Triple Win Property Management Blog | Second Nature

Learning to Empower your Property Management Employees | Second Nature

Written by Tony Cline | Apr 24, 2025 2:00:00 PM

Tony Cline has over 20 years of experience in property management. After purchasing a real estate and property management brokerage in Denver, Colorado, he spent more than two decades as managing broker. Today he's focused full time on his work as a Property Management Success Coach. Tony is a Second Nature Triple Win Mentor.

Managing a team is hard, especially when you run the company. You want to empower your teams to be more than just button pushers, while also keeping a high level of execution and not putting your business at risk.

It starts with hiring the right people, identifying their strengths, and putting them in the right seats. But beyond that, you have to make sure you’re giving them the room they need to learn, grow, and sometimes fail.

Learning to let go of control over every detail, and instead trust your employees, will help you see more success, keep your best employees longer, and establish yourself as a true leader of your business.

Getting started with hiring

When I was just ramping up my property management business in Colorado, I fell into one of the classic traps that small business owners face. I just wanted to put butts in seats. I wasn’t hiring with intention.

When you’re in grow-at-all-costs mode, it’s easy to start hiring whoever you can for whatever roles you can. But the danger is that you put people in the wrong positions and you don’t set them up for success.

The lesson I learned very quickly was that I needed to be looking for people who were passionate. First, they needed to be passionate about the type of work we were doing. Second, they needed to be passionate about the types of properties we were managing.

I learned that I needed people on my team who were bought into the long-term vision. They needed to have the same core values as we did if they were going to be successful. And beyond that, I wanted people who had the desire to learn, take on a challenge, and become better.

Putting people in the right spots

The specific skillset and attitude you need might vary by role. For example, in a sales position, you want people who have the drive to own everything, and may even have aspirations of becoming their own boss some day. But in operational roles, you may need people who are more focused on the small details, who like to get in the weeds and solve problems. 

Each person has a specific role to fill. I think of it like getting dressed in the morning; it doesn’t do much good to have 5 pairs of pants but no shirt.

Learning to let go of control

When I first started leading a property management business,I started out as too much of a control freak. I didn’t want people who would challenge my ideas or thoughts. I thought I was the smartest person in the room, and it was my business, so I was in charge.

As a result, I held back my team. I didn’t give them ownership over their work. And it hurt my business.

But then, in 2006, I got sick, and it became absolutely necessary to hand over control. It was the only way for my business to survive. I couldn’t own everything. I had to give people the opportunity to step up. And when I did, there were people there who really flourished. They just needed to be given the space to do it.

It’s one of the most important lessons I’ve learned in business. People need to have authority and ownership to excel in their role. You need to give them direction, and then you need to get out of the way.

You can’t steer a parked car; you have to be in motion to change direction.

Getting comfortable with the occasional mistake

One of the biggest sticking points for a lot of leaders—especially in property management—is a fear that, if they give responsibility to someone else, that person will make a mistake.

I have two responses to this: First off, mistakes are inevitable. Of course they’re going to happen, but that’s okay. Second, the stakes really aren’t that high. We’re not driving ambulances and getting lost on the way to the hospital.

Really, what’s the worst that can happen? If we’re late getting a payment out to an owner, maybe we’ll get an upset phone call. We’ll feel like we have egg on our faces when we have to apologize. But we’ll all move on from it and we’ll find a way to make it right.

Realistically, holding back your employees is costing a lot more than letting them make a mistake. When you create an environment where it’s okay to make a mistake, you create an environment of trust. And when you have that, you have a successful workplace where people want to work.

Besides, why have someone on your team if you aren’t going to trust them to take on responsibilities and grow?

 

Holding onto your best people

Keeping talented team members is tough. Turnover is a big issue in all small businesses, but especially property management. There’s a ceiling on growth, and a lot of good employees hit it pretty quickly. There just aren’t that many positions to grow into when your team is only four or five people. And that means there’s no big promotion or big raise that they’re working for.

I believe you can still keep your best and most ambitious contributors. You just need to give them something worth working for.

I always say that people will suffer for a cause, but they won’t suffer just because. You need to give people a north star to work towards, and you need to hire people who believe in what they’re doing. When people are bought in on your company vision, and when the work they’re doing is directly tied to it, they can continue to grow even in the same role.

Final thoughts

One thing that I try to bring into my leadership style every day is believing in people more than they believe in themselves. I truly believe people are capable of more than they think they’re capable of. Everyone carries some level of impostor syndrome, and a great leader can help them overcome it by believing in them, coaching them, and empowering them.

When I see that someone has the right values and they’re bought in, that’s when I start to give them more and more guidance on how to improve. Most people will rise or fall to the level of your expectations, so set your expectations high, and then give them the support to meet it.