• What types of solution could genuinely solve this?
  • Is there anything that would change how we approach this completely?
  • How do I compare products that look completely different on paper?
  • Implementation timelines measured in months or years, with no clear reason why.
  • Changes to workflows require external consultants or the vendor’s own development team.
  • The system comes with pre-built logic that doesn’t quite fit your operation, and fighting it becomes the project.
  • Integration “works” in demos but needs significant support to hold up in production.
  • Questions about audit trails or calculation transparency produce vague answers.
  • How quickly can a domain expert change a workflow, without involving the vendor?
  • What happens when an acquisition adds new assets or changes the operating model?
  • Can you show me where the calculation logic lives and how it can be traced?
  • Who owns the configuration: your team, or theirs?