This evaluative case study explores how mentors or coaches, called Associates, support beginning in-service teachers in developing reflective teaching practices, as well as which practices are most effective in supporting beginning teachers. Using a definition of effective reflective practice and a tool for gauging progress toward becoming a reflective practitioner taken from previous research, researchers conducted an evaluative case study of one Associate and two beginning teachers across two school years. Findings suggest Associates should meet beginning teachers where they are on the reflective continuum. Implications include that Associates need meaningful professional development to support teachers in growing as reflective practitioners.