Teaching outdoor education, or leading outdoor recreation experiences, often involves teaching people how to perform certain skills. The quality of this instruction can become critical if the skill level of students has the potential to influence the students' level of safety and well-being, or their ability to focus on other learning objectives (see, Thomas, 2005). However, many outdoor leadership training pathways do not involve the formal study of motor skill acquisition. Also, physical education teacher training programs may not teach skill acquisition principles in ways that are specifically adapted to outdoor leadership settings. Skill performance in outdoor education may involve different timeframes, environmental circumstances may influence what counts as a skillful performance. In an outdoor leadership setting the definition of a skill might be highly practical or functional rather than normative. Suffice to say, it would seem that further consideration of skill acquisition principles may enhance the preparation of outdoor leaders. The terms outdoor leaders and outdoor leadership are deliberately used in this paper because they are inclusive of both outdoor education and outdoor recreation practice. In one of the few papers focusing on motor skill acquisition in the outdoor education literature, Higgins and Morgan (1997) provided a good example of how a potentially flawed understanding of skill instruction led to a common, but poor, instructional practice in a kayaking instruction context. They described how some instructors were taking a shortcut and teaching the pawlata roll to beginner kayakers so they could experience success in re-righting a capsized kayak. However, the pawlata roll requires a change in the kayaker's grip on the paddle, places less emphasis on the important role of hip-flick, and encourages an over-reliance on the paddle to re-right his or her kayak. Hence, the ultimate goal of developing a reliable and effective kayak roll that works well while paddling on the river is sacrificed in order to provide quick results.