If your only interaction with your IT provider is when it's time to renew a contract… it's time for a change.
Technology doesn't run on autopilot. Threats evolve. Systems age. What worked 6 months ago might leave you vulnerable today. That's why quarterly IT check-ins aren't optional—they're essential.
But what should you be asking? Here are 7 smart, straightforward questions that every business owner should ask their IT provider—every single quarter.
- Are There Any Urgent Vulnerabilities Right Now?
- Are antivirus and firmware fully up to date?
- Any systems unpatched or flagged recently?
- Have there been any close calls or red alerts? You don't want to find out the hard way.
- Are Our Backups Working—And Have You Tested Them?
- When was our last successful restore test?
- Are we backing up the right data, in the right places (local, cloud, hybrid)?
- Is backup data secure and compliant?
- Many businesses think they're protected… until they're not.
- Is Our Team Following Security Best Practices?
- Are there signs of risky login behavior or phishing click-throughs?
- Should we schedule more security awareness training?
- Is multi-factor authentication enforced everywhere it should be?
- Your weakest link is often a well-meaning employee.
- Is Anything Slowing Us Down?
- Recurring performance issues?
- Any aging hardware we've outgrown?
- Opportunities to optimize our systems or workflows?
- Slow systems hurt productivity—and morale.
- Are We Still Compliant With Key Regulations?
- HIPAA, PCI-DSS, GDPR… are we keeping up?
- Have requirements changed?
- Are we documenting and updating policies properly?
- Fines and audits aren't something you want to "wing."
- What Should We Budget For Next Quarter?
- Upcoming license renewals or hardware replacements?
- Projects or migrations we should prep for?
- Any expected changes in IT costs?
- No one likes surprise IT bills.
- What Are We Behind On?
- Any rising threats or industry trends we're ignoring?
- Are we lagging in areas like patch management or AI-based threat detection?
- What are other companies our size doing that we're not?
- Falling behind means falling vulnerable.
If You're Not Asking These—Or Your IT Provider Can't Answer—It's Time To Reevaluate
Your IT partner should meet with you quarterly, offer clear answers, and help you stay ahead—not just react after something breaks.
Not sure where your current provider stands? We offer free Security Assessments to give you a clear picture of where you are and what to fix before it becomes a problem.
Click here to schedule your FREE Introductory Call today!