Groundswell is New York City’s leading community public arts organization that engages artists, underserved, marginalized and economically disadvantaged young people, and community members in creating visible and permanent change in some of New York City’s most challenged neighborhoods. Over its 18-year history, Groundswell has employed thousands of artists, youth, and community members in the creation of upwards of 500 works of public art throughout all five boroughs of New York City. To make this happen Groundswell works with ‘Teaching Artists’ who build relationships with community partners and participating youth, families, and neighbors. Groundswell has invited us to engage these Teaching Artists in a process of reflecting on their own work and collaboratively developing a set of community engagement methods and strategies to improve their capacity to do this important work with New York City neighborhoods, youth, families, and partnering organizations. Students from The New School have been facilitating a community building process with Groundswell to collaboratively develop, implement, and document community engagement methodologies with teaching artists. As facilitators, the students have listened, observed, interviewed, and met with the community partner staff, participants, and community members. The goal has been to gain a deeper understanding of Groundswell’s work, concerns, hopes, and needs. The featured case studies below showcase: (a) multimedia elements recorded during the sessions with teaching artists; (b) external resources for teaching artists in the field, and (c) tools for sustaining the teaching artist community at Groundswell and the teaching artist as an individual. [Access details to the knowledge base can be found in the Appendix.] The work employs participatory methods of engagement such as strategic questioning, interviews, Groundswell project observations, deep listening, “code” development, and the co-creation of the knowledge base between teaching artists and our group. We implemented dialogues, ice breakers, guided self-reflection, and radical visioning activities.