Lama Tsong-kha-pa was an extremely intelligent person who beseeched the virtuous teachers of his time to teach him. He began his learning with the fundamentals - the doctrines and tenets. And spent his first few years of study broadly acquiring the doctrines from various sects. He also sincerely learned from all his teachers and extensively mastered the teachings received from all his teachers. By listening to the teaching of virtuous teachers, one obtains the wisdom arising from listening.
Global Lamrim 2, Lecture 0012
So what should we start doing to have a better understanding of teachings?