The Paperwork Doesn't Die

By Gary Payne, MBA Founder of FuneralCostOntario.ca The Fine Print A week or two after a funeral, somebody usually ends up at the kitchen table with a folder that was never supposed to become a project. There is the will, a death certificate, a bank statement, maybe something from an insurance company and a growing collection of notes about things that still need to be done. The folder gets opened, closed, moved out of the way for dinner and opened again the next morning. Eventually it stops looking temporary. We talk a lot about grief after someone dies, and rightly so, but not nearly as much about the administrative job that arrives with it. Someone who is still trying to absorb what happened may suddenly be calling banks, cancelling accounts and trying to understand government forms they had no reason to know existed a month earlier. You become the person handling it because your name is on the will, because you live closest or because everyone else has quietly decided you’re the one who can figure these things out. The mail keeps coming, which is one of the stranger parts. Renewal notices arrive. Bills show up. A company writes to the person who died because, as far as its computer is concerned, nothing has happened. You call, explain the situation and write down the name of whoever you spoke to because there’s a fair chance you’ll need it later. Before long there are dates in the margins, confirmation numbers on scraps of paper and reminders to call somebody back Tuesday. That kind of mess is actually where I can see AI being useful. Not because it knows how to settle an estate, but because it’s quite good at helping organize information when six browser tabs are open and you’re trying to remember what somebody at the bank said yesterday. It can turn a page of notes into a list, help sort what’s finished from what isn’t and explain a piece of bureaucratic writing that doesn’t make much sense on the third reading either. The important part is deciding where the facts come from. In Ontario, the Ministry of Finance says an Estate Information Return generally has to be filed within 180 days after the estate certificate is issued. Service Canada says the executor should apply for the CPP death benefit within 60 days of the death. The federal government’s Canada.ca site can also build a checklist based on someone’s circumstances. Those are useful facts, but I’d rather have AI read those pages than ask it to remember the rules on its own. That’s the same distinction I’ve come back to before: point, don’t answer. Open the Ontario page and ask, “What does this say I have to file, and when?” Give it the Canada.ca checklist and ask which steps might still need attention. If a bank sends a letter written in the peculiar dialect of financial institutions, let the machine translate the wording into ordinary English. The source stays in front of you. There’s a privacy wrinkle here too. An estate folder may contain account numbers, tax information and other details that don’t belong in an AI prompt simply because you want help understanding one paragraph. Remove what isn’t needed. In most cases, the useful question is about the wording or the process, not the dead person’s account number. That leaves AI in a less exciting role than some of the ones we hear about, but probably a more useful one. It isn’t the executor, it isn’t the government and it isn’t the accountant. It’s something you can use while doing a job you never expected to have, mostly to make the pile a little easier to understand. If its answer disagrees with the document in front of you, the document wins. There’s something odd about how little the administrative world notices a death. A person can be gone and yet the statements still arrive, the forms still have dates on them and somebody still has to close the account. Eventually the folder comes back onto the kitchen table and gets opened again. The paperwork doesn’t disappear when the person does. It changes hands. *Gary Payne is the founder of CVORReady.ca, a compliance platform for Ontario trucking companies.