Directing a demo instead of watching one
A standard demo is a rehearsed path through the product's strongest features. You learn nothing you could not have learned from the website.
The default demo is a presentation. The vendor drives, the sequence is practised, the data is clean, and the questions come at the end when there is no time to explore them.
It is a good use of the vendor's hour and a poor use of yours. The fix is to send the agenda in advance and insist on it. When comparing claims around remote employee monitoring, remote employee monitoring software gives one vendor’s framing to test against documentation, demos and references.
Send scenarios, not questions
Give each vendor the same three or four scenarios drawn from your real process, written concretely enough to be performed: a specific task, with specific awkwardness, from start to finish.
Scenarios beat feature questions because a feature question is answered yes. A scenario has to be demonstrated, and the demonstration reveals how many steps it takes, what it looks like, and whether the answer was really yes.
Comparability is the whole point. Three demos of three different things produce three impressions and no comparison.
Ask to see the ugly parts
Every product has areas that are older, less polished or genuinely awkward. These do not appear in a standard demo and they are where you will spend real time.
Ask directly: show us the administration screens, show us an error being corrected, show us what a new user sees on their first day, show us the reporting builder rather than a finished report. A vendor who navigates these comfortably is telling you something; one who deflects is also telling you something.
Have a user drive part of it
The most informative ten minutes of any demo is when someone from your team operates the product with the vendor watching, rather than the reverse.
It surfaces the difference between a product that is well demonstrated and one that is usable. Vendors sometimes resist, and reasonably so at this stage — but a flat refusal in a competitive process is worth noting.
Take the awkward questions in the meeting
Ask what the product does badly. Ask what kind of customer it is a poor fit for. Ask what the most common reason for churn is.
Good vendors answer these well, because a product that fits everybody fits nobody and they know it. The quality of the answer is one of the better signals available about what the relationship will be like after the sale.
Record and score immediately
Score against the agreed criteria within the hour, independently, before anyone discusses it. Impressions converge quickly in conversation and the loudest evaluator's view becomes the record.
With three demos over two weeks, this is the only reliable way to have three comparable assessments rather than one memory of whichever was most recent.
For independent security checks beyond vendor marketing, CISA resources and tools provides public guidance and tools.