It is clear that educators rely on a variety of instructional methods to change learners’ behaviors. What is less clear is how distance learning educators can foster deeper and more meaningful learning by taking into account a learner’s unique background, experiences, competencies, learning styles, personality type, and levels of self-directedness. This is a challenge for those educators wishing to create a learner-centered instructional environment at a distance. How can educators avoid the trap of “teaching to the middle,” providing materials that are too challenging for some learners and too simple for others? How can educators identify learners’ dependency level/self-directedness?