Ending the Triple Entry Tax: How to Automate Tedious Data Entry

Grant Calloway

Welcome to AI for Small Business. I'm Grant Calloway. Picture a financial planning office on a Tuesday afternoon. An adviser hangs up with a client and types a note about the call. Then types the same note into a second system. Then a third. Same sentence, three times. On the trading floor we'd have called that a fat finger waiting to happen. In a small office, it's just Tuesday.

Grant Calloway

I call this the triple entry tax. Nobody sends you an invoice for it, but you pay it every single day. At a firm called SMART Business Solutions on the Mornington Peninsula in Victoria, Australia, every client call and meeting had to be logged in three places: a document system called FYI, a financial planning system called Xplan, and a third called Dash. Three to five minutes a note. Around twenty notes a day, across four advisers and the admin team behind them. Your office might not run those exact programs. But I'd bet you have your own version. Job notes copied from email into the CRM. Invoice totals retyped into the accounting software. Same data, different window.

Grant Calloway

Now, here's why the timing matters. The JPMorgan Chase Institute looked at transaction data from about 4.6 million small businesses with Chase business accounts, from 2019 through 2025. They counted a business as an AI user when it paid for an AI service, so free tools aren't in the numbers. Firms that started in 2019 took 77 months, more than six years, to get ten percent of their group paying for AI. The firms that started in 2025 got there in about six months. Employer firms adopted at nearly twice the rate of businesses with no employees, with professional services among the leaders. My read: this isn't a fringe move anymore.

Grant Calloway

But before you go shopping, remember what we said in the Stop Automating Bad Plumbing episode. Automation laid over a messy process just makes the mess run faster. The SMART story is the proof. The firm's founder, Shannon Smit, had spent years writing down how work gets done, step by step, and that's the whole reason the next part worked. Hold that thought.

Grant Calloway

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Grant Calloway

Shannon started SMART in 2007 from a spare room. She'd learned systems at fourteen and nine months old, working a McDonald's counter, where every task had a checklist and the fries came out the same no matter which manager was on shift. She carried that into accounting. Document it, make it repeatable, and the next person can deliver the same result.

Grant Calloway

Her son Ryan, twenty years old and in the second year of an accounting degree, worked at the firm three days a week. He hated file noting most, so he automated it first. He used Microsoft Power Automate and Microsoft Copilot. The bot takes the note once and puts it into FYI, Xplan, and Dash with nobody touching the keyboard. According to the case study, that saves roughly one hour a day per person on the planning team, which adds up to over a thousand hours a year across the firm. And that was his first build.

Grant Calloway

Then comes the moment I find most interesting. Ryan turned to his mother and asked, quote, "So what do I do now? Is there not enough work for me? Have I just reduced my own work hours, and therefore my wage for the week?" End quote. Shannon laughed and said, "No. We'll find more work for you. We'll automate other things." Her broader rule, in her words: "I'm not trying to replace jobs." And: "I ask the team, what's the most boring, tedious part of your job that you hate? Let's automate it. Then you go and do something more exciting."

Grant Calloway

Ryan is now the firm's Systems Champion. Other staff walk over and ask him to look at the workflow they'd like automated next. Not everybody came along, though. Two team members opted out of the AI program after six months, and Shannon doesn't pretend otherwise. Change is hard, and some people don't want it. I'd rather hear that than a fairy tale. And her rule of thumb is worth taping to your monitor: "You can't automate something that you don't fully understand." Ryan could build that bot because the manual process was already written down.

Grant Calloway

This week's tool is Microsoft Power Automate, the same one Ryan used. It's software that moves information between your programs so a person doesn't have to retype it. It fits best for businesses of roughly five to a hundred people who already live in Microsoft 365. Power Automate Premium is listed at about fifteen dollars per user per month, billed annually, and there's a thirty day trial, though do check current pricing. One practical use: a staff member pastes meeting notes into a single intake form, and Copilot formats them and routes them into your practice management and billing tools. You don't need a developer. You do want somebody curious.

Grant Calloway

Here's your challenge, and it fits inside an hour. Call it the Triple Entry Audit. First, find one task where someone copies the same information into two or more systems. Second, ask that person to write the exact click path on paper: what triggers the task, what gets copied, which fields it lands in, and what a finished job looks like. Five steps, give or take. Third, pair them with the most tech curious person you've got, and sketch an automation with tools you already own. Power Automate works, or whatever you already have. And before anyone touches a keyboard, make the Shannon Smit promise out loud: this automation will not cut your hours. It frees you for better work.

Grant Calloway

The biggest takeaway? Write it down first, automate second, and tell your people what's in it for them. Ryan's first bot saved about an hour a day per person, but what made it stick was an owner who answered his question honestly. Markets reward the folks who do the boring work well, and so do small businesses. Try the audit this week.