Colder weather will force you to crank your stove a bit more which changes the whole way you tend it. (more frequent adding of coal, shorter time to shake down & reload due to increased fire temp & burning though allot more coal!)
Only experience with your stove & chimney will work. Shaking down is more of an "Art" than a "Science".......You want to shake down enough to get rid of the ash & settle the coal bed, but not so much that you compact the coal bed down so tightly that you cut off the air to the fire....Takes practice & it depends on how hot your stove is running.
See if any tips from this thread help: shaking a hand fired stove ?