Abbas, AdnanWohn, CalebHu, DonghanRho, Eugenia Ha RimLee, Sang Won2025-08-072025-08-072025-07-08https://hdl.handle.net/10919/137001Effective planning and reflection are essential for knowledge workers’ productivity and well-being, yet many struggle with them. While conversational agents (CAs) have shown promise, existing approaches rely on repetitive check-in without variance. We designed PITCH, a CA that checks in twice daily for morning planning and evening reflection while considering the morning conversation. Atwo-week field study with 12 graduate students demonstrated that engagement with PITCH increased their perceived well-being over time.We also evaluated a rotation strategy, which cycles through diverse topics every day, hypothesizing that rotation would mitigate wear-out effects and offer new perspectives. The results revealed that the specificity of a randomly chosen goal was perceived as being out of context and authoritarian, with most preferring the non-rotation version for consistency and flexibility. These findings highlight the potential of CAs to support knowledge workers and offer design considerations for varying conversations to provide topical diversity.application/pdfenCreative Commons Attribution 4.0 InternationalArticle - Refereed2025-08-01The author(s)https://doi.org/10.1145/3719160.3736634