In real estate, speed matters, but certainty matters more.

When a seller says, “I’m motivated,” your instinct might be to run the numbers, make an offer, and try to beat your competition to the punch.

But the best deals rarely go to the fastest investor. They go to the most informed one.

Asking the right questions, early, clearly, and confidently, separates the real opportunities from the distractions. It protects your time, sharpens your offers, and puts you in the driver’s seat from the start.

This article gives you a complete framework of what to ask a motivated seller before you make an offer, and why each question matters.

You’ll find:

• 30+ proven questions, broken into categories

• How to phrase them without sounding robotic or pushy

• What seller responses really tell you

• Callout boxes with red flags and quick filters

Let’s dive in.

Start With the “Why”

Uncover the motivation behind the motivation

The reason they’re selling tells you more than anything else.

Don’t skip this part, even if they’ve already said they’re “motivated.”

Key Questions:

• “What’s got you thinking about selling right now?”

• “What’s changed recently that’s made this a priority?"

• “If everything went perfectly, when would you be out of the property?”

• “Are you considering selling to solve a specific issue, or more just exploring options?”

• “What would need to happen for this to feel like a win for you?”

What You’re Looking For:

• Timeline urgency: Are they moving? Behind on payments? Done being a landlord?

• Pain vs. possibility: Are they escaping something, or chasing something?

• Emotional tone: Are they bitter, burned out, uncertain, hopeful?

Pro Tip: The best follow-up phrase? “Tell me more about that.”

Qualify the Property

Know what you’re buying, and what you’re inheriting

Even if you can see the photos, walk the property, or check tax records, you still need to ask.

Why? Sellers will often reveal conditions, quirks, or obstacles they’d never include in a listing or mention unsolicited.

Core Questions:

• “Can you tell me about the property’s current condition?”

• “Have there been any major repairs or renovations recently?”

• “Are there any issues you’re aware of that need attention?”

• “Is the property currently vacant, occupied, or tenant-occupied?”

• “Is anyone else living in the property who might need relocation assistance?”

• “Have you had any offers before now?”

What You’re Listening For:

• Undisclosed issues: Foundation, mold, roof, HVAC, plumbing, and hoarding.

• Tenant complications: Evictions, leases, squatters, uncooperative occupants.

• Repair tolerance: Whether they want top dollar for a fixer.

Red Flag: “I haven’t seen the property in years.”

This usually means you’re walking into a mess.

Get Clear on Ownership & Authority

Don’t negotiate with the wrong person

This is one of the most overlooked (and dangerous) parts of the seller convo.

Too many investors waste hours crafting the perfect offer, only to find out:

• The person they’re talking to is not the decision-maker

• The property is tied up in probate, divorce, or disputes

• Multiple heirs don’t agree on the sale

Smart Questions:

• “Are you the only person on the title, or are there others involved?”

• “Has the title been transferred recently or is it still under your name?”

• “Are there any liens or legal matters connected to the property?”

• “Are all decision-makers on board with selling?”

• “Is there anything that might delay a closing, like probate or court approvals?”

Pro Tip: Ask early.

Sellers usually appreciate your professionalism when you phrase it like: 

“Just want to make sure we don’t run into title issues late in the game, mind if I confirm a few quick things?”

Uncover the Financial Picture

Numbers tell the truth, but only if you ask the right ones

Motivated sellers often won’t volunteer what they owe, but they also won’t lie if you ask directly and respectfully.

Critical Questions:

• “Is there an existing mortgage on the property?”

• “Are you current on payments, or behind?”

• “Do you know the approximate payoff amount?”

• “Are there any other debts tied to the property, like liens or second mortgages?”

• “If you had to guess, what would it take to walk away clean?”

Why This Matters:

• It tells you how flexible they can be.

• It reveals whether they’ll net anything from a traditional sale.

• It opens the door to creative financing, if you’re open to it.

Look For: Signs they’re upside down, want debt relief, or are open to terms.

Test Their Price Expectations

Price reveals priority and realism

Many sellers won’t name a number first. That’s okay.

But it’s your job to gently smoke out their expectations, so you don’t waste time pitching a price that would never fly.

Suggested Questions:

• “Have you thought about what you’d want to walk away with?”

• “What kind of number would make this an easy yes for you?”

• “Have you gotten any offers already? What were they?”

• “If I were to offer cash and close quickly, would you expect a discount, or are you aiming for full market value?”

• “If we could make the process painless, is there some flexibility in price?”

A seller who won’t even discuss price isn’t motivated; they’re fishing.

Confirm Urgency (Without Forcing It)

Serious sellers have serious timelines

“Motivated” means nothing unless it’s backed by a deadline.

Use this set of questions to gauge just how urgent they really are.

Go-To Phrases:

• “What happens if it doesn’t sell in the next 30–60 days?”

• “Do you need to sell before a certain date?”

• “Is there a specific event pushing the sale, like a move, tax bill, or property issue?”

• “Are you already working with an agent, or going solo for now?”

• “Would you consider holding onto the property if you don’t get your number?”

Green Light: A seller who says, “I can’t carry it another month” is ready.

Yellow Light: “I’m in no rush, just curious.”

Feel Out Flexibility & Fit

Beyond price, can this deal work for both sides?

Now that you’ve gathered most of the “hard” facts, move into the soft variables:

• Will they accept terms?

• Are they open to fast or delayed closings?

• Do they want to avoid repairs, showings, or inspections?

Smart Filters:

• “Would you prefer to sell it as-is, or are you open to doing any prep work?”

• “Would you consider selling on terms, or are you looking for all cash?”

• “Is timing or price more important to you?”

• “Would a quick close help, or would you need time to transition?”

• “If we handled everything, no fees, no commissions, just a clean sale, would that be appealing?”

Goal: Find the seller’s priorities so you can structure the right offer, not just guess the right price.

Wrap It All Into One Key Question

End with clarity, not confusion

Once you’ve covered the essentials, land the plane by asking the question that pulls it all together:

“If I came back with a fair number that solves the problem we talked about, and made it simple for you, would you be ready to move forward?”

Their answer tells you:

• If they’re really motivated

• If they’re still unsure

• Or if you’ve got more work to do

This is your litmus test.

If they hesitate, it’s fine. But now you know why, and you can follow up accordingly.

BONUS: Questions You Should Avoid

Even great investors can tank a deal with the wrong tone or timing. Avoid these phrases:

• “Why haven’t you just listed with an agent?” (Feels judgmental)

• “What’s the lowest you’ll take?” (Too aggressive, too early)

• “Are you desperate to sell?” (Even if true, they won’t admit it)

• “If I give you cash, will you take a hit on price?” (Sounds exploitative)

• “Is this the best you can do?” (Puts them on the defensive)

Respect builds rapport. Rapport closes deals.

Final Word: Ask Smarter. Offer Smarter.

If you want better deals, you need better questions.

Motivated sellers aren’t unicorns; they’re people with problems. Your job isn’t just to buy houses. It’s to listen, ask, and structure offers that make sense for both sides.

Ask like a pro, not a script reader. Listen like a partner, not a predator. And remember: The seller’s first answer is just the start.