Guide
Questions to ask before choosing an IT support company
The questions worth asking an IT support company are the ones with a specific, checkable answer: what your on-site visits cost, when a restore was last tested, who answers the phone at 9am, and what happens to your documentation if you leave. Vague questions get rehearsed answers. This guide gives you twenty specific ones and, more usefully, what a good answer sounds like.
By James 12 min read
How to use this list
You do not need all twenty. Pick the eight most relevant to your business and ask them in writing, because a written answer is a commitment and a verbal one is a memory. Every provider you are considering should get the same list, which also makes the answers comparable.
What you are listening for is specificity. "We pride ourselves on rapid response" is not an answer. "Priority 1 is one hour, here is what counts as Priority 1, here is last quarter’s average" is. The gap between those two sentences is the whole assessment.
About cost
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What does a visit to our office cost, including travel?
What a good answer sounds like: You want a number and a coverage area, not "it depends". If visits are included, ask where the boundary is and what happens outside it. This is the single biggest hidden variable between two quotes.
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What is not covered by the monthly fee?
What a good answer sounds like: A good provider has this list ready because they are asked constantly. Expect project work, hardware, licensing and out-of-hours. Be wary if the answer is "nothing, it is all included", that is not a real offer.
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Is Microsoft 365 licensing included in that figure?
What a good answer sounds like: Usually it is not, and at £10 to £20 per user per month it materially changes the comparison. Ask, and normalise both quotes before comparing them.
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How does the price change when we add or lose staff?
What a good answer sounds like: Look for monthly trueing-up in both directions. Some contracts let you add users mid-term but not remove them until renewal, which is expensive if your headcount moves seasonally.
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When and by how much can the price change?
What a good answer sounds like: An annual review clause with no cap means the price can move by any amount. A cap or an index link is reasonable to request.
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About the service
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Who actually answers the phone at 9am on a Monday?
What a good answer sounds like: Ask whether it is an engineer or a triage layer, and whether it is the same people each time. For a small business the answer matters more than the ticketing system they use.
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What is your response commitment for a fault that stops us trading?
What a good answer sounds like: Look for a defined severity level described in business terms rather than technical ones, plus an actual figure. Then ask what last quarter’s performance against it was.
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How many clients does each engineer look after?
What a good answer sounds like: Rarely asked and highly revealing. There is no perfect number, but a provider who has never thought about it is telling you something.
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What happens if our issue needs a third-party vendor?
What a good answer sounds like: You want them to own the case rather than hand you a phone number. "We will raise it and manage it through to resolution" is the right answer.
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Do you support home workers on the same terms?
What a good answer sounds like: Increasingly important and often quietly excluded or capped. Ask specifically.
About safety
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When did you last perform a test restore for a client of our size?
What a good answer sounds like: The best question on this list. A provider who tests restores will answer immediately with a rough date and a story. One who does not will talk about backup success rates, which is not the same thing at all.
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What exactly is backed up, how often, where is it held and for how long?
What a good answer sounds like: Four separate answers. Vagueness on retention is common and matters: some sectors need years, and most default arrangements do not provide them.
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Is multi-factor authentication included or chargeable?
What a good answer sounds like: It should be included and it should be assumed. A provider treating MFA as an upsell in 2026 has the wrong baseline.
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What is your own security posture?
What a good answer sounds like: They will hold administrative access to your entire estate. Ask what protects that access, and whether they hold Cyber Essentials themselves.
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Have you had a security incident affecting a client, and what happened?
What a good answer sounds like: An honest yes with a clear account is more reassuring than a no. Supply chain compromise of IT providers is a known attack pattern and the mature answer acknowledges it.
About the relationship
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Can we see the documentation you would produce for us?
What a good answer sounds like: Ask for a redacted sample from another client. A provider who documents properly is pleased to show you. One who does not will explain why documentation is unnecessary.
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What does the first 30 days look like?
What a good answer sounds like: You want an audit, documentation, and a written list of what they found, including the uncomfortable parts. If onboarding is just installing an agent, the relationship starts blind.
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What is the notice period, and what do we get back if we leave?
What a good answer sounds like: Thirty days, and everything: documentation, credentials, a restorable backup. No exit fee. Read this clause before the rest of the contract.
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Can you give us two references from businesses our size in our sector?
What a good answer sounds like: And then actually call them. Ask the reference what has gone wrong and how it was handled, which is far more informative than asking whether they are happy.
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What would you change in our setup in the first three months?
What a good answer sounds like: Asked at the end of a walkthrough, this separates providers who looked from providers who pitched. A good answer is specific, prioritised, and includes at least one thing that does not make them any money.
