This study compares two tools used to observe and assess how teachers support student learning: the LEGO Foundation's Engage tool, formerly PLAY, and the World Bank's Teach Primary tool. The goal was to evaluate their similarities and overlaps in their measurement of teaching practices. Nine experts reviewed both tools in detail, carefully matching items from PLAY to those in Teach Primary. Results indicate that about one-third of the items are closely matched, showing that PLAY is built on a solid framework to capture engaging teaching practices. Another third of the items did not have a precise match, meaning each tool separately captures unique aspects of teaching that the other does not. The study also looked at how well the scores of the two tools aligned using accurate classroom data from Ethiopia, Peru, and Sierra Leone. The results showed a small positive relationship between the two tools, meaning they measure related but different aspects of teaching. The study also found that how PLAY is structured may need some adjustments to reflect better the skills it is designed to measure. By combining expert opinions with data analysis, this study provides strong evidence that both tools are valuable but serve different purposes. The findings highlight the importance of using multiple approaches to assess teaching quality. The study also offers recommendations for improving tool improvement and suggests the following steps on how classroom observation tools can help support improved teaching and learning worldwide.