A Day in the Life of a Rental-Focused Chicago Realtor

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Last week I described what I did during an average day when I worked as a leasing agent for a local landlord. That was the first half of my real estate agency career. Today we’ll be doing the same thing but looking at the second half when I was working for a real estate brokerage as a Realtor focusing on rentals.

I’m going to start out by saying that in this article I will be revisiting a job that was one of the worst experiences of my life. Not the absolute worst, but certainly one from which I’ve needed a long time to recover. This was due mostly to the culture of the company. The work itself was been mostly enjoyable. The buildings were beautiful. My employer was sterile, cold and totally unequipped to provide support for what they hired me to do.

Things have probably changed at that company since I left. They created a specific rental division. They started putting more money into the rental part of the business. They realized that by ignoring rentals they were missing 60% of the Chicago market. But when I was there things were very different and I had to do a lot of pioneering work for my sponsoring branch office.

The Brokerage

In 2010 I realized that I had reached the top of my earning potential at the landlord’s office and opted to shift into residential real estate sales. I chose a smaller branch office of a large local real estate brokerage. I originally went with the intention of focusing on small apartment building sales, but things didn’t turn out that way.

I entered the real estate market at the bottom of the recession when the majority of residential sales were foreclosures or short sales. There was no money available for financing small apartment building transactions. Buyers were skittish of getting into a market that had soured so badly, with the exception of very wealthy buyers who were completely alien to my entire previous agency experience in low to mid-income vintage apartment leasing. Condo sales were out of the question as project after project failed underwriting.

As it turned out, I was rather uniquely positioned within my new office to handle the one area of the residential market that hadn’t gone south: I could still do rentals. But there was a catch that I hadn’t anticipated. Nobody else in my office did rentals. Nobody really knew how to do them. Not even my boss was familiar with the CRLTO except to be vaguely aware of its existence. Not only did they not understand rentals, but they largely hated working rental transactions with a passion. This wasn’t just a localized issue with my particular office either. The head office actively discouraged agents from working rentals and didn’t even provide a valid paperwork structure for processing them.

Other agents had their listings blasted to a ton of websites but few of those sites specialized in rentals so I had to set up my own ad syndication automation. Other agents didn’t have to worry about things like pulling credit reports and criminal histories since all of that is handled by mortgage brokers when you’re dealing with sales. I had to contract out my own credit reporting. Other agents had templates for brochures, flyers and marketing materials but they were all structured for sales. I had to do all of my own graphic design and layout to customize them for rentals. Other agents had free access to professional photography of their listings through the brokerage. I had to do my own photos, including any post-processing and uploading them to the MLS.

It wound up being quite the passive-aggressive environment. The other agents resented me for doing rentals and made a lot of snide comments about my work, but they would forward over their underwater sellers so that I could temporarily find tenants until the market recovered. They would want to keep younger clients on their list of referrals even if those clients weren’t ready to buy yet, so they would send those clients to me to help them find apartments that would last them a few years. Many of the other agents and my boss were landlords themselves and would bounce questions off of me about how to comply with the CRLTO. I wound up holding seminars in the office to teach other people the finer points of the CRLTO, a task which was not only above my pay grade but something that really should have been handled by a licensed attorney rather than the youngest agent in the office.

I did some sales transactions, all assisting buyers. I didn’t get my first sales listing until I had been there for 5 years and was already completely done with the whole situation. But I did a lot of rentals. In fact I led the office in closed transactions for 2 out of the 5 years I spent there. I carved out a little niche for myself as the rental agent of the office and I was fine with that since there were very few agents in the entire city of Chicago who repped for renters. Apartment locators practice dual agency. Plenty of agents will rep landlords. The number of good agents from all brokerages throughout Chicago who actually repped renters were so few that we got to know each other quite well. I was closer to them than I was to anyone in my office.

The scene has changed quite a bit in the years since I left, as several brokerages including my own have now created their own rental divisions. But from 2010-2015 I stuck with an office that couldn’t support me, a boss who couldn’t train me and coworkers who largely devalued my work.

When reading my schedule below, the other thing to remember is that I do not under any circumstances use my phone while driving. Phone time is phone time and it stays off while I’m in the car. This means that my day had to be structured somewhat more precisely than other agents. In other words, the day I’m about to describe is not going to be that of your standard Realtor nor your standard apartment locator. But it worked for me and a case study is a case study even if it’s a statistical outlier.

The Standard Work Day

As with last week this will describe a standard mid-summer weekday. On Saturdays I would do nothing but showings. On Sundays I would usually help another agent in the office by sitting an open house for them in the late morning and then do more showings in the afternoon. There were no regular days off in brokerage.

