The pole height classification functions very similar to the midspan. The default shortcut is 'p' for pole height and will immediately prompt you to begin calibrating the height stick. Place all 5 calibration markers accurately at their correct heights inside the white squares.
The key difference for pole height photos is the placement of the pole top marker. The pole top marker will create a useful attribute later on and is required for pole loading. You want to place the pole top marker where you see the top of the pole, often just above crossarms.