The world is concerned about young people’s preparedness to face challenges in the workplace, as well as society’s ability to respond to the social and economic issues of the twenty-first century. To respond to this challenge in the past decade, the education systems in East Africa have incorporated life skills and values into their policies and curricula; however, the actual implementation and incorporation of teaching and learning practices that foster these skills in the classroom is mostly unexplored. It has also been noted that tools used to measure 21st century skills in non-Western contexts have been borrowed from Western literature. This leaves no room for different understandings and conceptualisations of the skills to be measured. The Assessment of Life Skills and Values in East Africa (ALiVE) team addressed the gap in existing literature by exploring the understanding of collaboration, problem solving, self-awareness, and respect in the East African context through rapid ethnographic interviews. Each of these constructs are represented in the education systems of Kenya, Tanzania, and Uganda. The researchers interviewed a total of 368 participants (80 from Kenya, 55 from Tanzania, and 95 from Uganda). Of these, 76 participants were adolescents; 78 were parents; and 76 were teachers. What emerges prominently in the East African context is that personal identity incorporates more communitarian than individualistic features compared to the Western descriptions of the self. As a consequence, when designing a data collection tool for assessing life skills in the East African context, there are several conceptual, ethnographic, and epistemological elements to be considered—not only at the initial stage of conceptualising the framework of a tool, but also in the process of tool development, data collection, and data analysis.