Effective leadership is a collaborative effort, requiring a degree of complementarity in how people enact roles of leadership and followership. Using a novel online vignette methodology, we experimentally tested how three contextual factors influenced coaches’ responses to challenge-oriented acts of followership as well as investigated two potential mechanisms. Coaches (N = 232) watched videos of an athlete provided unsolicited challenge-oriented feedback to a coach. Videos varied by the (a) athlete’s status, (b) presence of third-party observers, and (c) stage of the decision-making process. Following the video, we assessed coaches’ evaluations of the athlete. Challenge-oriented followership was perceived more favorably when enacted by an athlete in one-on-one (versus in a group) and before a decision has been reached (versus after a decision is reached). Coaches may appreciate proactivity from athletes in positions of followership, but challenge-oriented followership behaviors enacted at the wrong time and place can elicit negative reactions.