How to Grow Your New Chicago Real Estate Business

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You’re ready to commit to a career in residential real estate and jump in with both feet. Now comes the important question: How are you going to grow your business? 

There are as many ways to build a real estate business as there are brokers, and it’s important to spend some time thinking of a strategy that will be right for you. As you get started, consider what type of business model you would like to create, how you can emphasize your unique expertise and talents, and who you can turn to when you have questions or want to talk about your progress toward your goals. As with most facets of real estate, there is not necessarily a right or wrong way. It’s about finding the way that works for you as an individual, and sticking with it consistently over time. 

In my perspective, the path to growing your new Chicago real estate business comes down to three main parts: 

  1. Identify who you are, and what you like to do.  
  2. Work with your managing broker and team to develop a detailed business plan that includes specific tactics — including some that appeal to you, and some that you expect to find more challenging. 
  3. Execute your plan and monitor your results.

Oftentimes, people starting their career spend all of their time learning, and not enough time doing. Real estate is a profession that rewards action versus inaction — so while it’s important to have a strategy and a plan in place, keep in mind that there are a lot of different ways to be successful. The brokers who get the most out of these early days are going to be the ones who fully execute on a plan. 

Curious about how you can define and execute your own path to success? Let’s break down each of those steps in a bit more depth: 

Identify Who You Are 

Working with your Designated Managing Broker and the team in your office, identify what makes you, you — including your personality style, your strengths, your background, and your goals. 

In the Lincoln Park office, we typically try to support brokers by helping them develop lead generation and relationship building strategies that support their personality style. There are ways to be successful for every personality type that’s out there. One of the things that we do most frequently is to really get to know the person that we’re coaching and training so that we can most effectively support them. 

For instance, for someone who is extremely introverted, networking events and sitting open houses all of the time may not be suited to them, at least at first. Not only would this strategy not help them work toward their goals, but it also lowers the likelihood that their passion for the industry will continue. 

There are many ways for new brokers to develop self-awareness and start figuring out their preferred approach, including completing personality profiles or working through exercises. In conversations with your Managing Broker, you may also realize that you have a very good understanding of yourself. 

For example, If I ask a question like: “Would you rather give a presentation in front of a group of people or sit one on one and have a conversation?” Some people will say, “I love giving presentations.” If that’s the case, then we can discuss strategies tailored for that person. However, if someone says giving a presentation in front of a group is their worst nightmare, then I realize that this is somebody that I will probably have to work with to get to that level. That strategy shouldn’t go as number one on the list, and there are other paths to explore. 

With that said, we also strongly encourage brokers to get outside of their comfort zone every so often. In my personal experience, there are things I’ve done in my real estate career that I initially thought I would dislike. But once I started, I realized that I could be successful by going down an unexpected path — and it’s something that I can continue to develop and do. 

Develop a Business Plan

Successful real estate agents get their business and build their “pipeline” from many sources. We’ll explore some of these sources in more detail in a moment. To keep it simple for now, there are two main “buckets” of business for people starting a career in real estate: people you know, and people you don’t know. It’s important to access both of these channels — while recognizing that it may take some time and planning to get started, based on your background. 

On the front end, there are really two different categories of people that get into the real estate business: those for whom this is a first career, and those who are transitioning careers. When real estate is your first career, it’s often a bit easier to brand yourself as a real estate broker and dive into building relationships and generating leads headfirst. 

When you’re transitioning careers, it’s important to rebrand yourself, so that the people in your sphere start to see you as a real estate authority. This can take some time upfront. As a result, people who had a previous career are probably going to be more successful in their first three or four months generating real estate opportunities from people they don’t know. In these early days, their goal is going to be to get in front of as many new people and build as many relationships as they possibly can.

At the same time, they will also want to find ways to rebrand themselves as a real estate expert to the people in their sphere, personally and professionally. This comes from education, such as hosting seminars and events. On a smaller level, it can come from asking people the right questions, and consistently adding value. Once you’ve established this credibility with your network, they’re more likely to start sending referrals or working with you directly. It’s unusual that there’s an “on/off” switch. More often than not, brokers who are transitioning careers usually have to take a little time to lay the groundwork and develop their brand in order to start getting these opportunities. 

