The National Staff Development Council recommends that principals devote 10% of the school budget and 25% of teacher time to professional development (PD). While PD requires time, it is crucial that the time be organized, carefully structured, and purposefully led to avoid the waste of human and financial resources. Despite the millions of dollars spent on professional development nationally, student learning outcomes continue to stagnate or dwindle, discipline issues continue to skyrocket, and teacher moral plummets. This may be due, in part, to leaders paying little attention to learning transfer. Culture plays a key role in one’s ability to learn because learning is a social endeavor. Because our schools worldwide are more and more diverse, professional development that is grounded in culture is paramount for educators whose goal is to improve learning outcomes for all students. Because attending professional development does not necessarily equate to the implementation of knowledge or skills, this conceptual paper proposes a Culturally Proficient Professional Development (CPPD) framework that includes a Multidimensional Model of Learning Transfer (MMLT). The MMLT and its rubrics aim to be culturally responsive tools that school leaders in PK-12 schools can use to organize, deliver, and assess professional development offerings while also enhancing learning transfer and improve educators’ cultural proficiency. Considering culture as the main enhancer or inhibitor to transfer is innovative and useful because schools spend large amounts of money and resources on PD, yet the money invested does not often produce the desired outcomes.