It's simply down to practice, me thinks.
Not mindless repetition, mind, but really thinking about all the variables
Then you get to know that ...
this PCB supplier uses smaller pads that heat up quicker,
that .05 solder flows faster than the other, but
gotta be quick with the .08 solder or it's too much,
this tip takes longer to reheat between quenchings,
change the tip out for gnds on back of pots,
guitar cavities are more awkward to work in than unboxed pedals,
temp settings for: different tips, types of solder, components...
etc
AH... Erik beat me to it!
It's not cheating if you reheat and get a good solder-joint — that's the goal and I score accordingly.
Like when the top thins out too much and I have an excess on the other side — reflow it and/or solder-sucker up the excess...