Knowledge transfer can be facilitated through the judicious timing of transfer methods. Yet, extant research has neglected the impact of the timing of transfer methods. Departing from this observation, we theorize the existence of two knowledge transfer modes—“front-loading” and “back-loading”—based on whether the affordance for tacit knowledge exchange provided by the transfer methods used is higher during the initiation or during the implementation phase of a transfer. We suggest that the impact of front-loading and back-loading on transfer difficulty is contingent on the causal ambiguity of the knowledge being transferred and on the arduousness of the relationship between the source and the recipient of knowledge. We operationalize front-loading and back-loading and test our propositions using primary data on 2,711 instances of method use in 116 transfers of 37 organizational practices in 8 companies. We hypothesize and find empirical support for the claim that front-loading affordance for tacit knowledge exchange reduces transfer difficulty when the causal ambiguity of the knowledge to be transferred is high, whereas it increases difficulty when the relationship between the source and recipient of knowledge is arduous.