If your parents are getting older and moving into retirement living, or they have passed and the house is now yours to deal with, the honest first step is to get organized early. I have handled this many times, usually with several siblings and a lot of personalities in the mix, and the families who struggle are almost always the disorganized ones. It costs them in stress, and often in money.
Start by being clear about who actually has the authority to sign, which is not the same as who cares most or who the family listens to. While your parent is alive and mentally capable, the decision to sell is theirs, full stop. A power of attorney for property generally lets you act on their behalf, usually when they are unable to or ask you to, but it does not override a capable parent's wishes or give adult children the right to sell the home out from under them. Once a parent has passed, authority shifts to the estate trustee named in the will, and whether you need probate before you can sell depends on the circumstances, including how the property is owned and how title is held, so do not assume one way or the other. Sort this out early with an Ontario estate lawyer, so you know who can sign and what the timing looks like before you are trying to list under pressure.
If your parent is still alive and you are even thinking about this, the time to get advice is now. Good estate planning can sometimes reduce complications later. But the specific moves people hear about, like adding a child to title, can carry serious tax, legal, ownership, and family consequences, and they can backfire. This is not something to do on a neighbour's suggestion. Talk to an Ontario estate lawyer and an accountant before you change anything.
Then there is the family itself, and in my experience the hardest problems are interpersonal, not legal. One sibling usually takes the lead, which helps, but it is rarely smooth. People disagree on what to do, how to do it, and who to hire. One thing I will say plainly: do not hire a family friend or a relative who happens to be an agent. It puts your family dynamics on display, and the moment you pick someone one person knows, everyone else feels overruled. A neutral third party removes a whole layer of drama. A simple approach that works is to interview three agents and let the family settle on one together. To be clear, that is about keeping the peace, not about overriding anyone. Whoever holds the legal authority, the attorney while your parent is alive or the estate trustee afterward, is still the one who decides and signs. Getting everyone consulted just prevents the situation I have seen too often, where one disgruntled sibling tries to hold up the listing, or balks when a good offer is finally on the table.
The hardest part, though, is rarely the paperwork. It is the parent who does not want to leave the home they have lived in for decades, and the children trying to move things along. Usually the money from the house is what pays for the retirement residence or the daily help they now need, and that is not cheap, so there is real pressure underneath it all. My honest view is that it is seldom worth forcing someone at that stage of life to do something they are not ready for. What you can do is prepare around the decision rather than around the house: research the options, get the legal and financial advice in place, understand the timeline, and look at where they might go next, all while respecting that it remains their home and their call. Any work on the house itself should wait for their consent or the proper authority. Then, when they are ready, or a spot opens or a health change makes staying impossible, you can move quickly instead of scrambling.
There is a practical reason to wait, too. It is genuinely hard to show a home well when it is fully lived-in and someone would have to leave for every appointment. The sale tends to go better once there is full buy-in, or once the parent has comfortably settled into their next place, because an empty or calmly staged home is simply easier to present and to schedule around. I have had the reverse situation as well, where the owners were completely on board but could not manage the logistics. One home had so much showing demand that the owners, who were quite elderly and could not reliably get their medications sorted and be out the door in time, were genuinely better off staying in a hotel for a couple of days while we ran the showings. You adapt to the people.
It is worth being clear about the difference between a living parent selling their own home and an estate sale after a parent has passed, because they are not the same. An estate sale is typically sold as is, since the estate trustee often has limited personal knowledge of the home and cannot reasonably speak to its condition. When a living owner sells, they usually do know the home, and what has to be disclosed depends on the facts and the law, which is a conversation for your lawyer and agent rather than a default setting.
Here is something candid about estate sales. Buyers often assume an estate seller is motivated and will take less, and family members, understandably, are sometimes eager to settle things and move on. Neither of those means the home should sell at a discount. When proceeds are split several ways, it can feel like a price cut barely matters to any one person, and that is exactly how money gets left on the table. My job is the opposite: to protect the family's financial interests through proper preparation, pricing, marketing, and negotiation, so the sale reflects what the home is actually worth.
The most common mistake I see is the one I already warned about, letting a hard call slide by hiring a relative to keep the peace. I was once interviewed for a listing where the family clearly wanted me, and they chose a relative instead who did not know the area, the market, downsizing, or estate sales. Bringing in someone unfamiliar with the local market, on top of the family dynamics already in play, tends to create more tension rather than less, because when things get complicated, the person who pushed for the family member ends up owning that choice. The harder decision up front is almost always the easier road later.
A last word for whoever is carrying this. It is a heavy and often lonely job. You will second-guess yourself, wondering whether this is what your parents would have wanted, and your siblings may ask you the same. A good agent should be an advisor in that, helping you think it through and reassuring you that you are doing right by them. If you are facing this, now or somewhere down the road, I am glad to walk you through it and take as much of the weight off as I can. These are hard enough times without doing it alone.