The #1 Negotiation Mistake That’s Killing Your Deals (and How to Fix It)

Real estate expert Tom Toole explains why assuming the outcome in negotiations can cost agents deals, referrals, and long-term client relationships. Tom breaks down the mindset shift agents need to make, replacing assumptions with data, options, and curiosity-driven questions.
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BAM Fest 2026

Join Sharran Srivatsaa, Chris Smith, Selene Hanna and a huge Mystery Guest for a live breakdown of the AI and content strategies driving more closings right now. Completely virtual and 100% free. Click HERE to reserve your free spot today.

You’re in a negotiation. You’ve written a solid offer. And then, before even presenting it, you start second-guessing. 

“The seller’s not going to go for that.”

“The buyer can’t go any higher.”

“They’ll probably walk if I push this.”

Sound familiar?

Here’s the problem. When you assume the outcome, you’re not just psyching yourself out. You’re robbing your clients of real options. 

And you’re killing deals before they ever get off the ground.

It’s one of the most common mistakes I see agents make. And it’s one I’ve made myself. If you want to win more deals, retain more clients, and protect your income, it’s time to drop the assumptions and start leading with questions.

Assumptions Kill Deals

I’ve fielded the same call more times than I can count:

“Tom, the buyer’s capped at this number. The seller’s never going to go for it.”

“They want X, but I don’t think it’s even worth asking.”

When you think like this, you’ve already taken the pen out of your client’s hand. You’re writing the ending for them without even giving them a shot at the full story.

Here’s what you need to remember:

  • The decision-makers are the buyers and sellers. Not you.
  • Your job is to guide, not to control.
  • You’re not there to predict the outcome. You’re there to provide clarity, data, and options.

And when you do that well, you’ll be surprised how often people make the opposite choice from what you assumed they would.

Fear-Based Forecasting Is Hurting You and Your Clients

The moment you start forecasting disaster, thinking “They’re going to back out” or “We’re going to get a hard no,” you’re not protecting anyone. You’re injecting fear into the process.

And fear is paralyzing.

It keeps you from having the real conversation. It leads you to avoid follow-ups. It causes you to hold back on options that might actually work.

When you lead from fear, here’s what happens:

  • You under-deliver
  • You stop advocating
  • You avoid the tough (but necessary) conversations

That’s not leadership. That’s self-sabotage.

Replace Assumptions with Curiosity

The best agents don’t make assumptions. They ask better questions.

Instead of saying, “They won’t do it,” start asking:

  1. What’s the best thing that could happen if we submit this offer or ask for this repair?
  2. What’s the worst thing that could happen?
  3. What’s the likely outcome?

These three questions shift your mindset. They get you out of fear and into strategy.

From there, use open-ended discovery questions to explore what really matters to your clients:

  • “What would need to happen for you to feel confident moving forward?”
  • “What’s holding you back from getting started right now?”
  • “How would you feel if we lost the house over this issue?”
  • “If we push back on this term, what’s the potential upside, and are you okay with the risk?”

Questions like these move the conversation forward. They also show your clients that you’re not trying to push an agenda. You’re trying to help them make a decision they can live with.

Present Options, Not Predictions

Let’s say your client wants to get into a specific school district. That’s their driver. That’s their “why.” You can anchor your guidance in that.

Try something like:

“You told me this home puts you in the right district. So, here are our three options:

* Move ahead as is
* Walk away
* Try to negotiate the terms

Which one feels best to you?”

Assumptions Don’t Just Kill Deals. They Kill Referrals.

Let’s take it past the transaction.

How many of your past clients never hear from you again? Probably more than you’d like to admit. The data says over 80% of buyers would refer their agent again. But fewer than 20% actually do.

Why? 

Because most agents assume those clients aren’t going to refer them. So they stop showing up.

I can’t tell you how many deals I’ve done that started with a birthday call. That’s it. I wasn’t asking for anything. I just kept the relationship warm. And when the moment came, they remembered.

This is the same mindset mistake. Assuming the outcome instead of staying engaged and present.

Assume Nothing. Be Ready for Everything.

Your role isn’t to forecast how every negotiation will play out. It’s to give people the tools, insight, and space to make the right call for themselves.

That means:

  • Providing real-time market data
  • Offering clear options with pros and cons
  • Leading with open-ended questions
  • Staying connected with past clients
  • Letting go of the need to control the outcome

When you stop assuming and start asking, you’ll close more deals, retain more clients, and position yourself as a trusted advisor. Not just a transaction handler.

So stop deciding for your clients. Start helping them decide for themselves.

Want to hear how all this plays out in real agent-client conversations? Join me, Byron Lazine and Lisa Chinatti for the live roleplay in BAMx every Tuesday morning at 9:00 Eastern.

Weekly role play is the not-so-secret differentiator for agents who are committed to improving their negotiation and objection-handling skills and bringing their A-game to every conversation. 

I look forward to seeing you in there! 

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About the Author

Tom and his team catapulted to the #1 ranked team in Pennsylvania, a title held since 2018. Known for strategic business operations, Tom shares sales techniques and business tactics as a sought-after speaker throughout the United States. He also hosts Toole Time, Tom’s Take, and Agent Hacks and is a moderator for the 5AM Call.

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