So far I've gotten about 9 in extended, here's what I've done to get "outtakes", don't know if they all count, though.
NO SPOILER TAGS BELOW, I'M TIRED OF THEM
(all in extended play, some might not work, but seemed like outtakes to me)
Click on the trinket on the table
Look out the window at the office
Look at the paintings at the office
Talk to Pom-pom
Talk to Pom-pom again
You know what, Just talk to pom-pom until he repeats himself.
Click on the Helicopter set
Talk to Renaldo