It’s been a long day of negotiations. Everyone has been at it since nine in the morning and now the sun is going down. There have been heated discussions about the value of accounts, the use of money, equitable true-ups, and what is “fair.” The parties are frustrated and exhausted, the lawyers have been at each other’s throats much of the day, and finally everyone thinks an agreement has been reached.

It’s at this point, late in the day, that one of the siblings recalls mother’s ring, or the Christmas ornaments, or some other piece of personal property. The intrinsic value is low but the emotional, sentimental value at this moment in time cannot be overestimated. The negotiations come to a screeching halt and the parties, infused with adrenaline, dig in over this last item. In their view, they have given all they are going to give, and that ring, or the ornaments, or whatever it is, should go home with them.

What is to be done? How is the settlement that was so close rescued?

The usual answers are known well enough. The parties can draw lots. They can bid for the item like an auction. If it’s a photograph, perhaps it can be duplicated. The possibilities are only limited by the physical characteristics of the item and the imagination of those in the room.

But the mechanism is not really the point, and choosing among them is the smaller half of the problem. What rescues the settlement is that the parties agreed to a method before either of them knew who it would favor. When that happens, the one who walks away without the ring can blame luck. When it does not, the only thing left to blame is a sister.

That distinction decides whether the agreement survives the drive home.

Personal property is almost never pleaded. It does not appear in discovery, because no one propounds an interrogatory about ornaments. And clients rarely raise it in preparation, because they are embarrassed to. A person who will discuss undue influence for an hour without flinching finds it undignified to say that what they actually want is a quilt. So the subject waits until the worst possible hour, when everyone is tired and every reserve of goodwill has already been spent on the money.

There is also an asymmetry that shapes the whole conversation and usually goes unremarked. One sibling is typically living in the house, or holds the key to it, and has had the property for two years. The other has a memory and a list. The one in possession does not experience themselves as holding anything hostage. The one outside experiences very little else. Any method that leaves the current holder deciding what is fair will be received as no method at all.

So the better way is to move the whole subject weeks earlier, out of the exhausted hour and into a quiet one.

In the pre-mediation conference calls I ask counsel to solicit from each party a list of non-negotiable property. The items with so much sentimental value that the party is not willing to give them up. The deal breaker stuff. Collected in advance, those lists let the mediator see where the real conflict lies and where the easy agreements can be reached before anyone sits down.

What comes back is often shorter than counsel expect, and it overlaps far less than the parties fear. A good part of what one sibling cannot live without, the other has not thought about in a decade. That portion of the problem dissolves the moment it is written down, which is worth doing for its own sake. What remains is a small number of genuinely contested items, and a short list at ten in the morning is a negotiation. The same list at seven in the evening is a crisis.

For what remains, the room can choose its method with a clear head. Lots drawn for order of selection, with the parties then taking turns until the list is exhausted. Sealed numbers on the two or three items nobody will yield, with the difference credited back in the distribution, which converts a contest of will into a contest of preference. Duplication where the object is standing in for something else, a photograph copied, a setting reproduced, a set divided rather than kept whole. And an auction of last resort, agreed to in advance precisely so that no one has to use it.

Whatever is chosen, put the logistics in writing with dates. Who has access to the house and when, who pays the movers and the storage, what happens to whatever no one claims and the deadline after which it goes. More personal property agreements fail on the moving truck than on the allocation, because two people who have just divided their childhood are then asked to coordinate a Saturday.

A word on tone belongs here as well. The room’s instinct, once the money is done, is to treat this part as comic relief. It is not comic to the person asking, and it costs a mediator nothing to say so.

Nothing here is legal advice for any particular matter, and the allocation of personal property carries tax and title consequences that belong to the parties’ lawyers. But disappointment at certain aspects of a negotiated settlement is part of the system. Parties can absorb a great deal of it. What they cannot absorb is the belief that the system itself was unfair, and an agreement carrying that belief is at risk of not surviving.

Ask early. Decide the method before anyone knows who it favors. Then the loser can blame bad luck, which is the only thing in the room that no one has to forgive.