
It's budget season. In most of the mid-market companies I talk to, the 2027 IT budget is being built the way it's always been built: take last year's actuals, add a few percent, and argue about the projects at the bottom of the list.
That approach has two blind spots. It doesn't look far enough ahead at what's coming off support, and it assumes prices that have already changed. After 25+ years on both sides of the budget table, I've learned that the first blind spot is the one that puts the business at risk.
This year I worked with three companies that were all late on Windows 10. In each case the Windows 11 upgrade never made it into the annual operating plan (AOP). When leadership finally recognized it had to happen, the project was shoehorned into a PMO that was already fully committed, and other priorities slipped to make room.
Windows 10 wasn't the only one:
I've now seen this same pattern at multiple companies. It isn't a technology problem. It's a planning problem: end-of-support and compliance deadlines are known years in advance, yet they keep getting left out of the plan. (If you run SAP ECC, the same applies to its 2027 end of mainstream support.)
Before anyone debates new initiatives, CIOs and IT leaders should answer one question: what in our environment is coming off support or falling out of compliance in the next 24 months?
Once the must-do list is set, check the prices underneath it.
Many Central Florida mid-market companies don't have a CIO in the room when the IT budget is set, and that's exactly when one pays for itself. A fractional or interim CIO can find the end-of-support deadlines that aren't in your plan, pressure-test your 2027 budget and build a roadmap your CFO can defend.
Let's Talk About Your 2027 BudgetSenior IT leadership for budgeting, roadmaps and vendor negotiations, part time.
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