#14: Kylie Jenner
Most people would probably agree that it is better to ask and be told the same thing a million times over than not to ask questions and horribly screw up a situation. Especially when working for a world-famous celebrity, chances are that you will want to be extra cautious about not screwing things up.
For some reason, Kylie Jenner seemed perplexed when her assistant asked her what flavor smoothie she wanted to drink every morning… Can you imagine what would happen if Jenner was given the wrong flavored smoothie? Even though it might seem annoying, it is better this happens than the alternative.