Having a technical backgound, my first attempt was to try to dive in the product and look at it with a bottom-up approach. After few days installing, configuring and playing with some Maximo product i found myself lost and decided to step back in my chair and take some time to study some ITSM (IT service management), AM (Asset Management) and Maximo stuff from a higher level.
The IBM Tivoli Information Center is a good source of information but I think it is not the right place to start. IBM Redbooks have a more tutorial style so are more approriate for me. Searching for the word 'Maximo' i found several books. Here are the query results.
Among them I have selected the Certification Study Guide Series: IBM Maximo Asset Management V7.1. It may be boring but it is very useful to understand the asset management business and have an overview of Maximo features.