It is clearly understood that the design teams have a critical role to play in achieving circularity in the built environment. However, little attention has been given to the demolition industry and its contribution at the design stage of construction. The purpose of this paper is to investigate the role of the demolition industry in the movement towards the circular economy through exploring the benefits and challenges of involving demolition contractors at the design stage of construction. This study reports the findings from 12 in-depth interviews undertaken with professional demolition practitioners. The following questions were asked: Are there benefits to involving a demolition contractor at the design stage? What roles and responsibilities might be appropriate for the demolition contractor at the early stages of design? What knowledge does the demolition contractor possess that is of value to designers and clients? And what challenges might arise? The findings show that early demolition contractor involvement is more likely to ensure that end-of-life factors are considered at early phases of design. The input of a demolition contractor at the design stage will encourage designers to design for deconstruction; thus, fulfilling a closed-loop concept. However, a series of challenges were also revealed. Results show that adversarial relationships, cost, and time are the biggest challenges to involving a demolition contractor at the design stage. This study shows the essential need to revise the current linear models followed within the construction cycle and articulates the important role the demolition industry has in the continued movement towards a circular economy.