Beyond the Contract: Lessons from My First Contract Deep Dive

I was sixteen when I landed my first office job. The owner of a masonry company needed someone to organize expenses and agreements. That meant going through hundreds of pages of contracts and creating some kind of system. The office manager set me up and shared her woes of keeping everything straight for decades.

To say I was lost is an understatement. I had no idea what I was looking at. So I started at the beginning. Pen and paper in hand (because that was all the rage back then) I made a list. What did the company promise to do? What did we promise to do? The list grew fast, pages for every agreement. I noticed something else too: some obligations kicked in at the start of the contract, others at the end, and some required monthly reporting.

That led to my first meeting with the owner and the office manager. It took an hour to explain what I found in just two contracts. The owner’s reactions were mixed. Shock, anger, and a little disbelief. “These are all the things you said you would do” didn’t go over well. “These are the things they said they would do” made him angrier because he didn’t think it was enough. Cue the rookie mistake: “You should really read these contracts before you sign them.” Ouch. Then came the blame game, first the office manager, then the family friend lawyer. One thing became clear: I was spending my entire summer dissecting contracts to find every sneaky term.

Fast forward more than two decades. From small businesses to global giants, step one has never changed. Read the contract. Know what you’re responsible for. Know what they’re responsible for. And know how often you have to do it. 

Sincerely, your friendly neighborhood contract detective