Your IT provider shouldn’t just be a name you call once a year to renew a contract. For small to medium-sized businesses, technology is at the core of everything—productivity, data protection, client communication, and compliance. Yet many business owners treat it as a ‘set it and forget it’ system, assuming everything is running smoothly until something breaks.
The reality? IT needs proactive attention and regular alignment with your business goals. That’s why quarterly check-ins with your provider aren’t just good practice—they’re essential.
But here’s the problem: Most SMBs don’t know what to ask.
So here’s your quarterly IT check-in cheat sheet—seven essential questions your IT provider should be ready and able to answer clearly, honestly, and without tech jargon.
1. Are There Any Vulnerabilities We Need To Address Right Now?
Security threats are evolving daily. Your systems might be up-to-date today, but that could change tomorrow. You should be asking your provider:
- Is our antivirus and endpoint protection current?
- Are there any systems missing critical patches?
- Have you observed any attempted breaches or suspicious behavior recently?
This isn’t being paranoid—it’s being proactive. Waiting until something happens is no longer an option.
2. What’s The Status Of Our Backups? And Have You Tested Them Lately?
Backups are a critical safety net. But just having them isn’t enough. You need to know:
- When was the last time a test restore was done?
- Are we backing up all essential files and systems?
- Are backups stored offsite, in the cloud, or both?
- Are our backups encrypted and protected against ransomware?
A failed backup can turn a small issue into a devastating loss. Don’t wait to find out the hard way.
3. Are All Employees Following Security Best Practices?
Employees are often the weakest link in a cybersecurity chain. Even one misclick can take down an entire network. Ask:
- Have there been any recent incidents of risky user behavior?
- Are staff members trained on phishing and other social engineering tactics?
- Is multifactor authentication (MFA) enabled across all accounts?
Your IT provider should be monitoring for this and bringing recommendations to you—not waiting for you to ask.
4. How Has Our Network Performance Been? Anything Slowing Us Down?
Performance issues cost more than frustration. They impact productivity, customer service, and employee morale. Check:
- Are there recurring slowdowns or outages?
- Are we using outdated hardware or unsupported software?
- Are there bottlenecks or misconfigurations we can fix?
Often, a small investment in upgrades or optimization delivers huge returns in efficiency.
5. Are We Still Compliant With [HIPAA, PCI-DSS, GDPR, etc.]?
If your business handles sensitive data, compliance is non-negotiable. Ask:
- Are we up to date with our industry’s regulatory requirements?
- Have any standards changed that affect how we store or access data?
- Do we have the documentation needed to prove compliance in an audit?
Noncompliance isn’t just risky—it can be expensive and legally damaging.
6. What Should We Be Budgeting For Next Quarter?
Good IT is planned—not panicked. Your provider should help you stay ahead. Ask:
- Are there any upcoming software renewals?
- Is any hardware reaching end-of-life status?
- Are there anticipated projects that require IT support?
Planning helps you avoid emergency spending and makes budgeting predictable and efficient.
7. What Trends In IT Or Cybersecurity Are We Behind On?
Staying current with tech isn’t about chasing trends—it’s about staying secure and competitive. Ask:
- Are there new security tools or protocols we should adopt?
- Are we falling behind in terms of performance compared to similar businesses?
- Are there upcoming threats or shifts in the IT landscape that we should prepare for?
Being proactive helps you move with confidence, not catch up after the fact.
If You Aren’t Having These Conversations, That’s a Red Flag
If your IT provider can’t answer these questions—or isn’t initiating these conversations—you may not be getting the level of support your business deserves.
The best IT partnerships are based on prevention, performance, and planning.
Need help evaluating your current IT setup or want to get a second opinion? We offer FREE Security Assessments for SMBs just like yours. We'll help you pinpoint risks, optimize performance, and ensure your systems are ready for what’s next.
