Questions to ask before you sign with an IT provider

Questions about scope

Start with what is in and what is out. Ask for a written list of the services included in the monthly fee, and a separate list of the things that are billed extra. Ask specifically about new staff setups, laptop replacements, printer issues, Microsoft 365 changes, mobile phones, home internet problems and support for your industry software. These are the grey areas where misunderstandings tend to start.

Then ask how they define a project. Some providers treat installing a single new computer as routine; others quote it as a project. Neither is wrong, but you need to know which applies. A useful follow-up is to ask for three examples of work they would quote separately and roughly how those quotes are calculated, so you can picture what an ordinary year looks like.

Questions about response and support

Ask how staff request help: email, a portal, chat or a phone line. Ask who answers, whether it is a technician or a call-taker who passes messages on. Ask what the response targets are for urgent, normal and minor issues, and how often those targets are actually met. A provider who reports on their own performance is usually one who takes it seriously.

Ask what happens outside office hours, and whether after-hours work costs extra. Ask how onsite visits work: are they included, how quickly can someone attend, and what areas do they cover? If you have more than one location, check that each site gets the same level of service, not just the one closest to the provider's office.

Questions about security

Ask which security controls come as standard. Look for endpoint protection with monitoring, email filtering, multi-factor sign-in, patching, backup monitoring and some form of security awareness training. Ask who reviews security alerts and how quickly. A tool that raises alerts nobody reads offers little protection, however impressive its name. Ask to see a sample of the monthly security report you would receive.

Ask how the provider protects their own systems, because they hold the keys to yours. Do their technicians use multi-factor sign-in on every tool? Is access to client systems logged? What happens if one of their staff leaves? Supply chain attacks, where criminals break into an IT provider to reach its clients, are a real risk, and a good provider will be comfortable discussing how they guard against them.

Questions about access and ownership

Ask who will own the admin accounts for your Microsoft 365, domain name, firewall and backups. The answer should be your business, with the provider granted access. Ask whether they will give you a copy of all credentials on request, and how quickly. Ask whether your domain name and Microsoft licensing are registered in your company name or theirs.

Ask what documentation they will keep about your systems and whether you can have a copy. Network diagrams, asset lists, licence records and configuration notes belong to the business that paid for them. Getting this agreed at the start is far easier than negotiating it at the end of a relationship that has gone sour.

Questions about the contract

Ask how long the minimum term is, how much notice you must give to leave, and whether the contract renews automatically. Ask how and when prices can increase. Ask what exit assistance they provide and whether it is charged. A provider that is confident in its service rarely needs a long lock-in to keep clients.

Ask how changes in headcount are handled. If you add five staff in a busy season and then drop back, can the monthly fee follow? Ask about any setup or onboarding fee, what it covers and whether it is refundable if the first months go badly. Get every answer in writing as part of the agreement, not just in an email.

Questions about reporting and reviews

Ask what reports you will receive and how often. Monthly summaries of requests, response times, patch status and backup results let you see whether the service is working. Ask whether someone will meet with you regularly to discuss bigger issues, such as ageing hardware, security improvements or upcoming licence changes, and plan the year ahead.

Finally, ask what they would want to know about your business. A provider who asks good questions about how you work, what keeps you awake and where you are heading is more likely to give useful advice than one who only talks about their own tools and certifications. The questions a provider asks you are often the best preview of how they will work once you are a client.