26 Questions To Ask Before Joining A Chicago Real Estate Brokerage

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Structure & Value

What is your company’s value proposition—why would an agent want to work here?

What would my commission split be at your company? Is it fixed or does it change?

What monthly fees would I be responsible for?

Does the broker or manager actively sell real estate?

What structured training do you offer for: new agents experienced agents? top producers?

How does your company view or support agents who want to build a team?

Culture & Opportunties

What traits do you look for to ensure an agent is a good fit for the company?

Is there room to grow into leadership, mentoring, or other real estate-related roles?

What do you expect from your top-producing agents?

Are commissions negotiable with clients? Can I make that decision myself?

How would you describe your company culture?

What are the production levels of your top 10 agents?

Tools, Tech, & Fees

Does your company invest in local, regional, or national advertising? Why or why not?

What tech tools do agents receive (e.g. CRM, personal website)? Are there additional costs?

Beyond the commission split, are there transaction or admin fees per closing?

Are there charges for things like photocopies or printing? If so, how much?

What structured training do you offer for: new agents experienced agents? top producers?

Leads, Support, & Success

Will I receive leads from the brokerage? If so, how are they distributed?

What does the company do to help increase the production of its agents?

What lessons or values did leadership carry forward from their own real estate careers?

How have your past experiences shaped the way your brokerage is run today?

Results & Performance

What percentage of your agent roster has not produced in the past 6 months?

How quickly do new agents typically get into production?

On average, how many homes does an agent at your company close per year?

Does the broker or manager actively sell real estate?

What habits or behaviors set your top producers apart from those who struggle?

Contacts & Exit Strategy

If I leave the company, what does your independent contractor agreement say about my listings and pending sales?

If I have pending sales at the time I leave, will I be paid on my current split?

Reflection

Which company felt most aligned with my values, goals, and vision?

Where did I feel the most supported, both now and for my future growth?

Which company offered the best training, mentorship, or leadership development opportunities?

How does each brokerage’s culture match what I’m looking for?

Which leadership team would I trust to invest in my success?

Beyond commission splits and tech, which company truly feels like home?