Introduction
You already know the house stopped working. The kids are sharing a room. The dining table is somebody’s office. You drive past the turnoff to a better commute twice a day.
So you start thinking about listing. And the first thing most families do is call an agent, sit down for fifteen minutes, and sign something. There are questions to ask before you list, and almost nobody gets to them.
That is the part worth slowing down.
Moving up is not one transaction. It is two, happening at the same time, each one dependent on the other. Plenty of agents are good at selling a house. Plenty are good at buying one. Far fewer are good at running both at once while the clock is going.
After 18 years in Markham, here are the seven questions I would want any family to ask before they sign anything. Including with me.
Why do the questions to ask before you list matter if the market sets the price?
Because the market sets the price of each house. It does not set the gap between them.
That gap is where the entire move-up decision lives, and it is the thing an agent either understands or does not. Two families in identical houses can move up in the same month and end up tens of thousands of dollars apart, based on sequencing, conditions, and what they knew before they listed.
Question 1: Will I be working with you directly, or does someone else take over once I sign?
Some brokerages sign you with the person you met, then hand the file to a buyer agent, a listing coordinator, and an admin. That is not automatically bad. It is only bad if nobody told you.
Question 2: What is my net cost to move up?
This is the one that matters most, and it is the one most likely to get a vague answer.
Your net cost to move up is not what your house sells for. It is the gap between what you sell for and what you buy for. That number is the actual cost of the decision.
Here is why it changes everything. In a hot market you might sell for a hundred thousand more. You would also be buying into that same hot market, competing with waived conditions, and paying far more on the purchase. Sell high, buy higher. In a softer market you sell for less, but you buy for a lot less, and you keep your financing and inspection conditions.
The gap between the two numbers is the whole decision
Question 3: How do you handle selling and buying at the same time?
This is a logistics puzzle, not a mystery. The tool is a condition of sale, which means your purchase only goes through if your current home sells first. It is your protection against owning two houses at once.
In a hot market, sellers will not look at that condition. Too many cleaner offers on the table. In today’s market, many sellers will consider it. That is a real advantage right now, and it will not last forever. If you want the full sequence, I broke it down in how long it actually takes to upsize in today’s Markham market.
Question 4: If I renovated instead, would that solve my problem?
This is a test, and a fair one. You are asking an agent to talk you out of a commission.
Sometimes renovating is the right answer. If the problem is a dated kitchen or a bathroom that has had it, renovate. But renovation cannot fix location. It cannot fix lot size. It cannot fix a forty minute drive to your kid’s school.
Plenty of families renovate, then move anyway two or three years later. They paid twice to solve the same problem.
Renovation cannot fix location, lot size, or a forty minute drive
Question 5: What happens if my house does not sell in time?
You are about to make the largest financial commitment of your life on a timeline. Ask what the plan is when the timeline slips, because sometimes it does.
Question 6: How do you price my current home, and why that number?
There are two ways to price a house. You can price it high to flatter the seller and win the listing, then grind through reductions for two months. Or you can price it at market value to create competition and sell it properly.
Ask which one they are doing, and ask them to show you the comparable sales behind the number. If you want a sense of what the current market actually supports, here is what $1.2M buys you in Markham right now.
Question 7: Have you ever told a client not to move?
If the answer is no, ask why not.
An agent who has never once told someone the timing was wrong, the numbers did not work, or the house was not right has either had a very unusual career or has never put a client ahead of a transaction.
The questions come before the signature, not after
What if I ask these and the agent gets uncomfortable?
That is the information. You are not being difficult by asking. You are doing the thing that protects the next two years of your family’s life.
A good agent will be glad you asked, because these are the questions that separate them from whoever is quoting a lower commission down the street.
What does the wrong choice actually cost?
Not a commission. Commissions are the smallest number in this whole conversation.
The real cost is three more years in a house that stopped working. Three more years of the kids sharing a room, of the long drive, of the office at the dining table. Those years do not come back, and your kids are growing up right now. I put actual numbers to that in what it actually costs to stay in a home you’ve outgrown.
Ready to run your numbers?
If you are somewhere between thinking about it and doing something about it, the useful next step is not a listing appointment. It is knowing your net cost to move up.
I will run it with you. No pressure, no pitch, just the actual number so you can decide with information instead of guesswork.
