"How Am I Supposed to Do That?"

A Tactical Question Every Agent Should Have in Their Pocket

By: Chris Morgan, VP of Sales at Real Geeks

If you've ever been deep in a negotiation—whether over price, repairs, commissions, or timelines—you’ve probably found yourself stuck between your client’s expectations and what’s realistically possible.

It's that moment when the seller wants full price and wants to sell it "as-is."

Or when the buyer is asking for $15K in concessions, and your gut is screaming “Come on, really?”

There’s a question that can help you in those moments. A question that doesn’t spark conflict but invites clarity. It’s from former FBI negotiator Chris Voss, and it’s this:

“How am I supposed to do that?”

This isn't just a throwaway line. It’s a tactical pause button.

And when used with the right tone—curious, calm, even a little puzzled—it can shift the entire dynamic of a negotiation.

Why This Works in Real Estate

In real estate, we’re not just navigating contracts—we’re navigating emotions. Behind every offer is fear, urgency, ego, or attachment.

The beauty of “How am I supposed to do that?” is that it quietly hands the problem back to the other side without starting a fight.

It invites them to see the friction their ask is creating.

You're not saying “no”. You're saying: help me understand how to make this work.

When to Use It

1.  The buyer lowballs, but wants everything included:

“How am I supposed to do that, given where the comps are coming in and what the seller’s already agreed to?”

2.  The seller refuses to make a single repair:

“How am I supposed to do that when the buyer’s inspection clearly flagged safety concerns?”

3.  The client wants your full attention, but also wants to list below market:

“How am I supposed to give this my all when we’re positioning it under value in a competitive market?”

This isn’t about being difficult. It’s about asking the other party to walk a mile in your shoes.

You’re nudging them to solve the puzzle with you, not against you.

The Magic is in the Delivery

The power of this tactic lies in tone. Think less “grumpy parent,” more “genuinely curious guide”.

Deliver the question in a way that feels:

✔  Calm

✔  Slightly puzzled

✔  Warm, not defensive

You’re essentially saying: I want to help you get what you want. But this ask? It doesn’t line up with the facts. Can we rework this together?

Use It, Then Listen

This question buys you space. It draws out more detail.

Most of the time, you'll hear something like this in response:

“Well, I just thought maybe we could…”

“I don’t know, maybe there’s another way…”

“I guess we could come up a bit…”

Boom. Now you’re having a real conversation. Not just pushing back on their requests, but moving things forward in a way that feels cooperative.

Final Thought: It’s Not a Trick, It’s a Tool

In a market where margins are tight and clients are stressed, agents who can calm the chaos and guide negotiations gracefully are the ones who win.

So next time you’re backed into a corner—on price, on timing, on anything—don’t react. Pause. Breathe. Then say:

“How am I supposed to do that?”

And let them come toward you.

If you want more ways to handle moments like this—and the systems to back you up—Real Geeks can help. We build tools and strategies that help agents win more deals, and win them with less stress.

Let's talk.

- Chris Morgan | VP of Sales, Real Geeks