The article examines the tensions one superintendent in the USA experienced as he evaluated principals in a high-stakes environment that had undergone numerous transformations at the central office. Using qualitative methods, primarily, shadowing techniques, observations and debriefing, the following tensions emerged and were examined in light of the work of the superintendent evaluating principal performance: (1) discrepancies between principal performance when compared to performance data, (2) length of time in the principalship compared to results, (3) finding the right balance between student achievement data and other indicators of principal performance, (4) what types of achievement data are important and when these data are made available, (5) credence paid to complaints about structural changes implemented by the principal, (6) balancing the principal self-evaluation rating scores with the final evaluator scores and (7) accounting for personal factors such as relationship to principals and knowledge about principal capabilities. Each of these tensions contributes to the difficulty a superintendent may feel when conducting the principal evaluation process.