Adaptive expertise represents the combination of both efficient problem-solving for clinical encounters with known solutions, as well as the ability to learn and innovate when faced with a novel challenge. Fostering adaptive expertise requires careful approaches to instructional design to emphasize deeper, more effortful learning. These teaching strategies are time-intensive, effortful, and challenging to implement in health professions education curricula. The authors are educators whose missions encompass the medical education continuum, from undergraduate through to organizational learning. Each has grappled with how to promote adaptive expertise development in their context. They describe themes drawn from educational experiences at these various learner levels to illustrate strategies that may be used to cultivate adaptive expertise. At Vanderbilt University School of Medicine, a restructuring of the medical school curriculum provided multiple opportunities to use specific curricular strategies to foster adaptive expertise development. The advantage for students in terms of future learning had to be rationalized against assessments that are more short-term in nature. In a consortium of emergency medicine residency programs, a diversity of instructional approaches was deployed to foster adaptive expertise within complex clinical learning environments. Here the value of adaptive expertise approaches must be balanced with the efficiency imperative in clinical care. At Mayo Clinic, an existing continuous professional development program was used to orient the entire organization towards an adaptive expertise mindset, with each individual making a contribution to the shift. The different contexts illustrate both the flexibility of the adaptive expertise conceptualization and the need to customize the educational approach to the developmental stage of the learner. In particular, an important benefit of teaching to adaptive expertise is the opportunity to influence individual professional identity formation to ensure that clinicians of the future value deeper, more effortful learning strategies throughout their careers.