With people you don’t know, it typically takes less time to grow relationships and build opportunities — as long as you’re professional, knowledgeable, and prepared. There are many different avenues for Chicago brokers to build relationships with the people outside their sphere, including: 

  • Business networking groups
  • Chamber of commerce events
  • Open houses
  • Online lead generation
  • Digital and print advertising

For people within your personal and professional network, it’s all about taking time to show that you’re engaged, informed, and learning about how to better support them and add value to their process. Generating opportunities from people in your sphere might include: 

  • Hosting informational seminars (such as “Things You Need to Know Before Buying a Multi-Unit Property” or “Best Ways to Prepare Your Home for Sale”)
  • Doing an audit with homeowners in your network to evaluate whether or not they have a homeowner’s exemption attached to their property. This is a quick way you can put some money back in their pockets. 
  • Provide a free property review, giving people a quick, free analysis of the value of their home. Doing simple, no-strings-attached things for your connections once a year can start bolstering your credibility.

Execute, Monitor, and Adjust Over Time

You’ve taken some time to strategize and create a plan; now it’s time to put it into action.

Be intentional and consistent with your actions as you follow your plan. In real estate, you get from it what you put into it. Set the bar high, collaborate with your Managing Broker to find ways to reach your goals, and then implement the activities on a regular basis that will help you get there.

As you create and execute a plan, make sure that you’re doing some things that you think you’re going to like, while also taking on some things that you think you might find challenging or are a little skeptical about. This might mean cold-calling cancelled or expired listings, creating mail campaigns, or running online ads. 

Be intentional, and don’t try to take on too much at once. Start with a smaller number of lead generation sources, and expand as you master them. So, instead of having ten things that you only do to a level two, have two things that you do to a level ten. You will get much better results that way. 

Too often, people try to move too quickly from one thing to the next. For example, an agent may say that they’re going to try open houses. However, if they do one open house without getting a deal, they’ll get frustrated and immediately move on. If sitting open houses is a lead generation strategy you want to pursue, then you need to commit to it for a period of time — not a week, but months. Be consistent, commit to a plan, measure and monitor just as you would with anything else, and if you need to tweak, then you tweak. 

Finally, keep in mind that there has to be someone who can help you define and execute your strategic approach. If you’re always on your own or find yourself hitting walls trying to figure things out, you will benefit from having someone to bounce ideas off of. 

To continue using open houses as an example, let’s say you’ve done two without generating any leads. Rather than giving up, it may be a question of refining your approach. As a supportive Managing Broker, I may be able to get a sense of what’s happening, and help you find better questions to ask. We’ll dig deeper before we move on to the next thing. Too often, frustration grows and is not properly diagnosed because agents don’t have the support team around them that can ask the questions that need to be asked. 

Want to Talk About Building Your Chicago Real Estate Business?

Customization is one of the great features of our industry, and there is no right way to start building a successful career. It’s all about finding what works for you. 

As the Designated Managing Broker of Baird & Warner’s Lincoln Park office, I aim to spend as much time as necessary with new brokers to make sure their business plans and goals are ambitious yet achievable,. Along with the management team, I schedule regular check-ins throughout the year to closely monitor how agents are making progress. 

I believe in an individualized approach, encouraging every broker to maximize his or her own natural style, strengths, and opportunities with my support and the support of the office as a whole. It is important that we formulate a custom business plan for each broker, and provide support that is ongoing and constantly evolving as the broker’s career and goals grow.

We strive to create a collaborative environment where our brokers use the innovative tools and support we provide to build thriving, sustainable businesses. Have any more questions? Want to keep the conversation going, or learn more about Baird & Warner — Lincoln Park? I always welcome the opportunity to discuss your real estate career. Whether you are considering a career change or looking for a new partner in your existing business, I truly look forward to connecting.


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