My earliest memories of learning are from conversations with my mother. I was homeschooled, and these took place at the kitchen table and at the grocery store and just about anywhere else. In 9th grade, I had the great opportunity to attend a classical, liberal arts high school. Fortunately, “going” to school felt less foreign when the format felt so familiar. Each day, we experienced some new shared phenomenon—a text or a lab or a mathematical problem or a philosophical idea—before being expected to engage it through conversation. This has always felt right to me.
The primary medium by which tradition is passed from one generation to the next is the word, whether written or spoken, but this transmission has never been simply unilateral. The strength of humanity is in the power of conversation around the things we transmit—discussion and debate as a way ofhonoring the past, engaging the present, and discerning for the future. Government has worked best when it rested not on the strength of arms, but on the strength of argument. As a colleague of mine noted, the thing missing from our national political conversations today is the presence of authentic conversation. Instead, we find politicians speaking over each other, hoping only to achieve a newsworthy soundbite.
“When I am contradicted,” says Montaigne in On the Art of Conversation, “it arouses my attention, not my wrath. I move towards the man who contradicts me: he is instructing me. The cause of truth ought to be common to us both.” The ability to step outside our own perspective and listen carefully is fundamental to learning. In conversation, the goal is not to win from an entrenched opinion. Rather, we should attempt to understand the perspective of our interlocutor.
We should first reach for clarifying questions before dogmatic assertions; to work from a first principle rather than unquestioned presumption; to entertain nuance and to preserve respect. Faith in the common pursuit of truth allows us to approach an issue from different perspectives. This approach refines and brings clarity to both perspectives.
In my career teaching, as well as recruiting and developing teachers, authentic conversation has remained at the core. As a teacher, I sat among 22
seniors huddled in an old movie theater comparing their study of limits in calculus to the theology of Aquinas. For these students, the discussion was not just an intellectual exercise—it united them in their very humanity. Training and coaching educators has simply been an occasion to serve as a conversational midwife, and it is no surprise that our headmasters will often say that the best interviews with teacher candidates will feel more like good conversation. There is a shared common love, but also a shared spirit of inquiry. Developing the skill of conversation during conflict is one of most sought-after areas of growth for new leaders. When exposed to more audiences and even deeper levels of conflict, the demand for effective listening tools becomes even more necessary. Strong leaders identify the need to be good counselors who navigate the waters of emotion and trust in order to produce healthy communities.
Indeed, whether the setting is the kitchen table, the classroom, or a congressional hall, our best work together is forged through human conversation—places where there is a shared common love, but also a shared spirit of inquiry. Our tradition demands that we listen carefully and contribute to the conversation. Our greatest responsibility for the next generation is to create the freedom for them to carry that tradition forward.
Jerilyn Olson is the Chief People Officer of Great Hearts, overseeing recruitment, human resources, and professional. She has worked for the organization since 2005, beginning as a teacher. She has a bachelor’s degree in Government and Literature from Claremont McKenna College and a master’s degree from the University of Dallas. She and her husband have three children and reside in the Phoenix area.