10 Questions to Ask Before You Hire an IT Company
A good IT provider should be able to answer every one of these clearly, without hedging - including us. For each question, here's why it matters, what a good answer sounds like, what should concern you, and a useful follow-up if you want to dig deeper.
Do you monitor my systems 24/7, or only respond after something breaks?
Why it matters: There's a real difference between "we'll fix it" and "we caught it before it became a problem."
A good answer sounds like: "We have automated monitoring running continuously, and we can show you exactly what got flagged this week and what we did about it."
What should concern you: Vague reassurance with no specifics - "oh yeah, we keep an eye on things" - and nothing to back it up.
Useful follow-up: "Can you show me your monitoring dashboard right now?"
What's your actual response time for a critical outage - in writing?
Why it matters: "Usually pretty fast" isn't an answer.
A good answer sounds like: A specific number tied to a written agreement - e.g., "critical issues get a response within one hour, guaranteed in our service agreement."
What should concern you: No willingness to put a number in writing, or the number only exists verbally.
Useful follow-up: "What happens if you miss that response time - is there any accountability built in?"
Do you test my backups, or just run them?
Why it matters: A backup that's never been restored is a guess, not a safety net.
A good answer sounds like: "We do test restores on a regular schedule and can show you the results of the last one."
What should concern you: "The backup job runs every night" with no mention of ever actually restoring from it.
Useful follow-up: "When was the last time you actually restored a full backup, and can I see the results?"
What happens if my main contact is out sick or on vacation?
Why it matters: You need a team that knows your setup, not one person who's irreplaceable.
A good answer sounds like: "You have a whole team with access to your documentation and setup, not just one person."
What should concern you: A single freelancer with no backup plan, or an honest "things would probably wait until they're back."
Useful follow-up: "Who specifically would handle an emergency if my main contact were unreachable?"
Can you show me what you're actually monitoring on my network right now?
Why it matters: If they can't show you, it's worth asking why.
A good answer sounds like: They pull up a real dashboard or report on the spot.
What should concern you: They can't produce anything concrete, or get defensive about the question.
Useful follow-up: "Can I get a copy of this report on a regular basis, not just when I ask?"
Do you have real experience with my industry's specific software and compliance needs?
Why it matters: Generic IT support and industry-specific IT support are not the same thing.
A good answer sounds like: Specific examples of similar clients and the exact software or compliance frameworks they've worked with.
What should concern you: A generic "we work with all kinds of businesses" with no specifics.
Useful follow-up: "Can I talk to a current client in my industry?"
What's included in my monthly fee, and what turns into a surprise invoice?
Why it matters: Get this in writing before you sign anything.
A good answer sounds like: A clear, written breakdown of what's covered and what isn't.
What should concern you: Reluctance to put pricing or scope in writing, or "it depends" with no elaboration.
Useful follow-up: "Can you send me a sample invoice from a client with a setup similar to mine?"
Who actually owns my data, licenses, and passwords if we ever part ways?
Why it matters: You should always have full access to your own accounts.
A good answer sounds like: "You do, always - we can hand over full access the same day if you ever leave."
What should concern you: Hesitation, or licenses/domains registered under the provider's own account instead of yours.
Useful follow-up: "Can you show me where my domain and licenses are currently registered?"
Can I talk to a current client who's been with you two-plus years?
Why it matters: Long client relationships say more than any sales pitch.
A good answer sounds like: They offer a name or number without hesitation.
What should concern you: Excuses about confidentiality for a simple reference call, or only offering brand-new clients.
Useful follow-up: "Do you have anyone in my specific industry I could talk to?"
What's your process when you genuinely don't know the answer to something?
Why it matters: Everyone hits this eventually - what matters is what happens next.
A good answer sounds like: "We escalate internally or bring in a specialist - we won't guess with your systems."
What should concern you: Defensiveness, or a claim that this never happens.
Useful follow-up: "Can you give me an example of a time this happened and how you handled it?"
Want a personalized answer instead?
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