Our research reveals actionable ways for managers to (1) successfully manage salespeople’s avoidance of relatively large opportunities, (2) better understand the role of conversion uncertainty in salesperson decision making when prospecting, and (3) effectively manage salespeople’s decision making when prospecting by altering their benefit–cost calculus and uncertainty calibration and paying attention to salespeople’s portfolio characteristics. Furthermore, salespeople should be aware of the biases their past performance success and experience create in their decision making when prospecting.