June 05, 2025
If you're only talking to your IT provider when you
renew your contract, you're doing it wrong.
Technology isn't a "set it and forget it" part of your
business. It's constantly evolving, and so are the threats that come with it.
That's why quarterly IT check-ins are nonnegotiable if you want your business
to stay protected, productive and competitive.
But here's the thing: Most business owners don't
know what to ask.
So today, we're giving you a cheat sheet. These are
the questions your IT provider should be ready to answer every single quarter -
no tech-speak, no vague promises, just straight answers that keep your business
running smoothly.
1. Are There Any Vulnerabilities We
Need To Address Right Now?
This isn't just about checking boxes. You need to
know:
●
Is our antivirus up-to-date?
● Are there unpatched systems?
● Have we had any near misses
or red flags lately?
You're not being paranoid - you're being prepared.
2. What's The Status Of Our Backups?
And Have You Tested Them Lately?
Backups are like seat belts: You don't think about
them until you really, really need them. Ask:
● When was the last time you
tested a full restore?
● Are we using the right backup
strategy? Off-site? Cloud? Hybrid?
● Are we backing up the right
things?
● Is everything being backed up
and stored securely?
You'd be shocked how many businesses think
they're backed up…until they're not.
3. Are All Employees Following Security Best Practices?
It
only takes one team member clicking the wrong link to bring the whole
network down. Ask:
● Have there been any unusual
logins or risky behavior?
● Do we need another round of
phishing training?
● Are employees using
multifactor authentication?
Bonus points if your IT provider brings this up before
you ask. That's how you know they're watching.
4. How Has Our Network Performance Been? Anything
Slowing Us Down?
Slow
systems = slow teams = lost productivity (and money). Ask:
● Are there any recurring
performance issues?
● Are we outgrowing our
hardware or software?
●
Is there anything we can optimise to speed things up?
Even small tweaks can make a big difference.
5. Are We Still Compliant With [Cyber Essentials, ISO27001, GDPR,
etc.]?
Regulations
change. So do the rules about how you store and protect data. Ask:
● Are we meeting the standards
for our industry?
● Have any requirements
changed?
●
Do we need to update policies, software or training?
Fines for noncompliance aren't cheap. Stay ahead of them.
6. What Should We Be Budgeting For
Next Quarter?
Good
IT is proactive. Ask:
● Are there any software
licenses expiring?
● Any equipment nearing the end
of its life?
● Any upcoming projects we
should be planning for?
This
helps you avoid surprise expenses and plan like a pro.
7. What Trends In IT Or Cybersecurity
Are We Behind On That Are Making Us Slower Or More Vulnerable?
Technology doesn't stand still - and neither do
cybercriminals. Ask your IT provider:
●
Are there new tools or best practices we're not using
yet?
● Are we lagging behind in any
security protocols or performance benchmarks?
●
What are other businesses our size doing that we're
not?
● Are there any rising threats
that we need to be more cautious of?
Falling behind on emerging trends doesn't just slow
you down - it leaves you exposed. A great IT partner will keep you ahead of the
curve, not playing catch-up.
You AREN'T Having These Conversations? Red Flag
If your IT provider doesn't have clear answers to
these questions - or worse, if they aren't offering to meet with you quarterly
in the first place - you might not be getting the support you need.
Technology
changes fast. Cyberthreats move faster.
You need someone who's not just reacting when
something breaks but actively working to prevent the break in the first place.
We offer FREE Security Assessments to help business
owners like you get a clear view of their tech setup - what's working, what's
not and how to fix it before it turns into a problem.