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Booking software: the questions that expose a bad fit

Every demo shows you a calendar, and the calendar always looks fine. What makes venues switch again a year or two later never shows up in a demo. It's in how the system handles your courts, where your money lands, what the move costs you, and what the contract says. These are the questions that bring all that out — including the ones we'd least like to answer.

If you only ask four

  1. Whose account do payments land in — yours or theirs?
  2. Can I export all my customer and booking data myself, today?
  3. How much notice do I have to give, and what happens to saved card details when I leave?
  4. Can you set up my most awkward booking — not a simple court hire?

1. Who owns your customers, payments and data

Start here. These three answers shape everything else, and they're the hardest to undo later. You can work around clumsy scheduling. It's much harder to recover once you find out you don't control your own customer list.

Whose account do payments land in?

If the answer is "ours, and we pay you out", here's what that means day to day. Your money arrives when they run payouts, not when your bank would have settled it. Refunds and chargebacks go through their support queue. And every saved card and recurring membership payment sits in their account, not yours.

That last part is the one to watch. It means leaving them requires every member to enter their card details again — a switching cost dressed up as a technical detail.

A bad answer sounds like: a long explanation of why their built-in payments are simpler. They might well be simpler. That wasn't the question.

Can I export my customers and bookings myself, right now?

Not "is there an export" — every vendor says yes. Ask to see it during the trial, and look at what's actually in the file: contact details, booking history, membership status, credits left, marketing consent. An export with names and emails but no credit balances or consent status won't get you to another system.

Who owns the customer relationship?

This one mostly matters with marketplaces and consumer apps, where the honest answer is "we do". That can be a fair trade if they bring you players you'd never have reached on your own. What matters is knowing which deal you're in before you build your business on it. We go into that trade-off on the Playtomic comparison.

2. Your courts and classes — where demos hide things

Every system demos well on the easy case: one court, one hour, one person. Your venue isn't the easy case. The gap between the two is where your next two years of workarounds live.

Ask them to set up your most awkward booking

Don't let the demo pick the example. Bring your own — the thing your current system can't do, or does badly. Real ones we hear:

  • An 11-a-side pitch that also splits into two 7s or three 5s. Selling one has to close the others.
  • A session that needs a boat, a qualified driver and a free seat before you can sell it at all.
  • A beginner swim lane at four to one, running next to an improver lane at eight to one — same pool, same time.
  • One parent paying for two children, in different squads, on different nights, at a sibling rate.
  • A 90-minute padel slot where four players each pay their own share.

If the answer involves duplicate courts, made-up customer accounts, or "you'd just do that by hand", you've found your future weekly admin. Count the clicks, then multiply by the bookings you take.

Can you price each court separately?

One price for the whole venue is a warning sign if your courts genuinely differ: indoor and outdoor, floodlit and daylight, a show court and a back court. If everything has to share a price, you'll underprice your best courts to avoid overpricing your worst.

What happens to a cancelled slot?

Ask whether a cancelled booking goes back on sale automatically. It sounds like a small thing. It decides whether a generous cancellation policy protects your revenue or leaks it. A slot someone hands back that you can't resell costs you exactly what a no-show costs you.

3. Money: what it really costs

Is it commission, a subscription, or both?

Commission looks cheap while you're small and hurts once you're busy, because the fee grows exactly as you grow. A flat subscription works the other way round. Do the sums on the volume you expect in two years, not the volume you have today. A vendor charging commission usually won't do those sums for you.

What's actually in the top tier?

Ask for the list, not the tier name. "White-label" on its own means at least four different things: a branded booking page, that page on your own web address, the booking form built into your website, and your own branded mobile apps. Vendors price these at different tiers while using one word for all of them. We've set out which is which on our own white-label page, and it's worth asking every vendor to do the same.

What are the setup, onboarding and migration fees?

These sit outside the subscription and often aren't on the pricing page at all. Ask for the total first-year cost in writing, migration charges included.

4. Moving across, and what to ask early

Moving systems is where the real risk sits, and almost nobody asks about it while choosing, because it feels like a problem for later. It isn't. These answers decide whether you can switch at all.

What actually comes across?

Customers and future bookings are the easy part. The rest is what matters: active memberships and their renewal dates, unused class-pack credits, wallet balances, customers on account and their terms, and marketing consent. Anything not on that list, your staff will retype by hand or lose.

Can we run both systems at once for a while?

Switching everything over in one go, mid-season, in a busy venue, is asking for trouble. Ask whether the old system can be made read-only while your team learns the new one. Ask specifically whether you can get through one full renewal cycle before you turn it off. Recurring memberships are where a bad move does lasting damage: a member charged twice, or not at all, is a member you may lose.

What happens to our existing booking links?

Customers bookmark booking pages, and your ads may point at one. Those links need to redirect to the new ones, not break.

5. The contract

Three questions. All dull. All much better asked now than later.

  • How much notice do we have to give, and is there a minimum term? Year-long tie-ins are common. They're not automatically bad — they often buy you a lower price — but you should choose one, not discover it.
  • What happens to saved card details when we leave? If payments run through the vendor's account, each member usually has to set their payment up again somewhere else. Ask them to talk you through how that works. How readily they answer tells you how often they've had to.
  • How and when do prices go up? Ask about their last two increases and how much notice they gave.

6. A short scorecard

If you want one page to take into a demo, this is it. Score every vendor honestly, us included.

  • Payments land in our own account — yes / no
  • We can export everything ourselves, credits and consent included — yes / no
  • Our most awkward booking works without a workaround — yes / no
  • We can set prices per court, not just per venue — yes / no
  • Cancelled slots go back on sale automatically — yes / no
  • Usage reported by hour and by court, not just totals — yes / no
  • The move brings memberships, credits and consent with it — yes / no
  • We can run both systems through one full renewal cycle — yes / no
  • Total first-year cost, in writing — yes / no
  • We know the notice period and how to leave — yes / no

We publish this knowing you can hold us to it, and knowing we don't win every row. A marketplace will beat us at bringing you new players. A studio-only platform may suit a studio better. A venue that switches for the wrong reason leaves within a year, and that costs us more than never signing them.

Want to run the scorecard against Real Sports Bookings? The free Starter plan covers enough for you to test most of it yourself. Or get in touch and we'll go through it with you — including the rows where our answer isn't the one we'd like.

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