We address the question of how participants in a small world experiment are able to find short paths in a social network using only local information about their immediate contacts. We simulate such experiments on a network of actual email contacts within an organization as well as on a student social networking website. On the email network we find that small world search strategies using a contacts position in physical space or in an organizational hierarchy relative to the target can effectively be used to locate most individuals. However, we find that in the online student network, where the data is incomplete and hierarchical structures are not well defined, local search strategies are less effective. We compare our findings to recent theoretical hypotheses about underlying social structure that would enable these simple search strategies to succeed and discuss the implications to social software design.