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Flag missing tax documents against last year's return before prep starts, with an AI document checklist

who Conner Kelderman, CEO and founder of Track, a CPA-led tax and bookkeeping firm in Minneapolis (seven people, 850+ clients a year), in a Filed customer story

The problem

The team spent 1 to 2 hours per return just getting ready to do the tax work: building workpapers from scratch, checking by hand whether all the documents were in, and going back and forth with clients about missing forms. Reviewers were catching missing documents in March.

What happened

Kelderman reports saving over an hour per return in manual prep work, catching missing items before the April deadline, and clients commenting that the process felt more organized. Expanding Filed to all returns was a plan at the time. Vendor customer story: the figures come from Filed, which sells the tool.

Quoted in the source: Conner Kelderman, CEO and founder, Track. Source: Filed customer story: How Track Reclaimed Tax Season with AI · Added 2026-10-19.

How to set it up yourself

1. What Track does: before a return is prepared, an AI checklist compares what the client sent with what last year's return says they should have (an HSA last year means a Form 8889 is expected) and flags the gaps.
2. For each client, list the forms that should recur from last year (W-2s, 1099s, 1098, K-1s, HSA, childcare). The prompt below turns that into a per-client checklist, using a client number instead of a name.
3. When documents come in, check them against the checklist and send one email listing everything still missing, instead of several.
4. Have the preparer confirm the gap list before it goes out; a missing form may simply not apply this year.

Copy-paste prompt

Here is a summary of last year's tax return for client {CLIENT NUMBER, no names}: {FORMS AND LINE ITEMS}. Here are the documents received so far this year: {DOCUMENTS RECEIVED}. 1) List every document I'd expect this year based on last year, and why. 2) Mark which are received and which are missing. 3) Draft a short, friendly email asking the client for only the missing items, with a one-line reason for each. Don't assume anything changed unless the documents show it; mark uncertain items as [ASK CLIENT].

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