This article describes the retrospective case study of a core group of academic experts who worked with student researchers and local government leaders under the umbrella of the Challenging Sustainability initiative. Run by New Zealand's Massey University-Wellington in calendar years 2011 and 2012, the objective of the initiative was to improve the sustainable use of agricultural land. Research was planned to determine improvements to agriculture at rural, peri-urban, and urban locations in Hawkes Bay, Manawatu, and Wellington City, respectively. During the process, visual strategic planning was adapted to help manage the Wellington City subproject, using proprietary software. This approach was subsequently used to help manage the Challenging Sustainability initiative as a whole because it appeared that visual strategic planning could help advance a number of subprojects. However, as the overall initiative neared completion, it was unclear how the initiative's management team, as a whole, had benefitted from using visual strategic planning processes. The authors used Q Methodology to help create this retrospective case study, which analyzes how the management team viewed the use of visual strategic planning to help manage their work. The assumption that visual strategic planning can facilitate both greater transparency and more sophisticated collaboration was borne out in the Q Methodology results. However an additional finding-that participants needed more time and experience to understand the value of the visual tools-was indicated. Further research is required to test the hypothesis that a visual approach to complex planning is a genuine improvement upon more text-dependent processes.