Engaging professional adults in an online environment is a common challenge for online instructors. Often the temptation or commonly used approach is to mirror face-to-face strategies and practices. One premise of this study is that all strategies used in an online environment are assessment strategies, and as such should be considered for their value in measuring student experiences. This research study investigated student responses within a principal preparation course to the use of twelve assessment strategies that included: work samples, "Twitter" summaries, audio recordings, traditional papers, screencast/videos using "YouTube", group projects, open discussion, paired discussion, response to video, field experiences, quizzes, and interviews. The redesigned course used in this research allowed the researchers to experiment with both traditional and innovative strategies within an online environment to determine how students perceive the value of each assessment strategy. Student experiences were measured in terms of level of enjoyment, level of engagement, and the extent to which students believed the assessments would result in the creation of knowledge that could be transferred to future professional practice. The results indicate that students prefer assignments that are less traditional and which fully incorporate the technological tools available.