with your Team

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

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

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

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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