A Day in the Life: Working with a Less-Experienced Property Manager

I’ve worked in property management for a few years now, and I’ve seen my fair share of challenging situations. But nothing quite prepared me for the day I had to work alongside one of my new colleagues—let’s call him John. John had just been hired as a property manager, and while he had all the right qualifications on paper, it quickly became clear that his “street smarts” in property management were a little lacking.

The day started like any other. I was in the office, catching up on emails and reviewing tenant feedback when John popped his head in. He had a perplexed look on his face, which wasn’t unusual. But this time, it was different—he looked a bit panicked.

“Hey, um, can you help me with something?” he asked, clutching a file.

“Sure, what’s up?” I replied.

John sat down across from me and opened the file, showing me a lease agreement that seemed…off. It was filled with scribbled notes, highlighted sections, and some odd markings I couldn’t quite make sense of. The lease was for a new tenant who was scheduled to move in later that afternoon.

“Okay, so I’ve got this lease for the new tenant, and I’m just not sure about the rent amount… it doesn’t match what was in the listing,” John said, scratching his head.

I took a look at the paperwork. Sure enough, the rent amount on the lease didn’t match what was agreed upon when the listing was posted, nor did it align with what had been discussed in the initial phone calls.

“How did this happen?” I asked, trying to stay calm. The lease had already been signed by both parties, which was a bit of a red flag.

John’s face turned pale. “Well, I… I didn’t check the online listing against the lease before sending it to the tenant. I thought it was all set.”

I blinked. “John, you’ve got to double-check those details. Especially when it comes to rent. That’s one of the most critical parts.”

“I know, I know! I just… I was really busy trying to get the unit ready for move-in today,” he stammered.

At this point, I was trying to figure out how to fix this mess. The move-in was in a few hours, and we couldn’t afford to have a tenant showing up expecting one rent price, only to have a different one on the lease. I quickly called the tenant, who was understanding but clearly frustrated that the mistake had been made. Luckily, she wasn’t moving in until later in the day, so I had time to get everything sorted.

After hanging up, I turned to John. “Okay, we need to amend this lease, get a corrected version signed, and send it over to the tenant ASAP. We also need to make sure the rent change is updated in the system before she arrives.”

John nodded, but I could see he was overwhelmed. I knew he was still getting the hang of things, but he seemed to be in over his head.

We spent the next few hours getting everything straightened out. I walked him through updating the system, correcting the lease, and explaining why double-checking these details was vital to avoiding legal headaches down the line. He listened, but I could tell this was a lot for him to process in one go.

Once everything was fixed and the tenant was happy with the new arrangement, I sat down with John for a quick debrief. “Listen,” I said, “I know you’re still learning the ropes, but these little details—like checking the rent and confirming everything matches—are the backbone of property management. If you get those wrong, it creates big problems.”

“I get it,” John replied, looking sheepish. “I’ll be more careful moving forward. Thanks for stepping in and helping me out.”

“No problem,” I said, trying to keep it light. “Just… remember to slow down a bit. No one expects you to be perfect, but making sure the basics are covered is the bare minimum.”

The Aftermath

The next few weeks were a bit of a learning curve for John. There were a few more small slip-ups, like not following up on maintenance requests or missing key details in tenant communications. But each time, we worked through the issue together. Slowly but surely, John started to get more comfortable in his role.

It was clear that John had the potential to be a great property manager—he just needed time and more hands-on guidance. What I learned from this experience wasn’t just about how to fix mistakes. It was about patience. When you’re working with someone who’s not quite “there yet,” it’s easy to get frustrated, but the key is helping them build confidence and competence over time.

Now, months later, John is a much stronger property manager. He’s still not perfect, but he’s made significant improvements. And I know he’s learned that, in property management, attention to detail really is everything. It’s not just about making sure the rent matches the listing—it’s about building a reputation for reliability, trust, and consistency.

Would I say John was the smartest or most naturally skilled person I’ve worked with? Probably not. But with a little guidance and a lot of patience, I’ve seen firsthand how someone can learn and grow, even when they start off a little slow. And sometimes, that’s all it takes.