Our answers to the awkward ones
On-site visits are included within about 15 miles of Mansfield on the Support and Complete plans, with visits scheduled and travel quoted before we set off beyond that. Restores are tested on a schedule and we will tell you the date of the last one for a client of your size. The notice period is 30 days, there is no exit fee, and your documentation and credentials come with you.
Three answers that should end the conversation
"We would need to do a full audit before we can indicate any pricing." An audit before a detailed proposal is entirely reasonable. Refusing to give any indication of a per-user range for a business of your size is a negotiating position, not a technical limitation.
"Our clients do not really need backups tested, the system reports success." Backup software reporting success and a backup restoring are different claims. A provider who conflates them has not been through a real recovery, or has and did not learn from it.
"You would need to sign a three-year term to get that rate." Length of term is a commercial preference, and there are legitimate reasons for it on large deals. On a ten-user support contract it exists to make leaving expensive. Ask what the twelve-month or rolling price is; if there is not one, you have your answer.
One question to ask yourself
Before any of the above: what is actually going wrong at the moment, and what would have to be true in six months for this to have been worth doing?
Businesses that answer that clearly get better proposals, because they can steer the conversation instead of receiving a standard pitch. Businesses that cannot answer it tend to buy on price, which is how most bad IT relationships start.
Questions worth asking about your own business first
Providers give better proposals to buyers who can describe their own situation, and most small businesses cannot, because nobody has ever asked them to. Twenty minutes of preparation changes the quality of every conversation that follows.
Write down your user count, your machine count, and whether you have servers. Write down what happened the last three times something went badly wrong, and how long it took to resolve. Write down which single system, if it stopped for a day, would stop you trading. That last one is the most useful sentence in any IT conversation and it is the one most rarely said out loud.
Then write down what you actually want to be different in six months. "Fewer problems" is not an answer a provider can quote against. "Nobody waits more than an hour, and I stop being the person who fixes the printer" is.
How to run the comparison without wasting three weeks
Speak to three providers, not seven. Beyond three the proposals blur, the process drags, and the decision gets made on whoever chased hardest rather than whoever fits best.
Give all three the same written brief, including your user count, server count, sites and the eight questions from this guide you care most about. Identical inputs are the only way to get comparable outputs, and a provider who cannot answer a written brief in writing is telling you something about how they will handle a ticket.
Ask each of them to walk your premises, or at least to see the estate remotely. A provider who quotes without looking is quoting a template, and the number will move once they arrive.
Finally, weight the decision toward the things that are hard to change later. Price is negotiable and reviewable. Whether the provider will actually put an engineer in your building, and whether the same person will know your setup in a year, are structural. Those are worth paying a little more for and they are what most buyers under-weight.
Frequently asked questions
If the answer is not here, ask us. You will get a straight one, from someone who does the work.
Mon–Fri, 9am–5:30pm
What are the most important questions to ask an IT support company?
What a visit to your office costs including travel, what is not covered by the monthly fee, when they last performed a test restore for a client your size, who answers the phone at 9am, and what you get back if you leave. Those five separate most providers quickly.
Should we ask for references?
Yes, from businesses of similar size in a similar sector, and then call them. Ask the reference what has gone wrong and how it was handled rather than whether they are happy; the second question has only one answer.
How do I compare two IT support quotes fairly?
Normalise both to an annual total for your actual business: twelve months of per-user fees, plus server fees, plus last year’s on-site visit count at their rate including travel, plus licensing and backup if charged separately. The per-user headline on its own is not comparable.
Is it reasonable for a provider to refuse to quote before an audit?
Refusing a detailed proposal is reasonable. Refusing to indicate a per-user range for a business of your size is a negotiating position rather than a technical limitation, and it is worth naming as such.
Should our IT provider hold Cyber Essentials?
It is a fair thing to ask, since they will hold administrative access to your whole estate. More important is what protects that access day to day: how their own admin accounts are secured, and whether they can describe it without hesitating.
What should the first month with a new provider look like?
An audit, full documentation, and a written list of what they found including the parts you will not enjoy reading. If onboarding consists of installing a monitoring agent, the relationship is starting blind and the first surprise will be yours.
How many IT providers should we ask?
Three. Beyond that the proposals blur, the process drags on, and the decision tends to get made on whoever chased hardest rather than whoever fits best. Give all three the same written brief so the answers are genuinely comparable.
Should we let a provider audit us before deciding?
Yes, and how they behave during it is the most useful data you will get. A provider who walks the site, asks about your busiest period and tells you something uncomfortable is showing you how the relationship would work. One who arrives with a proposal already written is showing you that too.
Should we prepare anything before speaking to providers?
Twenty minutes of it changes every conversation that follows. Write down your user count, your machine count, whether you have servers, what happened the last three times something went badly wrong, and which single system stopping for a day would stop you trading. That last sentence is the most useful one in any IT conversation and the one most rarely said out loud.