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In an increasingly polarized society, navigating polarization is endemic to U.S. educational leaders ‘futuring’ positive change, challenging some leaders. Leveraging a Vertical Development lens, this study investigated educational leaders’ conflict experiences. Data included a Subject-Object Interview to understand participants’ vertical development stages and conflict experiences, triangulated with MyWorldView leadership profiles. Analysis included scoring Subject-Object Interviews for vertical developmental perspectives and grounded theory analysis of Subject-Object Interviews to unearth conflict experiences. MyWorldView was AI-assed through Global Leadership Associates. Findings suggest that leaders navigating conflict from earlier stages described working to develop inner fortitude and burning out in heightened conflict situations, while developmentally mature leaders described forging connections across differences during conflict and mentoring others. Implications include supporting leaders’ vertical development.