This study reports a cognitive-response-based analysis of advice planning. Through an examination of full-time employees’ thought generation pattern when they plan to offer suggestions to their supervisor (Study I), this study identifies five distinct types of thoughts involved in advice planning and provides evidence of the association between thoughts (e.g., assessment, goal-oriented, and caution) and message qualities. These results are replicated in Study II when the same data collection procedure is used to examine advice planning in a friendship context. While advice message qualities are determined to a certain extent by advice givers’ thought content, results from Studies I and II also suggest that such a process is further moderated by people’s cognitive elaboration. That is, heightened degree of effortful thinking in deciding how to give advice, as compared with low effortful thinking, results in a greater number of caution thoughts and advice messages that contain a larger number and more diverse set of reasons.