Finding the Right Fit: What Questions Should You Ask the Recruiting or Managing Broker?

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As you move forward in your career in real estate, finding the right office will be one of the most important factors in determining your future success. Because no two real estate offices are the same, it’s extremely important that you do your homework on the front end to find the environment that will be a great fit.

One of the biggest steps in choosing the right office to launch your Chicago real estate career is to sit down for an interview with the office’s Recruiting or Managing Broker. This interview can be an opportunity to learn more about the things that matter most to you — including office culture and values, training and coaching opportunities, management and support structure, technology, and more. 

In my view, these discussions should be far more collaborative than most traditional job interviews. As a Designated Managing Broker who regularly speaks with potential new real estate brokers, I do want to make sure that you’ll be a good fit in the office. But just as importantly, this interview is about making sure this setting will be a good fit for you

It is extremely important to find the right environment that will help drive your success for years to come. I know this is a big decision. That’s why, at Baird & Warner Lincoln Park, we encourage you to be as systematic and thorough as possible when looking for the right office. 

First, create a list of the offices in your area. Next, research each brokerage firm by talking to friends and spending time on their websites. This can help give you a sense of the brokerage’s values, history, training and coaching opportunities, and resources. Start reaching out to a few local offices for more information. From there, you can start whittling down your list by making eliminations based on reputation, location, and responsiveness to your inquiry. 

Finally, as the last step, try to interview at least three Managing Brokers or Assistant Managers. When you choose an office, these are the people who will infuse your experience with education, counsel, and mentoring throughout your career, so it’s important to talk with them in some depth. Look for someone you can trust, and who will be a good match for your needs and goals as you enter this next chapter in your career. Do you trust them to be responsive and accessible? Do you think their teaching style and training schedule will work for you? Are they someone you will be able to turn to for management and support? 

Questions to Ask During Your Real Estate Interview

Looking to make the most of your real estate interview? It helps to go in with a few questions prepared for the Managing Broker, so that you can be sure to cover the topics that are most important to you. 

As a rule of thumb, I always encourage people to dig deeper when going into this sort of interview. Be prepared to ask for details and don’t be afraid to follow up. For example, instead of saying, “tell me about your training program,” digging deeper may mean asking a question more like: 

“What can I expect on a day-to-day basis in terms of manager interactions — not just on week one or week two, but on month one and month two? Can you give me a detailed outline of what training looks like from day one, all the way through the end of year one?”

The Managing Broker should be prepared, and more than happy to answer your questions.

Want to get your list started? Here are a few types of questions that can help you learn more and see if the office is the right fit for your style and goals:

  • “Besides the corporate- or company-level training program, what can I expect in the office? Who is available to help me with everyday questions?” Going into a new office, it helps to have an understanding of the specific administrative and management staff that is there. I would be interested in learning who these people are, and how they work. 
  • “Who are my go-to resources for all questions?” For example, who would you talk to if you had a transactional question? Who could you speak with if you have a tool or resource question? What would be a reasonable response time to expect? 
  • Who would help me write a business plan? Do you write business plans with your brokers, and if so, who would be the one to help me?” At Baird & Warner, we emphasize training and coaching, which means that as a Designated Managing Broker, my full-time focus is on equipping brokers with the tools, information, and education they need to feel confident in all aspects of launching and maintaining a real estate business, at every stage of their career.
  • “What does the office-level training and coaching calendar look like?” How often can you expect to meet with the management team in the office? For example, in the Lincoln Park office, we like to schedule regular check-ins throughout the year to closely monitor how agents are making progress toward their goals. 
  • “Can I have contact information for brokers who have been hired into your office in the last twelve months so that I can talk to them?” Interviewing people who have recently been in your shoes is a great way to find out about their experience with learning and settling in at the office.
  • “Do you believe it’s important to be present in the office to learn?” While things are operating differently right now due to social distancing, I do believe in the importance of being present — whether you’re attending virtual training classes or you’re physically present in the office and learning from your peers. I believe you need to be present to collaborate and develop relationships. 
  • “What tools and resources does the company provide to help me in year one?” What marketing materials, tools, and technology does the company make available? This is particularly important for new agents. What tools and resources does the company provide to help you launch your business on the front end — not just give you support when you have more listings down the road?
  • “What do you look for when you’re hiring a broker to your office/What criteria do you look for in a broker?” Getting a sense of what the Manager sees as common characteristics and traits of very successful real estate brokers can help you understand their style and their training strategy, while also helping give a sense of whether you share similar philosophies and goals. 

What Questions Should You Expect? 

As I mentioned earlier, I feel that this should be a highly collaborative process. In general, there are a few questions and topics that I like to address during these conversations, such as: 

  • “What’s your background, and how did you start considering residential real estate as a career path?” Usually, I find that new-to-the-business brokers have some pretty deep, interesting stories. After all, in real estate, you truly are starting a business, and you need to understand what it really means to start a business. People who have spent more time considering that aspect of things are usually a better match in our office. 
  • “Do you know anyone else who is running a successful residential real estate career?” I’m always curious what a new broker’s perceptions of residential real estate are when they walk into the office. Have they spoken to anyone else about getting started in real estate, and what did they have to say? For new brokers, I believe in the value of picking as many people’s brains as possible, and I also find that people have very strong opinions on what it means to start a real estate career. Experienced professionals may be pretty negative (“it’s super hard, don’t ever do it”) or very enthusiastic and encouraging (“it’s fantastic, and this is what you should look for…”). 
  • “From your perspective, what does success look like in your first year?” Real estate is a career that you need to jump into with both feet — and actionable, achievable goals. I’m curious about what new agents might expect as they enter their first year. This includes the financial side of things. In real estate, it is more than likely that you won’t see your first paycheck for 45 to 60 days. Have you clearly defined what it takes for you to survive financially, and what it will take for you to thrive? 

I’m not here to sell you on anything, or to sell you on joining Baird & Warner. Instead, I’m here to see if we are a good match — that’s it. When we sit down for an interview, I want you to feel free to ask any question you want to ask. I promise I will be transparent and give you my honest opinion on it. But understand that it is just my opinion, and that is why I encourage you to speak to as many people as you possibly can. 

Want to Get the Conversation Started? 

Whenever you’re ready to start the discussion, I’m excited to share more about the Lincoln Park office and my thoughts on a career in real estate. 

When I was getting started in real estate, I wanted a strong, ongoing training program, a culture that was high-energy and collaborative, and a brand with a reputation for integrity that brought me credibility in the market. Today, as Managing Broker of the Lincoln Park office, I take ownership in creating and maintaining an office culture that promotes continuous improvement, and a culture and brand that I can be proud of.

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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