12 questions to ask any PMS vendor before you sign

Every property management system demos well. That is what a demo is for. The salesperson knows the shortest path through the software and they will take it, not because they are dishonest but because that is what a rehearsed forty minutes looks like.

These twelve questions are the ones that do not have a rehearsed answer. Ask them in this order. The first four decide whether the rest are worth asking.

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The four that come first

1. "Can I edit a transaction after it has been posted?"

If the answer is yes, you have learned the most important thing about the system in the first minute.

An editable posting means the books tell you their current state and nothing about their history. When a guest disputes a charge, when a card issuer sends a chargeback, or when your accountant reconciles a month you have already filed, the question is always the same: what did this say on the 14th? A system with an edit button cannot answer it.

Ask the follow-up: "then how do I fix a mistake?" The answer you want involves the words reversal, authorization and reason, and it involves a record of who did it. "It's fine, you can just change it" is a system optimised for the demo rather than for the audit.

2. "Show me the tax on a package."

Blend breakfast into a nightly rate, or bundle anything with a room, and ask to see the tax break down.

Accommodation tax applies to accommodation only. If the system computes it against the blended total, you over-collect on every package you sell, invisibly, for as long as you own the software. If it stores one tax total per transaction rather than each tax as its own component, your remittance is a reconstruction rather than a query.

Ask to see a remittance report, not a tax summary. Then ask whether it can tell you which portion somebody else remitted.

3. "What happens to my data if you go out of business?"

Every vendor has an answer to this. Only some of them have a mechanism.

You are listening for exports you can run yourself, without a support ticket, covering guests, reservations and the transaction ledger, plus something that preserves your closed periods. "We'd of course help you migrate" is not a mechanism, it is a sentence, and it requires the company to still exist at the moment you need it.

Ask where the data is resident, and ask it as a fact question rather than a compliance one.

4. "How long before a new hire can check someone in alone?"

Watch whether the answer is a number of hours or a description of a training programme. Those are two different products, and the second one bills you every season.

For a seasonal property this is not a soft question. It is paid in full every year, during the two weeks you have least time to give it. There is a whole guide on the arithmetic.

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The four about the work

5. "What stops somebody doing the wrong thing?"

Be specific. Ask about checking into a room that is still occupied. Ask about checking into a room that has not been cleaned since the last guest. Ask about taking the same payment twice.

Three possible answers, and they are very different: the system blocks it, the system warns and lets you proceed deliberately, or the system cheerfully allows it and you find out later. The mix tells you how much supervision the software expects from you.

6. "Where does the day's work come from?"

Ask them to show you the screen a staff member opens at 8am. Then ask who maintains the list on it.

If the answer is that somebody assembles it, that somebody is you, every morning, forever. If it derives from the state of the property, ask what happens when the state changes at 11am.

7. "Show me a guest whose company pays for the room but who pays for their own extras."

One reservation, or two? If the system fakes it with a second booking, your occupancy is wrong, your room count is wrong, and one guest can be checked out twice.

Follow with: move that guest to a different room mid-stay, then print their bill. It should be one document describing one stay.

8. "What does the housekeeping screen say about tomorrow?"

A list of dirty rooms is not a forecast. You are asking whether the system can convert tomorrow's departures into cleaning time and a number of people, using your cleaning times rather than an industry average.

Then ask whether a same-day turnover automatically outranks a stayover, and who has to tell it that.

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The four about the money and the exit

9. "Where does a deposit appear in the revenue report?"

The correct answer is that it does not. A deposit for a stay that has not happened is a liability, and it should be reported as one until the guest arrives, then earned night by night.

If deposits land in revenue on the day they are taken, every seasonal property using that system has a revenue chart that peaks in the spring and a year-over-year comparison that means nothing.

10. "Do you connect to the channels I actually use?"

Name yours out loud rather than accepting a logo wall. Then ask the question that matters: "is that live today, for a property like mine, or is it in progress?"

A logo on a website is not a connection. Ask what happens to a booking from that channel today, and ask whether the system distinguishes a channel that invoices you monthly from one that charges the guest and remits you the net. Those produce different folios, and treating them the same either chases a guest for money they already paid or zeroes a folio they still owe.

11. "What is the real price at my size, for three years?"

Get the per-unit or per-booking basis, the minimum, the setup or onboarding fee, the migration cost, the charge for additional users, the payment processing arrangement, and what happens at renewal.

Then ask the one that gets skipped: "what does it cost to leave?" Not the notice period. Whether your data comes with you, in what format, and whether that is included.

12. "Can I talk to a property like mine that uses this?"

Not a case study on the website. An operator, on the phone, with a property of roughly your size and shape.

A young company may not have one yet, and there is a version of that answer you should accept: "not at your size, here is who we do have, and here is what is genuinely unproven." What you should not accept is a smooth pivot away from the question.

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The one instruction for the demo itself

Ask them to hand the keyboard to somebody who has never seen the software.

Not you, and not the salesperson. Bring the person who will actually be behind your desk in July, or any capable adult who was not in the meeting. Give them one task: a guest is standing here, they are on the list, check them in and take payment.

Then stop talking and watch. Where do they hesitate? What do they read? Do they find the next action, or do they go hunting for it?

Ten minutes of that tells you more than the other forty, because it measures the only cost that recurs every season for as long as you own the software.

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A note on where this came from. We wrote these questions and we sell a system, so read them with that in mind. The test of a list like this is not whether the vendor who wrote it comes out well. It is whether the questions would still be the right ones if we had never existed, and whether we answered every one of them on this page instead of the three that flatter us. Take the list to every vendor on your shortlist, including us, and give the same weight to what each of them does with question four.