By Brett Kaufman. 8 years using relationships to build sales pipelines, from political fundraising to a 7 figure business to running matchmaking for two communities. Over 1,000 introductions facilitated.

The best questions to ask a business broker over coffee are about their pipeline and their sellers, not their fees: what is coming in the next few months, what kills their deals, which buyers they call first, and what they need from you. Bring about eight, let the broker talk, and leave with one next step.

Those are the questions to ask a business broker when you are a buyer and the goal is the next deal, not this one. The list is below, with what each answer tells you and what to do with it.

I have never sat across from a broker as a buyer. I have made over 1,000 introductions between deal makers, operators and investors. For the broker side I used what brokers and searchers say in public, linked below.

Here is the scene. You finally get 30 minutes with the broker who handles half the exits in your city. You spend 20 of them pitching yourself. You ask about multiples, then fees. He is polite. You leave with nothing you did not already know, and he leaves with no reason to think of you first.

What should you do before coffee with a business broker?

Do three things: read their current and recent listings, write your box in one line, and have your profile and funding ready to send that afternoon. The Kellogg searcher who wrote about why searchers frustrate brokers advises “aggressively trimming your initial question lists,” and that applies to a coffee as much as a CIM. A broker’s time is the thing you are asking for.

If this is your first contact, send a short email first so they know your box before you sit down. How to get on a broker’s first call list covers what they are screening for.

What are the best questions to ask a business broker?

These 12 are grouped by what you are trying to learn. You will not ask all of them. Pick the eight that fit this broker.

Question	What the answer tells you	What to do with it
Their pipeline
What are you working on that is not listed yet?	Whether you can be in the first window	Ask to be called when it is ready
What do you expect to bring to market in the next few months?	Their timing	Set your next touch around it
Of what you have now, what is closest to my box?	How well they understood you	Ask for the NDA the same day
Their buyers
Which buyers do you call first when a listing comes in?	What a first call buyer looks like to them	Become that, in writing
What do your best buyers do that others do not?	Their pet peeves, in reverse	Do it on the very next teaser
What makes you stop sending a buyer deals?	The fastest way to get cut	Never do it
Their sellers
Why are your sellers selling right now?	Retirement, burnout, health, partners	Shape how you talk to owners
What do sellers care about besides price?	Employees, legacy, timeline	Put it in your profile
Who refers sellers to you?	CPAs, attorneys, wealth managers	Meet the same people
Their market
What timelines are you seeing from LOI to close?	Whether your financing fits	Line your lender up to match
How much seller financing are you seeing?	How much equity you really need	Adjust your box
What kills deals for you?	Where buyers fail in diligence	Fix it before your next LOI

You can check a broker’s market answers against public data. The IBBA and M&A Source Market Pulse survey for Q2 2026 found Main Street deals taking 6 to 10 months on average, and seller financing under 10% of most deals. If a broker tells you something very different, that is worth a follow up question, not an argument.

What should you not ask a business broker at a first meeting?

Skip the questions that make the broker work for you before they trust you:

1. “What are your fees?” The fee is between the broker and the seller who hired them. It is not your question.
2. “Can you send me everything you have?” That asks them to do your filtering.
3. “What is the owner really like?” on a live listing before you have signed an NDA.
4. “What multiple will this sell for?” The broker works for the seller. You will get the seller’s answer.
5. A list of 30 diligence questions about a teaser. Save them for after the NDA, and trim them first.

What should you say about yourself?

Say less than you planned. One line of background, one line of box, one line of funding. The IBBA blog piece by Michael Fekkes of ENLIGN Business Brokers on what defines a serious business buyer describes the buyer brokers want as someone who “knows what they want and what they can afford.” You can show that in under a minute and spend the rest of the coffee listening.

Then close with the one question that matters most: “What do you need from me to be one of the buyers you call first?” Write the answer down.

What should you do in the 24 hours after?

Send what you promised the same day, and capture what they told you before you leave the parking lot. Here is how I would run it.

1. In the car: note the two or three things that matter. What is coming, who they call first, and anything personal they mentioned.
2. Same afternoon: send your profile, proof of funds if asked, and a two line thank you that references one thing they said.
3. When their next teaser lands: reply within 48 hours with a yes or a pass with one reason. PrivSource’s guide for new buyers calls this the habit that keeps you among the buyers who get listings first.
4. When the timing they gave you arrives: text them about it. “You mentioned a few HVAC owners getting close to a decision this fall. Still funded and still looking in Charlotte if one gets there.”

That last step is where the coffee pays off. I learned it in political fundraising. After every call I wrote down what mattered to that person, and I used it the next time we talked. People notice when you remember what they said months later.

The two page buyer profile brokers remember is the thing to send that afternoon. If the broker you had coffee with went cold, what to text a broker after six months has the words, and the business broker relationship playbook has the whole system.

The system that remembers the coffee for you

That is why I built FRONT OF MIND. Leave the coffee and say the broker’s name and a sentence out loud, or snap their business card, and it is filed. Later it opens on your 10 minutes for today, and that broker shows up with one line saying why today: a follow up is due, they posted a new listing, they are going cold. Every draft is a text style message, 40 words max, nothing sends without your tap, and it learns from your edits. Your contacts are encrypted, no one on our team looks at them, and you can export or delete anytime.

Start free with your first 25 contacts and see which broker comes up first.

See how it works