8:00am. (Optional) Photo shoots of listings on the west and north sides of the street, home inspection tours for buyer clients, sales closings. These all had to happen very early in the morning. Alternately if I had an afternoon meeting scheduled this would become my graphic design slot for the day.

11:00am. Schedule showings for the next day. This usually involved calling the listing agent to work out key pickup or requesting a showing using an online calendaring website. Notify my own office of any anticipated drop-offs or pickups during the day. I would do these at my home office if the 8am slot was empty, otherwise I would do it in my car.

Noon. Return calls and emails from the overnight and morning hours.

2pm. Design or pull marketing materials for the evening showing tours and send to the office color printer for pick up at 4pm. Photo shoots of buildings on the east side of the street. If I absolutely had to go into the office for any reason for meetings, training, etc. this is when I would do it.

4pm. Pick up marketing materials at the office and check my mail. Briefly wave at the boss to make sure he knew I was still alive.

4:30pm. Showings until 8pm. If I was representing a landlord I would try to be present for any showings coming through because I found a lot of the sales agents who didn’t respect the rental market would send their clients to view a place unaccompanied. (This is against the law, by the way.) I would usually place a lockbox with the keys on the property and allow renters’ agents that I trusted to show without me being present provided the unit was vacant. If I was representing tenants I would be on tour with them and driving them from location to location. Unless I was really overloaded with listings I would alternate days between landlord side and tenant side. As with the previous job each showing took about half an hour. However, I was now covering the entire city plus suburbs to the north and northwest as far out as Schaumburg, so time in transit was much much longer.

Dusk. (Optional) Photos of buildings on the south side of the street. These are always the toughest to shoot and I would often just have to Photoshop out the sky to get rid of the sun.

8pm. Return calls and emails from the afternoon and evening. Send notification warnings to tenants occupying in my own listings for any showings coming up in the next two days.

9pm. Process paperwork from the evening showing slot, including applications, credit reports, leases and updating any listings in the MLS with new prices or status changes. Completed background checks would go to my clients for review or, if I was representing the tenants, they would go to the listing agent for their review first.

11pm. Work on the next article for my marketing blog, which at the time ran three days a week.

1am. Review and amend my personal audit log for the day containing a record of all conversations and phone calls. Check schedule for the next day, set alarm accordingly, go to bed.

A Standard Showing, Broker style

First I had to get the keys. In a large complex the front desk staff usually had them on hand and would loan them out in exchange for a business card. For smaller buildings some agents kept them in lockboxes chained to the fence or discreetly hidden elsewhere on the property. Others kept them at their office and I’d have to stop by twice to pick them up beforehand and return them afterwards.

Then I had to find the place and park. GPS and a solid knowledge of streets, alleys and building address numbering is crucial for doing this efficiently. Many agents will work a very small territory so they can learn the good parking spaces very well. As the only agent working rentals in my office I didn’t have that luxury.

When showing an occupied apartment as a tenants’ agent I could never be sure if the current tenants had been properly notified so I always gave a dry run knock about 15 minutes before I needed to enter. I’d schedule the occupied ones at the start of a tour so I could come back around later in the day if needed. Occupied or not, once inside every apartment got the same treatment that I’d do for the apartments at the old job. Lights on, open the blinds, open the doors, hide the obvious personal info of current occupants. Closing up was the same routine in reverse.

If it was a place I’d never seen before I’d have to very quickly case the place on my own as my clients were doing the same thing. An agent’s eye starts from the top and works downwards to the floor. I would look at ceilings and places where walls were interrupted by things like windows, joints and electrical outlets. I would look at heating ducts and tread patterns on the floors. I would consider if clutter was due to messy tenants or insufficient closet space. I would think about all the things my old boss hated to maintain in a building and look at those places in every apartment I showed. I would always track down the breaker box and point it out to my clients.

The Earliest Form of RentConfident Reports

I started screening landlords when I was representing tenants at this job. The first reports did were rudimentary and sought primarily to balance out the screening work I was doing for my landlord clients. As a Realtor I had quick access to a lot of data that is far more buried for members of the public so I could very rapidly assemble a landlord profile that was sufficient for clients with whom I’d already established a line of communication. The versions that RentConfident uses are far more robust since that line of communication isn’t there between our report research staff and our customers, but the core data has remained the same for all this time.

“I Am Not a Lawyer, But..”

Realtors are not supposed to provide legal advice to their clients unless they have a license to practice law in the state where they’re working. Buyers and sellers regularly hire attorneys to represent them in real estate sales transactions. With rentals this isn’t the case. At the landlord’s office I had the luxury of working directly for an attorney and using his paperwork. At the real estate brokerage I no longer had that layer of supervision. There were a lot of times when I had to walk very close to if not over the line between real estate agency and legal agency.

There were a lot of times when I would have to approach a situation with a preface of “You really need to talk with an attorney about this, but the way we used to do handle these situations is…” There were a lot of times when I had to crib from old paperwork I’d squirreled away after other jobs to create leases and riders because my office didn’t have the right documents available for me to use. There were plenty of times when I thought about throwing in the towel and heading off to law school instead. Everything they teach you about agency in training classes for new sales agents is turned on its head when it comes to rentals. You will find yourself doing things that you know are technically wrong. You will gently fracture numerous laws every day just so you can clean up after the untrained locator agents who are shattering far more severe laws. It’s a very uncomfortable environment.

Paparazza Power

If any new agent were to ask me about doing rentals in Chicago, the one bit of advice I would give would be to hone your photography and your skill with Photoshop. Very few brokerages will spring for VHT photos on a rental listing since the profit margins on them are so small. A stellar photo portfolio in this era will bring in more interest than anything else you can put in the listing.

That being said, being thorough in your listings is also extremely helpful, especially if you’re working a listing that is likely to attract relo clientele. While not everyone knows how to search and sort through an MLS website, the competent clients do and so do their agents. It’s always a pleasure to work with competent people. Court them by putting in that extra effort. In residential brokerage it’s certainly important to connect with your clients on an emotional level but it’s also crucial to understand and fully utilize the tech that’s available to those in the industry.

Freedom and Selling Out

As an agent I was always an independent contractor. I set my own hours, I planned my own day, I got no benefits and was paid almost entirely on commission. But at the property management office the arrangement was far closer to an employee/employer relationship than the situation I was in at the brokerage.

There is a definite shift in demeanor required when moving from property management agency to free agency. As a property manager representing one or a handful of landlords I was at liberty to present myself in a manner that’s relatively close to my own personality with only a light professional gloss on it for the sake of propriety. A showing with a landlord’s agent is as much an introduction to the staff as it is an introduction to the property, so unless you want to be faking it every single day it’s much better of an idea to just be yourself when meeting prospective tenants so there’s no misconceptions about how you operate.

In free agency one is entirely the servant of the clients. You must cultivate the sense that you are completely on the side of the client no matter what and looking out for their best interest. I had to suppress a lot more of my real personality for this job. My values had to match my clients’ values at least temporarily. The hairstyle, makeup and wardrobe would change from hour to hour. In one day I could be a Christian or a Buddhist, a liberal or a conservative, a New Englander, a southerner, a south sider or a Brit. I had to alter my own aesthetic preferences to seek out what the client wanted in a home.

The End of it All

I left because RentConfident was more important and I knew that designing our research engine would take all of my attention for several months. I left because after 10 years of hustling around Chicago I had done everything I could. I left because I was ill. But I also left because throughout the entire time I was there my boss was pressuring me to take on sales listings, and when I finally got one I didn’t enjoy the experience. After 10 years of rentals it was too slow and too formal. I had been hoping for almost five years that breaking into that one remaining aspect of the business would make things all better, but it just made everything much worse.

I quit in the middle of a listing. Another agent in the office took it over from me. I mailed my office key back in and they mailed to me the few items that were in my desk. I avoid that block now if I’m driving through the area. Neither side of that experience came out of it unscathed. Four years later, a check of the website tells me that 14 of the 30 agents that I worked with are still working there, along with my former boss. All of the top producers and anyone I actually got along with have moved on to other companies or other offices.

There’s a lot of things I learned from brokerage, and not all of it is industry related. Flexibility, self-direction, tolerance and my own limits thereof. Understanding the values that people share openly and the ones that they hide. How to speak across generation gaps and how to discern which members of a group are dominant. Staying rational when everyone around you is getting emotional. All very valuable things.

But in retrospect the most important thing I’ve learned is how to recognize the signs of burnout in myself. I didn’t recognize it soon enough, in fact I was overdue to take a break by at least 18 months by the time it all came to an end. That’s something that I’ve only started recovering from recently, four years after leaving the business. Burnout is a very real thing and quite common in the real estate industry. If you’re a consumer looking for an agent it’s important to ask them how many hours they’re working in a week and how often they get to take a vacation, as their burnout could negatively affect the level of service they provide to you.

RentConfident is a Chicago startup that provides renters with the in-depth information they need to choose safe apartments. Help us reach more renters! Like, Share and Retweet us!

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Kay Cleaves

Founder and owner of RentConfident. She's the primary developer of the website and research engine code. She's spent over 10 years working in the Chicago rental industry and has assisted with over 1200 leases.