Objective: Reducing sedentary behavior (SB) is an important public health concern. The purpose of this study was to explore motivation to acquire a standing desk and strategies for using a standing desk through one-on-one interviews. Methods: Thirty-seven university employees (89% staff; 51% women) participated in the study. Data were collected using a semi-structured interview guide and brief demographic questionnaire. Results: Data analysis yielded five themes about motivation to acquire a standing desk: (1) pain management; (2) health risk; (3) movement opportunity; (4) workspace flexibility; and (5) productivity and three themes about typical use strategy: (1) task-dependent; (2) time-dependent; and (3) threshold. Conclusions: Motivating factors for using a standing desk should be considered when encouraging standing desk use. Interventions should provide realistic strategies to establish a sit-stand routine that address employees’ unique job demands and preferences.