Nobody adopts software

Before I showed up, the company started moving to a new accounting system, and a person everyone trusted pushed back directly to the owner. He sided with her and the migration was reversed. I heard that story early, and I heard it told with some pride. A firm that manages other people's farmland runs on the confidence of landowners who have been clients for decades, and that confidence wouldn't survive a botched month in the accounting office.

The company sells farmland at live auction, sometimes sixteen tracts at once, and a bidder can take one tract, a combination, or the whole farm. Somebody in the back of the room has to know, at every moment, which set of bids wins. For years that was a spreadsheet, and a new bid combination took two or three minutes to work out while the auctioneer stalled and the room waited.

I sat through a sale before I wrote a line of code. Then I built a board that resolves a new combination in seconds and puts it on every screen in the hall. It ran for the first time in June 2026 at a sixteen-tract sale in Ohio, alongside the old spreadsheet, so if the board was ever wrong the spreadsheet still held the room.

One small thing from that build stayed with me more than the math. An early version showed estimated totals with a tilde in front of them, the way a programmer writes “about.” From forty feet away a tilde reads as a minus sign, and a dollar figure with a minus sign in front of it, in a room where people are bidding real money, is a problem. I cut the tilde.

The AI came second, and the AI is where I got things wrong.

I built the company an assistant that knows its own documents and its own people and answers in plain language, with citations. Staff sent in more than a hundred suggestions over the first few months and about two thirds of them shipped. That part worked. The thing was being used.

Then in August an appraiser asked it about farmland sales in a county in Ohio, and it invented one. It described a sale that never happened, complete with made-up contamination readings, and presented it as something it had found. When he pressed, it told him it hadn't run a search at all. The log showed it had.

I'd built a tool for people whose signatures go on appraisals, and it had misled one of them twice in one conversation. The fix went in the same day: a gate in the code that refuses to let a claim through unless it can point at the source it came from. The assistant says it doesn't know far more often than it used to.

There were smaller lessons of the same shape. A shared document with a colon in its filename became invisible in every list while the upload screen kept saying it had worked. For weeks the activity log that was supposed to show who was using the tool recorded the person being helped instead of the person doing the helping, so our heaviest user looked like she'd never logged in.

In August the owner asked me to take the company's technology seat, part time, alongside the building. I said yes mostly because of the week-after problem. An outside firm hands over a binder and leaves. The person who has to live with what got built keeps the people around them using it, and that's a different job.

At a company meeting in early September the public version of the assistant ran live, in front of the whole staff, for ten minutes. Seventy-five messages. The first question a colleague typed used a county name the way locals say it, and the assistant drew a blank. Somebody else asked why it didn't know the county coverage printed on the company's own map. Good questions, both of them, and both fixed within a day, tested against a battery of questions built from what the room had typed.