The advancement of artificial intelligence technology has enabled chatbots to mimic human conversations to the point of being nearly indistinguishable from humans. This study investigates the impact of chatbot proactivity on user experience, considering task types and user characteristics. Experiments were conducted using proactive and non-proactive chatbots for business-related and non-business-related tasks, evaluating user characteristics (age, gender, AI experience level, education level, personality traits) and user experience (perceived usefulness, perceived ease of use, perceived satisfaction, trust). The results showed that proactive chatbots were positively evaluated in terms of perceived usefulness, perceived satisfaction, and trust, but no significant difference was found in perceived ease of use compared to non-proactive chatbots. Additionally, task types and user personality traits (extraversion, agreeableness) significantly influenced user experience. This study highlights the critical role of chatbot proactivity in providing satisfying interaction experiences and emphasizes the importance of designing chatbots considering task and user characteristics.