A demo is a performance of a product working. That is not a complaint — you would do exactly the same — but it means the default demo tells you very little about what the thing does in your building in month six.
The questions below change what you learn from an hour. Several are uncomfortable to ask. A few of them are uncomfortable for us to answer, which is the reason they are in here rather than in a competitor's blog.
First: make them run it on your data
The highest-value thing you can do is refuse the sample dataset. Send an export from one of your own systems before the call and ask them to load it.
A demo on curated data shows you the product's best day. A demo on your data shows you your duplicate rate, your missing phone numbers, and whether their matching survives contact with a real host stand at eleven at night.
If a vendor cannot or will not do this, that is an answer in itself. Sometimes a fair one — a genuinely early product may not have the ingest built for your platform yet — but it should be said plainly rather than deflected into a follow-up call.
Questions about identity
This is the part that decides whether anything else on the screen is true. Four questions, and the answers vary far more than the marketing does.
- What happens when two guests share a name? The correct answer involves not merging them. Any product that merges on name similarity will eventually combine two real people, and there is no undo that restores either history.
- Show me why you decided these two records are the same person. You want a reason — matched on phone, matched on email — rather than a confidence score with nothing behind it.
- What do you do with a phone number attached to two hundred guests? That is the host stand's own number, typed in to get past a required field. A good product notices and quarantines it. A bad one merges your entire Saturday into one very loyal person.
- Can I un-merge, and what happens to the visit history when I do? Ask them to do it on the call.
Questions about the six months after the demo
Nearly every failure in this category happens after the contract is signed and has nothing to do with features.
- Which of my systems can you read today, in production, with a customer live on it? Not "we support" and not the roadmap. Today.
- What does week one cost me in my own staff's hours? A number, not "minimal setup."
- Who operates this in month six? The most common failure here is not a bad product. It is a good product nobody has time to open. Ask who that person is at their existing accounts and what their job title is.
- What breaks when one of my sites changes reservation platform? It will happen, probably during your contract.
- When a number looks wrong, what do I do? There should be a way to see the underlying records yourself rather than a support ticket and a wait.
Questions about ownership and exit
Ask these early, while everyone is still being charming about it.
- Can I export everything, myself, in a format I can open? Have them demonstrate it rather than confirm it.
- Whose data is this? Specifically: can they use your guest data to build or improve anything they sell to somebody else.
- What happens to my data when I leave — deleted on request, and within what period.
- What is the contract length and what happens at renewal? Ask what the price did for their existing customers at the first renewal.
- Who at your company can read an individual guest record, and is that logged.
The awkward ones, including for us
Every vendor in this category, ourselves included, has a set of questions they would rather you did not open with. Ask them anyway, and treat a straight answer as a signal in its own right.
For what it is worth, here is how we would answer them at the time of writing. If any of it has changed by the time you read this, ask us again and make us say it out loud.
- How many restaurants are live on this today? Ask for a number rather than an adjective. We are early, and we would rather tell you exactly where we are than gesture vaguely at "groups like yours."
- Which integrations are live and which are pending? Reservation platforms approve partner integrations on their own timetable, and ours are in progress rather than complete. A vendor who describes a pending integration as a live one has told you how they will describe everything else.
- Can I speak to a customer who is not in your case studies? If the answer is a slide instead of a phone number, note that.
- What does your product do badly? A vendor who cannot name anything is either too new to know or comfortable saying things that are not true, and neither is what you want across a three-year contract.
- What do you not do at all? We do not take bookings, run a floor, or process payments. A product that claims all of it is describing a much larger project than the one you are being quoted for.
- Where did that statistic come from? If a slide puts a figure on how many regulars a restaurant loses each year, ask for the source and then go and read it. We do not publish that number anywhere, because we could not find a version of it we would be willing to defend.
What a good answer sounds like
Specific, checkable, and occasionally unflattering. "We match on phone and email, we never match on name alone, and a chunk of the records in your file matched nothing at all because they have neither" is a good answer, even though the last clause is bad news for both of you.
A bad answer is the demo continuing. Watch for the pivot to a different screen, the phrase "we can take that offline," and any sentence about philosophy.
Write the answers down during the call, in your own words. Three weeks later four demos blur into a single product that does everything, and that product does not exist.