Vendor demos are designed to impress. To make a sound decision, you need to drive the conversation with pointed questions that surface what marketing materials gloss over. This checklist organizes the questions that matter most, grouped by topic.
Reliability and infrastructure
- What is your historical uptime, and where can I see your status page?
- How is your network redundant? What happens if a data center fails?
- How do you handle calls during an outage on my end?
- What network requirements must I meet for good call quality?
Pricing and contracts
- What is the all-in monthly cost for my exact configuration, including fees and taxes?
- Which features cost extra, and how much?
- What is the contract term, and what does early termination cost?
- Can I keep my phone numbers if I leave?
- How does pricing change as I add users or locations?
Security and compliance
- Is call traffic encrypted? How about stored voicemails and recordings?
- What access controls protect my account and data?
- For healthcare: Will you sign a Business Associate Agreement?
- How do you handle and report security incidents or breaches?
- Where is my data stored, and who can access it?
Support and onboarding
| Question | Why it matters |
|---|---|
| What are your support hours and channels? | Outages do not respect business hours |
| Is onboarding assistance included? | Migration is where projects often stall |
| What is your typical response time? | Slow support during an outage is costly |
| Will I have a dedicated contact? | Continuity matters for complex setups |
Features and integrations
- Which of the features I need are included versus add-ons?
- Do you integrate with my existing software, and how?
- How do you handle 911/E911, and what do I need to configure?
- Can I see analytics and call reporting?
Migration and portability
- How does the transition from my current system work?
- How long does number porting take, and what could go wrong?
- What downtime, if any, should I expect during cutover?
Reading the answers
Pay attention not just to what a vendor says but how they say it. Clear, specific answers signal a mature provider. Evasive or vague responses, especially on uptime, security, or total cost, are red flags. A vendor that will not commit to a written quote or refuses to discuss a BAA when you handle PHI is telling you something important.
Bring the questions to a trial
The best vendors back up their answers in a trial. Use the evaluation period to verify the claims that matter: test support responsiveness, confirm call quality on your network, and validate that promised features work as described. Good questions start the conversation; a real-world trial finishes it.