Learn 7 signs your IT relationship may be failing, how to evaluate your MSP, and ways to improve support with co-managed IT, cybersecurity services, and cybersecurity testing.
Working with a managed service provider (MSP) should be a relationship. Like any relationship there are red flags to watch for when it comes to your business needs. As your business and technology evolve, your IT provider should grow with you, not hold you back or struggle to keep up. The challenge is that the signs aren’t always obvious with Managed IT.
Here are seven signs your IT relationship may be breaking down and what to watch for before it impacts your business.
1. You Feel Like You're Managing the Relationship
What this looks like:
- You’re constantly following up on tickets
- You’re coordinating vendors or internal fixes
- You’re asking them what should be done next
A good IT partner should reduce your workload, not add to it. When issues come up, their job is to resolve them quickly and support your employees, not slow them down.
Most MSPs work with multiple clients so not every issue can be fixed instantly, but if you constantly have to follow up on tickets and act as the “go-between,” something is off. They should know what to work on, where to go, and should be managing this process, not you. Which leads to our next sign:
2. Communication is Inconsistent
What this looks like:
- You only hear from them when something breaks
- No regular check-ins or planning calls
- Updates are unclear or overly technical
Strong IT relationships rely on clear, ongoing communication. They don’t just reach out when something goes wrong, they provide updates and make sure your business is secure and running smoothly.
Without communication, issues go unnoticed until they become problems.
Like any relationship, communication is one of the most important aspects. If you don’t know your MSP team or feel comfortable reaching out with questions, that’s a red flag. This doesn’t mean knowing them inside and out rather feeling comfortable to ask questions. Your MSP should also be providing clear answers as to why things may have gone wrong. It should feel like a partnership, not a one-sided relationship.
3. Billing Feels Unclear or Changes Frequently
What this looks like:
- Monthly invoices vary without explanation
- You’re not sure what services are included
- Unexpected charges appear
A healthy IT relationship should have clean billing. You should always understand where your charges are coming from and what services you’re paying for. While not every invoice will look the same because of unexpected issues or hardware replacements there should still be a clear explanation behind any changes.
Without that visibility, it becomes difficult to know whether you’re getting value, and in some cases, businesses can end up overpaying without realizing it.
4. Reactivity Instead of Proactivity
What this looks like:
- Frequent downtime
- Recurring issues
- No improvement over time
Reactive IT is fixing problems after they happen. Proactive IT is preventing issues before they occur. Businesses today need ongoing optimization and proactive support to reduce the risk of issues before they happen. While it’s unrealistic to prevent every problem, recurring issues should be addressed so they don’t continue happening.
If the same problems keep coming up or your MSP isn’t taking steps to prevent them it’s a sign they’re not operating effectively. This not only leads to repeated disruptions but can also slow down your business over time.
5. There’s No Clear IT Strategy or Roadmap
What this looks like:
- No long-term technology plan
- No budgeting guidance for IT investments
- No discussion of future risks or growth needs
If your MSP is only focusing on IT and isn’t helping you plan for the future, it may be a sign of a lack of organization or long-term focus. This is where a vCIO (virtual Chief Information Officer) can play an important role. A vCIO helps with strategic planning by guiding decisions around technology, budgeting, and long-term goals.
Having a clear IT roadmap allows your business to align budget, growth, and security so your technology evolves alongside your needs. Your MSP doesn’t need to have every detail figured out from day one, but there should be a defined plan early in the relationship to provide direction, insight, and long-term value.
6. You Don’t Know How Secure Your Business Actually Is
What this looks like:
- You assume security is handled
- No reports or clear explanations of protections
- No testing or validation of your defenses
Security without testing is just blind trust. While security findings can sometimes be complex, you should still have visibility into what’s being identified and addressed. If you never hear about risks, vulnerabilities, or improvements, that’s a red flag.
One way to gain that visibility is through a vulnerability scan, which is a tool that checks your systems for known security weaknesses. If a scan reveals multiple vulnerabilities, it may indicate that your MSP isn’t effectively managing your cybersecurity and it also gives you a starting point to create a plan for fixing those issues.
7. Your IT Provider Struggles to Keep Up as You Grow
What this looks like:
- Slower response times over time
- Gaps in service coverage
- Your needs are evolving but their capabilities aren’t
Many small managed service providers (MSPs) work well early on, but as your business grows, they can become stretched too thin. They may take on more clients than they can fully support, or simply lack the resources needed to keep up with increasing demands.
This can lead to gaps in service, where day-to-day support is handled, but long-term strategy and growth take a back seat. It’s not always an easy conversation to have, but it’s important to put your business first and ensure your IT provider is prepared to scale with you.
How to Test if any of These Signs have Happened
Security testing is an important way to not only reduce the risk of cyber attacks, but also to verify that your MSP is effectively protecting your business.
A vulnerability scan is a quick, cost-effective way to identify known security weaknesses in your systems. It gives you a clear picture of where potential risks exist.
A penetration test (often called a “pen test”) goes a step further. It simulates a real-world cyber attack to show how a hacker could potentially access your environment and what could be compromised.
Both of these approaches provide valuable insight not only helping strengthen your defenses, but also giving you greater confidence that your IT provider is actively safeguarding your business.
How to Strengthen Your IT Support Without Starting Over
Just because one or several of these signs apply to your situation doesn’t necessarily mean you need to switch providers right away.
There are ways to strengthen your current setup without completely replacing your MSP. For example, adding specialized cybersecurity services like cybersecurity-as-a-service or penetration testing as a service, can bring in experts who focus specifically on protecting your environment. These services work alongside your MSP to strengthen your security without disrupting your existing relationship.
Another option to consider is co-managed IT support. This approach allows you to bring in additional expertise to support your internal team or fill in gaps your current provider may have. It can also be a useful way to evaluate how a new MSP would work within your organization before making a full transition.
What to Do if Your IT Relationship Isn’t Working
If you’re unsure where things stand, take a step back and evaluate your current IT provider. Ask questions, review what services are actually being delivered, and make sure they’re meeting expectations. The goal is simple: ensure your IT support aligns with your business and delivers the value you were promised. If it does not align with what was discussed start looking at other providers or a co-managed framework.
Whether you’re exploring a new MSP or just need extra support through a co-managed approach, the team at Usherwood is here to help you find the right fit. Fill out our evaluation form to get started and take the first step toward a more efficient IT department.
