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Your team assures you everything’s under control, but you’re not so sure.

Can you really trust that the right checks are in place? Is your investment in software and systems delivering real value, or just eating into your budget? How long would it take to recover if a breach happened tomorrow?

You don’t have the time to sort through it all. Between meetings, firefighting, and driving the business forward, digging into the weeds of your IT operations falls to the back burner. But ignoring it isn’t an option.

This is the reality for many executives. And while your IT team may be doing a decent job, do you really know what's going on behind the scenes? The risks you don’t see could cost you big—both in dollars and reputation.

So, let’s get real. Here are the top five things you need to know about your in-house IT team.

5 Signs Your IT is Failing (That Every Exec Should Know)

1. Spending without real value

Be honest—when’s the last time you did a deep dive into what your IT budget is actually being spent on?

Not just the dollar amounts, but where that money is going. Are you getting real value? Or are you paying for software, services, and tools that aren’t pulling their weight? This is what we call software bloat—those shiny tools you’re paying for but never use.

One organization we worked with was shelling out $900 a month for a network switch. $900. For one switch. They had no idea it wasn’t supposed to cost that much. That’s not just a small mistake—that’s budget bleed, plain and simple.

What’s even worse? It’s not an isolated incident.

If you haven’t sat down with your IT team to go over what you’re paying for, versus what you’re getting, you’re probably leaving money on the table.

If they can’t give you clear, confident answers to the questions below, it’s time to take a closer look.

What to Ask Your IT Team →

  • "Are we fully utilizing the software we’re paying for?"
  • "Are there cheaper, better alternatives?"
  • "Can you guarantee the value we're getting from each tool or service?"
5 Signs Your IT is Failing (That Every Exec Should Know)

2. Redundancy (or lack thereof)

Here’s a question that’ll keep you up at night: What happens if your top IT person decides to take a two-week vacation? Worse—what if they quit?

Do you have someone who can step in? Or will your entire system fall apart the minute they’re gone?

This is where redundancy comes in. No, not the boring kind of redundancy. We’re talking about ensuring no single person holds all the knowledge. Because if one person is the only one who knows how to fix the network, you’ve got a problem.

It’s common, especially in smaller companies, to rely on a “one-man IT show.” But that’s a single point of failure. It’s a ticking time bomb that could cost you big if things go wrong. And we’ve seen them go as wrong as they can. An organization reached out to us after their IT team died in a tragic accident. Not only were they mourning the loss of two people, but they now had no one to manage their IT and keep their business operational.

If the answers aren’t crystal clear to the following questions, you might need to rethink your approach to IT staffing.

What to Ask Your IT Team →

  • "Who else knows how to manage our critical systems?"
  • "Do we have backups in place for key roles?"
  • "What’s the plan if someone leaves or is unavailable?"
5 Signs Your IT is Failing (That Every Exec Should Know)

3. Incident response and backup plans

Let’s get one thing straight—if you’re running a business today, you will be attacked. Maybe not today. Maybe not tomorrow. But eventually, a cyberattack or data breach will happen. The only question is: How ready are you?

If your answer is, “We’ll figure it out when it happens,” that’s not good enough.

Your in-house IT team should have a clear incident response plan in place, ready to go at a moment’s notice. If they don’t, you’re setting yourself up for disaster.

The average cost of downtime during an outage? $427 per minute. How much is your company willing to bleed before getting back up and running?

If your IT team can’t give you specifics, you might want to consider a third-party audit to help you shore up your defenses.

What to Ask Your IT Team →

  • "Do we have a documented incident response plan?"
  • "How often do we test our backup and recovery processes?'
  • "How long would it take to fully recover from a breach?"
5 Signs Your IT is Failing (That Every Exec Should Know)

4. Validating IT’s performance: fact vs. fiction

“I’m not a tech expert, but I trust my IT team.”

We hear this all the time. And trust is important, but as an executive, it’s also your job to verify.

Are they really keeping everything up-to-date? Or are they telling you what you want to hear?

Here’s the truth: Most executives can’t tell the difference between an efficient IT operation and one that’s barely treading water. The only way to know for sure is to dig into the data—or have a third party do it for you.

What to Ask Your IT Team →

  • "How often are we performing system audits?"
  • "When was our last third-party audit?"
  • 'What are the most common issues we face, and how are they being resolved?"
5 Signs Your IT is Failing (That Every Exec Should Know)

5. The hidden costs of a dysfunctional IT culture

Your IT team’s performance doesn’t just impact your systems—it impacts your people.

If your internal IT team is slow to respond to employee issues, if they’re brushing problems under the rug, or if they’re hard to work with, it’s costing you more than you think. Frustrated employees lead to lower productivity, higher turnover, and overall dissatisfaction across the board.

And if employees feel like they’re not being heard? They’ll start finding their own workarounds. Tools you don’t know about. Unsafe practices you haven’t approved.

If your employees aren’t happy, it’s a sign something’s broken. And fixing it could save you a lot of headaches (and money) down the road.

What to Ask Your IT Team →

  • "How satisfied are you with our internal IT support?"
  • "What’s the most frustrating part of working with IT?"
  • "Do you feel supported when it comes to technology needs?"

The case for outsourcing: why it might be the smarter move

After reading this, you might be thinking, “Is it even worth it to keep IT in-house?” And that’s a valid question. Outsourcing your IT can seem like a risk, but in many cases, it actually reduces your risk while giving you access to deeper expertise.

When you outsource to a Managed Services Provider (MSP), you get a team of specialists who live and breathe this stuff. They’re not just putting out fires—they’re preventing them from happening in the first place. And the best part? They’re always there. No more scrambling when your IT guy goes on vacation. No more wondering if your backups are solid. No more single points of failure.

The Bottom Line

Your IT team is the backbone of your business. If you’re not 100% sure they’re delivering the value, performance, and security your company needs, it’s time to start asking hard questions.

Whether you keep your team in-house or look into outsourcing, the most important thing is knowing what’s happening behind the scenes. Because when it comes to IT, what you don’t know can hurt you.

Talk to one of our IT experts to see if you’re truly getting the most out of your current IT solutions. Because if you’re not getting answers that make you feel confident, it’s time to take control.

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