This paper aims to understand the involvement of cognitive versatility in scenarios of tension between decision-makers. The paper uses a qualitative case study of human resource allocation for digital product creation at a UK-based car manufacturer. Data retrieved through meeting observations, qualitative interviews, workshops, and internal documents were analyzed and triangulated. Three main findings were made. First, managers suggested in interviews and communication with the organization that Human Resource (HR) allocation decisions are rational, based on aligned metrics across digital product opportunities. While managers compare opportunities against each other, for example, annualized monetary savings, a tendency towards familiar types of work with familiar metrics was evident. For example, supply chain cost savings were justified more easily than customer experience improvements. Second, the HR allocation process favors digital product opportunities presented by managers who have stronger relationships with the executives and are better at convincing the wider management team, for example, through powerful storytelling, thereby bypassing objectified comparisons of opportunities. Third, managers over-rationalize and simplify the complexity of reality. For example, the HR allocation process assumes that all employees in the same role perform equally well within different team and product environments. As a result, previous knowledge, experience, and relationships have been widely ignored, leading to HR reallocation transaction costs. The lessons gleaned from the case study suggest that (1) managers and their HR allocation decision-making are not as rational as they think and say they are, (2) surfacing some of the hidden, intuitive decision influences might improve decision outcomes, and (3) ensuring to fully account for the strategic value of unfamiliar digital products might help managers to understand the real value of opportunities.