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.
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:
Each step is vital to setting up your team for success, so let’s walk through them one by one.
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 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:
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.
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.
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.
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.