The planning process in the UK is a highly complex system, developed over many decades, and is in the process of rapid transitions into digital planning. Among these transformations is a desire to move from an outputs-based assessment to an outcomes-based assessment process. This is challenging, and in this paper, the authors explore the variety of factors that make outcomes assessment challenging. The authors first studied the literature to understand how outcomes are complex, ranging across different sectors and practices, identifying 359 indicators related to outcomes. The authors then conducted a knowledge mapping exercise to understand the characteristics of the indicators in multiple themes. The authors also invited practitioners for an interview on their perspectives of outcomes assessment, definitions of outcomes, barriers to outcomes, the benefits of outcomes assessment, and how practitioners envision a world with outcomes assessment. The authors conclude the paper with future directions of research.