median-labs/close-the-books/ask-the-founder

Ask the founder

The scarcest resource in a catch-up is the owner's attention. Everything here is about spending it well.

A list of thirty questions gets zero answers. Five specific ones get five answers, and usually a sixth thing you did not know to ask.

Five questions that are not in this round

The bank's own balance, the For Review count, the feed state, the reconciled date and the bank rules come off a QuickBooks screen rather than out of memory, so they have their own short round with the screen named against each one. See read-the-screen. Asking them here mixes a lookup in with questions that need the owner to remember something, and the lookup is the half that gets skipped.

The other list of questions

What a return needs is a separate list, raised out of the chart rather than out of a stuck transaction, and ready-to-file builds it. Those questions live in the same store and come out in the same rounds, so books.py questions batches both together and books.py answer records both the same way. The difference is where they come from: this skill asks what a categorization is blocked on, and that one asks what the firm filing the return will otherwise chase in April.

Hard gates

• Never ask what the books already answer. Mine the history first. Asking

where a vendor goes when the last forty transactions all went to the same place wastes the one thing you are short of and makes the tool look like it is not paying attention.

• One question per paragraph, each ending in a question mark. An implied

question gets an implied answer.

• Never ask for a decision you should be making. "Should this be an expense

or an asset?" is usually your job. "Was this trip for the Berlin office or personal?" is theirs. The test: does answering it require knowing something that happened in the world, or knowing accounting?

• Record every answer with a date and a source. An undated answer is

indistinguishable from a guess in a month.

• Ten at a time, maximum, ordered by what unblocks the most work.
• Never answer one on their behalf, and never leave one blank. Where they

cannot answer, record that they could not and why: books.py answer Q03 --cannot "the invoice is with our former bookkeeper". A stated unknown can be chased. A blank reads downstream as a no.

Run it

python3 bin/books.py questions --profile profiles/mine.local.json --round 1

Writes questions/round-1.md, drawn from what the profile could not settle and what the categorizer parked. Each question carries the vendor, the amount, the date and, where it helps, what you will do with each possible answer, which often lets them answer in one word.

Record answers as they come:

python3 bin/books.py answer Q03 "Berlin office, business trip" --on 2026-09-12

Round two does not open until round one is answered. Two open rounds means neither gets finished.

What a good question looks like

Not: "Can you clarify some uncategorized transactions?"

But: "There's a 4,200 payment to Fabrikam Freight on 14 March that doesn't match anything else that year. Was that a one-off shipment, or the start of something recurring?"

The second one can be answered from memory in ten seconds, standing up, on a phone. That is the bar.

Questions that come up in almost every catch-up

Worth asking early, because each one unblocks a category of work: who was keeping the books and when did they stop; which of these accounts are still open; are there accounts not in QuickBooks at all; which card is the real one where two look alike; are any of these payments personal; did anything unusual happen this year, such as a raise, a loan, a sale, or a new entity.

What good looks like

Every question specific enough to answer from memory. Every answer stored with its date and who gave it. Nothing asked twice. And the count going down each round, which is the only real measure that this is converging.