Teamwork or collaboration is recognised by many governments and international agencies as an essential life skill and competency in the workplace. Employers almost always rank teamwork among the top competencies expected of college graduates. In Singapore, SkillsFuture Singapore (a government agency driving skills equipping at the national level) identifies it as a core skill, and it is reflected in the MOE (Ministry of Education) framework for 21st Century Competences. At the Singapore Polytechnic (SP), collaboration skill is one of our graduate attributes. To hone collaboration skill, many educational institutions incorporate collaborative exercises and teamwork projects as learning experiences for students. While such learning activities increase the opportunities for team interaction, putting students in a group does not necessarily lead to the development of teamwork skills. To effectively develop teamwork skill, teamwork learning activities need to be carefully designed and integrated throughout the course. Empirical studies have shown that teamwork skills improved after students were systematically given explicit teamwork instruction, opportunities to practise teamwork skills and formative feedback on their teamwork skills across their curriculum. This paper describes how teamwork skills development and measurement is holistically and systematically supported and developed in SP. The journey starts with an educational innovation project by an academic staff which led to a small-scale pilot project in AY20/21 before scaling to an institution-wide roll-out to all students joining SP in the AY23/24. The goal of this teamwork project is twofold: firstly, to develop teamwork skills systematically over a three-year diploma course, and secondly, to obtain psychometrically reliable and valid teamwork scores to inform the development of teamwork skills in SP students, leading to the award of a Teamwork Metric at graduation. The metric enables the quantification and evaluation of collaborative performance, providing a critical foundation for assessing and improving teamwork skills within an educational setting.