Healthcare innovation is the development of new or improved healthcare policies, systems, products, technologies, services or methods of delivery, which aim to improve outcomes for people within healthcare. The Clinical Skills Development Service (CSDS) is one of the world’s largest healthcare simulation and training providers, which works towards healthcare improvement through training, collaboration, and innovation. This project provided the opportunity for academics to contribute new knowledge in Design Thinking strategies for healthcare innovation to the CSDS team. This was achieved through: (i) delivering a new-to-the world Design Thinking approach with an Observation Strategy suitable for use in the context of healthcare practices and (ii) a workshop protocol that was tested through first-hand experience with the CSDS team. Through this project we learned that the healthcare context is highly regulated, and therefore constrained in the technologies they are approved to employ. From the design team perspective, the inability of the healthcare sector to use creative online tools such as Padlet or Miro highly constrains the opportunity to explore different creative interactions across team members. From a healthcare professionals’ perspective, it was evident that some Design Thinking workshops require a longer iterative process to effectively identify opportunities for innovation, which is an area of emphasis in the healthcare sector. Two key aspects of this collaboration were the opportunity to expand our understanding of how quality improvement in healthcare can be achieved through design, and how a team combining two different worlds of knowledge and processes can meet in the middle to develop and deploy improved experiences through a co-design approach.