Every hotel PMS demo goes well. The salesperson is competent, the interface is clean, and the feature list covers everything you asked about. Then you are two years in, and the problems are things nobody demonstrated.
These are the questions that surface those problems while you can still walk away. Ask every vendor the same list and compare the answers, not the demos.
Data and exit — ask these first
Deliberately first, because the answers tell you the most and vendors expect them last.
"Can I export all my data, myself, at any time, without asking you?" Reservations, guests, rates, invoices, folio history. In a usable format — CSV or JSON, not a PDF report. If the answer involves raising a support ticket or a fee, that is a lock-in mechanism, and you are being told the plan.
"If I leave, what happens to my data, and how long do I have?" You want a defined export window and clear deletion terms in writing.
"Is there an API, and can I use it on my plan?" An API that exists only on the enterprise tier is not an API you have.
"Who owns the guest data?" It should be you unambiguously, in the contract. Check what the vendor is permitted to do with it.
Money — the whole number, over three years
"What is the total monthly cost for my property, with every module I have discussed?" Get the number for your actual room count, not the headline price.
"What is not included?" Setup, data migration, training, support tier, extra users, extra properties, API access, each integration.
"What happens at renewal?" Introductory pricing that rises sharply in year two is common. Ask for the increase to be capped in the contract.
"Is there a per-booking or per-transaction fee?" Some pricing is per-room-per-month; some takes a cut of bookings. Over a year these are very different, and the second scales against you.
"What is the contract term and the notice period?" A three-year lock with a 90-day notice period is a different product from a monthly rolling agreement, whatever the demo showed.
Migration — where implementations actually fail
"Who does the data migration, and what exactly moves?" Future reservations, guest history, rate plans, invoices. Get the list in writing. "We will help you" is not a plan.
"What happens to bookings made during the switchover?"
"How long from signature to going live, for a property my size?" Then ask for a reference customer of similar size who went live recently, and actually call them.
"What does training include, and what does it cost?" Including for staff who join after go-live — turnover is a fact of front-desk life.
Support — the difference that shows up at 2am
"What are your support hours, in my time zone?"
"Is support a person or a ticket form?" Ask how to reach a human when the system is down at 23:00 on a Saturday. If there is no answer, that is the answer.
"What is your uptime, and where is it published?" Ask for a status page. A vendor without one is asking you to take availability on trust.
"What happens if the internet goes down?" Can you still check a guest in? Some systems have an offline mode; most do not. If not, what is the documented manual procedure?
The operational specifics
"Show me a real check-in, on the live system, at the speed a receptionist would do it." Not the sales walkthrough — the actual sequence, including a walk-in with no reservation.
"Show me the night audit."
"How do I move a guest to a different room mid-stay?" A frequent, awkward operation, and a good test of whether the system was designed by people who have worked a front desk.
"How do I split a bill between two guests?" Another one that is either two clicks or twenty minutes.
"Does it work on a phone or tablet?" Housekeeping in particular.
"Does it handle my languages, my currency, my tax rules and my invoice format?" Check the legal invoice requirements in your country specifically — this is where regional vendors beat international ones and where an otherwise good product becomes unusable.
Integration reality
"Which channel managers and payment providers are you actually connected to today?" Not "we can integrate with anything". Which ones are live, in production, right now, for existing customers.
"How fast does availability propagate to channels?" Seconds or minutes matters. Fifteen-minute polling is how you oversell.
"When an integration breaks, who fixes it?"
Before you sign
- Get a trial with your own data, not a demo with theirs.
- Have the person who will use it daily test it, not only the owner.
- Call two reference customers of similar size, and ask them what they wish they had known.
- Read the contract's termination, price increase and data clauses specifically.
- Confirm the total three-year cost in writing.
Disclosure, and why this list is shaped this way
GrandStay is a hotel PMS. We are one of the vendors you would be asking these questions.
We wrote the data-and-exit section first, and made it the sharpest, because those are the questions that are least comfortable for any vendor to be asked — including us — and they are the ones that determine whether you are a customer or a hostage. A vendor who answers them cleanly is worth considering. One who does not has told you something important, and you should believe them.