This study examined the quality of start–up planning of two Early Head Start (EHS) agencies and its association with staff satisfaction, burnout, and turnover a year after program implementation. Respondents (N = 65) completed interviews and surveys at two time points. Data were analyzed in the context of the Head Start's EHS Organizational Readiness Chart. Both programs addressed salient aspects of organizational readiness, including establishment of a leadership team, forging of community partnerships, and hiring and training of staff. The two agencies differed on several elements including goals and timeframes, dynamics of start–up planning teams, challenges encountered, and utilization of community partnerships. Higher quality of start–up planning was associated with lower burnout, higher satisfaction, and lower staff turnover during the first year of program implementation. These results indicated that strategic start–up planning is an important predictor of EHS staff well–being and stability, especially during early stages of program implementation.