Smallholder farmers, those producing on less than 5 acres, remain the backbone of agricultural production: smallholder farming is the livelihood of more than 50 per cent of the population in most developing countries. With this rising demand, agribusinesses, both local and multinational, are growing and increasingly seeking to source production from smallholder farmers. While such business relationships have been formally occurring for decades in certain export crop value chains, there is now growing pressure from export market countries for “fair trade” and “sustainably produced” products, which actively engages those at the base of the pyramid. Given this growing potential, how can smallholder farmers make decisions to optimize their relationships with businesses along the agricultural, and other, value chains? This How To Do Note examines parameters affecting how smallholder farmers engage with business to maximize new opportunities; provides a decision tree for smallholders when entering into relationships with aggregators and businesses; and examines the potential challenges faced by both parties.