Roadmaps

9 articles

· 1 min read

The Windows 10 estate: year-two math

Consumer ESU runs out in October. Enterprise ESU doubles every year. If the fleet is still on 10, the spreadsheet decides this one.

#windows#eol#planning

· 2 min read

The first ninety days of a roadmap

A modernization roadmap earns trust or loses it in its first quarter. What to schedule in days 1 through 90, and what to refuse to.

#roadmaps#planning#delivery

· 2 min read

Decommissioning is a project

Turning things off is scoped work with an owner, a sequence and a budget. The modernization industry's least favorite fact.

#roadmaps#decommissioning#cost

· 2 min read

The vendor contract time bomb

The estate's biggest risks are filed in procurement, not running in production. Reading the contracts folder like an engineer.

#roadmaps#vendors#licensing

· 3 min read

What we tell boards about rewrites

The full-rewrite pitch reaches every board eventually. The four questions that separate the rare good one from the expensive kind, with numbers.

#rewrites#roadmaps#strangler-fig

· 2 min read

Leave it alone, on purpose

The most underused line on any modernization roadmap. When not touching a system is the correct engineering decision, and how to make it stick.

#roadmaps#strategy#risk

· 1 min read

Put January 2027 on the wall now

Windows Server 2016 extended support ends January 12, 2027. Thirteen months is exactly enough time, which means it is almost too late.

#windows-server#eol#planning

· 1 min read

Pin the migration to the LTS

.NET 10 shipped this month with three years of support. That release cadence is your planning tool. Use it.

#dotnet#roadmaps