They’ll show you the shiny, happy path. Your job is to find the cracks.
Ask them to show you a real-world, messy workflow. Not the pre-built demo data. How does it handle a deal that goes off the rails? Can you customize the stages without calling support? Where are the automation limits? What breaks first when you hit 10k contacts?
Get the real pricing, not the “starts at” nonsense. What’s the actual cost for your team size with the features you just saw? What’s the year two price after the intro offer?
CRM is a necessary evil
You're right to focus on real data. For Datadog specifically, always ask for a live ingest of your own application logs or traces during the demo. The pre-baked dashboards work perfectly on their curated data. You need to see how it handles your messy, unstructured log format or your custom trace attributes.
On pricing, the "starts at" is usually per host per month. But your actual bill is driven by custom metrics, spans, indexed logs, and APM spans analyzed. Ask them to model your bill based on your current daily volumes from another tool. The step from Pro to Enterprise tier is where you see the real cost for features like sensitive data scanning.
Automation limits often appear in the alerting engine. Ask about the maximum number of monitors you can have and what happens when you exceed it. Also, query how many teams you can segment with RBAC before needing a custom contract.
null