December 15, 2021
What are you supposed to ask in a software demo?
Most operators I talk to don't have a good answer to that. They book the demo, they show up, the sales rep shares their screen, and for 45 minutes everything looks polished and possible. Then the call ends and the operator has a feeling - "seemed nice, seemed capable" - but no real data. A week later they're guessing between two platforms based on vibes.
I've been on the other side of that table. When we were building our booking system I sat through demos from every major platform to understand what the competition was doing. And I can tell you: vendor demos are sales pitches. Every one of them. That's not a criticism - it's just the format. The rep controls what you see, in what order, for how long. Your job is to redirect that into a qualification call. You do that with questions. Specifically, these 25.
I've grouped them by category. Work through them in order. If a rep dodges or deflects on more than two, you've learned something important.
This is the section most operators skip because they feel awkward talking about money up front. Don't skip it. Hidden fee structures are where operators get hurt, and the demo is the right time to surface them - before you've signed anything.
A story about question 1: I know an operator who asked a vendor exactly that - "do you take a cut on my direct bookings, even the ones that come in off my own website widget?" The sales rep talked for about two minutes without answering. Then redirected to screen-sharing the dashboard. The operator thanked them politely, ended the call, and signed with someone else. Two minutes of dodge is a real answer. It means yes, or "we haven't decided yet," and neither is good.
Features are what the demo will focus on most, because features are what look good on a screen. Ask the questions that don't look good on a screen.
The demo experience tells you nothing about what happens at 7am on a cruise ship day when something breaks and you have 60 guests arriving in 90 minutes. Ask these before you need the answer.
Every operator I know who has switched booking systems has a story about the migration. Usually it involves a spreadsheet and several days of manual entry. That's because they never asked this question before signing.
This is the section almost nobody asks, which is a shame because it's the most useful one.
A vendor who can't name three references in your region either doesn't have customers there yet or doesn't want you talking to the ones they do have. Both are worth knowing.
After the call, score it. Give one point for every clean, direct answer. Zero for every deflection, redirect, or "I'll follow up on that." If the score is below 18 out of 25, the platform has things to hide. Maybe small things. Maybe not.
The goal here isn't to catch anyone lying. It's to enter a 12 or 24-month working relationship with actual information instead of a good feeling. A good feeling doesn't hold up when you're two months in and the payout is sitting in a bank account in a country you don't operate in, or the support ticket from Tuesday is still open on Friday.
We built Junglebee specifically for Caribbean tour and charter operators, which means every one of these questions has a published, specific answer - including the pricing, which lives on a public page because that's how it should work. But use this list on any vendor, including us. Operators who go into demos with the right questions end up with the right software. The ones who don't end up switching again in 18 months.
