Why People Still Matter in Big Transactions
Big real estate deals move money, land, and laws. But they also move people. Behind every spreadsheet and closing binder, there’s someone writing the check, signing the lease, or making the tough call on a zoning change. Lose sight of that, and you risk losing the deal—or worse, losing trust.
According to CBRE’s 2024 Global Investor Intentions Survey, over 65% of real estate investors are now prioritising relationship-based deals over purely opportunistic ones. Relationships are being factored into risk. That should say everything.
When real estate transactions get complicated, the human element becomes more important—not less.
Complex Doesn’t Mean Cold
A complex deal often involves multiple stakeholders. Lawyers, developers, lenders, city officials, tenants, investors. It’s a lot. Terms get dense. Timelines get tight. But the key players? Still people.
Michael Fralin, a senior real estate attorney with over 20 years in the game, knows this well. At one point, he was helping launch SomeraRoad Inc. as their first hire. The company had zero assets and no systems. Five years later, they had $2 billion in assets and dozens of employees.
“Most of the time, we were figuring it out on the fly,” he said. “And the thing that kept deals moving wasn’t the perfect document. It was that people trusted we’d figure it out.”
When Deals Get Messy, Communication Saves Them
Every deal breaks somewhere. The schedule slips. A lender changes terms. An environmental issue pops up. It’s not a matter of if—it’s when. What matters is how you handle the break.
One developer shared how their financing fell through two days before closing. They were ready to walk. Their attorney picked up the phone—not to negotiate, but to listen. That call kept the client calm enough to regroup, restructure the stack, and close three weeks later.
Pick up the phone. Don’t hide behind redlines. Don’t let issues fester over email. Talk like a person. Solve like a partner.
Read the Room—Not Just the Term Sheet
The more people involved, the more emotional complexity you’ll face. Some deals stall not because of numbers, but because someone feels steamrolled or unheard.
If a city planner looks annoyed, stop. If a lender keeps asking the same question, ask why. If the client’s CFO goes silent after a walkthrough, something’s off.
Use the meeting before the meeting to check tone. Use the post-call recap to confirm understanding. The soft stuff avoids the hard stops.
Action Steps for Keeping Deals Human
Here’s how to keep people in the loop without slowing the deal down.
1. Start With Context, Not Conditions
Before you talk about terms, ask for goals. What does success look like for each side? What are they trying to avoid?
This frames the deal around outcomes, not clauses.
2. Translate the Documents
Don’t just send a 65-page agreement with “let me know if you have questions.” Summarise key points. Bullet the changes. Highlight risks that might cause concern.
Even the smartest clients appreciate clarity.
3. Ask People How They Want to Communicate
Some want calls. Some want text. Others want Monday updates and Friday recaps. Match their style, not yours.
4. Build in Buffer Time for People Problems
Deals don’t just get delayed by documents. They get delayed by human stuff—team turnover, illness, decision fatigue.
Add time. Expect silence. Plan for real life.
Data That Backs It Up
A 2023 PwC real estate outlook report found that 81% of real estate execs said “internal communication breakdowns” were a top reason for failed or delayed transactions.
It wasn’t financing. It wasn’t regulation. It was people not talking to each other well.
Harvard Business Review also found that deals with regular human check-ins (weekly calls or touchpoints) had 24% higher close rates than those managed purely through written updates.
Communication is not a courtesy. It’s a deal accelerator.
Legal Can Be Human, Too
Lawyers often get blamed for slowing down deals. But the best ones make things faster. They explain. They anticipate. They manage expectations like pros.
Michael Fralin once told a story about a stalled bond financing project. City approval kept slipping. Instead of pushing more paper, he walked the city’s lead attorney through the deal structure in person. Not over Zoom. Not in a memo. In the same room. The approval came two days later.
Sometimes your job isn’t to push—it’s to sit down and explain.
Good Deals Feel Fair
The final structure should reflect more than risk allocation. It should reflect shared wins. When one side feels like they got the short end, they delay, renegotiate, or disappear.
To avoid this:
- Give people face time during key decisions
- Be transparent about trade-offs
- Avoid legal tricks that look smart but feel shady
- Make sure both sides can explain the deal to their teams without blushing
Trust doesn’t come from terms. It comes from tone.
Don’t Just Close Deals—Build Deal Fluency
Every complex deal is a chance to get better. After closing, ask your team:
- What surprised us?
- Where did people get confused?
- What did we assume that we shouldn’t have?
Then fix the process. Build checklists. Train junior staff. Write up the sticky spots. The next deal will go smoother—and feel better.
Wrap-Up: Make People Your Secret Weapon
The deals that close well—the ones that come back around—are the ones where everyone feels heard. Complex structures aren’t the problem. Cold structures are.
The human element isn’t fluff. It’s not extra. It’s the grease that keeps the gears turning.
Structure your deal like a pro. Communicate like a human. That’s how you win.
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