IBBAinsights: Winter 2025
IN THIS ISSUE: “A Thankful Reflection on an Extraordinary Year” Letter from the 2025 IBBA Chair. Plus, Insights on AI use in Business Brokerage, Trends in Search Funds as Buyers, A Tribute to Steve Mariani, and more!
The business brokerage world is shifting faster than most people realize. Technology has already changed how buyers search, how sellers prepare, and how deals move from start to finish. But nothing is reshaping our industry more than artificial intelligence. It is not a small upgrade. It is a complete shift in how the best brokers will operate moving forward.
Let me start with this: I do not believe AI will replace business brokers anytime soon. The work we do—guiding people through big decisions, building trust, solving deal problems, and managing human emotions—cannot be automated. People still want a human voice and a human point of contact at the center of a transaction.
But here is the reality: the broker who does not use AI will be replaced by the broker who does. Not because the software takes the job, but because another broker, armed with it, becomes ten times more effective. This is not a small edge. This is not a five-percent improvement. One AI-powered broker can easily outperform three to five brokers who rely only on old methods.
The good news? You do not need to become a tech expert to win this game. You just need to adopt the right habits. And the single habit that changed my entire business is this: recording every seller interview when taking a new listing.
Every time I take a listing, I conduct a full seller interview on video. I ask the seller to walk me through the story of the business: how it started, how it grew, what they do each day, who their customers are, who their competitors are, and why they are selling. Then I record it. AI transcribes the entire thing. And that transcript becomes the foundation for everything that follows. And yes, AI also gives me the exact interview question I use for the new listing’s specific industry.
I now refuse to take a listing unless the seller agrees to be interviewed on camera. It is simply too valuable, and I’ll tell you why it’s a deal breaker for me.
It solves the biggest inefficiency in brokerage: everyone repeating the same questions. Buyers ask the same things. Brokers give the same explanations. Sellers tell the same story again and again, and they get burned out. Everyone is drained before a real deal conversation even begins.
But when buyers hear the story directly from the seller on video, they retain the information better. They understand the tone. They catch details that get lost in long documents. They feel more connected to the business.
Inside my system, it tracks how much of the interview the buyer actually watches. If they watch for only a few minutes, AI triggers follow-ups to either re-engage them or confirm they are passing. If they watch eighty percent or more, they enter a different workflow geared toward next steps and deeper questions.
And I do not allow buyers to meet the seller—Zoom or in person—until they watch the entire interview. It is one of the best buyer filters I have ever used. The meeting quality skyrockets. The seller stops repeating the basics. And the conversation becomes about deeper, more meaningful questions.
But that is not the main reason this practice matters.
Most brokers think the biggest benefit is saving time. And yes, it saves an enormous amount of time for both the broker and the seller. But that is not the real value.
The real power is this: the transcript of the seller interview contains enough content to build the entire CIM. Every section. Every detail. Every story. With the right AI prompt, you can turn the transcript into a polished, complete CIM very quickly.
On average, it takes me about twelve minutes to go from a full transcript to a ready-to-publish CIM.
The key is having an expertly crafted prompt that tells AI exactly how to structure, format, and write the document. And here is something most brokers get wrong:
They take work. They take trial and error. You must adjust them, refine them, and test them across multiple listings. Your first prompt will not be your best prompt. Your second will be better. Your tenth will be sharper. And once you have it dialed in, it will become one of the most valuable tools you own. Designing effective AI prompts or Prompt engineering is a skill set you must learn, not just for business brokerage; the principles will apply to nearly everything else you do in life that incorporates AI.
This is the difference between casual AI users and true AI-powered brokers.
Casual users ask general questions.
Power brokers build systems.
Casual users copy and paste random prompts that they get from others (don’t do this).
Power brokers build and refine their own prompts until the output is precise.
Casual users get inconsistent results.
Power brokers get predictable, repeatable, high-quality results.
This is why your prompt becomes an asset—something you build over time, and it starts with developing this skill set.
Another major shift in my workflow is something most brokers never consider. I treat the executive summary as a living document, not a fixed one.
When qualified buyers meet the seller on Zoom, I record that meeting as well. AI transcribes it, identifies the new questions buyers ask, and updates the CIM and Q&A section. After three or four qualified buyers—especially ones with industry experience—the document becomes incredibly complete.
This produces two benefits:
I receive messages almost daily from buyers thanking me for the clarity and structure. Even private equity groups comment on how thorough the package is.
But here is the key:
Accuracy depends on giving AI clear instructions.
If your inputs are sloppy, your outputs will be sloppy. If your prompts are vague, your summaries will be vague. AI is powerful, but only when the broker is disciplined in how they use it.
There is another advantage most brokers miss: sellers love this process. It shows them you are organized, prepared, and running a real system—not winging it. They see the difference. They feel the difference. They trust you more.
Sellers want efficiency. They want fewer interruptions. They want a broker who protects their time. This system gives them exactly that.
Here is where it gets exciting. Each deal becomes a live AI bot that connects to my email. When a buyer sends questions, AI reads the email, scans my full database of information, and drafts the perfect reply before I even start my day. All I do is review the drafts, make quick edits, and hit send.
his eliminates almost all repetitive email work. Questions that used to take hours across multiple buyers now take minutes.
AI will not replace brokers. But brokers who refuse AI will be replaced by brokers who embrace it. The gap will widen every year.
And here is the most important thing: you do not master AI overnight. Your first prompt will be rough. Your first transcript workflow will feel new. Your first automations will need tweaking.
But every improvement you make becomes permanent. Every refined prompt becomes an asset. Every workflow becomes a system that saves you hours every week for the rest of your career.
This is not about working harder.
This is about working at a level others cannot match.
The future of brokerage belongs to the brokers who evolve—one prompt, one system, one improvement at a time.

Trent Lee, CBI, MCBI, M&AMI
[email protected]
IN THIS ISSUE: “A Thankful Reflection on an Extraordinary Year” Letter from the 2025 IBBA Chair. Plus, Insights on AI use in Business Brokerage, Trends in Search Funds as Buyers, A Tribute to Steve Mariani, and more!
Dear IBBA Members, As I close out my term as Chair of the Board of Governors, I find myself reflecting with immense pride and gratitude on all that we have accomplished together over the past year. It has truly been a landmark year for the IBBA—and it’s thanks to the dedication, passion, and professionalism of […]
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