Most IT plans are wish lists. This one runs on dates.
An item only earns a place on your roadmap if something external forces it — a vendor stops shipping security updates, a warranty expires, an insurer asks a question you have to answer honestly. That constraint does the prioritising for you, which matters when nobody at your company wakes up thinking about IT.
- The deadlines already on your calendar. A dated end-of-life register — Windows, Office, SQL Server, Exchange, Windows Server. Most companies find at least one that has already passed.
- Why Windows 10 is a hardware problem, not an upgrade problem. And why the free workaround you read about doesn't work on a single properly-managed business PC.
- The Windows 11 trap nobody warns you about — getting there isn't the finish line, and one version is already out of support.
- A five-year lifecycle — plus the end-of-sale trap that means a brand-new firewall can arrive with two years of support left.
- Let your insurer write the first draft. What carriers now refuse to bind coverage without — and the "Windows 10 voids your policy" myth, which we went looking for and couldn't find.
- What the claims data says to fix first — and why it probably isn't what your IT company is selling you.
Five worksheets you actually fill in
A deadline register, an asset inventory, a five-year refresh schedule, a business-impact sheet, and a prioritisation matrix — printable, and pre-filled with the dates that already apply to you. No prices anywhere: licensing and hardware costs move too fast for a printed figure to stay honest.
Get the guide
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