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Human interactions across settings shape young people’s learning and development, and building adult expertise in facilitating productive interactions takes deliberate practice and reflective experience. However, relational practices are not consistently part of adult learning for those who work with youth. We describe a 2-year design study to develop the Simple Interactions Leadership Program, a professional learning workshop focused on relational practices. We refined the program across 3 iterations with library and after-school staff (with a total of 41 participants). Iterative changes included adding participant-driven “try-it-out” projects, adding external accountability features, and combining staff from the library and after-school sectors. Using artifacts and memos from workshops and participants’ reflections, we found that these features incrementally improved participants’ engagement, depth of learning, and sense of professional community—which we suggest are three central goals for related professional development efforts. As a collective youth-serving field, we need effective and scalable ways to help adults recognize and strengthen their relational practices with young people. The Simple Interactions Leadership Program offers a flexible structure for professional learning focused on building expertise in relational practice while sustaining change and improvement through continuous reflection within communities of practice.