Sleep hygiene is a recommendation to help improve sleep quality; many persuasive technologies have been designed in human–computer interaction (HCI) studies to support sleep hygiene routines. However, a critical challenge is that users intentionally do not follow the recommendations because these often conflict with the user’s preferences or circumstances. To overcome this problem, we propose an alternative interaction strategy by which users can negotiate their sleep hygiene activities. Instead of emphasizing idealized rules for users, goals mutually agreed between the user and the system may support adherence to sleep hygiene. To explore the potential and experience of negotiating sleep hygiene goals, users and design researchers engaged in improvisational role-playing to simulate negotiations. We found that negotiation could support positive attitudes and self-efficacy in adhering to sleep hygiene practices. We discuss the balance between flexibility and authority as the primary characteristics of negotiation, and how to design negotiation-based interactive systems.