You need to distract Dougal, and it has to be once. You will be tasked with making breakfast for yourself.
1. Get Dougal to interact with the string on the cupboard door and with yourself to get the bowl.
2. Now, you'll get dougal to interact with the door, distracting him, then you must quickly interact with the bag of oats hanging from the wooden beam in the top right screen.
If you're not fast enough, the dog won't let you go on top of the cupboard, and the achievement/trophy is void. You'll have to dashboard out of the game quickly and then reboot it to possibly restore the achievement or trophy.
Achievement/trophy pops once you make it on top of the cupboard.