By BRITECITY Team | 15+ years experience
Published December 20, 2025
Expertise: Managed IT Services, Cybersecurity, Cloud Computing
Don't sign a contract without asking these critical questions. Expert guide to evaluating managed IT service providers and avoiding common pitfalls.
Before hiring an MSP, ask about: contract terms (length, termination clauses), response time guarantees (in writing), what's included vs. extra (especially security), pricing structure (per-user, hidden fees), and references from similar businesses. The answers reveal whether an MSP will be a true partner or an expensive disappointment.
Picking an MSP is a big decision. A good one feels like part of your team. A bad one brings surprise bills, slow support, and security holes.
After 17+ years in IT, we know what works. Here are questions to ask—and answers that show if a provider earns your trust.
Most MSPs lock you into 1-3 year deals. A few offer month-to-month.
Good Answer:
"We offer month-to-month agreements. We believe we should earn your business every month."
Red Flag:
"Our minimum is 3 years, and there's an early termination fee equal to the remaining contract value."
Know the exit plan before you sign.
Good Answer:
"You can leave anytime with 30 days notice. We'll help transition you to your new provider smoothly."
Red Flag:
"The contract is binding, but we can discuss service improvements if there are issues."
Your passwords and network docs should stay yours.
Good Answer:
"All documentation is yours. If you leave, we provide a complete handoff package at no extra charge."
Red Flag:
"Our documentation is proprietary. We can provide basic information during transition."
"Fast" means different things to each MSP. Get exact numbers.
Good Answer:
"We guarantee 1-hour emergency response for phone emergencies, in writing. If we miss it, here's what happens..."
Red Flag:
"We respond as quickly as possible. Usually same day for emergencies."
If your team works late or weekends, you need support then too.
Good Answer:
"Our help desk is staffed during business hours, with 24/7 emergency support available by phone."
Red Flag:
"Business hours only. After-hours support is available at $200/hour with 4-hour minimum."
Some problems need hands-on help. Know the process and costs.
Good Answer:
"On-site visits are included in your monthly fee. We come out when needed, no extra charge."
Red Flag:
"On-site visits are billed at $150/hour plus travel time, with a 2-hour minimum."
Hidden costs often hide in security add-ons. Get a full list.
Good Answer:
"Everything: EDR/MDR, email security, DNS filtering, dark web monitoring, security training, and 24/7 threat monitoring. All included."
Red Flag:
"Basic antivirus is included. Advanced security is an add-on package starting at $50/user/month."
Attacks happen. You need a clear response plan ready.
Good Answer:
"We have a documented incident response process. Here's our playbook. We'll contain, investigate, remediate, and provide a full report."
Red Flag:
"We'll handle it. Security incidents are treated as high priority."
HIPAA, SOX, and PCI rules need specific know-how.
Good Answer:
"Yes, we have X clients in your industry. Here are references. We understand [specific requirements] and can help with audits."
Red Flag:
"We can figure it out. Compliance is pretty similar across industries."
Know exactly how billing works.
Good Answer:
"$X per user per month. That covers everything except projects you request. Here's a detailed breakdown."
Red Flag:
"It depends on your environment. We'll need to do a full assessment before we can provide pricing."
This is where surprise bills come from.
Good Answer:
"Projects you specifically request (new server, office move, etc.). Everything else—support, on-site, emergencies—is included."
Red Flag:
"After-hours support, on-site visits, new user setup, security tools, backup recovery, and projects are additional."
A line-by-line quote shows what you really pay for.
Good Answer:
"Absolutely. Here's the breakdown: per-user fee, per-device fee, and exactly what's included in each."
Red Flag:
"We prefer to keep pricing simple with a single monthly number. It covers what you need."
Size and industry match matters.
Good Answer:
"Here are three clients in your industry, similar size. Feel free to call them directly."
Red Flag:
"Our client list is confidential, but we have great reviews online."
How long clients stay tells you a lot.
Good Answer:
"Our average client tenure is 5+ years. Here are some we've worked with for 10+ years."
Red Flag:
"We're growing fast, so most of our clients are relatively new."
Staff changes happen. Know the backup plan.
Good Answer:
"All documentation is centralized. Your backup contact already knows your environment. Transitions are seamless."
Red Flag:
"Your account manager knows everything about your setup. They'll be with you for the long term."
Bring this to MSP meetings. Score each answer from 1 to 5.
Score: 40-50 = Excellent | 30-39 = Good | 20-29 = Concerns | Under 20 = Pass
Here's how we answer these questions:
We welcome tough questions. Ask us anything in a free call.
Book a Free ConsultationThe sales process shows how the MSP will treat you later. Watch for:
If they're hard to work with in sales, expect the same during service. Trust your gut and use this checklist to decide.
Get personalized advice based on your specific situation. No pressure, just honest guidance.