Succession planning is a very crucial aspect of family business continuity. The successful transition of family businesses is especially important for small and medium scale family businesses which constitute the beginning phase of most businesses. This paper explores two critical aspects of succession planning, namely the decision to keep business ownership within the family and the transfer-readiness of family businesses. This study assessed potential correlates of these two constructs using data from small and medium scale farm and non-farm businesses in Midwest US. Results from a probit estimator showed that farm businesses were more likely to be kept within the family (P<0.01). For the full sample, the number of generations involved in daily management, the readiness of the senior management to delegate control, and the owner experience were found to be good correlates of the decision to keep the business within the family. For farms, we also found some correlation between the perception of the business as being successful and the decision to keep the business in the family (P<0.1). Results from the probit and bivariate probit models showed that capital and the number of generations in management are the most consistent correlates of transfer-readiness for the full and farm samples. Finally, we found that female owners of farm businesses were less likely to be ready for business transfers than their male counterparts (P<0.01).