Two hundred and twenty-one business executives completed the Big Five NEO-RI-R (Costa & McCrae, 1992; an inventory of normal personality), the Hogan Development Survey (HDS) (Hogan & Hogan, 1997; an inventory of career derailing tendencies) and the Motives, Values and Preferences Inventory (MVPI) (Hogan & Hogan, 1999; an inventory of ten core occupational values). Correlational and regression analyses revealed modest but predictable relationships between all personality traits (except Neuroticism) and the values, particularly Recognition, Power and Security. The personality traits accounted for most variance with respect to Aesthetics, Altruism, Security and Power. Correlations and regressions for the HDS and MVPI showed that the values most related to “flawed interpersonal style” were Recognition, Affiliation, Power and Security. Step- wise regressions indicated that the HDS accounted for incremental validity over the Big Five in predicting core work values. Implications of these findings were considered.