The thinking behind our question guides

We publish a lot of questions. Questions for your mother, for your father, for grandparents, for the aging parent you've been meaning to sit down with for three years. They're free, they're not gated behind an email address, and you can print them and never think about us again.

People occasionally ask why. The short answer is that the questions are the part we've thought about hardest, and hoarding them would be a strange way to prove we know what we're doing. The longer answer is below, along with what we believe about what makes one question work and another fall flat.

The test a question has to pass

Most bad life-story questions fail in one of two directions. They're either too small to open anything, or too big to answer.

"Did you like school?" is too small. It has a floor and a ceiling, and the ceiling is one word. Your father says "sure" and looks at you, and now you're both waiting. Anything a person can dispatch with yes, no, or fine is a door with no handle.

"What was your childhood like?" is too big. Few people have that answer loaded. Asked to summarize eighteen years on the spot, people often reach for the version they've said before — times were hard, we didn't have much, we got by — and that version is a wall, not a window. It's smooth and rehearsed, sanded down over forty years of retellings until there's nothing left to catch on.

The questions that work sit between those. They're open enough to need a story and small enough to have one. "What was in the icebox on a bad week?" can't be answered yes or no, and it can't be answered in the abstract either. You have to go look. And when someone goes to look, they come back with the linoleum and a story they've never told, because the icebox had never come up.

Anchor it to something a person can see

The move underneath most of our good questions is the same: point at a physical thing.

Rooms, meals, prices, the route to school, what a machine sounded like, what a person wore, who sat where at the table. Memory doesn't store the summary of 1961. It stores the kitchen. Ask about the kitchen and 1961 comes along for free: the job that paid for the house, the sister who wasn't speaking to anyone. Ask about 1961 and you get a decade-shaped shrug.

This is also why our lists lean specific in ways that look almost trivial on the page. A question like "what did your grandmother's hands look like?" reads like a small question. It isn't. It's a door into the woman, her work, and the fifty years that shaped both.

The best question is usually the one you didn't plan

Here's the part that makes a printed list an odd product to build a company around: the list stops being useful a few minutes in.

Your mother mentions, in passing, a neighbor named Sal. That's the question now, not number seven on your sheet. "Who was Sal?" turns into "why did he stop coming by?", and you're somewhere no list could have sent you, because no list knew Sal existed. One pulled thread beats ten prepared questions, and the whole skill is noticing the thread while it's still going past.

That's harder than it sounds when you're the one holding the phone, watching the recording timer, aware that your father is being patient with you. You hear "Sal" and don't register it, because you're already reading the next question on the sheet. It's an easy failure to fall into, and I've fallen into it myself, in my own family, with a list I wrote.

Why we give them away

Which brings me to the real reason the guides are free.

A written list of questions can do the first half of the job. It tells you what to aim at. What it can't do is sit in the room and notice Sal, and that's not a gap we can close by writing a better list. It's a gap that closes when somebody whose only job is listening is the one asking. That's what we built. Loristry interviews the person by voice and asks the follow-up, so you get to be their kid instead of their interviewer.

So the guides are the part of our thinking that fits on a page. Plenty of families will take them, do this themselves with a phone on the kitchen table, and never need us. That's a fine outcome. It's a much better outcome than the guides not existing and the conversation not happening.

If they're useful, use them. If you get a few questions in and realize you'd rather be listening than steering, you know where we are.

— Scott