Question-asking is a crucial aspect of human interaction. Questions fuel engagement, stimulate thought processes, foster learning, and facilitate information-seeking behavior. Yet, scarce empirical research exists on question-asking, or its relation to related cognitive capacities such as creativity, curiosity, and intelligence. The use of digital games as a research medium offers significant advantages for studying cognitive processes in natural settings. As such, this study empirically investigates how people ask questions in an online serious game. To do so, we developed an online game—Spot the Spy—where players are required to find a hidden spy amidst a crowded room, by asking a chatbot agent questions that guide them in their investigation. Our game thus offers to investigate question-asking in natural settings empirically, and optimal question-asking strategies, which we conducted in two studies. Study 1 (online, N = 103) focused on game development and exploratory validation, whereas Study 2 (in-lab, N = 100) focused on replication and extension. In both studies, participants completed a series of cognitive tasks assessing creativity, curiosity, and intelligence before playing the game. Our results highlight strategies related to optimal performance in the game, as well as how players’ gameplay correlates with their cognitive abilities, especially with intelligence. Specifically, we found that higher intelligence scores were associated with more effective questioning strategies and better game performance. These insights highlight the potential of gamified environments to enhance our understanding of cognitive processes and advance the development of educational and training tools that foster strategic thinking and question-asking capacities.