If you’ve outsourced your IT, you’ve likely done it for one of two reasons—you wanted to get out of the weeds and focus on running your business, or you knew you needed help staying secure and competitive in a digital world. Or both. 

But as time goes on, it’s fair to wonder—are you getting the value you expected? Is the money you’re spending on managed IT services actually working for your business? 

If you’re asking this question, you’re not alone. 

Let’s walk through how to evaluate your current provider honestly and what you should expect from a strong IT partnership. 

A lot of IT companies will send monthly reports filled with metrics. Things like patch completion rates, antivirus status, or uptime percentages. While those numbers matter, they don’t mean much if you don’t know how they’re impacting your business.

Real value looks like this:

Your team isn’t dealing with annoying tech issues every week —or at least, significantly fewer than when you started working together.

You haven’t had a major outage in a while—and if you did, it was handled quickly.

Your staff feels supported, not frustrated.

Your business-critical apps are running smoothly.

Think back to when you first partnered with your IT provider. The goal isn’t zero issues (that’s unrealistic), but you should see a clear reduction in the daily “noise”, meaning fewer help desk tickets, fewer employee complaints, fewer fires to put out. Some businesses will always need regular support, but the problems should feel more manageable and less disruptive than they used to be.

Most MSPs say they’re proactive. But what does that actually mean? 

Being proactive means your IT company is spotting and fixing issues before they affect you. That includes: 

Monitoring systems in real time 

Catching early warning signs of hardware failures 

Closing vulnerabilities before they can be exploited 

Regularly testing backups (and not just assuming they’ll work) 

If your IT support is mostly fixing problems after you report them, you’re in a reactive relationship—one that might be costing you more in downtime than you realize. 

A good managed IT provider should be meeting with you regularly—not just to review tickets, but to talk strategy. 

If you’re not having quarterly (or at least bi-annual) reviews that cover: 

Upcoming projects 

Your business goals 

Tech improvements to support growth 

Security concerns and compliance risks 

…then you’re missing out on one of the biggest values of outsourcing: executive-level guidance. 

Many SMBs don’t have a CIO or CISO in-house. Your IT partner should be filling that gap, helping you plan for the future and not just reacting to the present. 

Let’s be blunt. Security can’t be “assumed.” Just because you have antivirus software and someone updates your computers doesn’t mean your business is protected. 

You should know: 

Is there a written incident response plan? 

Are we using MFA everywhere it matters? 

Are employee accounts being audited regularly? 

Do we run phishing simulations or awareness training? 

Are backups encrypted, tested, and stored offsite? 

Cybersecurity isn’t one product. It’s a system of layered protections—and your provider should be walking you through what you have, what you’re missing, and how they’re closing those gaps. 

Keep in mind: Not every business needs enterprise-level security measures, but every business needs appropriate protection for their industry and size. Your IT partner should help you understand what’s baseline protection versus advanced measures for your specific situation. 

As your business changes, so do your tech needs. But many businesses keep paying for licenses or services they no longer use—because no one is reviewing them. 

Your MSP should be helping you audit tools, consolidate vendors where possible, and make sure you’re not overpaying. 

Here’s a simple question to ask: When was the last time your IT partner helped you reduce costs—not just sell you something new? 

While we’ve covered what good IT support looks like, here are some warning signs that your current relationship isn’t working: 

Communication red flags: 

• You consistently get technical jargon instead of business explanations 

• Support tickets sit for days without updates 

• You have to chase them for monthly reports or check-ins 

• They seem surprised when you ask about your current setup 

Service red flags: 

• The same problems keep recurring without permanent fixes 

• You’re always hearing “that’s not covered under your plan” 

• Emergency response times keep getting longer 

• Your team complains more about IT issues, not fewer 

Strategic red flags: 

• They’ve never asked about your business goals or growth plans 

• All conversations are about fixing problems, never preventing them 

• They can’t explain how their services tie to your business outcomes 

• You feel like you’re managing them instead of them managing your IT 

If several of these sound familiar, it’s not about finding small fixes—it’s about finding a new partner. 

If you ask your current provider any of the following: 

“What exactly are we paying for?” 

“How are you measuring success?” 

“What are you doing each month to reduce risk?” 

“Can I see the last time our backups were tested?” 

“If someone clicked a bad link right now, what happens next?” 

…you should get a clear, confident answer. Not a vague response, not tech-speak, not a deflection. 

Transparency isn’t a luxury. It’s a requirement. You deserve to know how your business is being protected and supported. 

If you’re not sure whether your current IT support is worth it, that’s a signal. 

Because when IT is working well: 

Your business runs smoothly. 

Problems are rare—and when they do happen, they’re handled fast. 

You sleep better at night knowing your data and operations are protected. 

Your team trusts the systems they use every day. 

And you know what you’re paying for. 

Final Thoughts 

Managed IT shouldn’t feel like a mystery. You’re not paying for a black box—you’re paying for outcomes. Uptime. Security. Support. Strategy. Peace of mind. 

If you’re not sure you’re getting those outcomes, it might be time for a conversation. Sometimes that conversation is with your current provider—many issues can be resolved by simply setting clearer expectations and asking for better communication. Other times, it means exploring whether a different partner might be a better fit. 

Either way, you deserve clarity about what you’re paying for and confidence that it’s working for your business. 

No pressure. Just clarity.