As design thinking became popularized, practitioners in the field pointed out that design thinking rarely takes stakeholders and contexts into account as a result of focusing solely on end-users. We believe such a limitation can be complemented with speculative design, which critiques the future that an idea depicts and interrogates relationships with social, cultural, economical, and political systems. This paper, through pilot interviews with 10 participants and a thematic analysis on interviews with 12 participants, explores possible interaction between design thinking and speculative and critical depiction of the future. Speculative and critical inquiries allowed the participants to consider various social contexts and stakeholders, and further helped them shape and brainstorm the ideas’ potential values and challenges faced during adoption. The overall critical speculation influenced various steps of the design thinking process. The paper contributes to the literature by reporting a novel application of speculative design to the conventional design thinking process. In the future, we hope to further explore other elements of speculative design and their impact on design outcomes.