Most IT support companies sound alike. Everyone is “responsive”, “proactive” and “trusted”. The difference only shows up when something breaks, and by then you have already signed. These ten questions help you find out what a provider is actually like before you commit.
1. Who will I actually speak to?
Ask whether you will deal with a named person or a ticket queue, and whether the person who answers can fix things or only log them. Continuity matters: a team that knows your setup solves problems faster than one that starts from scratch each time.
2. What exactly is included?
Get the scope in writing, in plain English. Does it cover every device and user, or only some? Is remote support included? What counts as a project rather than support? Vague scope is the most common source of surprise invoices.
3. How is it charged?
Per user, per device, fixed monthly or time-based, all can be reasonable. What matters is that you understand it. Ask about call-out fees, out-of-hours work and anything charged separately, so the monthly figure is the real figure.
4. How do you handle security?
Ask what they do by default: patching, multi-factor authentication, endpoint protection and email filtering. If a provider cannot explain this simply, that tells you something. Be wary of anyone claiming accreditations they cannot show you.
5. What happens to our backups?
Who checks they ran, how often are restores tested, and is your Microsoft 365 data covered? See our guide to Microsoft 365 backup for what to look for.
6. Can you show me how you document our systems?
Good documentation is what lets a provider deliver consistent support, and what lets you leave if you ever need to. You should own your documentation and your administrator access.
7. What happens when it goes wrong?
Ask for an example of a real incident and how they handled it. Listen for ownership: did they take responsibility, communicate clearly and follow up afterwards?
8. Will you tell me when something is not worth buying?
An independent provider is comfortable saying no. If every answer involves a product they happen to resell, ask how they decide what to recommend.
9. Are you local, and does it matter?
Much support is remote and quick, but some things need a person on site: a failed switch, a new office, a conversation about what you really need. If you are in Dorset or Hampshire, ask how quickly someone can actually visit. Our local support pages explain how we cover the area.
10. How easy is it to leave?
A confident provider is happy to explain how a handover works, and does not rely on long lock-in contracts to keep you. Our guide on changing IT providers without disruption shows what a good exit looks like.
If you would like to put these questions to us, we are happy to answer them. You can talk to a real engineer with no hard sell, or see what our managed IT support includes.