The endeavor to support creative and innovative activities within the construct of testing, grading, and rewarding in a standardized, reliable, and equitable way is a significant challenge for every subject. Technology education supports the development of a critical and inquisitive disposition (Williams 2011), yet one can question the capacity to effectively and validly measure the capabilities that enact this disposition. This chapter highlights the importance of integrating professional judgment as a means of supporting a more effective assessment of the evidence and actions that allude to the characteristics of a technologically capable person. The chapter discusses the proximal and distal effects of using adaptive comparative judgment (ACJ) as a means of judging evidence of capability so as to demonstrate the validity of the assessment method while supporting the pragmatic requirements of formal education. The chapter also discusses critical aspects of the impact assessment practices have from the perspective of the teacher and the student. The chapter concludes by presenting ACJ as a central approach to effective assessment “as” learning.