Hi Reader

I want to talk about a critical skill you need if you want to be a successful buyer who lands solid deals and, more importantly, actually closes them: "Deal Empathy."

Here's what it's all about:

Most people think deals fall apart because the numbers don’t work.

After sitting through enough closings—and just as many deals that never made it there—I don’t think that’s true.

In most failed deals I see, the math was fine. The valuation was defensible. The financing was workable. The legal issues were solvable. On paper, there was no obvious reason the deal shouldn’t have closed.

And yet, it didn’t.

What actually went wrong usually had very little to do with the spreadsheet and everything to do with what the seller was reacting to underneath it. Not consciously. Not always rationally. But consistently.

You experience a deal as a transaction.
Your seller experiences it as a risk event—often the largest and most personal one of their life.

When that pressure shows up, behavior changes. Sellers fixate. They hesitate. They dig in. And to you, it can feel emotional, irrational, or sudden.

But once you’ve seen this play out enough times, those reactions stop being mysterious.

That’s where Deal Empathy comes in.

Deal Empathy isn’t about being “nice” or giving sellers whatever they want. It’s the ability to accurately understand what the seller is protecting at each stage of the deal—and to structure, communicate, and negotiate in a way that accounts for that reality.

That’s what this issue is about.

This isn’t theory. It’s pattern recognition I've developed from going through the reps, from real deals—what sellers fixate on, what they resist, and what quietly drives their decisions as a transaction moves from LOI to closing.

If you develop Deal Empathy, three things tend to change:

• Your LOIs land with less friction
• Your deal structures face less emotional resistance
• Your closings get smoother instead of more fragile

The strongest buyers don’t just price risk.
They design deals that absorb it.

The Asymmetry You Don’t See—Until It Starts Hurting the Deal

You experience a deal as an opportunity.

Your seller experiences the same deal as a loss event.

From your seat, the deal represents upside: more income, more control, a future that improves if things go right. From the seller’s seat, the deal represents exposure—loss of control, loss of identity, loss of certainty, and the risk that something goes wrong after they thought they were done.

That asymmetry explains why positions that feel reasonable to you can trigger unexpected resistance on the other side of the table.

You’re trained to optimize price, structure, and leverage. Under pressure, sellers optimize for safety, familiarity, and closure. When those priorities collide, deals don’t usually blow up immediately. They weaken. They drag. And then one “small” issue becomes the excuse to stop.

Deal Empathy is the skill of seeing that collision before it happens.

Inside the Seller’s Head: What Deal Empathy Reveals

What follows are 10 recurring seller thought patterns I see across industries, deal sizes, and personalities. Lessons learned from over 160+ deal closings and just as many or more that never got past LOI, or died a violent death late in the process.

Sellers rarely articulate these thoughts clearly—but if you practice Deal Empathy, their behavior becomes readable.

And if you don’t account for these dynamics early, they don’t disappear. They resurface later—usually as rigidity, delay, or sudden resistance at exactly the wrong moment.

1. Cash at close is the only money that feels real

To you, price is price. To the seller, cash at close is the only money that feels settled.

Seller notes, earnouts, rollovers, and contingent payments may be economically sound—but psychologically, sellers discount them heavily. Future money feels conditional. Cash feels final.

Without Deal Empathy, it’s easy to assume structure buys goodwill automatically. In reality, structure often feels like continuing risk to the seller—not added value.

This is especially a problem with SBA 7(a) deals where seller notes are heavily subordinated to the loan - almost to the point where some sellers reluctantly agree to the deal even when their lawyer is screaming that there's a good likelihood they'll never see the money if anything goes wrong.

2. Time doesn’t feel neutral—it feels risky

You might assume that if nothing is wrong, time doesn’t matter. 60, 90, 120 days until closing? As long as it closes right?

Sellers don’t experience it that way.

As deals stretch out, uncertainty compounds. Silence breeds doubt. Momentum breeds confidence. Depending on the seller, the business, what they're hearing from their friends, and the deal, this time risk can start kicking in as early as 60 days or less.

I’ve seen deals with no material issues start unraveling emotionally simply because they lost pace. Deal Empathy means understanding that managing time is part of managing risk—not just process.

Realistic and communicated timelines, regular check-ins, and staying at the front of the line with your SBA lender all play into mitigate time risk.

3. Once the news breaks, the risk becomes real

One of the most underappreciated seller fears shows up once the deal starts to feel public.

Once a seller tells employees, customers, or key vendors—even indirectly—the business environment changes. If the deal falls apart after that, the seller isn’t just disappointed. They’re exposed.

If the deal falls through, they may not have a viable business that they can either step back into, or even to put back on the market.

Deal Empathy means recognizing that late-stage hesitation is often about protecting the business, not extracting leverage.

This is also why seemingly normal diligence asks, like requesting to interview key employees, access vendor lists, or review customer data, might be rejected hard.

4. “I don’t want this following me forever”

Post-closing liability is emotionally charged for sellers, even when the dollar amounts are modest.

In practice, sellers care more about how long liability lasts than how much it might be. A long tail feels like unfinished business.

