The most expensive thing in real estate is not a bad house. It is a confident answer that turns out to have been a guess.

Confidence is easy to produce and difficult to assess, particularly when you are new to something and everybody in the room sounds certain. So rather than trying to judge whether someone knows what they are talking about, ask questions where a guess and an informed answer sound obviously different.

These eight work on anyone. An agent, a mortgage broker, a contractor, a landlord, a relative with strong opinions. Use them on me too.

One. What is that number based on?

Somebody tells you the house is worth $1.2 million, or that rents in the area are rising, or that you should offer eight per cent under asking. Ask what the number comes from.

An informed answer names a source and a period. A guess restates the number more firmly.

Two. How many sales is that built on?

Every average has a sample size behind it, and the size changes how much weight it can carry.

To take a real example, King recorded 20 sales in July 2026 and Vaughan recorded 272. An average built on 20 transactions moves considerably when one unusual property trades. An average built on 272 does not. Both are real numbers. They are not equally reliable.

Three. What is the median, not the average?

The average is the total divided by the count, so a handful of expensive sales drags it upward. The median is the middle sale, so it describes the typical property better.

When the two sit far apart, the average is telling you about the top of the market rather than the middle. In Toronto C14 in July 2026 the average was $891,304 and the median was $643,000. Quoting only the first would give a very misleading impression of what a typical home there costs.

Ask for both. Anyone who works with this data has both.

Four. What would change your mind?

This is the single most useful question on the list, and it is almost never asked.

Someone who has reasoned their way to a position can tell you what evidence would move them off it. Someone who has simply adopted a position cannot, and will usually treat the question as hostile.

Five. What is the case against this?

Ask whoever is recommending something to argue the other side for a minute.

If they cannot, they have not considered it, which means the risks they have not mentioned are risks they have not thought about rather than risks they have weighed and dismissed.

Six. What does this cost me per month if it goes wrong?

Most real estate decisions are framed as outcomes. Will it sell, will it rise, will it rent. Reframe as exposure instead.

If you are carrying two properties for three months, what is the monthly figure? If the tenant leaves and the unit sits empty for two months, what is the monthly figure? If the closing slips by three weeks, what does that cost?

A number you can look at is a decision you can make. A worry you cannot quantify simply follows you around.

Seven. What happens on the date this does not work?

Every plan needs a review date decided in advance and written down.

If the property has no offer by day thirty, what specifically happens on day thirty one? If the renovation is not finished by the fifteenth, what then? Deciding this while you are calm is a completely different exercise from deciding it while you are not.

Eight. Have you done this specific thing before, and what happened?

Not have you sold houses. Have you sold a house like this one, in this situation, and how did it turn out.

The honest answer is sometimes no. That is a perfectly good answer when it comes with a plan. It is the answer that dodges the specific and returns to the general that should give you pause.

Turning this on myself

It would be poor form to publish that list and not answer it, so here is one of them.

Have I done this specific thing before? A client of mine had a listing cancelled before he came to me. This is what he wrote afterwards:

"He created momentum with multiple offers, pushed terms that protected us, and helped us land a sale price above asking, with a closing timeline that worked perfectly for our move."

Mike Groves, seller

That is one client, saying one thing, about one house. Which is precisely the point of question two. Ask me for more than one.

How to use the list

You do not need all eight in one conversation. Two or three will tell you most of what you need to know, and the atmosphere of the answers will tell you the rest. People who know their subject tend to enjoy these questions. People who do not tend to find them irritating.

That reaction is itself information.

If you want a straight answer

Ask me anything on this list about your own situation. If I do not know, I will tell you I do not know, and then I will go and find out.

Text me at 647-931-5151.

Danny Macedo, Macedo Real Estate Group, Royal LePage Supreme Realty, Brokerage. Selling in Toronto and York Region since 1996.

Market figures from the Toronto Regional Real Estate Board Market Watch report for July 2026. The testimonial is a real client review, published with the reviewer's name as given.