Choosing a managed IT provider is one of the highest-leverage technology decisions a small business makes — you're picking who holds the keys to everything, usually for years. Yet most businesses choose on a referral and a sales meeting, and find out what they bought later.
I don't sell managed services — when clients need one, I help them run the selection. These are the ten questions that do the most work in those evaluations. Ask them all, in writing where it matters, and pay as much attention to how they're answered as to the answers.
1. What exactly is included — and what's billable on top?
Get the specific list. Onboarding? Projects? After-hours? New-employee setup? Security tooling? The gap between "unlimited support" in the pitch and the exclusions in the agreement is where surprise invoices live. You want the boundary written down before you sign, not discovered after.
2. What are your actual response and resolution commitments?
Not "we're really responsive" — numbers, in the contract, by severity. How fast is acknowledgment vs. an actual human working the issue? What happens at 2 a.m.? What's the remedy if they miss the target? A provider who won't commit to numbers is telling you something.
3. Who, specifically, will work on our account?
You're often sold by the A-team and serviced by whoever's available. Ask about team structure, whether you get consistent technicians who learn your environment, and staff turnover. Ask to meet the person who'd actually own your account — not just the sales engineer.
4. Who owns our documentation, credentials, and licenses?
The answer must be you. Admin passwords, domain registrar access, Microsoft 365 tenant, network documentation — all of it should be yours, documented, and accessible to you on request. If any of it lives only in their systems under their name, you don't have a provider, you have a landlord.
5. How would we leave?
Ask it plainly and watch the reaction. A confident provider has a clean offboarding process: documentation handover, credential transfer, cooperation with the successor, defined timelines. Contract length, termination notice, and early-exit fees tell you whether they retain clients with service or with lock-in.
6. Do you make money on the products you recommend?
Resale margin, vendor rebates, commissions — most MSPs earn some or all of these, and it shapes their recommendations (here's how to spot it). It doesn't disqualify them as an operator. But a provider who answers this question plainly is one you can work with; one who dances around it will dance around other things too.
7. How do you secure your own company?
Your MSP is your single biggest cyber risk: their access is the master key, and attackers know it. Ask about MFA on their tools, how they store client credentials, background checks, their own security certifications or audits, and whether they've had an incident. A provider who secures clients but can't describe their own controls hasn't thought hard enough.
8. What will we see every month?
Reporting separates managed from merely monitored. You should regularly see: tickets and response performance, patch and backup status (including test restores), security posture, and upcoming recommendations with honest reasoning. If the answer is "you'll get an invoice," keep looking.
9. Can we talk to two clients our size who've been with you 3+ years — and one who left?
References they hand-pick still tell you something, but tenure and size-match matter most: a provider great at 10-person shops may drown at 60. The "one who left" ask is a stretch — but how they respond to it is informative.
10. What does the price look like in year three?
Get the escalation terms in writing: what triggers increases, caps, and what happens to per-seat pricing as you grow or shrink. A low year-one price with uncapped escalators isn't a low price — it's an introductory rate. Run the numbers at your expected size (the decision checklist applies here in full).
The short version
Make the scope, the numbers, the people, the exit, and the year-three price explicit before you sign — and make sure everything about your environment stays yours. If you'd like independent help running a selection like this — building the shortlist, sitting in the meetings, reading the agreements — that's a fixed-fee project I do regularly, with no stake in who wins. Book a call and tell me where you are in the process.