What this looks like is seemingly unreasonable seller positions on "market" structures like reps and warranties, survival periods, indemnities, and even who's responsible for warranty claims.

Deal Empathy helps you see that these fights aren’t about legal nuance—they’re about closure (hint, arm yourself with this knowledge and try to resolve disputes here direct with the seller, not through their lawyer who's already been given orders to "protect me at all costs" by the seller).

5. Sellers mentally check out earlier than you think

Once a seller decides to sell, they often start disengaging emotionally—even while they’re still operating the business. Some people call this "taking their foot of the gas" - but it goes beyond checking out of running the business.

So when you ask for one more report, another call, or extended involvement, it doesn’t feel incremental to them. It feels like unpaid work attached to something they already believe they sold.

Deal Empathy explains why cooperation often drops late in the process—and why pushing harder at that stage usually backfires.

Solution? Front-load your requests instead of dribbling them out throughout, and work with the broker team whenever possible (good brokers can help get things done for you without bogging down the seller, literally and emotionally).

6. The business is personal, even when the seller says it isn’t

I’ve yet to see a seller who was truly indifferent about what they built.

For many owners, the business represents years of sacrifice, pride, and identity. If you treat it like a commodity, you may not get punished immediately—but you’ll lose trust quietly.

Deal Empathy means respecting the emotional asset alongside the financial one.

Remember this when you talk about future plans with "their baby." Even if you're planning big changes with systems or employees keep them to yourself. Also, make sure to respect seller titles in correspondence and deal agreements. For instance if they call themselves "Chief Executive Officer" of their company, don't just call them "owner." And if they prefer "CFO" don't use "Treasurer" instead.

7. Once the deal feels “real,” sellers become afraid of change

There’s a point where the seller has already crossed the finish line emotionally.

They’ve told their spouse and even business owner friends.
They’ve imagined life after the business.
They’ve mentally spent some of the money.

After that point, changes feel threatening—even reasonable ones. Without Deal Empathy, buyers misread this as stubbornness. With it, you recognize it as fear of reopening something that already felt settled.

This is the reason why retrades are so tricky and risky. Even if you have all the evidence (underperforming financials, late discovered customer concentration, bank required note restructures) to share, sellers will feel like you're proposing an unfair change (which feels like a major emotional threat). Approach these fundamental deal changes with caution, Deal Empathy, and support from your deal team. I see more deals dying at this juncture than any others.

8. Under stress, sellers trust familiarity more than expertise

When pressure rises, sellers default to people they’ve always trusted—even if those people have never done a deal like this.

Longtime CPAs. Family lawyers. Business friends with outdated anecdotes.

Deal Empathy helps you recognize that you’re often negotiating with fear filtered through a trusted voice—not pure logic.

I recommend two key tactics here. 1) Strongly encourage sellers to hire deal counsel. I even have a non-binding requirement that sellers do this in every LOI I draft. 2) If you've got a particularly sticky issue to air out, consider working through the broker. The broker is also in this trusted seller advisor camp, but unlike an inexperienced long-time advisor, they've seen lots of deals (so know what's market) and have a unique incentive to close (since that's how they get paid).

9. Sellers are hypersensitive to “free work”

By the time you’re deep into a deal, sellers often feel like they’re already done.

So requests that feel minor to you can feel like unpaid labor to them. This especially comes into play when negotiating terms of transition services or post-closing consulting. These are obviously critical to the value of the business you're buying, but tread carefully here. Some things I recommend against here include wanting too much transition services for free (after they "transition" the business to you, any further consulting work should be on an hourly basis), and being any more demanding on their schedule and availability than what they're used to. If, as the working owner they've been working 20 hours a week and mostly remote for the past year, requiring them to be on-site 40 hours a week even for a few transition weeks can feel like an unreasonable and potentially offensive requirement.

Deal Empathy explains why sellers sometimes react emotionally to small asks late in the process—and why preserving goodwill matters more than squeezing efficiency at the margin.

10. At the end, sellers want certainty more than optimization

Early on, sellers talk about maximizing value.

Late in the process, they want closure.

After months of negotiation and emotional strain, clean beats clever. Certainty beats upside. Trust beats optimization. This requires that your proposed structure at LOI meet those same criteria. Deals that are overly complicated from the start, even if they get accepted in principal at the LOI stage, can start to unravel when the going gets tough and deal fatigue starts to set in.

Deal Empathy lets you recognize when the finish line has shifted—and adjust accordingly.

Final Thought: Why Deal Empathy Wins Deals

Deal Empathy doesn’t mean overpaying.
And it doesn’t mean capitulating.

It means understanding that deals are closed by humans under stress—not spreadsheets in isolation.

The strongest buyers don’t win by being aggressive.
They win by being precise.

Strong LOIs don’t just allocate economic risk.
They reduce psychological risk.

And once you understand what your seller is protecting, negotiations stop feeling adversarial—and start feeling predictable.

Deal Empathy comes from pattern recognition across real deals.
Reply here or reach out on X @lawyer4smbs with what you’re seeing.

Cheers!

Eric

Your "Deal Emphathy decoder."