The use of artificial intelligence (AI) chatbots for urban planning in the literature is exploratory, fragmented, and lacking collaboration with practicing planners. Moreover, the potential for chatbots to complement or replace daily planning processes is not well understood. This study does not involve evaluating the performance of chatbots or selecting the most suitable tool; instead, the study sought to engage planners in the development of a chatbot to leverage existing question-answer data and socialise planners with the potential usefulness of AI for repetitive planning tasks. In-depth workshops were conducted with managers and planning officers in a state government planning agency in Australia. Insights were gained through discussion about planners subconsciously adapting to different jargon used in questions, how planners review and reuse previous answers, how recording questions and answers will aid the planning team, and low-risk pathways for planning officers to start using chatbots as an internal resource before making them public.