50 Questions to Ask HR Software Vendors Before You Buy

Don't Just Watch the Demo—Grill the Vendor

Sales representatives for HR software are trained to highlight strengths and gloss over weaknesses. They will show you a perfectly configured environment with fake data that looks beautiful. But your company isn't fake, and your data is messy.

To get to the truth, you need to ask specific, sometimes uncomfortable questions. We've compiled the ultimate list of 50 questions, organized by category, to help you cut through the marketing fluff and find a tool that actually works for your business.

💰 Pricing & Contracts (The Hidden Costs)

Avoid "sticker shock" after signing the contract. Vendors love to hide implementation, training, and module fees.

1. What is the Total Cost of Ownership (TCO) for year 1, including implementation, training, and setup fees?
2. Does the monthly price include all modules shown in the demo, or are some considered "add-ons"?
3. Is there a setup or implementation fee? If so, is it one-time or recurring?
4. Is pricing based on "active employees" or "total records" (including terminated employees)?
5. What is the cost for additional administrators?
6. Are there overage charges for file storage or database size?
7. Is support included in the base price, or is "Premium Support" an extra line item?
8. Is there a contract minimum length? (e.g., 1 year, 3 years)
9. What is the cap on annual price increases? (Can you write "max 5% increase" into the contract?)
10. What is the cancellation policy? How much notice is required?

🚀 Implementation & Onboarding (The Timeline)

Sales says "2 weeks." Reality often says "3 months." Get them to commit to specifics.

11. What is the realistic timeline for go-live for a company of our size?
12. Do we get a dedicated implementation manager, or just access to a help center?
13. What level of data migration do you handle? Do you import historical data/documents, or just current snapshots?
14. How much time will my team need to dedicate to implementation each week?
15. Do you offer training sessions for my administrators? What about for managers/employees?
16. What are the most common reasons implementation gets delayed?
17. Can we run a "parallel payroll" (if buying payroll) to test accuracy before switching?
18. Do you provide templates for communicating the launch to our employees?
19. What happens if we miss our go-live date? Are there penalties or extra costs?
20. Can you provide a reference from a client who went live in the last 6 months?

🛠️ Features & Usability (The Real Workflow)

Don't let them drive the demo. Ask to see your specific workflows.

21. Can I see the mobile experience for a regular employee requesting time off? (Ask them to show it live on a phone, not a slide).
22. How customizable are the reports? Can I create my own columns/filters without calling support?
23. Show me how a manager approves a request. Is it via email, Slack, or do they have to log in?
24. Does the system handle [Unique Policy, e.g., "unlimited PTO" or "complex shift differentials"]? Show me.
25. How does the system handle multi-state employees or international contractors?
26. Is the Org Chart auto-generated from employee data?
27. Can we customize the onboarding workflow for different departments (e.g., Sales vs. Engineering)?
28. Is there an "audit trail" that shows who changed a field and when?
29. How does the search function work? Can I search by partial name, nickname, or job title?
30. What new features were released in the last 6 months? (Tests their innovation speed).

🔗 Integrations & Technical (The Connection)

A siloed tool is a useless tool. Verify connectivity.

31. Does this integrate natively with our Payroll provider / ATS / Accounting software?
32. Is the integration real-time (API) or file-based (SFTP/CSV)?
33. Is there an extra cost for enabling API access?
34. Do you support Single Sign-On (SSO) via Okta/Google/Microsoft? Is that extra?
35. What happens if the sync fails? Who gets notified?
36. Can we build our own integrations? Is the API documentation public?
37. Does the system integrate with Slack or Microsoft Teams for notifications?
38. Can we export ALL our data easily if we decide to leave? In what format?
39. How often is the system down for maintenance?
40. Do you have a public status page where we can see historical uptime?

🔒 Security & Support (The Safety Net)

Your employee data is sensitive. Ensure they treat it that way.

41. Are you SOC 2 Type II compliant? Can I see the report?
42. Where is the data hosted physically? (US, EU, etc.)
43. Is data encrypted at rest and in transit?
44. Who owns the data—us or you?
45. What is your disaster recovery plan? How fast can you restore backups?
46. What are your support hours? Are they 24/7 or just 9-5 EST?
47. Is support US-based or outsourced?
48. What is your average response time for a critical ticket?
49. Do we get a dedicated Customer Success Manager (CSM) post-launch?
50. If we leave, do you delete our data permanently after a set time?

🚩 Red Flags to Watch For