10 Questions to Ask an MSP Before You Sign

Choosing a managed IT provider is one of the most consequential vendor decisions a small business makes. The wrong choice means years of slow response times, surprise bills, and IT that holds your business back instead of moving it forward.

Most contracts run 1-3 years. These ten questions will help you evaluate any MSP — including us — before you commit.

1. Where are your technicians physically located?

This matters more than almost anything else. A national MSP with technicians across five states will have a very different on-site response capability than a local provider whose team is based in your county. Ask specifically: where is the closest technician to my office, and what is a realistic on-site arrival time for a critical issue?

2. What is your actual response time SLA — and what happens if you miss it?

“We respond quickly” is not an SLA. A real SLA specifies: response time by ticket priority, resolution targets for different issue types, and what compensation you receive if those targets are missed. Any MSP worth considering should be able to hand you a document that defines these terms precisely.

3. Who will be my primary contact?

You should have a named account manager — a specific person who knows your environment, attends your quarterly business reviews, and is accountable to your relationship. If the answer is “you’ll call our help desk,” that’s a meaningful differentiator to note.

4. How do you handle after-hours emergencies?

“24/7 support” can mean a live engineer monitoring your systems or it can mean a voicemail box and a callback in the morning. Ask specifically what happens at 2am on a Sunday when your server is down. Get the actual escalation process in writing.

5. Can I see a sample of the monthly reports you provide?

Every managed IT client should receive regular reporting on system health, uptime, tickets resolved, patches applied, and security status. If the MSP can’t show you a sample report, they probably don’t produce meaningful ones.

6. What security tools are included in your base price?

Many MSPs quote a low per-user rate that doesn’t include antivirus, email security, or backup — then sell those as add-ons. Ask exactly what is included and what costs extra. The difference between “managed IT” and “managed IT with real security” can be $30-50 per user per month.

7. What is your backup and disaster recovery strategy?

Ask: how often are backups taken, where are they stored, how quickly could you restore my systems after a ransomware attack, and when did you last test a restoration? Untested backups are not backups. A good MSP does regular recovery drills.

8. Do you have experience in my industry?

Healthcare, legal, and financial services businesses have specific compliance requirements (HIPAA, GLBA, SEC, FINRA). An MSP that primarily serves retail shops may not have the compliance expertise to keep a medical practice audit-ready. Industry experience matters.

9. What is your offboarding process?

This question tells you a lot. An MSP that makes it difficult to leave — by retaining passwords, delaying documentation, or structuring contracts to create switching costs — is not a partner. A good MSP documents your environment thoroughly, gives you full administrative access to all systems, and makes transitions clean.

10. Can you provide three client references in businesses similar to mine?

References are the most valuable signal available. Ask for businesses in your size range and industry, and actually call them. Specifically ask: how do they handle on-site visits, how do they communicate when something goes wrong, and would you sign with them again?

---

The right MSP should welcome all of these questions. Evasiveness, vague answers, or pushback on standard contract terms are red flags worth taking seriously.

If you’re evaluating CyanLink Technologies alongside other providers, we’re happy to answer every question on this list — in writing, upfront. That’s the standard we hold ourselves to.