It is February. Love is in the air. People are buying chocolate, making dinner reservations, and pretending they enjoy romantic comedies again. So let’s talk about relationships.

Specifically, the kind of IT relationship that feels like a bad date.

The kind where you call for help and hear nothing back.
The kind where a “fix” works for one day and then the problem comes right back.

If you have lived through that, you know how exhausting it is. And if you have not, you have avoided a very common small business headache.

Many business owners are still stuck in the IT version of a bad relationship:

  • Hoping it will get better
  • Making excuses
  • Saying “they’re cheap” like that makes the stress worth it
  • Continuing to call even though trust is already gone

And like most bad dates, it did not start this way.

The Honeymoon Phase

At the beginning, everything felt great. The IT person was responsive, helpful, and quick to fix problems. Things were set up. Issues were handled. The business thought, “Perfect. This is taken care of.”

Then the business grew.

The tech stack became more complex. Security threats became smarter. The team got busier. And the relationship changed.

The same problems started appearing again. Response times slowed. You heard the familiar phrase, “We’ll take a look when we can.”

So business owners did what people often do in bad relationships. They adapted their business around someone else’s bad behavior.

That is not partnership. That is survival.

 

The Voicemail Black Hole

You call. You leave a message. Maybe you send an email. Then you wait.

Hours pass. Sometimes days.

Meanwhile, employees are stuck. Work cannot get done. Deadlines slip. Customers grow impatient. You are paying people who cannot do their jobs because IT support is nowhere to be found.

That is not support. That is the tech equivalent of someone saying “I’m on my way” and then disappearing.

Healthy IT relationships do not leave you hanging. Problems are acknowledged quickly, triaged quickly, and fixed properly. Even better, many issues never happen at all because someone is watching your systems before they fail.

 

The Arrogance Problem

This one hurts the most.

Eventually, they show up. The issue gets fixed. And you are made to feel like you should be grateful they fit you into their schedule.

You hear things like:

  • “You wouldn’t understand.”
  • “That’s just how it works.”
  • “You should have called sooner.”
  • “Try not to do that again.”

It feels like being blamed for having a problem they were hired to solve.

A good IT partner does not make you feel foolish for needing help. They make you feel relieved that someone competent is handling it.

Technology should not be a test of patience or character. It should be boringly reliable.

The Workaround Trap

This is where things quietly get dangerous.

Because support is hard to reach, your team stops calling. They start creating workarounds. Files get emailed instead of stored properly. Data gets saved on desktops. Passwords get shared in text messages. Random tools get purchased just to keep work moving.

Not because employees want to break rules.
Because they want to do their jobs without waiting two days for help.

You see it in small ways at first. Like an office where the Wi-Fi drops every afternoon, so meetings are silently scheduled around the dead zone.

That is not technology working. That is your business learning to tiptoe around broken systems.

And workarounds lead to quiet disasters: security gaps, compliance risks, duplicate tools, inconsistent processes, and knowledge that disappears when someone leaves.

 

Why Tech Relationships Go Bad

Most small business IT relationships fail for the same reason many real relationships fail. Nobody is maintaining them.

Technology is often handled reactively. Something breaks. Someone calls. It gets patched. Everyone moves on until the next problem.

That is like only talking to your partner during arguments. You are technically communicating, but you are not building anything stable.

Meanwhile, the business keeps changing. More employees. More data. More software. More compliance pressure. More attacks aimed directly at companies like yours.

The IT approach that worked for five people and one shared folder does not survive a growing, modern business.

 

A good IT partner does more than fix problems. They prevent them. They monitor, patch, and maintain systems quietly in the background so issues do not appear during payroll, tax prep, or your biggest deadline of the quarter.

That is the difference between firefighting and fire prevention.

What a Healthy Tech Relationship Feels Like

A good IT relationship is not exciting. It does not create drama. It feels calm.

It looks like:

  • Systems that behave during deadlines
  • A team that does not dread updates
  • Files stored in one clear, reliable place
  • Fast responses that fix issues correctly
  • Tools that fit how your industry actually works
  • Data that stays secure and compliant
  • Growth that does not break everything

The biggest sign you are in a healthy tech relationship is simple. You stop thinking about IT most days because it just works.

 

The Big Question

If your IT provider were a person you were dating, would you keep seeing them?

Or would your friends say, “Seriously? You are still dealing with that?”

If you have normalized bad tech behavior, you are paying twice. Once in money. Once in stress. And neither one is necessary.

Know Someone Stuck in a Bad Tech Relationship?

If this sounds like your business, it may be time for a reset.

If this does not sound like you, there is a good chance you know someone it does. Feel free to share this with them. We are happy to help.