Post-secondary career school educational leaders are charged with formulating sufficient, ongoing, and effective faculty development programming to ensure the delivery of quality education in their unique trade-expert led institutions. Classroom observations, which include substantive feedback exchanges from trained personnel are well documented as an evidence-based practice; yet, further research was recommended in new settings to expand what is known about the perceptions and experiences of personnel who engage in this key development practice. The purpose of this research was to obtain an in-depth understanding of career school class observation practice and the perceived effectiveness of that practice as performed by career school trade experts. Faculty development and constructivism theories formed the framework for this multiple case study. A purposive sample of three schools, from a U.S. based National Career School (NCS) chain, formed the units for analysis and one observer plus two instructors from each site formed a participant base of nine career school educators. Data were collected through face-to-face interviews and on-site observations. Data were coded and analyzed using a constant comparative approach, and the use of NVivo software aided in the identification of themes. The researcher found that NCS career school trade-experts engage in a classroom observation practice that aligns with evidenced-based methods; and despite the lack of pedagogical expertise, the practice is experienced in the career school setting as structured, purposeful, ongoing, and effective. The emergent themes related to practice effectiveness were (a) prescriptive institutional formats, (b) feedback focused on teaching techniques, and (c) sustained practice. Findings are useful for school practitioners charged with forming an effective classroom observation practice as a component of their faculty development program. Recommendations were made to (a) repeat this multiple case study with another cross-section of career schools to further verify emergent themes; (b) construct a qualitative study to compare the effectiveness of the observational instruments; and (c) conduct a longitudinal study to observe the impact of increased and sustained observation practice. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]