Red Flag #2 — They Love Hearing Themselves Talk and Rarely Ask Questions
After years of lending money, investing with operators, raising capital, and doing real estate deals, I’ve learned to pay attention to something that has very little to do with a spreadsheet:
How much does the person across the table actually listen?
Some people can talk for an hour about their accomplishments, their portfolio, their knowledge, their returns, and why their deal is incredible.
But they rarely ask a question.
That gets my attention.
This is Red Flag #2 in my series about warning signs investors and lenders often overlook.
The Smartest People I Know Are Still Learning
There’s nothing wrong with being confident. If you’re responsible for millions of dollars or hundreds of properties, you better know what you’re doing.
But confidence and believing you know everything are two very different things.
Some of the best operators I know are constantly asking questions:
What am I missing?
What could go wrong?
How would you handle this?
What are you seeing in the market?
Is there a better way to do this?
They understand something important:
No matter how experienced you become, there is always something you don’t know.
Markets change. Financing changes. Insurance changes. Construction costs change. Laws change. Deals go sideways in ways you’ve never experienced before.
The moment you believe you’ve figured everything out is often the moment you become vulnerable.
Listen to How Someone Talks About Their Success
When I’m evaluating someone, I’m not only interested in what they’ve accomplished.
I’m listening to how they talk about it.
Does every conversation eventually come back to them?
Do they constantly remind you how successful they are?
Do they dismiss other people’s ideas?
Do they interrupt when someone challenges their assumptions?
Or can they admit:
“I don’t know.”
Those might be three of the most valuable words an operator can say.
Because someone who knows what they don’t know can surround themselves with people who fill those gaps.
Someone who thinks they already know everything probably won’t.
Humility Is a Risk-Management Tool
This isn’t just about personality.
It’s about protecting capital.
Real estate has a way of humbling people.
A project runs over budget. A contractor disappears. Financing changes. Insurance doesn’t cover what you expected. A property doesn’t sell. Tenants stop paying. The market shifts.
What happens when reality proves the operator wrong?
A humble operator adjusts.
An arrogant operator may keep defending the original decision because admitting they were wrong is harder than changing direction.
When your money is involved, that’s a major difference.
I Expect Improvement
I don’t expect perfection from myself, my team, borrowers, or operators.
Perfection isn’t attainable. Improvement is.
I believe you should constantly be trying to do better today than you did yesterday.
And frankly, I don’t think that deserves some huge celebration.
It should be expected.
Good operators study their mistakes. They ask other people questions. They build better systems. They surround themselves with people who are better than they are in certain areas.
That’s how organizations get stronger.
Don’t Just Listen to the Pitch. Watch the Person.
None of this means someone who talks a lot is dishonest.
And being confident, outgoing, or passionate about your business certainly doesn’t make you a fraud.
That’s not the point of this series.
One characteristic isn’t proof of anything. Patterns are what matter.
But when someone constantly talks about themselves, rarely asks questions, can’t accept criticism, and seems convinced they’re the smartest person in every room, I’m going to look much harder at everything else.
Because when I’m deciding whether to trust someone with money, I’m not only underwriting their property.
I’m underwriting their judgment, humility, character, and ability to adapt when things don’t go according to plan.
The best operators I’ve met don’t need to prove they’re the smartest person in the room.
They’re too busy learning from everyone else in it.
Final Thought
When you’re evaluating an operator or borrower, pay attention during your next conversation.
Don’t only ask yourself:
“Did they give me good answers?”
Ask:
“Did they ask any good questions?”
That answer may tell you more than you think.
Don’t just underwrite the deal. Underwrite the person.
