The 21st century educational landscape has changed the way schools undertake instructional supervision and assessment. Technological developments paved the way for a shift in skills requirements from learners which is termed as 21st century skills. This study utilized a comprehensive literature review to investigate the current issues and concerns in instructional supervision and assessment. It also determined conditions that would make these processes effective vis-à-vis the needs of the current times. The study showed that there is a need for a collaborative and trust-based type of supervision. There should be regularity, continuity, and quality in supervision with a provision for adequate funding and capacity building. For instructional assessment, a HOTS-based assessment in conformity with international assessment standards is appropriate to the current times. An online or e-assessment should also be considered.