Researchers and practitioners in the field of human-computer interaction (HCI) are increasingly confronted with wicked problems. Inspiring speculative thinking among users is an effective approach to reconcile wicked problems. Although existing work explores various ways to inspire speculative thinking through interaction, there is a lack of systematic exploration regarding which interaction strategies can effectively inspire speculative thinking and subsequently reconcile wicked problems. This research aims to explore the obstacles and strategies for inspiring speculative thinking and therefore reconcile wicked problems. Drawing on eight semi-structured interviews with participants with different backgrounds, I used thematic analysis to identity themes. I found that the obstacles include: (1) limited consideration of grand intentions, (2) restricted sensory engagement in interactive communication, and (3) difficulty in changing behavior. I also reveal three interactive design strategies for effectively stimulating user speculation, thereby reconciling wicked problems: (1) attracting participatory interactions, (2) eliciting emotional resonance, and (3) creating cognitive resonance. The first contribution is expanding interaction design strategies and methods in the speculative design domain. Interactive devices are crucial in stimulating user speculation and creating effective paths for reconciling wicked problems to envision a desirable future. This study contributes to the field of speculative design, interaction strategies, providing implications for interaction design practices.