How do I know if my current IT company is doing a good job?

If you’re asking this question, something probably feels off. Trust that instinct.

Many business owners don’t know what good IT looks like because they’ve never experienced it. They assume slow responses, recurring problems, and being kept in the dark is just “how IT is.”

It’s not.

15 Warning Signs Your IT Company is Failing You

Communication Red Flags

1. You can’t get a straight answer When you ask a simple question, do you get jargon, deflection, or “it’s complicated”? Good IT partners explain things clearly.

2. You don’t know who to call Is there a clear point of contact? Or do you feel like you’re starting from scratch every time?

3. Radio silence between problems If you only hear from your IT company when something breaks (or when the invoice arrives), there’s no proactive relationship.

4. They don’t document anything Ask for documentation of your network. If they can’t produce it, they don’t have it. That’s a problem.

Performance Red Flags

5. The same problems keep happening If your email server crashes every few months, that’s not bad luck - that’s bad IT. Root causes should be identified and fixed.

6. Response times are slow (or undefined) What’s their SLA? If they don’t have one, that’s concerning. If they have one and miss it regularly, that’s worse.

Good benchmarks:

Critical issues: 15-30 minutes
Standard issues: 1-4 hours
Low priority: Same or next business day

7. You’re always waiting for updates You shouldn’t have to chase your IT company for status updates. They should proactively communicate.

8. Projects always run over budget and timeline Occasional surprises happen. Constant overruns indicate poor planning or scope creep they’re not managing.

Strategic Red Flags

9. No technology roadmap When’s the last time your IT company sat down to discuss your business goals and how technology supports them? If the answer is “never,” you’re missing out.

10. They’re always reactive, never proactive Good IT finds problems before you do. If you’re always the one discovering issues, monitoring isn’t working.

11. Your technology is outdated Are you running Windows versions that are out of support? Software that hasn’t been updated in years? Old equipment? Your IT company should be flagging this.

12. No security improvements in years Cyber threats evolve constantly. If your security posture hasn’t changed in 2+ years, you’re falling behind.

Business Red Flags

13. Billing surprises Unexpected charges, unclear invoices, or costs that keep creeping up indicate poor communication or intentional vagueness.

14. They hold your data hostage Do they control access to your own systems? Can you get your passwords and documentation if you leave? Some providers make this difficult on purpose.

15. High turnover or no continuity If you’re constantly dealing with new technicians who don’t know your environment, institutional knowledge is being lost.

What Good IT Support Looks Like

If you’ve only experienced mediocre IT, here’s what you should expect from a quality provider:

Responsive Communication

Clear point of contact
Defined response time SLAs (and they hit them)
Proactive updates on issues and projects
Regular check-ins (quarterly at minimum)

Proactive Management

Issues caught before you notice them
Regular maintenance and updates
Capacity planning before you run out of resources
Security improvements keeping pace with threats

Strategic Partnership

Annual technology planning
Budget forecasting for upcoming needs
Recommendations aligned with your business goals
Help evaluating new tools and vendors

Professional Operations

Complete documentation of your environment
Smooth onboarding for new employees
Organized project management
Clear, understandable invoicing

Accountability

They own problems until resolved
Root cause analysis on recurring issues
They admit mistakes and fix them
Transparent about what’s working and what isn’t

Questions to Ask Your Current Provider

If you’re unsure about your IT company, schedule a meeting and ask:

“Can you show me documentation of our network?”
“What’s our current security posture, and what should we improve?”
“What’s your average response time for our tickets?”
“What proactive monitoring do you have in place?”
“What should we budget for technology next year?”
“Can you walk me through what’s included in our agreement vs. extra?”

A good provider will answer these confidently with specifics. A bad one will fumble, deflect, or get defensive.

When to Make a Change

Consider switching providers if:

You identified 5+ warning signs above
They can’t answer basic questions about your environment
The same problems keep recurring
You feel like IT is a constant headache
You don’t trust them

How to Evaluate New Providers

When shopping for a new IT partner:

Get referrals from similar businesses - Not just any references, but businesses your size and industry
Ask about their onboarding process - How will they learn your environment?
Understand their support model - Who answers the phone? Where are they located?
Review the contract carefully - What’s included? What’s extra? What’s the exit clause?
Meet the team - You should know who’s supporting you

The Transition Fear

Many businesses stay with bad IT providers because switching seems scary. What if the new company is worse? What if the transition causes problems?

Valid concerns. Here’s the reality:

A professional transition looks like:

Thorough discovery and documentation
Parallel support period (overlap with old provider)
Gradual transition of services
Clear communication throughout
90-day stabilization with extra attention

A good new provider will:

Never speak poorly of your old provider
Find issues and fix them without judgment
Be patient during the learning curve
Over-communicate during transition

The short-term disruption of switching is almost always worth escaping a bad IT relationship.

Think your IT company might be underperforming? We’re happy to provide a second opinion with a free IT assessment. No sales pitch - just an honest evaluation of where you stand. Request an assessment.