Once we are sold on something, the reality sets in. You are going to put your stamp on it, pay for it, roll it out. You need to start looking for reasons *not to buy*. So, here's the ultimate catch all...
"Does it do [_____]?"
Make [_____] really seem important. Ensure [_____] is critical to your current process. There, good, a reason not to buy. You can't live without [_____].
Then the vendor counters with a question: "Of all the named users in your system, how many of them use the system on a daily basis?" You answer with something like "We have 8000 users. About 1000 log in per month. About 150 use it every day."
The vendor asks: "What what is the value if all 8000 users accessed the system every month? And 1000 or more were using it per day?"
The vendor didn't even acknowledge [_____]? How rude.
The truth is that you have people out there trying to do a job. You need to capture their documents to make your organization efficient and compliant. This generally doesn't mean you need to give them an extra fly-out menu option, or an extra feature. It means you need to give them a tool that stays out of their way.
Some vendors will heap [_____] onto a pile of features that will get used by 150 people a day.
Shinydrive is a technology that will enable all 8000 of your users with no training. We are sorry it doesn't do [_____].