Focusing on the problems of assessing the speaking skills of secondary school students, this paper provides one example of how those problems were addressed in the Massachusetts speaking assessment. The paper identifies four requirements for measures of speaking skills: (1) feasibility, (2) reliability, (3) validity, and (4) freedom from bias. The discussion of these requirements is followed by a general discussion of issues related to developing measures of speaking skills. The paper concludes with a description of the Massachusetts speaking assessment and with data on the reliability, validity, and bias of the assessment instruments. (Author/FL) Primary type of information provided by report: Procedures (Theoretical).