According to Biggs' theory of constructive alignment, when designing and delivering a course (not only of entrepreneurship) educators should consider a coherence between the learning outcomes, the teaching and learning activities and the assessment practices. Assessment in this context is defined as an educational practice serving to fill the gap between the desired outcomes and what the student has actually achieved; not only is assessment essential to promote learning in students, but also permits teachers to reflect on and enhance their programmes. This chapter concentrates on how to assess a sense of initiative and entrepreneurship (SIE) among students, in educational settings. It will do so by drawing on literature of key competences and entrepreneurial education. The key finding is that assessment cannot be a 'one size fits all' process, but should be tailored to the institution and environments, with the active collaboration of the stakeholders. The final part of the chapter shows three best practices of entrepreneurial education in Ohio with a focus on assessment and the development of the SIE questionnaire for the evaluation of the way teachers educate for a SIE. Keywords Assessment • Entrepreneurial education Sense of initiative and entrepreneurship • Key competences Competence-based education This chapter explores the relevant literature on assessment through three streams: the assessment of competence, the assessment of key competencies and the assessment of entrepreneurial education. Within this scope, assessment is different from evaluation; while the former implies the learner's appraisal, the latter refers to the appraisal of providers, training methods or educators. The first section presents competence assessment with a suggested switch from psychometric to edumetric approaches, and the second describes the assessment of key competencies. In both assessments of competence and key competencies, formative assessment ('for' learning) plays a key role. The third section continues with the assessment of entrepreneurial education at secondary and tertiary level, with the literature evidencing an existing gap in assessment practices especially at secondary level. In enterprise, education forms