all you need to do is reach under the truck and squeeze the rear shock bladder, it should be firm, you can do this before you start it in morning or after it has sat a few or even several days. the pump will normally run for a few seconds each time you cycle the key from off to run regardless of anything. no need to go on a lift or see a mechanic unless the bladder is flat or visibly blown out. both shocks run on 1 air line that T's off of 1 line so it doesn't matter which side you squeeze both shocks will be either inflated or flat, they should never be flat unless you have a leak, visibly blown out or it has sat for a really long time. If they are flat from just sitting overnight then you have a leak. if they are very firm and the pump never runs then the pump relief valve may be defective.
if you are in doubt, turn on the truck grab you kids or a friend and stand on the back bumper so you have some weight on it and you should hear the pump kick on and lift the truck an inch or so