Recent Ministry of Education (MOE) policy in New Zealand has encouraged schools to create Innovative Learning Environments (ILEs); environments that provide flexibility and openness so learning can be personalised according to each individual’s strengths, abilities, languages, and cultures. Together, with the focus internationally of moving towards 21st century learning, many secondary schools are questioning their traditional single cell environments and are moving towards ILEs. It is apparent, as these open, flexible spaces are created, it is not just the physical environment that changes; an entire culture shift is required as teachers readjust their traditional roles and develop new skills. This study explores the experiences and support given to teachers as they transition from single cell classrooms into such an environment, and how this might differ for longer-tenured teachers compared to recently appointed teachers. The research focused on a single case study of a New Zealand secondary school. An individual, face-to-face interview with the leader in charge of professional development was conducted, followed by two separate focus group interviews with each selected group of teachers to gain their perceptions and experiences. Then a review of relevant documentation was carried out so the documented support could be identified and compared to the teachers’ perceptions of their experiences. The findings from this case study identified both the challenges and support experienced by the participants. Both focus groups commented on expecting a pedagogical change but not the cultural change that accompanied the transition into the ILE. Their combined experiences indicated there was no single solution to supporting teachers in their transition but instead suggest the culture of the school was a significant factor. Providing structures and processes that allow collaborative practices and trust to develop were identified as essential for building a culture where teachers learn from each other. This case study may have implications for the support of teachers particularly in new schools that only have ILEs, as it has highlighted the shift needed in both cultural and pedagogical change by teachers as they transition into an ILE, and the type of culture leaders can encourage in their schools to support this.