46 crucial questions for your software selection
46 questions across 7 categories to compare every vendor fairly and choose the right software, without costly surprises later.
46 crucial questions
Grounded ways to choose with confidence
Focus your selection on what truly has impact, instead of the slickest demo.
Ask questions that reveal what the vendor would rather keep quiet.
Expose hidden costs and risks before you put your signature down.
Needs & scope
- 1. Which concrete business problem must this software solve?
- 2. Which processes are in scope and which deliberately are not?
- 3. What are our must-have features?
- 4. Which features are nice-to-have?
- 5. How many users work with it now, and in 3 years?
- 6. Which measurable result do we expect within 12 months?
Functionality & fit
- 7. Does the standard version cover our core processes, or is customisation needed?
- 8. How much can we configure ourselves without the vendor?
- 9. How well does the software fit our sector?
- 10. Which sector-specific features are included by default?
- 11. How user-friendly is the system for our staff?
- 12. Does the software work fully on mobile too?
- 13. How does the software scale as we grow?
Integrations & technology
- 14. Which of our current systems must it connect to?
- 15. Are those integrations standard, via API or expensive custom work?
- 16. How does data exchange between systems work?
- 17. Does the solution run in the cloud, on-premise or hybrid?
- 18. Which security certifications does the vendor hold (e.g. ISO 27001)?
- 19. Where is our data stored and is that GDPR-compliant?
Implementation & migration
- 20. How long does a realistic implementation take?
- 21. Who is responsible for the data migration?
- 22. How is our existing data cleaned and migrated?
- 23. How much time does the implementation cost our own team?
- 24. Which onboarding and training is included?
- 25. What does the plan look like per phase?
Costs & contract
- 26. What is the total cost over 3 years (TCO)?
- 27. Which costs are not in the quote?
- 28. How do licence costs rise with more users or modules?
- 29. Which implementation and migration costs are one-off?
- 30. What do support, updates and maintenance cost per year?
- 31. What is the term, notice period and price indexation?
- 32. Do we take our data with us when we leave (no lock-in)?
Vendor & support
- 33. Does the vendor have references in our sector and size?
- 34. May we speak with an existing customer?
- 35. How financially healthy and stable is the vendor?
- 36. Who becomes our fixed point of contact after purchase?
- 37. What are the support hours, channels and response times?
- 38. Which SLA guarantees do we get on uptime and recovery?
- 39. How often do updates come and are they included?
Future & risk
- 40. What's on the product roadmap for the next 2 years?
- 41. How smoothly are major updates rolled out?
- 42. How dependent do we become on this one vendor?
- 43. How easily can we switch later?
- 44. Does the software fit our AI and automation ambitions?
- 45. What happens if the vendor is acquired or changes course?
- 46. Which exit strategy and data export is guaranteed?
Good to know
They bring structure to your selection. Instead of relying on a slick demo, you test every vendor on the same points, from 3-year costs to adoption and support. So you compare like with like and choose on facts.
For example: 'What is the total price over 3 years, not the monthly price?', 'Are the integrations standard or expensive custom work?' and 'Do we take our data with us if we leave?'. The guide contains 46 such questions across 7 categories.
For anyone in an SME facing a software choice, whether ERP, CRM, WMS or an Agentic AI solution. Whether you're a director, operations manager or project lead: these questions keep you in control.
As a polished, formatted 6-page PDF. Once you fill in the form, you can download the guide straight away — ready to save, print or share with your team.
A wrong choice quickly costs tens of thousands of euros and months of time. 6 in 10 implementations disappoint, rarely because of the software itself, but because of a choice that didn't fit the business. Good questions upfront prevent that.
We match you, free and independently, with the software and vendors that fit your organisation. You use this guide yourself in your selection; alongside that we put together a well-founded shortlist for you.
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