Navigating the Coaching Landscape and Fostering Community through PeerSphere

By LeeAnne Lavender, PeerSphere Storyteller

Empowering educators and leaders through coaching, Samantha Chesler has become a driving force in the PeerSphere community by leading two impactful peer learning networks: coaching in education and women in leadership. From her unique journey to her values-led coaching philosophy, Samantha’s story is one of passion, purpose, and community building.

Journey to Coaching: From the Classroom to PeerSphere

Samantha’s international education journey began in 2007 when she ventured overseas. In the years since then, she has worked in nine different schools; it was during her last five years of teaching in Singapore when she made the pivotal decision to transition from full-time teaching to become a coach.Β 

“It was a big decision,” she reflects. β€œI miss the camaraderie of being in a school community, but I have reached out to so many people and have found a community that’s all over the world. It’s amazing to work with educators in so many different places.”  

In addition to working independently, Samantha is also a member of the team at Making Stuff Better (MSB), a UK-based organization that places coaches in schools and offers coaching programs for educators. In her private business, she extends her coaching expertise to life coaching, making a significant impact on schools from the outside.

Samantha’s coaching philosophy revolves around values-led leadership. She believes in leading from a point of view grounded in one’s values.Β 

“What we do is one thing, but the way we show up, the way we are, is crucial,” she emphasizes.Β 

Coaching in Education: Bridging Gaps and Transforming Schools

Samantha met PeerSphere co-founder Michael Iannini in 2019 when he came to Samantha’s school in Singapore.


β€œI was in the first cohort of teaching and learning mentors in my school, and Michael came to coach us,” remembers Samantha. β€œWe really connected and would hop on a zoom and chat every now and then. Then I met Ewen and connected with the peer learning communities. It’s been wonderful to engage with the PeerSphere networks.”

In Samantha’s Women in Leadership PeerSphere peer learning network, Samantha collaborates with co-host Claire, using coaching tools and exploring techniques like the Polaris method for goal-setting and values awareness. The goal is to empower women leaders, addressing challenges such as self-doubt, confidence building, and the ability to own their positions and use their voices.

The Coaching in Education Peer Sphere network is diverse, catering to individuals at various coaching levels. Samantha facilitates discussions on versatile topics which recently included the art of listening and how this skill can be taught to tutors, students, and teachers.Β 

Having seen over a thousand students pass through her life as a teacher, Samantha brings a unique perspective to coaching. She identifies gaps in the education system, aiming to address the shift towards productivity and results over building community and nurturing students’ human skills.

The Coach Approach: Making an Impact

Samantha’s coaching journey has been reinforced through hosting PeerSphere sessions. She sees hosting as a way of extending her coaching skills and expertise with even more people.Β 

“It’s about the work and the impact. I go into every session thinking, ‘What do I want people to feel like coming out, and what tools do I want people to have to use tomorrow?'” she shares.

Samantha’s commitment to the coach approach is evident in her efforts to grow the CoachUp conference in Singapore. Her mission is clear: to invite more people into coaching experiences and to foster safe spaces for empathy, self-awareness, and values-led leadership.

β€œIn some ways, my two PeerSphere communities are overlapping because the coach approach is so versatile,” says Samantha. β€œOne of the biggest things about coaching is to pause and be in a relationship with a listener. I am there to listen and ask. I am a mirror and I can reflect back what I’m hearing.”

As Samantha continues to impact education and leadership from the outside, her story serves as an inspiration for those seeking transformative change in the educational landscape.


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