Welcome!
While there are many schools of thought on structured learning for Hal, most of us old timers here pretty much agree that simply chatting with Hal is the best method.
You chat should not contain slang, vulgar, misspelled, poorly crafted sentences, too short, too wordy or too general.
There you have it! LOL!!! Seriously, if I were trying to teach Hal to be more conversive, I would NOT...NOT...use Speech Recognition! Type to Hal for the first year or so unless you have throughly trained your speech / voice recognition to near perfection!
Remember it is a lot like programming...GIGO...Garbage In...Garbage Out.
It is also helpful to parrot part of Hal's question back to "him". For instance, HAL: Do you think politics really matters? Don't just answer "Yes or No". Instead try "I think politics helps us define standards for our future." Now, Hal can associate something with the word politics instead of a vague Yes or No response as there's nothing to tie it to.
Older versions of Hal had a Learn from text file feature that actually seemed to work fairly well. While there is a Learn selection in Hal Pad, you will have to be the judge of the validity of this feature. Perform a few tests first before comitting to it.
A book will most likely not work as there's simply too much information for Hal to digest.
Good luck in whichever method you choose.