Having Hard Conversations: Five questions to consider

May 14, 2025

Read Jennifer's latest article on NASSP (National Association of Secondary School Principals).

Excerpt:

Hard conversations are an inherent part of school leadership. More often than not, as a principal or an assistant principal, you will engage in hard conversations, and you will need to do so in productive ways. Speaking with clarity and courage and addressing difficult situations both humanely and directly is a part of your day-to-day work.

Five questions to ask yourself before having hard conversations with faculty and staff can help you have useful and productive hard conversations with greater chances of success. These questions cannot be asked and answered within a short period of time, and some of the answers need collective action at your school. Yet, if you move toward making these questions more common and more considered, the chances of having hard conversations with positive results will increase.

These hard conversations go beyond speaking up when truly unsafe actions are taking place, such as drug or alcohol abuse, mental health issues, or anything that creates unsafe working conditions. These hard conversations focus on implementing strategic goals, curricular initiatives, teaching standards, job descriptions, and living out the norms of collaboration to foster a positive culture of learning and ensure the well-being of all who work at your school.

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Jennifer Abrams

About Jennifer Abrams

Jennifer has been recognized as one of "21 Women All K-12 Educators Need to Know" by Education Week's 'Finding Common Ground' blog. She considers herself a "voice coach," helping others learn how to best use their voices – be it collaborating on a team, facilitating a group, coaching a colleague, supervising an employee and being an all around better human being in all types of interactions.

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    Praise for Jennifer

    “A thousand things are unspoken, implicit, buried in our educational lives. The invisibility of issues enforces the ineffective status quo. Change–personal, educational, institutional–requires that we speak OUT LOUD about what we know and believe. Jennifer Abrams brings decades of experience and years of training across the world to this usually overlooked essential act of finding our effective voice about what matters around learning.”

    Eric Booth, renowned art educator and author of Tending the Perennials: The Art and Spirit of a Personal Religion and The Everyday Work of Art: Awakening the Extraordinary in Your Daily Life