I have had mild success in waking up another (family member) using questions to draw them out more. You have to be careful not to get then to the point of shutting down though.
How you went about it seems like you were able to plant seeds... You could show him the whole line of kings, working forward in time, showing how long they ruled and show how the time line doesn't match 607...
You can use ONLY JW material for this, as their times line up with secular times (number of years ruling does, but the actual dates/years are diff) someone posted the whole time line w/ organizational references here a while back (less than a year ago I think ) alot is in the insight books, you may need to find some old WTs and KMs too though
That being said, walking someone up and getting then to want to leave are 2 very different things.. The first may be easy if done right and by the right person (close family may be ok, but a friend from the hall may not be) but the second may be impossible depending on circumstances and personality of the newly awakened