Cutting a busy season down to size by removing work instead of automating it

The situation

Crestline ran tax and advisory work for closely held businesses across northeast Ohio. Fourteen people, four partners, and a filing calendar that turned every January into a nine-week sprint.

Client documents arrived three ways: email attachments, a portal the firm had paid for since 2021, and — for the older accounts — a physical drop box in the lobby. The portal saw maybe fifteen percent of the volume. Everything else got downloaded, renamed by hand, and filed into a shared drive whose structure was a matter of individual opinion.

Nobody could say how long any of this took, because it happened in the gaps between real work.

What we found

The firm asked for automation. What they had was a process problem wearing an automation costume.

Three specific failures:

1. Three intake channels meant three sets of habits. Staff could not build muscle memory around a system that behaved differently depending on how the client felt like sending something.
2. No naming convention meant search was useless. Six people had six schemes. Finding last year’s depreciation schedule meant asking whoever handled that client.
3. The portal was never the default. It was offered, not required, so it lost every time to the client’s email client.

The automation the firm wanted — routing rules, OCR, a document classifier — would have run on top of all three problems and produced faster chaos.

What we did

Process first. We sat with two staff through a full week of intake and wrote down every step, including the ones nobody counted as steps. Then we removed the ones that existed only because of the previous step.

One channel: the portal became mandatory, with the drop box retained for four legacy accounts because forcing those clients would have cost more in relationship than it saved in time. Email intake got an autoresponder pointing back to the portal.

One naming convention, enforced at upload rather than corrected afterward. Retention rules encoded so the shared drive aged its own contents instead of accumulating forever.

Only then, automation: an intake routing rule, a nightly sync into their document management system, and nothing else. The classifier they had asked about never got built, because after the process work there was nothing left for it to classify.

The part worth stealing

We wrote the process document before we wrote any configuration, and we handed it over as a plain document — not a diagram inside a tool the firm would have to keep paying for to read.

The test of whether a system has been documented is whether it can be rebuilt by someone who has never met the person who built it. A flowchart trapped in a vendor’s account fails that test the day the subscription lapses.

The most valuable hour of the engagement was the one where we listed the eleven steps and asked which four could simply stop. Nobody had been given permission to ask that before.