This list is designed for a technology leader. I'm going to assume that the person who is looking at this is technical enough to know what a database is and roughly how the internet works, but will be less technical than other reading lists that are out there.
So, to begin, the first thing you need is a picture. Words are great and important and you can't understand distributed ledger or blockchain technology without words. But it is also important to have a picture in your mind, so you can refer to it later.
Here is the best picture I have found describing bitcoin specifically: