When I start working with a new business client, I don't open a laptop and start fixing things.

I spend the first week listening and looking. In my experience, the gap between "what the company thinks its IT looks like" and "what it actually looks like" is the most important thing to understand before anything else. That gap is where the real problems hide — and it's almost always larger than the client expects.

Here is what I look at.

The Systems People Actually Use vs. the Official List

Every company I've worked with has a list of their IT systems somewhere. It might be a spreadsheet, a contract folder, a note in someone's head. It is never accurate.