Modern microscopy systems allow researchers to generate large volumes of image data with relative ease. However, the challenge of analyzing this data effectively is often hindered by a lack of computational skills. This bottleneck negatively impacts both research reproducibility and efficiency, as researchers frequently rely on manual or semi-automated analysis methods. Interactive image analysis workshops offer a valuable solution, equipping researchers with the skills and tools needed to automate image processing tasks. In this paper, we share our experiences and best practices from conducting such workshops, which emphasize the use of open-source software like ImageJ, FIJI, and Python-based tools such as JupyterLab and napari. We discuss key considerations for workshop design, logistics, and outcomes, while highlighting common pitfalls to avoid. Using two recent workshops as case studies, we also present strategies for optimizing participant engagement and learning. Our insights offer practical guidance for planning and conducting image analysis workshops and serve as a starting point for researchers looking to establish similar training initiatives and enrich their local imaging communities.