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2026-10-16

What I look for when a small office asks me about automation

When an office asks me about automation, I don't start with AI. I look for the work someone does the same way every day: portals, spreadsheets, typing the same data twice, and matching payments.

When an office calls me about automation, the first question is usually what AI can do for them. I get why. But I start somewhere else. It doesn't matter if it's an office on Central Avenue in Cedarhurst or a practice in Lynbrook. I ask what someone there does the same way every day.

Here is what I look for.

Logging into the same websites

A lot of offices have someone who logs into a few portals every morning. They download a report or a statement, rename it, and save it in a folder. It might take an hour. It happens every day. That is the first thing I'd want to see, because a program can do those exact steps. I wrote more about it on my portal automation page.

The spreadsheet everyone depends on

Most offices have one spreadsheet that holds everything together. Someone updates it by hand from emails, exports, or another system. When I see that, I ask where each column really comes from. Often the data already lives somewhere else and just needs to flow in on its own.

Typing the same thing twice

If a person reads something on one screen and types it into another, that is worth a look. It might be an invoice going into the accounting system, or a form going into a client file. This is where I'll sometimes use AI, for reading the messy document. The rest stays simple. See document automation for how that usually goes.

Matching payments

Deposits come in. Someone has to figure out which invoice or account each one belongs to. When the amounts don't line up, it can eat a whole afternoon. That kept coming up, so I built RecoNexus for it. There's more on my payment reconciliation page too.

Big PDFs nobody wants to split

Scanned packets with dozens of documents inside are common in offices that deal with forms and statements. SplitPilot splits them into separate files and names each one.

What I don't look for

I'm not trying to automate everything. If a task takes judgment every single time, or only happens twice a year, I'll usually tell you to leave it alone. The best place to start is the boring task that happens every day.

Around here

I'm based in Cedarhurst, so a lot of the offices I talk to are nearby in Lawrence and Woodmere. Others are a little further out in Valley Stream or Long Beach. The businesses are different, but the work that eats their week looks a lot alike.

Does your office have something like this? Tell me what's eating up your week and I'll tell you honestly whether it's worth automating. If it's a bigger build, my custom software page explains how I approach that.