Now available · Paperback August 3, 2026
The Legacy Trap
A Field Guide to Legacy to Cloud Transformation and the Team That Runs It
Cloud migrations rarely fail on the architecture. They fail on the team. This is the field guide for the leader who has the platform picked, the budget approved, and a group of infrastructure veterans being asked to become beginners again.
Written for IT directors, infrastructure leaders, and the CIOs who have to carry both the migration and the people running it.
Kindle available now. Paperback ships August 3, 2026.
Free · Sixteen files
The Retooling Toolkit
Every tool from the book. The Readiness Assessment, the Team Skills Matrix, the Capacity Math Calculator, the 90-Day Sprint Tracker, and twelve more. Nothing in the kit is theory. Each file solved a real problem on a real project.
The pattern
The trap is not the old system. It is the team that kept it running.
Your best infrastructure people are the reason the legacy platform never went down. They know where every workaround lives. They earned their standing on years of heroic saves at three in the morning.
Now you are asking them to throw that away and become beginners. Nobody says it in those words, so nobody addresses it, and the migration quietly stalls on people who will not admit in a standup that they do not understand Terraform yet.
This book is about that problem, and how to move a team through it without losing the people who made you reliable in the first place.
Inside
What you get
The identity crisis no one talks about
The senior engineer who ran your data center for fifteen years is being asked to become a beginner. Nobody names that out loud, and it is the single biggest reason migrations stall.
Who will make it, and who won't
Score people on skill, adaptability, and influence instead of tenure. How to tell early, and what you owe the people who are not going to make the jump.
Psychological safety in a break-fix culture
Teams rewarded for years on heroic 3am saves will not admit they do not understand Terraform. Change that before you change the tooling.
Getting ops teams to work like developers
Infrastructure as code, Git, pipelines, and the end of manual change windows. The mental model first, then the tools.
The 90-day retooling sprint
A practical playbook for a single sprint end to end, plus the honest arithmetic on how much change a team can actually absorb at once.
The team that runs what they build
Migration is the easy half. Governance, guardrails, KPIs that mean something, and letting go of the control you spent a career accumulating.
The author
Josh Siddon
Thirty years in IT, most of it spent inside the systems this book is about. Josh has run the migrations, inherited the undocumented platform, and sat in the steering committee where nobody wanted to be the one to say the date was gone.
He now runs ResiQ, a vendor-independent technology advisory. Operators pay him directly and no vendor pays him anything, which is the entire point.