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Have floor dry, rags or absorbent pads handy, there is a very good chance it will make a mess.
One of the auto shops I worked in years ago had a plastic garbage can lid with holes drilled in it around the center, this was placed on top of a drain pan to make a larger target that was easier to hit with the stream of fluid coming out of the corner of the pan.
I have done mine a few times now so got sick of the mess no matter how careful you are.
I now use a small cheap 12volt fluid transfer pump from ebay that has a thin hose that goes down the dipstick tube and the other side of the pump has a tube that I put into a bottle.
Turn it on and wait till it drains most of the trans fluid.
I have found that the bolts are sometimes overtightened, bending the pan at the bolt holes. This causes the trans fluid to leak. After removing the pan, I would use a straight edge, checking all the bolt holes to see that they are flat. If any are dimpled inward, I would use a ball-peen hammer and a block of wood to straighten them. To avoid this from happening, gently snug up each bolt, going around the pan in a criss cross pattern.
I would either suck as much fluid as you can out via the dipstick hole first or you could even just buy some vinyl hose at a home improvement store and shove it down the dipstick hole and siphon out as much of the fluid as possible. This will significantly lessen the mess you'll make when you take the pan off. It would also help a ton if you can jack the back up and get the car level.
Otherwise be prepared to make a big mess when the pan comes off. You could also buy an aftermarket pan to put back on with a drain plug on it or retrofit yours to include a drain plug for future changes.