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What to ask an IT company before you sign

Twelve questions to put to any IT provider in Canada, why each one matters, what a weak answer sounds like, and the answer we give to every one of them, including the awkward one about being a new company.

Topic
Computers and networks
Published
August 17, 2026
Length
10 min read
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In short

  • Twelve questions separate a provider who has thought about your business from one with a good brochure. Ask all twelve of everyone you talk to, including us.
  • Listen for numbers, dates and documents. An answer made of adjectives is a no.
  • Our answers to all twelve are printed below, so you can compare them against anybody else's before you spend an hour on a meeting.

Owners buy this badly for an understandable reason: the product is invisible. You cannot look at IT support the way you can look at a van, a lease or a room full of chairs. So the decision usually turns on who seemed nicer on the phone.

These twelve questions turn an invisible product into something you can compare. Print the page, take it to every provider you speak to, and write their answers in the margin.

We have printed our own answers under each one. That makes this a sales document, and it also makes it a document you can hold us to.

1. What does it cost, and where is that written down?

Why it matters. A provider who will only discuss price after a discovery call is a provider whose price depends on what they think you can pay. Published prices are a discipline: the number cannot change between the meeting and the invoice.

A weak answer sounds like "it depends on your environment", with nothing following it.

Ours. The prices are on the pricing page and they are the prices on the invoice. Small Office Support is $1,900 a month for 5 to 15 people. Essential Support is $3,400 a month for 10 to 40. Growth Operations is $8,900 for 30 to 150. A full department is quoted after the free audit, because we will not put a number on something we have not seen. The arithmetic behind those figures, worked out per person, is in what IT support costs, and the short answer is at how much does IT support cost.

2. What is inside the monthly fee, and what gets billed on top?

Why it matters. This is where the cheap quote becomes the expensive year. Every provider has exclusions. The good ones hand them to you before you ask.

A weak answer sounds like "everything is included", with no list.

Ours. Four things sit outside the monthly fee, and they are the same four for every plan. Hardware and software licences, billed at what they cost us with nothing added. Advertising money, which goes straight to Google or Meta. Large one-off projects, quoted at a fixed price before anyone starts. Work from a higher plan than yours, quoted before it starts, with your monthly fee changing only when you say yes.

3. When I call, how fast does a person get back to me, and who is it?

Why it matters. Response time is the product. Everything else is machinery that supports it.

A weak answer sounds like a number of minutes with no explanation of what happens inside them, or a promise of round-the-clock cover from a company with six staff.

Ours. A person calls you back the same business day, usually within an hour. That person is your named account contact, and they know your business, so you tell the story once. We describe that person by role rather than putting a name and a photograph on the website, because the person who answers should be a commitment about the role instead of a marketing face.

4. What happens outside business hours?

Why it matters. "Round the clock monitoring" can mean a person watching, or an automatic alert arriving in a mailbox nobody opens until Monday. Both are sold with the same words.

A weak answer sounds like a slogan with no hours attached to it.

Ours. Your hours are written into your agreement, and they differ by plan. Essential Support covers business days. Growth Operations includes extended coverage hours, set out in the agreement. The full department has coverage agreed with you, including on-site visits. Ask us where the line falls before you sign, and it will be in writing when you do.

5. How long am I tied in, and how do I leave?

Why it matters. A long lock-in is a provider protecting themselves against their own service. The exit clause tells you what they expect you to think of them in a year.

A weak answer sounds like three years with an automatic renewal and a 90-day cancellation window.

Ours. Month to month. Thirty days written notice and the billing stops at the end of that period. Move up or down a plan on the same notice, in either direction. What the rest of the paper should say is set out in what should an IT contract say.

6. Do you take commission from the software and hardware you recommend?

Why it matters. A provider earning a margin on what they sell you has a reason to recommend the thing that pays best. You will never see that reason on an invoice.

A weak answer sounds like a change of subject, or "we have partnerships with the major vendors" offered as an answer to a different question.

Ours. We take no commission from any supplier we recommend. Hardware and licences are billed at what they cost us. Your monthly fee is the only money we make from you, which is what lets us tell you when the cheaper option is the right one.

