For heavy speakers, or weak backs - I recommend this:
Lay the speaker on it's SIDE ..... Lay the speaker stand on IT'S side, and slide the pole into the hole. (it's still laying on the floor at this point. Now, you can "wallk" the speaker up by lifting it on the stand to it's upright position. Much easier than raising it over your head, and searching for the hole.
I tell this to my female friends that do singles ....... really makes live easier!