Many users struggle when they have to use complex interfaces to complete everyday computing tasks. Offering intelligent, proactive assistance is becoming commonplace yet determining the right time to provide help is still difficult. We conducted an empirical study that aimed to uncover what user factors influenced following advice. Our results describe a user's background and expectations that appear to play a role in heeding assistance. Our work is a step towards understanding how to provide the right assistance at the right time and build proactive assistance systems that are personalized for individual users.