I'm only following the anime and I dont know if the manga or some guide says something about this, I dont think there is any hint in the anime about it. IIRC, it was said that Gran Torino started to train All Might in combat right away because he could handle the power of One for All at once. Midoriya in the other hand, everytime he uses One for All 100% breaks his body and to keep from harming himself he has to use One for All 5% or 20% later for what I've read in a wikia. Is it known why All Might could handle the power of One for All at once and Midoriya couldnt?
It hasn't been clearly stated in the manga but One for All is a stockpiling quirk that gains power from the current user and this power is transferred to the next when the quirk is transferred. With each transfer the power of the quirk increases which mean that when Nana gave All Might the quirk it wasn't as strong as when All Might gave it to Midoriya.