25 Questions to Ask CRM Vendors Before You Sign

Cost & Commercial Questions (1–6)

1. What is the all-in year-one cost — licenses, implementation, data migration, integrations, training, and support?
2. What does the three-year TCO look like, including expected license changes, add-ons, and upgrade effort?
3. Which of the features shown in the demo are extra-cost add-ons or higher tiers?
4. What are typical overrun percentages on projects like ours, and what causes them?
5. What happens commercially if we miss the go-live date because of your side?
6. What are the exit terms — data export format, cost, and timeline if we ever leave?

If the answers feel vague, model it yourself with The Real Cost of a CRM: TCO Beyond the License Fee.

Fit & Delivery Questions (7–13)

7. Can you demo our workflow — a rep's Tuesday, a service agent's queue — using our sample data?
8. How many implementations have you done for companies our size in our industry?
9. Who is actually on our project — names, roles, and % allocation — and can we meet them before signing?
10. What does your standard methodology look like week by week, and where do our people need to show up?
11. How do you handle requirements we marked must-have that need customization — effort estimates, not "it's configurable"?
12. What data migration approach do you use, and who is responsible for data quality?
13. Can we speak to two references who went live 18+ months ago — not last quarter's happy customer?

Training & Adoption Questions (14–20)

This is where projects are won or lost — and where proposals are thinnest. Push hard here.

14. What exactly does training include — role-based sessions on our configuration, or links to generic e-learning?
15. Who delivers the training — training specialists or the technical consultants who happen to be on-site?
16. Is training delivered in our environment with realistic data, or in a vanilla demo org?
17. What is the plan for managers and executives — the people whose behavior decides whether reps take the CRM seriously?
18. What happens after go-live — refreshers, new-hire onboarding, release-update training?
19. Which adoption metrics do you track post-go-live, and will you co-own targets contractually?
20. How do you run knowledge transfer so our internal admin can operate independently — and what does "done" look like?

Weak answers here are the single best predictor of the "we bought it but nobody uses it" outcome. For what good looks like, see Is Your Dynamics 365 Partner Helping You Succeed with Training?

Roadmap & Relationship Questions (21–25)

21. How are platform updates handled — who tests, who retrains users, and what does that cost?
22. What is your support model after hypercare ends — response times, channels, and pricing?
23. How do you propose we measure project success at 6 and 12 months, beyond going live on time?
24. What AI capabilities (e.g., Copilot) are included vs. paid, and what data hygiene do they require to be useful?
25. If adoption stalls six months in, what do you do about it — and is any of that included in this contract?

"Question 19 ended two of our three shortlisted partners. Neither could name a single adoption metric from a past project."

– CIO, professional services firm

One Question to Ask Yourself First

If you're replacing an existing CRM: can you prove the platform — not the enablement — is the problem? Most "CRM failures" I'm called into are training and adoption failures wearing a platform costume. Before spending months on vendor evaluations, spend five minutes on the free Training & Adoption Maturity Assessment. It scores your partner quality, knowledge transfer, and user confidence — and tells you whether you're about to solve the wrong problem.