The 5 Hardest Conversations in Real Estate (and How to Crush Them)

by Marguerite Crespillo

Let’s be honest—real estate isn’t always open houses, champagne closings, and HGTV vibes. Some days it feels more like a therapy session…with a lockbox.

After 30 years in this industry, I’ve had just about every conversation under the sun—and some that made me want to crawl under the kitchen island and hide. But the truth? The agents who win are the ones who know how to show up with confidence when things get uncomfortable.

Here are 5 of the hardest conversations you’ll have in real estate—and how to absolutely crush them like the badass pro you are:

1. “Your home isn’t worth what you think it is.”

A.K.A. The moment your CMA shatters a seller’s Zillow-fueled dreams.

Crush it with: Empathy + Evidence.

Start by validating their pride—it’s their home, not just a house. Then gently guide them with solid data. Use phrases like,

“I completely understand—it’s a beautiful home. Here’s what today’s market is showing us, and I want to position you for success.”

Bring visuals. Show comps. And remind them: you’re not there to flatter them—you’re there to help them move.

2. “This offer isn’t going to get accepted.”

A.K.A. The lowball heartbreaker or the unrealistic dream bid in a hot market.

Crush it with: Honesty + Strategy.

Try:

“I know how much you love this home, and I want to give you the best shot. Here’s how this offer stacks up—and here’s what we can do to make it more competitive.”

Make it collaborative. Show them you’re on their team—and that this isn’t your first rodeo.

3. “We’re going to need to lower the price.”

A.K.A. The mid-listing reality check.

Crush it with: Data + Direction.

This one can sting—but it doesn’t have to. Use your metrics: show online views vs. showings, days on market, and buyer feedback. Then confidently lead:

“The market is speaking. We can either wait and chase it down, or we can reposition now and get ahead of it.”

Stay solution-oriented. You’re not delivering bad news—you’re delivering a plan.

4. “This home isn’t the one.”

A.K.A. Talking a buyer out of a lemon they’ve fallen in love with.

Crush it with: Integrity + Insight.

Sometimes your clients fall for a house that’s about to eat their budget alive—or is in the wrong location, wrong condition, or just wrong. And it’s your job to speak up.

“I’ll support you in any direction, but I’d be doing you a disservice if I didn’t point this out…”

Be kind, but be clear. Long-term trust is worth more than a short-term sale.

5. “I’m not the right fit for you.”

A.K.A. Breaking up with a client (or knowing when to walk away).

Crush it with: Grace + Boundaries.

This one’s tough—but sometimes, the energy is off, expectations are unrealistic, or your values just don’t align. And that’s okay. 

“I want you to have the best experience possible—and I don’t think I’m the right person to give that to you.”

No drama. No shame. Just clarity. The right clients are waiting!

Pro Tip: Want to master these conversations (and more) without stumbling or second-guessing?

I created The Real AF Client Conversation Checklists: Buyer + Seller Edition to give agents like you exactly what to say in every tough moment. Scripts, strategies, and straight talk—no fluff.

CLICK HERE TO DOWNLOAD

Let’s stop avoiding the hard stuff—and start owning it like the pros we are.

 

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