The growing need for efficient and effective human decision-makers warrants a better understanding of how decision support systems (DSS) guide users to improved decisions. Decision support approaches utilize visual aids to assist decision-making, including trade-off diagrams. These visualizations help comprehension of key trade-offs among decision alternatives. However, little is known about the role of trade-off diagrams in human decision-making and the best way to present them. Here, we discuss an empirical study with two goals: 1) evaluating DSS interactivity and 2) identifying decision-making strategies with trade-off diagrams. We specifically investigate the value of interface interactivity and problem context as users make nine increasingly complex decisions. Our results suggest that problem context and interactivity separately influence ability to navigate trade-off diagrams.