In our world as business intermediaries, we spend a lot of time talking about valuation, deal structure, and managing expectations. And yes, those are all essential pieces of getting a deal across the finish line. But the more time I spend in this business, the more convinced I am that the most important part of our role as brokers isn’t just about negotiating the best price or most favorable terms.
It’s about listening. Really listening.
Because no two sellers are the same, and no two deals are either.
I recently worked with a second-generation business owner whose father started the company when he was just a boy. He’d been running it for nearly 40 years. Like most businesses, it wasn’t perfect, but it had a lot going for it and was a very desirable acquisition.
When we went to market, we attracted strong interest, and one buyer in particular stood out: well-capitalized, experienced in the industry, and ready to move quickly. On paper, it looked like a perfect match.
But something was off.
The conversations felt transactional. There was little effort to connect or understand the business beyond the financials. The buyer checked all the logical boxes, but something just didn’t sit right, and my client felt it too.
And that matters.
You can’t force a fit. I’ve learned over the years that if a seller doesn’t feel good about who’s taking over, if there’s unease or disconnect, it’s either not going to close, or they’ll live with regret.
So we walked away from the “best” offer.
Eventually, we found a buyer who brought a different kind of value. They took the time to learn about the company culture, asked thoughtful questions, and genuinely wanted to understand the story behind the numbers. And they listened, which was important, because my client? He was a talker.
The offer wasn’t nearly as high. The terms weren’t as strong. But it felt right.
Six months after closing, the seller told me:
“I don’t regret it. I’m sleeping at night. And I’m excited for what’s next.”
That’s the win in my book.
There’s a lot of talk in our industry about being advisors, not just brokers. What’s important to remember is that advising isn’t just about educating on valuation, deal structure or walking a client through LOIs. It’s also about knowing when to pause, when to ask better questions, and when to say, “This may not be the right fit.”
Sometimes our job is helping sellers say no.
No to the buyer that looks great on paper but doesn’t share the seller’s values.
No to the rushed timeline that leaves them feeling pressured into a deal they’re not ready for.
No to the offer that might be higher, but comes with conditions that don’t align with their goals.
This isn’t about being soft, it’s about being strategic and saving your time, effort while building stellar reputation in the process. Deals fall apart every day not because of numbers, but because of misaligned expectations, emotional triggers, or lack of trust. By understanding the human side, we reduce friction and build pathways to close.
Being a good advisor means you’re willing to walk away from the wrong deal, even when it’s the easiest one to close. That’s how you build trust that lasts well beyond the closing table.
We’ve gotten better at talking about value drivers and prepping businesses for the market. But are we doing the same when it comes to preparing our clients emotionally?
For a lot of sellers, this is more than a transaction. It’s an identity shift. It’s letting go of something they’ve built, often with their own hands, over decades. It’s the weight of “What’s next?” that starts to creep in as diligence moves forward.
Technology will continue to transform our workflows. Valuation software will get better. CRMs will get smarter. But what will always differentiate a great intermediary is their ability to build trust, navigate emotion, and create a deal that works for this particular seller.
And here’s the other benefit: sellers who feel heard are far more likely to stay engaged, cooperate in diligence, and refer you to the next client. Listening is not just a courtesy, it’s a business strategy.
If you want to put more emphasis on this side of your practice, here are a few ideas:
Instead of starting with valuation talk or diving straight into financials, focus on the seller’s bigger picture:
Create a simple framework that helps sellers identify what matters most to them, before the first offer ever hits the table. Ask them to rank key deal elements from most to least important: employee retention, brand preservation, seller involvement, timing, culture fit, terms, etc.
Use this as a reference point throughout the process. When it comes time to evaluate offers, you’re not just comparing numbers, you are also measuring alignment.
For example:
This kind of clarity leads to more confident decision-making and certainly fewer second thoughts after closing.
Take time after each buyer interaction to check in with your seller, not just on the facts, but on their gut feeling. Long before an offer is submitted, ask questions like:
These emotional cues can tell you just as much as any financial term down the road. Oftentimes they surface issues before they become deal breakers. Remember to listen
If two offers are on the table, walk through the pros and cons clearly and objectively. Show them how one may better align with their priorities, even if the dollar amount is slightly lower.
Sometimes a seller is financially ready, but emotionally not quite there. Part of our job is helping them recognize that.
There will be moments when they just need to vent – let them. And there will be times when the best move is to hit pause, even if you’re this close to getting the deal done. Take the break. Step back for a day or two.
It might feel counterintuitive in a fast-moving process, but giving the seller space to breathe can defuse tension, rebuild clarity, and ultimately protect the deal. And more often than not, they’ll thank you for recognizing what they couldn’t quite say themselves.
This work we do isn’t just transactional, it’s deeply human. Behind every sale is a person who spent years building something meaningful, and who deserves a thoughtful, respectful transition.
Yes, our job is to get the deal done. But our higher job is to get the right deal done.
As you head into your next listing meeting or offer negotiation, ask yourself:
Do I really know what matters most to this client?
Because sometimes, it’s not about the price. It’s about peace of mind, legacy, and knowing their story will continue, even when they are no longer running the business. That’s the kind of value you can’t calculate in a spreadsheet. And, honestly, that’s the kind of work that keeps me excited to show up every day.
Tanya Popov | MCBI, CM&AP
[email protected]
IBBA Magazine
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