I think there’s a lesson in here somewhere…

This week, I did our taxes. In the past, I’d handed that off to accountants, but we’ve simplified things and I was fairly confident that I could do it myself. The only complication was that we’d be filing jointly for Federal, but separately for State. No biggy, right?

I banged all the data into the basic TurboTax DIY web system, pulled stuff directly from banks and so forth, with no problems. But when it came to the State return, the system directed me to a dense page in the online help, which told me that I’d have to prepare two complete sets of returns – one joint, one separate – and file the Federal from the first and the States from the second. And because #reasons, I’d only be able to file by mail.

This sounded tedious, and error-prone. The obvious answer: upgrade to the premium TurboTax service, and let them do it for me. So I clicked Upgrade, and started a web chat with a Product Expert. (Not the Preparer, just a gatekeeper.) She told me I’d have to begin by uploading all my documents into the Checklist. “But I’ve already entered all the data, it’s in the system.” “Oh, no, we can only see the stuff that was imported electronically. None of the data that you typed yourself will transfer to the new return.” When I pointed out that this was crazy, she offered the following: “OK, I can drop you out of Full Service to let you get at the return you’d been working on. Then I suggest you screenshot each page. You can then return to Full Service and upload the screenshots, so that your Tax Preparer can enter the data.”

At first, I resisted. I tried to enter some of my data using the Full Service checklist, but it was completely useless. For example, there was a checklist item for Social Security income… but it only allowed you to enter one SSA-1099. If you have several, you’re SOL.

Reluctantly, I did what the Product Expert had suggested. I retraced my steps through the DIY web interface, and built up a folder containing 45 screenshots and 6 other documents, like photo IDs. I switched back to Full Service, and started to upload the files, to prepare for the call with my Tax Preparer.

After I’d uploaded 22 files, the system refused to upload any more.

First, I had a stiff drink. (I’ve moved from single malt Scotch to Bourbon recently.) Then I cancelled Full Service, and bought a copy of the Download/CD TurboTax Windows application. To my surprise, it successfully imported all the data I’d entered into the online service. I finished the whole Joint/Separate stuff in about an hour, with no significant issues. In part, this was because the UI of the Windows application was vastly superior to TurboTax’s web based services, and I had full control over the various versions of the return. The validation and issue resolution UX was crystal clear, highlighting each problem by showing the exact tax form fields involved. (In the online version, you have no visibility whatsoever into the relationship between the on-screen dialog and the resulting tax form entries.)

So what are the lessons here? It’s instructive that the only smooth data interchange occurred when I imported web data into the desktop app. I can imagine the desktop app team thinking, “These online services are likely to be problematic: let’s make sure we can always give the user a way of recovering by moving to the more reliable, old-school desktop environment.” Yes, there’s always a risk that the old desktop app will become an orphan in the world of web and mobile solutions, but I think TurboTax has managed to avoid that…. probably because accountants tend to be conservative. (And a good thing too!)