her mission is simple:
To help people show up with intention, speak with clarity, and lead with empathy—one conversation at a time.
The Voice Behind Conversation Compass
Esther Charlestin is the founder and Chief Conversational Guide of Conversation Compass LLC, a consulting firm that helps organizations navigate complex communication challenges and build cultures of trust and connection. With skill in strategic planning, facilitation, and human-centered leadership, Esther supports schools, nonprofits, and mission-driven teams through tailored consulting and transformative dialogue.
A sought-after keynote speaker, Esther delivers talks that spark reflection, challenge assumptions, and inspire action, drawing from her lived experience as an educator, public servant, and working mom. Whether guiding conversations or speaking from the stage, her work is rooted in empathy, equity, and the power of communication to drive lasting change.
From Campus Leadership to Consulting: Esther’s Professional Journey
Before founding Conversation Compass in 2023, Esther built a rich and varied career in educational and organizational leadership. She served as Dean of Climate & Culture at Middlebury Union Middle School, where she led school-wide behavior systems and coached staff to foster inclusive, student-centered environments. At Middlebury College, she worked as Assistant Director of Community Standards, overseeing the student conduct process and advancing restorative practices across campus.
Earlier in her career, Esther held key student affairs roles at Middlebury College and Bryant University, where she developed diversity and inclusion programs, mentored students, and supported them through academic and personal challenges. Her leadership extended beyond programming—she managed complex projects, coordinated cross-functional teams, and oversaw budgeting and strategic planning within her consultancy and institutional roles.
Esther holds a Master of Arts in Communication, Corporate Communication & Public Relations from Sacred Heart University and a Master of Arts in Teaching. She is also a graduate of the Vermont Leadership Institute and EMERGE Vermont, a political leadership program for women.
Work with esther
Partner with Esther to create spaces where dialogue leads to real impact.