It does everything except the one thing we actually needed.

We once bought a booking platform off the back of a demo that felt like it had been built for us. Group discounts, waitlists, a half-decent calendar view, an app that didn't look like it was designed in 2009. The salesperson nodded along to everything we asked. Ninety minutes in, we were mentally spending the time we'd save.

Three weeks into using it for real, we found the gap. Nothing dramatic — it just couldn't handle a booking that spanned two departure dates, which for us wasn't an edge case, it was a Tuesday. So we built a workaround. Then another one for the thing the workaround broke. Six months later we had a platform and a spreadsheet running side by side, and the spreadsheet was doing the important bit.

This isn't a story about a bad platform. Most of them are fine. The problem is that a demo is built to show you what the software does well, and every events business has a slice of its work that's slightly unusual — the way you handle no-shows, the odd payment plan a corporate client insists on, the one supplier who still wants a fax-shaped PDF. Nobody demos that bit, because it's not the bit that sells.

So you buy the eighty percent that fits and quietly absorb the twenty that doesn't. The absorbing is the expensive part, and it never shows up on the pricing page. It shows up as a person who's become the human patch between what the software promises and what your business actually does — usually without either of you deciding that was the job.

Give that gap long enough and the workaround stops being a workaround. It becomes the thing the business actually depends on, while the platform you pay a subscription for becomes the thing that just holds the data everyone's too nervous to touch. I've seen teams end up more constrained by the software they bought to give them freedom than they ever were by the spreadsheet it replaced, because now every fix has to route around a system that wasn't built to bend.

The tell is usually a phrase, not a metric. Someone says "I just do that bit manually" and everyone nods because it's been true for so long it doesn't register as a problem any more. That sentence is worth chasing. It's usually pointing at the exact seam where the templated part of your business met the part that's genuinely yours, and lost.

The only test that's ever worked for us is to bring the worst booking of last season into the sales call, not the average one. The multi-date group with a part-refund, a name change, and a supplier invoice that arrived in the wrong currency. Ask them to show you that, live, in the platform — not on a roadmap, not in the API docs, in the actual screen you'll be sat in front of at 6am on event day. Most platforms go quiet at that point, and that quiet is the most useful thing you'll learn in the whole sales process.

It doesn't mean walk away. Plenty of platforms are worth buying with eyes open about where the gap is and a plan for who owns it. What it means is that the twenty percent is the actual decision, not the eighty. If you want a second opinion on where that seam sits in your own booking flow before you sign anything, that's the kind of conversation I'm happy to have.