Vetting CS Software Platforms- What are the best questions to ask?

Chrissy Hines

Hi all! 
I'm currently vetting CS platforms for purchase- I was wondering if the community might share questions you're asking the providers when receiving a demo? I do have a list of questions, but I want to make sure I'm not missing something important that might come back to haunt me. What are some of your BEST questions in regards to what a CS software can do? Any pitfalls to look out for? As a note: we are not looking at the big guys (churn zero gainsight etc..). Thanks so much as always for your feedback.