Most accounting firms don't shop for IT support until something has already gone wrong — a server that died during a filing deadline, a staff member locked out of the client portal on the last day of tax season, or a cyber insurance renewal that suddenly asks technical questions nobody can answer. By then you're buying in a hurry, and hurried purchases are where firms get locked into the wrong contract for three years.

I run an IT firm in Barrie that works with accounting and other professional offices, and I'd rather you sign slowly. Here are the questions that separate an IT provider who actually fits an accounting practice from one who just has "accountant" on their website.

"What is your guaranteed response time — and what does 'response' mean?"

Every provider will tell you they're fast. Ask them to define it in writing.

The word to watch is response. Some contracts define it as "a human acknowledged your ticket." That can mean you got an email saying "we're looking into it" four hours later while your books software stays down. What you actually want defined is time to a working resolution or a concrete next step, and it should be shorter during your busy season, not longer.

Also ask what happens after hours. If your server dies at 6 p.m. on April 30, is that an emergency line with a real person, or a voicemail box that gets checked "first thing in the morning"? Your deadlines don't respect business hours, and your IT contract shouldn't pretend they do.

"How do you handle change freezes during tax season?"

A competent provider knows that January through April is not the time to migrate your practice management software, upgrade the server, or roll out a new line-of-business application. Ask directly:

Will you postpone non-urgent projects until after filing season?
Will you disable automatic major updates on our systems during that window?
Who approves any change at all between, say, March 1 and April 30?

If the salesperson looks confused by the question, that tells you they don't work with accounting firms in any real volume.

"Who holds the admin passwords — us or you?"

This one is uncomfortable, and it matters more than almost anything else on this list.

If your IT provider holds every administrator password, controls your Microsoft 365 tenant, and is the only person who knows how the server is configured, you don't have a partner — you have a dependency. It's not that most providers are bad actors; it's that firms change circumstances, providers get bought or busy, and one day you need to leave and discover you can't.

You should be able to get, on request and without drama:

Your own Microsoft 365 tenant as a tenant you own, with your firm as the owner and the provider as a delegated admin
Documentation of your network, server, and cloud configuration
A documented exit process

Some firms are now required to show exactly this for cyber insurance applications. "We can't access our own admin centre" is a bad answer to give an insurer.

"Is our Microsoft 365 data backed up — by whom, and can you prove restores?"

This is the single most common gap I find in professional offices. Many firms believe that because their email and files are in Microsoft 365, they're protected. Microsoft's shared-responsibility model says otherwise: they protect the *service*, not your firm against accidental deletion, an ex-employee's mailbox being purged, or ransomware encrypting your SharePoint libraries through a synced device.

Third-party backup for Microsoft 365 is inexpensive and settles this permanently. When you ask a prospective provider about it, don't accept "yes we do backups" — ask to see a restore test report. A backup that has never been test-restored is a hope, not a control.

"Can you help us answer our cyber insurance and PIPEDA questions?"

Insurance brokers and privacy obligations have quietly changed what "IT support" means for a Canadian professional office. Your policy application now asks about MFA, endpoint encryption, backup testing, and incident response. If you handle personal information of clients — and every accounting firm does — you also carry obligations around safeguarding and breach reporting under PIPEDA or provincial equivalents.

You don't need your IT provider to be a lawyer. But you do need someone who can produce, in plain English: whether MFA is enforced everywhere it should be, whether laptops are encrypted, when backups were last restored, and who to call in the first hour of an incident. Ask a prospective provider to show you what that evidence package looks like. Firms that can't show it will improvise at your expense later.

"What does your pricing actually include?"

IT support pricing has more hiding places than almost any professional service. Ask every candidate the same list:

Is support per user or per device, and what's the monthly number?
Are projects extra? (A new workstation, a software migration, a server replacement.)
What happens when something breaks *outside* business hours — is there a surcharge?
Are licences (Microsoft 365, antivirus, backup) marked up, and by how much?
Is there a contract term, and what's the exit notice?

The per-user monthly fee tells you little on its own. Two firms at the same headline price can differ by thousands a year once project rates and licence markups are added. You're looking for a provider who can state all of this on one page without hedging.

"Will someone actually drive to our office?"

Remote support handles most day-to-day issues, and a good provider should resolve the majority of things without a site visit. But accounting firms have physical reality: a switch that dies, workstations to deploy for a new hire class in January, a server that needs hands. Ask how onsite work is handled, by whom, and how quickly — and be skeptical of any firm that can't name a real person within driving distance of your office. Plenty of "IT support" operations selling into Barrie and Newmarket are call centres in another time zone with a local phone number.

A short checklist to take into the meeting

Guaranteed response and resolution times, in writing, with an after-hours path
Tax-season change freeze, agreed before January
You own your Microsoft 365 tenant and your documentation
Microsoft 365 third-party backup, with proof of test restores
Evidence package for cyber insurance and PIPEDA questions
Per-user pricing with project rates, licence markups, and exit terms disclosed
A named human who can be onsite in the Simcoe–York area

If a provider answers all seven without squirming, you've likely found a keeper. If you'd like a second opinion on a quote you already have — or a straight answer on any item above — that conversation is free, and it's the kind of thing we do for accounting firms in Barrie, Newmarket, and the surrounding corridor all the time.

IT support for accounting firms in Barrie — the full vertical plan
IT support for accounting firms in Newmarket — same plan, York Region response
Cloud migration services — server and email migration, fixed-fee

IT Support for Accounting Firms: What to Ask Before You Sign