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Questions to Ask a Real Estate Brokerage Before You Join
October 26, 2026 at 4:00 AM
by Rob Bergeron
Questions to Ask a Real Estate Brokerage Before You Join

Every brokerage sounds great in a recruiting meeting, including mine. The way to cut through it is to ask specific questions and get specific answers, in writing where it matters.

I'm Rob Bergeron, Owner–Realtor of Winner Realty in Louisville. Here's the list I'd want any agent to bring to any brokerage, mine included. At the end, I'll answer them for Winner Realty.

Money

  • What do I pay every month, whether or not I close anything?
  • What's the split? Is there a cap, and what's included in it?
  • What's the fee per closing, and who pays it?
  • Are there technology, desk, marketing, or brand fees on top?
  • Who pays for errors and omissions insurance?
  • Is there a sign-up or onboarding fee?
  • Do you pay a referral bonus if I bring in another agent?

Leads and deal flow

  • Where do company leads come from?
  • How many do agents actually get, and how are they handed out?
  • What do company leads cost me, as a referral fee or otherwise?
  • Can I work investor, commercial, or relocation deals here?
  • Do I keep 100% of the business I bring in myself?

Support

  • Who answers when a deal is falling apart at 7 p.m. on a Friday?
  • Is there contract-to-close or transaction coordination support, and what does it cost?
  • Who reviews my contracts, and how fast?
  • What training is there for where I am now, not where I was in year one?
  • What tools come included: CRM, e-signature, AI tools, marketing?

Contracts and leaving

  • Can I see the independent contractor agreement before I decide?
  • If I leave, who gets paid on my pending deals, and how much?
  • What happens to my listings and my database if I leave?
  • How much notice do I owe, and are there exit fees?

Culture

  • How many agents joined and left last year?
  • Can I talk to three agents here, without you in the room?
  • Do agents compete with each other for company leads?
  • What does the brokerage do in the community?

The question about agents leaving is fair to ask anyone. NAR's October 2026 analysis found 34% of agents who resign from a firm leave to join another real estate company, and bigger, multi-office firms are far more likely to call retention a top challenge. You deserve to know where you're walking in.

Our answers at Winner Realty

  • Monthly cost: $595 on our 100% plan, $100 on our 85/15 plan, $50 on our 60/40 plan. One-time $100 onboarding fee.
  • Per closing: $295 on every plan.
  • Company leads: residential and commercial leads in your inbox every morning at 6:30. We don't pay for portal leads. The referral fee on company leads is 25% on the 100% and 85/15 plans, 10% on the 60/40 plan. No fee on deals you bring in yourself.
  • Investor and commercial deals: yes, through Winner Commercial.
  • Support: our principal broker, Lisa Tucker, licensed in Kentucky and Indiana, and contract-to-close support from our COO, Colleen Reilly. Plus an AI assistant agents can text anytime.
  • Referral bonus: $500 for every agent you refer who joins.
  • Community: 1% of our net profits go to Hand in Hand Ministries.
  • Talk to our agents: please do. Call any of them and ask how they're supported.

For the full plan details, see our Join page. For the math on which plan fits your production, read Real Estate Commission Splits Explained.

Before you sign anywhere

Know the rules for leaving where you are now. In Kentucky, you can't practice in the gap between brokerages, and a 30-day clock starts with an email from the Real Estate Commission: How to Switch Brokerages in Kentucky. Indiana agents: How to Switch Brokerages in Indiana.

Book a time with me here, or text or email me at (502) 305-8915 or Rob@thewinnerrealty.com. You can see all three of our plans on our Join page.

Frequently asked questions

What should I ask a real estate brokerage before joining?

Ask what you pay monthly and per closing, what the split and cap are, where leads come from and what they cost, who supports you during a transaction, and what happens to your pending deals and listings if you leave. Ask to talk to current agents without the recruiter present.

What is the most important question to ask a brokerage?

What happens to my pending deals if I leave. It's the one agents forget, and it's decided entirely by your contract. Get the answer in writing before you sign.

Should I ask a brokerage how many agents left last year?

Yes. It's a fair question. NAR found retention is a top challenge for 53% of firms with 500 or more licensees, compared with 8% of firms with 1 to 10.