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. In response, the education systems in East Africa have incorporated life skills and values into their policies and curricula in the past decade. 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 in the East African context is how personal identity incorporates more communitarian descriptions of the self in contrast to the Western individualism. Consequently, several conceptual, ethnographic, and epistemological elements affected the designing of data collection tools, frameworks, the processes of data collection, and data analysis. The findings are explored with the book.   Download  https://link.springer.com/chapter/10.1007/978-3-031-51490-6_3