I'm currently managing a challenging situation where my small IT company, which has recently grown from under 50 to about 200 users after a merger, is in dire need of system upgrades. Previously, a Senior IT managed everything, and now that they're gone, I've been left without proper documentation or a clear understanding of our systems. I'm tasked with modernizing our outdated systems, but I don't have much detailed knowledge of what we actually have or how it all works. My remaining developer colleagues are either too busy or not very experienced, and the former Senior IT is considered too expensive for consulting. I'm trying to figure out how to modernize while navigating firewalls, server dependencies, and missing documentation. I mainly work in a Windows-based environment (IIS, MS SQL, .Net) and need strategies or tools to help sort through the chaos and document what I find. Any suggestions on how to tackle these upgrades or organize the systems would be greatly appreciated!
2 Answers
You’ve got a real challenge there! Begin with basic asset management to identify what each server does and who to turn to for help in case something goes down. It’s like putting together a puzzle; once you know what pieces you have, you can start figuring out how they fit together. Get everything documented, even if it's rough at first—this’ll help immensely later!
You've got quite the overhaul ahead! Start with getting documentation on all known systems down—use a simple, accessible platform for this, like DokuWiki or Google Docs. Aim to establish a minimum acceptable standard for your systems. Set up a plan for upgrades based on urgency, and always keep communication open with management about the risks involved in these legacy systems.
Good points! Plus, documenting changes systematically will protect you should anything go wrong.

Right! And don’t forget to learn from past mistakes in the company—sometimes old servers are still running because no one knew they were left behind after a business shift.