The purpose of the present study was to test the efficacy and appropriateness of the 4-point response option of the Principal’s Goals Scale of the SASS (1999–2000) survey. Competing dichotomous models with various conceptualizations were constructed and tested against the original polytomous conceptualization. Participants were 8,524 principals from whom 64% were males and 36% females. Principals’ goals were assessed using a 6-item scale anchored across points reflecting proximity to achieving a goal. The original polytomous conceptualization was contrasted to a dichotomous two-pole conceptualization using a model with freely estimated discriminations (two-parameter logistic model, 2PL) as well as the Rasch model assuming equal discrimination parameters. Results indicated that the 2PL dichotomous model provided the most optimal model fit. Furthermore, item-related, and person-related estimates pointed to enhanced accuracy and validity for the dichotomous model conceptualization compared to the polytomous model. It is suggested that a dichotomous scaling system is considered in subsequent measurements of the scale as a means of enhancing the accuracy and validity of the measured trait.