7. Whose name are our accounts in, and who holds the passwords?

Why it matters. This is the question owners wish they had asked. Accounts registered in a provider's name, or a domain registered under their account, turn a change of supplier into a negotiation.

A weak answer sounds like "we manage all that for you", with no mention of ownership.

Ours. Your accounts stay in your business name, with you as the owner on record and your domain registered to you. Passwords live in a business password vault that you and a second person in your business can reach. You can see everything we hold about your systems, at any time, without asking why.

8. How do you handle our private records?

Why it matters. Most Canadian businesses fall under PIPEDA. Health records in Ontario add PHIPA on top, Quebec adds Law 25, and Alberta has its own act. The duties are yours, and they do not transfer to a supplier.

A weak answer sounds like a list of certification acronyms with no description of what is actually done in your office.

Ours. We handle your data in line with PIPEDA, and with PHIPA where health records are involved. In practice that means access to records is limited to the people whose job needs it, logins are two-step, machines are encrypted, our own access is recorded, and anyone we bring in who touches personal information is covered by an agreement. In the full department we write the security and privacy programme down as a document you own. We claim no certification we have not earned, and you should ask any provider who claims one to show you the certificate and its date.

9. What happens in the first thirty days?

Why it matters. The documentation done at the start decides how fast everything afterwards goes. A provider who wants to skip it is telling you what the next year will be like.

A weak answer sounds like "we will get you onboarded", with no steps and no dates.

Ours. We agree the plan and the start date in writing. We take over your accounts and put them in your name. We put monitoring on every machine. We find your backups and test a restore rather than reading a report about one. We build the list of suppliers, renewal dates and written instructions most businesses turn out to be missing. Then we tell you what we found, including the parts that are fine.

10. What do I get back if we part company?

Why it matters. Documentation that lives only inside a provider's own tools is the most common complaint in this industry, and it is the one that costs the most on the way out.

A weak answer sounds like "we will help with the transition", with nothing written down.

Ours. Thirty days notice ends the agreement. You keep your accounts, because they were always yours. You get your documentation in a form you can hand to the next provider. The full department includes a written hand-over plan from the start, so the work can leave with you. The short answer on this one is what happens to our data if we switch providers.

11. You are a new company. Why should I trust you?

Why it matters. Somebody has to ask it, so we will. Every provider was new once, and the ones who dodge the question hide other things too.

A weak answer sounds like a client count, a star rating or a list of logos you cannot verify.

Ours. We are a new company and we have no long client list to show you. Judge us on the things you can check today instead of on a story about the past. Our prices are published rather than quoted in private. Our terms are month to month, so we have to earn the next month rather than rely on the last signature. The audit is free and ends in a written report you keep, whether or not you hire us. Your accounts stay in your name from day one. Every one of those is verifiable before you spend a dollar, and each one costs us something if we fail you.

12. We already have an IT person. Where does that leave them?

Why it matters. A provider whose only model is replacing your staff member has one answer to every situation.

A weak answer sounds like an immediate pitch to take the whole thing over.

Ours. Your person stays and we sit behind them: the escalations, the decisions about what to buy, the supplier calls, the after-hours cover, and the parts they do not cover. We work out the split on the callback. The trade-offs between employing someone, hiring a company and doing both are laid out in hiring someone for IT, or handing it to a company.

How to use the answers you collect

Count the questions answered with a document. A price list, a sample report, a written coverage schedule, a hand-over plan. Documents are the difference between a company that has done this and a company that intends to.

Watch what happens when you ask the awkward ones. Questions 6, 7, 10 and 11 are uncomfortable for a weak provider. How somebody behaves when uncomfortable is the most useful thing you will learn all week.

Ask the same twelve of everyone, including us, and write the answers down while you remember them. Three providers blur together within a day.

Ask us the twelve yourself

Leave your name and number on the contact page and a person calls you back the same business day, usually within an hour. Bring the list. We would rather answer twelve hard questions than send another brochure.

The free infrastructure audit is the other way in: we walk your systems and hand you a written report in plain English with the gaps in priority order. It costs nothing, there is nothing to sign, and the report is yours whatever you decide. What the day-to-day work covers is on the managed IT page, and what we cover in your city is under locations.


itopsi is a managed IT provider working with Canadian businesses from a Toronto base. Coverage, terms and monthly pricing are published on the site.

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