Article · IT Planning & Strategy
12 questions to ask before hiring a managed IT provider
The questions to ask an MSP before you sign, what good answers sound like, and the red flags that tell you to keep looking.
Most managed IT providers sound the same on a sales call. Everyone is “proactive,” “responsive” and “security-focused.” The way to tell them apart is to ask specific questions and listen for specific answers. Here are the ones worth asking, with what a good answer sounds like.
Support and response
1. When I call for help, who answers? A good answer names a real path: a help desk, the team behind it, and how you reach someone who knows your business. Be wary if every request goes into a ticket queue with no way to talk to a person.
2. How fast do you respond, and how fast do you fix things? Response time and resolution time are different. Ask for both, in writing, by priority level. “We’re usually pretty quick” isn’t an answer.
3. What happens after hours? Find out whether urgent problems are covered at night and on weekends, how you reach someone, and whether it costs extra.
What’s included
4. What exactly does the monthly fee cover, and what costs extra? Ask for a list. Common surprises are new-employee setup, projects, on-site visits, after-hours work, backups and security tools. The cheapest quote often leaves the most out.
5. How do you handle projects, like a move or a new system? Most providers quote projects separately. That’s normal. What matters is that you get a written estimate before the work starts.
6. Who owns our accounts and documentation? The right answer is you. Your Microsoft 365 admin accounts, domain names, passwords and system documentation should belong to your business, and you should be able to get them any time.
Security
7. What do you do to protect us, specifically? Listen for concrete things: multi-factor authentication on every account, email security, endpoint protection with someone watching the alerts, patching, and tested backups. Vague talk about “enterprise-grade security” without specifics is a warning sign.
8. How do you back up our data, and when did you last test a restore? A backup nobody has tested is a hope, not a plan. Ask how often restores are tested and how long getting back up and running would take.
9. Can you help with cyber insurance and client security questionnaires? More businesses are being asked these questions. A good provider can help answer them and close the gaps they turn up.
Fit and planning
10. Will we have regular planning meetings? Day-to-day support keeps things running. Planning keeps you from being surprised. Ask whether you’ll get regular reviews, a roadmap and budget forecasts. That’s the vCTO side of the work, covered in What does a vCTO do?
11. What does a typical client of yours look like? You want a provider that supports businesses your size and understands how you work. A firm built for 500-person companies may not be a good fit for a 15-person office, and the other way around.
12. What happens if we want to leave? Ask about contract length, cancellation terms, and how they hand over your accounts and documentation. A confident provider makes leaving straightforward, because they expect to keep you by doing good work.
Red flags
- They can’t tell you what’s included without a long sales process.
- They want to keep your admin passwords or domain in their name.
- Long contracts with steep cancellation penalties.
- No mention of multi-factor authentication or tested backups.
- You never talk to an actual engineer before signing.
For a sense of what managed IT costs and how quotes compare, read How much does managed IT cost?. Or ask us any of these questions directly. We’re happy to answer every one in writing.