A recruiting system demo is a performance. The data is curated, the path is rehearsed, and every click lands somewhere flattering. That is not dishonesty — it is how software is sold. It just means the interesting information is in the questions nobody plans for.
These are the eleven we would ask. Several of them are uncomfortable for us to answer too, which is rather the point.
1. What happens when nobody is logged in? Ask whether anything runs on a schedule. A great many systems describe alerts and reminders that only fire when a person opens a page. That may be perfectly fine for you — but you should know it before you design a process around a notification that will never arrive at 6am.
2. Show me the same candidate in four places. Open the board, the candidate record, the side panel and a report. Do they all say the same thing? Systems that calculate status per screen drift, and the drift shows up as arguments about whose number is right.
3. Can I add a pipeline stage? Then ask what happens to last quarter’s reports when you do. If the answer is cheerful and quick, they have not thought about it.
4. Who can see margin? Then ask how it is hidden. There is a real difference between a column that is not rendered and data that is never sent. Ask them to prove it with a browser open, not a slide.
5. What does export actually produce? CSV, PDF, both? An export is what you will fall back on for every report the system does not have. Find out what shape it comes in before it matters.
6. Can a candidate log in? Some firms want a candidate portal; some are relieved not to have one. Either is a fine answer. A vague answer is not.
7. What happens if two recruiters open the same record? Last write wins, silently, in more systems than you would like. Ask what your team sees.
8. What is on the roadmap versus in the product? Specifically: is there anything in the navigation that does not work yet? Menu items ship ahead of features more often than vendors admit, and a nav item is a promise to your team.
9. If I send a shortlist to a client, what can I see and what can I take back? Opens per person is useful. Being able to revoke is useful. Ask directly whether anything already downloaded can be recalled — the honest answer is no, everywhere, and you want to hear a vendor say so.
10. Who is your worst-fit customer? A vendor who cannot answer this either has not sold enough to know, or is not going to tell you. Both are worth knowing on a first call.
11. What will my team complain about in month two? Every system has one. Ask three of their customers the same question and see whether the answers match what the vendor told you.
What the answers are really telling you
You are not testing the product with these. You are testing whether the person selling it knows where the edges are, and whether they will tell you before you sign or after.
A vendor who says “we don’t do that, here’s what people do instead” is showing you exactly how the relationship will go when something breaks in month eight. A vendor whose product has no limitations is describing a product they have not looked at closely.
Take the list to every vendor you are evaluating, including us.
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