Before I became a real estate agent, I spent years as a public defender trying felony cases. One of the most valuable lessons I learned in the courtroom was that if you wanted to control the direction of a cross-examination, you needed to control the questions.
Of course, making small talk with a prospective buyer is nothing like cross-examining a witness. In court, I was often asking questions because I already knew the answer I wanted, but in real estate, I’ve learned that some of the best conversations happen when I’m genuinely curious about the answer.
Earlier this year, I spoke at the Tom Ferry Summit about charisma and how confidence isn’t something you’re born with but something you build through practice. Recently, I started listening to Vanessa Van Edwards’ book, Conversation: How to Connect with Anyone & Make Every Interaction Count, and found myself thinking about how much of her advice applies to real estate agents.
We spend so much time preparing listing presentations, studying comparable sales and practicing scripts, but how much time do we spend preparing for the conversations that happen before any of that?
Here are five small habits inspired by Van Edwards’ work, along with a few things I’ve learned from my own experiences.
How to level up your real estate conversation skills
1. Stop asking people what they do for a living
One of my favorite suggestions from Van Edwards’ book is surprisingly simple.
Instead of asking someone, “What do you do for a living?” try asking, “Working on anything exciting lately?”
Think about the difference.
The first question frames someone’s identity around their occupation, while the second gives them permission to talk about whatever they’re genuinely excited about.
Maybe they’re starting a business, training for a marathon or getting ready to welcome their first child. You’re giving them the opportunity to decide what’s worth sharing.
This particularly resonated with me because at the Tom Ferry Summit, I discussed how easily we allow our careers and accomplishments to define who we are.
We let our business tell us who we are, our bank account, our last transaction. And yet, one of the first things we ask someone when we meet them is what they do for work.
In real estate, we’re especially guilty of this. We meet someone at an open house and immediately start asking questions designed to determine whether they’re a potential client. But what if we started by learning something about the person instead?
2. Stop collecting facts and start looking for stories
Van Edwards has an entire chapter dedicated to asking for stories instead of facts, and I think this is one of the easiest lessons for agents to put into practice.
Think about how we typically approach someone at an open house.
- “Do you live in the neighborhood?”
- “How long have you been looking?”
- “Are you working with an agent?”
There’s nothing inherently wrong with these questions, but they tend to produce short answers.
What if instead of asking how long someone has been looking, you asked, “What’s been the most surprising part of your home search so far?”
Or at a listing appointment, instead of asking how long someone has lived in their home, you asked, “What originally made you fall in love with this house?”
Now you’re giving someone an opportunity to tell you a story.
Van Edwards discusses treating conversations like a scavenger hunt where you’re listening for little clues in what someone says and looking for opportunities to explore them.
Someone mentions their children are starting school, so you ask how they’re feeling about it. They tell you they’ve lived in the neighborhood for 30 years, so you ask what’s changed the most.
This reminds me of something I learned practicing law, where a good question is important, but what you do with the answer is often even more important.
You don’t need to memorize 50 conversation-starters. You need to listen better to the answers people are already giving you.
And when someone shares something meaningful, remember it. Make a note in your CRM, and ask about it the next time you speak. Remembering what matters to people is one of the simplest ways to show them that you care.
3. Look for common ground, but don’t manufacture it
I recently found myself sitting at a listing appointment discussing the delicate balance between maximizing a home’s sales price and knowing when to accept a good offer.
As agents, we have these conversations all the time because we explain market conditions, buyer demand, and the risks of holding out for a better offer.
But this conversation felt different because I’d recently put my own house on the market.
I shared that I’d been wrestling with the exact same dilemma. Of course, I didn’t want to leave a dollar on the table, but I also didn’t want to lose a great opportunity because I was holding out for something better that might never come.
As I shared my experience, I could almost feel the seller’s guard come down a little. I wasn’t trying to manufacture a connection because we genuinely had something in common.
Van Edwards discusses how powerful a simple, authentic “same here” can be.
I’m a husband and father of two young children, and when I’m working with a young family purchasing their first home, I can often relate to the uncertainty they’re experiencing.
But common ground shouldn’t be something you invent to make someone like you. It should come from genuinely recognizing where your experiences overlap. This is especially important in real estate because the conversations eventually become more difficult.
You might have to recommend a price reduction, explain why an offer isn’t as strong as it appears, or advise a buyer to walk away from a home they love. Those conversations are easier when you’ve already established that you understand what’s important to them.
Small talk isn’t necessarily something we do before the important conversation. Sometimes it’s how we build the trust necessary to have the important conversation in the first place.
4. Pay attention to what excites people
One of the more interesting concepts Van Edwards discusses is looking for conversational sparks. These are moments when someone’s energy changes because you’ve stumbled onto a subject they genuinely enjoy.
Maybe their eyebrows rise, they lean forward, or they suddenly become more animated.
Imagine you’re talking with a buyer about a neighborhood. You mention the restaurants, schools, parks and commute. They seem interested enough.
Then you mention the local farmers market, and suddenly, they light up and start telling you about their love of cooking. That’s probably worth exploring.
I’ve always talked with my hands, and I’m increasingly aware of how gestures, eye contact and body position can reinforce what we’re trying to communicate. Research has found that gestures accompanying speech can improve comprehension. That doesn’t mean there’s some magic hand position that makes people trust you, but it does suggest that how we physically communicate matters.
And don’t underestimate a genuine compliment. If you sincerely appreciate something about someone’s home or something they’ve accomplished, tell them. Better yet, ask about the story behind it.
The objective isn’t to perform charisma. It’s to become more attentive to the person standing in front of you.
5. Get comfortable with the possibility of rejection
Van Edwards explores the courage to be disliked, and I think it’s an especially important lesson for real estate agents. So many of us avoid conversations because we’re afraid of how someone might respond.
We hesitate to introduce ourselves at networking events or overthink what to say at an open house because we’re worried someone might think we’re salesy. But what if the objective wasn’t to make every person like you?
When I started creating real estate videos in 2018, hardly anybody watched them. For months, I’d spend my Sundays preparing a market update, finding someone willing to hold the camera, and sending the footage to an editor so I could publish another video on Monday.
And for a long time, nothing happened. But every week I kept the promise I’d made to myself to create another video.
Over time, I became more comfortable on camera, more confident in my ability to communicate and less dependent on how any individual video performed.
I think conversations work similarly.
You can promise yourself you’ll introduce yourself to three new people at your next networking event or commit to asking one thoughtful question at every open house. Not every interaction will go well, and some people simply won’t connect with you.
Confidence doesn’t come from knowing everyone will like you. It comes from knowing you’ll be okay when someone doesn’t.
Better conversations start before you open your mouth
I don’t think becoming more charismatic requires becoming the loudest person in the room or developing some larger-than-life personality. I think it starts with being comfortable with who you are, becoming genuinely interested in other people, and developing the confidence to initiate conversations without needing to control their outcome.
So the next time you walk into a listing appointment, attend a networking event or meet someone at an open house, don’t just prepare what you’re going to present, but instead prepare to have a better conversation.
Because sometimes the most important part of a listing appointment isn’t what you say about the house; it’s what you learn about the person who lives there.
