When the Numbers Look Too Good to Be True

I’ve never been great with numbers. It took me two goes to pass 5th form maths. So the fact I used to work for an accounting software company might seem like a strange twist of fate. That said, I did pass my one and only university accounting paper, so there’s that.

Over the last few months, we’ve been keeping a close eye on our numbers. The first month, we were in the red. The second month showed some solid improvements. And by the third month, things looked good, almost too good. You know that saying, “if it feels too good to be true, it probably is”? Yeah, that definitely applied here.

For the past couple of months, our numbers looked insane. I kept staring at them thinking, this can’t be right. This is unreal.

Even though I used to work at Xero, I never actually worked on the Xero product itself. I built tools for the teams behind the product, confusing I know. So there I was, poking around in Xero trying to figure out what was off. I spotted a few items marked as “unreconciled” on the accounts page. Thinking I was tidying things up, I deleted them all.

That triggered all those invoices to resend to customers who had already paid.

Not great optics. The next day, my wife messaged me saying, “How do I turn off the invoice reminders? People are calling, saying they’ve already paid.”

I’m used to staring at spreadsheets; they can be my happy place, but this was just painful. Searching Gmail for invoices, manually matching transactions, it turned into a nightmare of pain. But it needed to be done.

So I did what anyone would do in that situation: exported all the transactions from our bank in CSV format, exported everything from Xero, and began the slow, painful process of matching everything manually.

It took ages, but I tracked down most of the issues. Turns out we had been matching payments to invoices incorrectly, same with some bills. Here’s a key lesson: if you use search and find to match an invoice, Xero processes it as an invoice payment. But if you create one manually, it’s treated as a spend transaction, which is handled differently for GST and doesn’t link to the invoice. That difference can create a pretty big mess if you don’t watch it.

Is it all sorted now? Almost. The numbers we’re seeing now feel far more grounded in reality. They’re still good, just no longer too good to be true. And honestly, that’s probably where we need to be.

I’m now obsessed with the numbers and trying to automate as much as possible. I spent four hours the other night setting up email automation so invoices go directly to DocHub and then on to Xero. That should alleviate some of the cognitive load of manual work. We’re also looking at using our CRM to help with ordering stock, so we can track better and integrate directly with Xero.

Has anyone had a similar experience? What tools do you use to automate this kind of stuff?