Sales
The four questions I stole in Austin, Texas
Four questions from a room full of the industry’s best that flip a consult from performing to asking — and the hardest move in the business: shut up and listen.
By Austin Sizemore · May 2026 · 4 min
I flew into Austin, Texas, on Sunday night.
For anyone who knows me, you know Texas has never been my favorite. I’ve never lost anything here. But there’s something about being ten feet away from some of the most powerful leaders in the industry that makes the trip worth it every time.
I’m two days in with some of the most respected leaders in our industry. Jason Abrams. Jay Papasan. Wendi Harrelson. The kind of room where you shut up and take notes.
Here’s the thing I never take for granted as a leader: the chance to sit with people who are running businesses ten times the size of mine and figure out what they’re doing that I’m not.
And the theme that keeps surfacing in every conversation I’ve had so far is this:
We’re losing deals not because we don’t know enough — but because we’re talking instead of asking.
Think about your last buyer consult. Your last listing appointment. The last time a lead went cold after what felt like a “good” conversation.
How much of it was you talking? How much of it was you asking?
We’ve been trained to perform expertise. To walk in, demonstrate value, prove we know the market, prove we’ve done this before, prove we’re worth the commission.
But the agents closing at the highest level right now aren’t performing. They’re peeling.
Peeling the onion. Layer by layer. Until they actually understand what matters to the person sitting across from them — not what they assume matters.
The basic questions aren’t enough anymore. What are you looking for in your next home? Is time or money more important to you in this sale? Those are entry-level. Those get you a transaction. They don’t get you a client who tells five friends.
Here are four questions I’m taking home from Austin. Use them on your next appointment. Watch what happens.
1. “How do I win with you?”
This is the question that flips the entire dynamic. You’re not pitching. You’re asking them to define success on their own terms. Most clients have never been asked this. Most will pause. That pause is where the real conversation starts.
2. “How do I lose with you?”
This is the one nobody asks. And it’s the most important one in the conversation. You’re surfacing every objection, every fear, every past bad experience — before it shows up as a “let me think about it” three weeks from now. Get the landmines on the table. You can’t defuse what you don’t know.
3. “On a scale of 1 to 10, how direct can I be with you?”
This is permission. This is the difference between hoping your delivery landed right and knowing it will. If they say a 7, you know the lane. If they say a 10, the gloves come off. You’re not guessing anymore. You’re operating with consent.
4. “How do you want to be communicated with?”
Text. Call. Email. Mornings. Evenings. Weekly check-ins or only when something changes. This is the question that separates the agents who keep clients for life from the ones who get ghosted at week three. People don’t leave you because you’re bad at real estate. They leave you because you communicated on your terms instead of theirs.
Then do the hardest thing in our business: shut up and listen.
Ask these four questions on your next appointment.
Take notes. Real ones. In front of them. Let them see you writing down what matters to them. That single act — taking notes on what someone says — is one of the most underused trust-building moves in our industry.
The agents who win the next decade aren’t going to be the ones who talk the most. They’re going to be the ones who ask the sharpest questions and actually hear the answers.
That’s what I’ve got from days one and two in Austin. Two more days to go. You can count on me to bring back what’s worth bringing back.
Building with you, Austin Sizemore
Austin Sizemore is the CEO & Founder of Austin Sizemore Companiesand CEO & Team Leader of Keller Williams Realty Metro Atlanta — a market center, a producing sales team, and the operating systems behind them.