How are you doing?

Dana runs operations for a 60-person firm. She didn’t sign up to be the IT department, but somehow she is.

Her coffee is getting cold because the morning is already off the rails.

Two people can’t get into Outlook because their MFA prompts stopped showing up. The new hire from last week still doesn’t have access to the shared drive. A partner just forwarded an “urgent wire request” from the CEO that looks perfect: right tone, right signature, right everything. Except the CEO is on a plane.

Then there’s the list she keeps pushing to next week:

• The company is paying for Copilot licenses that almost nobody uses.
• Half the team is pasting client information into whatever free AI tool their friend told them about.
• The Azure bill went up again, and no one can explain why.
• The server in the closet runs Windows Server 2016, which loses extended support in January 2027.
• The new practice management app was supposed to “integrate with Microsoft 365.” It doesn’t.
• The cyber insurance renewal form asks questions she can’t answer with confidence.

None of this is a disaster yet. It’s just a steady drip of small problems, workarounds and “we’ll deal with it later.” Meanwhile, the business keeps growing, and the technology holding it together keeps getting more fragile.

How has her MSP allowed this to happen? She pays them every month, but for what?

By lunch, Dana is tired, hungry, and wondering whether this is just how things are now.