It’s February. Love is in the air.
People are buying chocolate, making dinner reservations, pretending they enjoy romantic comedies again. So let’s talk about relationships—the professional kind.
Specifically: tech relationships.
Have you ever had an IT relationship that felt like a bad date?
The kind where you reach out for help and get silence.
Or the “fix” works… briefly… and then the problem comes right back.
If you’ve lived through that, you know how draining it is.
If you haven’t—congratulations. You’ve avoided a very common business headache.
Because plenty of organizations—both small teams that outsource IT and growing companies with internal IT—are stuck in the technology version of a bad relationship.
They keep hoping it’ll improve.
They keep making excuses.
They keep saying, “Well, this is just how IT is.”
They keep calling… even though trust is already gone.
And like most bad relationships, it didn’t start this way.
The Honeymoon Phase
At first, everything worked.
Tickets were answered quickly.
Issues got fixed.
Someone “had it handled.”
Whether that was a solo IT provider, an MSP, or a partner supporting your internal team—it felt good. Reliable. Simple.
Then the business grew.
More people.
More systems.
More data.
More security threats.
More pressure.
And the relationship changed.
Problems started repeating.
Responses slowed.
The familiar phrase appeared:
“We’ll take a look when we can.”
So leadership did what people do in every bad relationship:
They adapted the business around someone else’s limitations.
That’s not partnership.
That’s survival.
The Support Black Hole
You call.
You submit a ticket.
You send a follow-up.
Then you wait.
Meanwhile:
- An employee is stuck
- A department can’t move forward
- Deadlines slip
- Customers feel it
You’re paying people who can’t do their jobs because IT—internal, external, or shared—is overloaded or unavailable.
That’s not support.
That’s the tech equivalent of “I’m on my way” followed by radio silence.
Healthy IT relationships acknowledge issues fast, triage clearly, and resolve them properly. Better yet—many issues never happen at all because someone is watching the systems before they fail.
The Arrogance (Yes, It Happens Internally Too)
Eventually, the issue gets fixed.
And then comes the attitude.
“You wouldn’t understand.”
“That’s just how the system works.”
“You should’ve reported it sooner.”
“Try not to do that again.”
Whether it’s an outside provider or an internal team stretched too thin, the result feels the same: the business is made to feel like the problem.
A good IT relationship doesn’t make people feel stupid for needing help.
It makes them feel relieved that someone competent is on their side.
Technology isn’t supposed to be a test of patience or character.
It’s supposed to be boringly reliable.
The Workaround Trap
This is where things quietly get dangerous.
Because help is slow or inconsistent, people stop asking.
They:
- Email files instead of using systems
- Save data locally “just in case”
- Share passwords over chat
- Buy unsanctioned tools to get work done
Not because they want to break rules—
but because they want to do their jobs.
You see it in small ways first.
Like the office where Wi-Fi drops every afternoon, so meetings are silently scheduled around it.
That’s not technology working.
That’s your business tiptoeing around broken trust.
And workarounds create invisible damage:
- Security gaps
- Compliance risks
- Duplicate tools
- Fragile processes
- Knowledge that disappears when someone leaves
Workarounds are what organizations build when they no longer trust their tech relationship.
Why IT Relationships Break Down
Most IT relationships fail for the same reason personal ones do:
No one is actively maintaining the relationship.
Many environments—outsourced or co-managed—run in reactive mode:
Something breaks → someone fixes it → everyone moves on.
That’s like only talking during arguments.
You’re communicating—but you’re not building stability.
Meanwhile, the business keeps changing:
More staff.
Remote work.
Cloud platforms.
Customer expectations.
Compliance pressure.
Smarter attacks aimed squarely at organizations your size.
What worked for a small team or a lighter environment doesn’t automatically scale.
A healthy IT partner—internal, external, or shared—doesn’t just fix issues.
They prevent them.
They monitor.
They patch.
They plan.
They communicate.
Quietly. Consistently. Before problems show up during payroll, tax season, or your most important deadline.
That’s the difference between firefighting and fire prevention.
One is chaotic and exhausting.
The other is predictable and mature.
What a Healthy Tech Relationship Feels Like
A good IT relationship isn’t exciting.
It doesn’t create drama.
It feels calm.
It looks like:
- Systems behaving during crunch time
- Employees not dreading updates
- Files living in clear, consistent places
- Support responding quickly—and fixing things right
- Tools that fit how your business actually operates
- Data that’s secure, recoverable, and compliant
- Growth that doesn’t break everything
The biggest sign you’re in a good tech relationship?
You stop thinking about IT most days.
Because it just works.
The Big Question
If your IT setup—whether outsourced, internal, or co-managed—were a relationship…
Would you keep investing in it?
Or would a trusted friend say, “You know this isn’t normal, right?”
If you’ve normalized bad tech behavior, you’re paying twice:
Once in money.
Once in stress.
Neither is necessary.
If your environment is solid—great.
This is for the many organizations that quietly know it isn’t.
Know a Business Stuck in a “Bad Date” Tech Relationship?
If this sounds familiar, book a 10-minute discovery call.
We’ll help you identify where the relationship is breaking down—and how to restore trust, clarity, and stability without drama.
If it doesn’t sound like you, that’s great.
But chances are you know someone it does describe.
Forward this to them. We’ll help.
[Book your 10-minute discovery call here]
If you’d like, I can:
- Tighten this for mid-market leadership audiences
- Add a co-managed IT callout section
- Adapt it into a sales enablement blog
- Rewrite it with Mirrored Storage continuity woven in
Just tell me where this will be published and who it’s for.
