1) Has he diversified his portfolio within the 11 sectors?
2) Does he go for capital appreciation stocks or dividend stocks?
3) How much time does he spend studying a company's financials (10K form) and charts?
4) Who is his favorite investor? Warren Buffet for picking great stocks and holding for many many years or someone like Bill Ackman who is a bit deceptive on his trading tactics (over the summer he said 'Hell is coming' a signal thought by many as "panic sell" whilst he was buying heavily)
5) What is the number he is seeking to retire? There's usually a number ranging from $1M and $200M.
6) Maybe ask him if he is seeking to get licensed as a CMT (reading chart patterns)?
Hope this helps, either way best of luck to him!