How a city of 7,000 modernized its entire IT stack in 18 months

The starting point: aging on-prem servers, an email system the vendor stopped supporting two years prior, a public WiFi network that occasionally rebooted itself, and an IT director who was retiring in 18 months.

The plan

We worked backwards from the retirement date. Whatever was running on day one of the new IT director's tenure had to be supportable, documented, and modern enough to last through their first budget cycle without an emergency.

The phases

1. Months 1 to 3: Inventory, documentation, security baseline. Discovered four servers no one knew about and three orphaned domains.
2. Months 4 to 8: Email migration, M365 hardening, MFA rollout. Council approval mid-phase for additional licensing.
3. Months 9 to 12: Network refresh, including segmentation and a new public WiFi that does not reboot itself.
4. Months 13 to 16: Backup and DR. Tested it twice with the outgoing director.
5. Months 17 to 18: Knowledge transfer, runbook completion, vendor introductions.

What we would do again

Tying the project plan to the retirement date gave it a forcing function nobody could argue with. We will use that frame again.