You know, when it comes to property management in Chicago, it’s easy to fall into the mindset of "keep the place clean, safe, and make sure rent gets paid." That’s what most landlords and property managers think is enough.

But let me tell you — after years of doing this and after a killer podcast we just recorded with Joey Coleman, I’m convinced that thinking is exactly what’s holding a lot of property owners back.

You’re missing the bigger picture. The resident’s experience.

Stop Thinking "Tenant." Start Thinking "Resident."

Words matter. Joey nailed this point.

When you say "tenant," you’re subconsciously saying this is transactional. When you say "resident," you remind yourself and your team that this is someone’s home.

We made this switch years ago at GC Realty. Clients instead of owners. Residents instead of tenants. And guess what? It’s changed how we operate — and how people feel living in our properties.

The First 100 Days: Where Most Property Managers Drop The Ball

Here’s the truth: signing the lease isn’t the win.
 Getting the lease renewed without a headache a year from now — that’s the win.

Joey broke down something that really resonated with me: There are 8 stages every resident goes through. Most Chicago property managers? They only focus on the first two — getting them in the door.

The biggest miss?
 Right after move-in, when doubts creep in.

• “Did I make the right choice?”

• “Is this landlord going to be responsive?”

• “Am I going to regret this in 6 months?”

This is when you need to step up. Not avoid them and "hope for quiet."

Move-In Day Is Not the Finish Line — It’s the Starting Block

Most property managers and landlords avoid move-in day. They just toss the keys and say "good luck."

Huge mistake.

Moving day is stressful — people are tripping over boxes, they can’t find their coffee maker, and nothing feels like home yet. This is when you should show up (literally or through small touches).

• Send a quick text or call: “Anything you need? How’s move-in going?”

• Leave a simple welcome kit. Even a note and a roll of paper towels shows you care.

• Give them helpful tips — where to park, how trash pickup works, or the best local pizza spot.

That’s proactive. That’s how you make them feel taken care of right off the bat.

Ease of Doing Business Is More Important Than You Think

Joey said it — and I couldn’t agree more:
 "If doing business with you is difficult, you’ve already lost."

Think about this:

• Still printing leases and asking people to hand-sign?

• Making them jump through hoops to submit maintenance requests?

• Sending 5 emails back and forth to renew a lease?

That’s old-school and drives people nuts. In Chicago’s competitive rental market, being easy to work with is your competitive advantage.

Not Everything Is a Yes (And That’s Okay)

I get asked all the time, "Mark, what about when residents ask for stuff that’s just a hard no?"

Joey nailed this one too.
 It’s about setting clear expectations upfront — and when the tough questions come, handling them with empathy.

“I totally get why you’d want new cabinets — and we do renovations on schedule to keep rents reasonable for everyone. While it’s not something we’re able to do right now, we’re happy to keep that in mind for future updates.”

It’s not about saying no — it’s about saying it the right way.

Forget the Logo Gifts. Make It Personal.

Look — no one wants a hat or calendar with your logo on it. That’s not a gift, it’s marketing.

If you really want to make an impression:

• Send a small gift after 3 months of on-time rent.

• Celebrate anniversaries in the unit.

• Acknowledge renewals with a thoughtful touch (not a generic email).

Joey told a story about a $35 golf ball that landed him a $35,000 deal — why?
 Because it was about the person, not the product.

Your Residents Can Be Your Biggest Advocates (If You Treat Them Right)

Here’s the bottom line — and Joey said it best:

"People don’t usually say 'I love my landlord' — but if you make it easy, proactive, and personal... they just might."

In a tight Chicago rental market, where word-of-mouth and reviews make or break you, turning your residents into advocates is the smartest thing you can do.

Stop thinking "keep it clean, safe, and collect rent."
 Start thinking "how do I make living here so good, they never want to leave?"

Need help delivering that kind of resident experience?
Check out our Tenant Placement Services or Request a Free Rent Analysis to make sure you’re competitive and your residents are happy.

This episode of the Straight Up Chicago Investor Podcast is a must-listen for landlords, property managers, and real estate investors in Chicago who want to step up their game. Featuring Joey Coleman, internationally recognized customer experience expert and bestselling author of Never Lose a Customer Again: Turn Any Sale into Lifelong Loyalty in 100 Days, this conversation goes deep into why resident experience can make or break your rental business. Joey, who has worked with global brands to transform client relationships, joined Mark Ainley of GC Realty & Development to discuss how his resident-focused strategies are especially critical for Chicago landlords navigating a competitive rental market.