rylla
@headincloud and aurafields: He's definitely the thoughtful, indecisive type! That's actually part of why the reading was done in the first place--he had some questions about how he'd do, given how indecisive he knows he is.
Personally, the HM is one of the hardest card to interpret. That's why I read this thread with all the excellent comments in it.
Once I had a very hart time/situation and I was getting the HM often. It would take too long to describe it so instead I am giving an example: like you would take care of someone who is sick and who you really love and you would bring all the sacrifices from all your heart but you would not know if that person will make it and you feel powerless and you are in suspense all the time with things out of your hand no matter what you do (in my situation things got resolved after a period of time so I just needed to keep going and wait it out).
So for me the HM isn't about leadership (as already pointed out by thirteen). And in my view the HM doesn't mean great leadership.
ThusSpokeZarathustra you addressed the question and, in my view, you also answered it (as I quoted you above). That's how I'd describe the qualities of that man re. leadership. So he may rely on the positive qualities of HM re leadership and he might try to pass those that are holding him up. If he looks honestly at himself (which he seems he does since he asked you a reading re his concern about being a good leader - it seems like he is questioning it instead of being self confident that he would be). Indecision could be a big issue here - a leader can't be indecisive or can't change his mind too often as a result. Good luck to him!
ETA: a leader can't have things out of his hands, he has to be on top of it, maybe you could advise him to be careful not to let things slip out of his hands (if he has inclination to do that)