I've Closed Nearly $1 Billion in Deals. The #1 Skill Had Nothing to Do With Numbers

Everyone talks about the numbers in this business—cap rates, NNN structures, absorption rates, comps. And yes, you need to know all of that cold.

But after 20+ years in this industry and nearly a billion dollars in assets marketed, I can tell you the deals that closed cleanly, and the relationships that lasted beyond one transaction, almost always came down to one thing that never shows up on a spreadsheet:

Empathy.

Empathy in CRE isn't a soft skill. It's a competitive advantage.

If you can't sit on your side of the table and genuinely understand what's happening on the other side—the pressures, the fears, the incentives, the politics—you're negotiating half-blind.

You might still win the deal. But you won't win the relationship, and in this business, the relationship is the annuity.

Every One of Your Deals Has Two Realities

The number one mistake I see agents make, especially early in their careers, is negotiating against a version of the other party that exists only in their head.

They assume the landlord is greedy.

They assume the tenant is being difficult.

They assume the buyer is lowballing and they feel they are being disrespectful.

The truth is almost always more complicated, and more human:

A regional retailer isn't slow-walking a lease because they don't want the space—they're waiting on a board that meets quarterly and won't approve capital outside that window.

A national client's real estate director isn't being cold and transactional because they don't care—they're managing 200 locations and get evaluated on cost-per-square-foot efficiency, not on how warm the relationship feels.

A local mom-and-pop tenant isn't nitpicking every clause because they're paranoid—this lease might be the single biggest financial commitment of their life, and if it goes wrong, there's no corporate parent to absorb the loss.

Understanding why someone is behaving the way they are changes everything about how you negotiate, communicate, and structure the deal.

Empathy isn't about being nice. It's about being accurate.

National and Regional Clients: Different Pressures, Same Need to Be Understood

When you're working with a national or regional account, it's easy to think you're negotiating with "the company."

You're not.

You're negotiating with a person inside that company who has quotas, internal politics, a boss to answer to, and a career to protect.

That real estate director doesn't just want a good deal—they want a deal they can defend internally without getting second-guessed.

If you understand that, you stop selling them on why the deal is good for them personally and start giving them what they actually need:

Clean data, defensible comps, and a rationale they can hand up the chain without having to translate it themselves.

You're not just closing a transaction, you're making someone else look good to their leadership.

That's empathy applied strategically, and it's exactly why national accounts come back to the same brokers deal after deal.

Local and Smaller Clients: The Stakes Feel Bigger, Even When the Dollars Are Smaller

On the flip side, when you're working with a smaller local client—a first-time franchisee, a family business signing their first lease, an independent investor buying their first building—the dollar amount might be smaller, but the emotional stakes are often much higher.

This might be their life savings.

Their identity.

Their big shot.

These clients don't need a broker who talks in institutional jargon. They need someone who can sit across from them, understand that fear is doing a lot of the talking, and translate the complexity of the deal into something they can actually make a confident decision on.

Empathy here looks like patience.

It looks like explaining a personal guaranty clause three different ways until it clicks.

It looks like knowing when to slow down instead of pushing to close.

Treat that client like they're "just a small deal" and you won't just lose the transaction—you'll lose every referral, every repeat deal, and every review they would have given you for the next twenty years.

Empathy Is How You Read the Real Deal Points

Every negotiation has stated positions and real motivations, and they're rarely the same thing.

The stated position might be price.

The real motivation might be timeline, risk, optics, or trust.

Agents who lack empathy negotiate against the stated position and often lose deals that were actually winnable, because they never uncovered what the other side truly needed.

Ask Yourself Before Every Call, Counter, and Negotiation:

What does this person need to walk away feeling like they won, regardless of what "winning" actually costs them?

What are they afraid of, and how do I address that fear directly instead of arguing around it?

What pressure are they under that has nothing to do with me or this deal?

Get those answers right, and you'll find deals close faster, with less friction, and with far fewer blown-up negotiations over things that were never really about the terms in the first place.

The Long Game

CRE is a relationship business disguised as a numbers business.

The agents who scale their book, who get the repeat national accounts and the referral-driven local business, are the ones who understood early that every person across the table—whether they represent a Fortune 500 real estate portfolio or a single storefront—is operating under their own set of pressures, fears, and definitions of success.

Learn to see the deal from their side of the table before you ever open your mouth on yours.

That's not weakness.

That's the skill that separates brokers who do a few deals from brokers who build a career.

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