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A Quick Note to Listeners:
Before this week’s interview, Will Parker and Jen Schwanke take some time to answer a listener question. This week’s question is:
I want to say yes to new opportunities outside my building without neglecting my first commitments to my school. Is it possible to do both?
Listen in to hear their response!
Meet Erika Bare & Tiffany Burns:
Tiffany Burns and Erika Bare are veteran educators and co-authors of Connecting Through Conversation: A Playbook for Talking with Students.
Tiffany brings more than two decades in education — from teaching at the elementary, middle, and high school levels, to instructional coaching and serving as an elementary principal before taking time to teach and support educators nationwide as part of the Connected Communicator movement.
Erika Bare has spent over 20 years in education as well, including roles as a special education teacher, administrator, and currently as a district leader committed to helping all students reach their potential. Together, they blend deep classroom and leadership experience with practical communication tools that help adults build stronger, more connected relationships with students.
They joined us on Principal Matters: The School Leader’s Podcast in Episode 369 to share insights from their work and strategies that empower leaders and educators to handle tough conversations with care and confidence. Now, they are authors of the new book, A School Leader’s Playbook for Tough Conversations.
Understanding the Challenge of Tough Conversations:
Tough conversations often create anxiety for school leaders, leading to sleepless nights and lingering stress. Tiffany Burns notes that, while most educators enter the profession to serve students, it is often the adult conversations — with staff, caregivers, and colleagues — that feel most complex and emotionally charged. In their book, Burns and Bare provide concrete strategies to help leaders prepare intentionally, reduce uncertainty, and approach conversations with purpose rather than avoidance.
The Importance of Relationship-Building:
A central theme of the conversation is the importance of building relationships long before difficult conversations arise. Erika Bare emphasizes the need for leaders to systematize relationship-building by intentionally scheduling regular check-ins and informal connections with staff. Simple habits — such as dedicating the first part of the day to walking classrooms and engaging in brief conversations — help staff feel seen, valued, and supported.
Will Parker reinforces this idea with the reminder: “Our systems support our habits.” When leaders prioritize relationship-building in their calendars, those behaviors become sustainable rather than reactive.
Strategies for Effective Communication:
Burns and Bare share several practical strategies for reducing tension and increasing clarity during tough conversations. One example involves responding thoughtfully when someone seeks immediate feedback or resolution. Instead of dismissing the concern or rushing a response, leaders can say:
“This conversation is important, and I want to give it the time it deserves. Let’s schedule a time to talk more.”
This approach honors the person’s concern while creating space for a more focused and productive conversation.
Another powerful strategy is the intentional use of supportive language. Bare highlights the impact of simple questions such as, “How can I support you?” This communicates empathy and helps leaders better understand what type of support is truly needed — whether emotional reassurance, problem-solving, or simply being heard.
Overcoming Obstacles to Communication:
Despite best intentions, school leaders often struggle to sustain these practices amid constant demands and crisis-driven work. Burns acknowledges how easily proactive relationship-building can slip as the school year intensifies. The solution, however, is not perfection — it is consistency and accountability. Leaders must protect their calendars, recommit to intentional habits, and recognize that meaningful connections are not optional extras but foundational leadership work.
Conclusion:
Tough conversations do not have to be overwhelming. When leaders invest in relationships, communicate intentionally, and build supportive systems, difficult moments become opportunities for trust, growth, and clarity. By applying these practices, school leaders can transform anxiety-producing conversations into meaningful moments of connection and leadership impact.
If you want to connect with Erika Bare and Tiffany Burns, you can learn more about them at their website.
