2025 Timely Challenge Conference | Learning Journeys

Speaker: Thad Persons, The Westminster Schools

This interactive workshop equips school leaders with approaches to build sustainable talent pipelines in today’s challenging recruitment landscape. Participants will explore data-driven strategies to identify, attract, and secure exceptional educators who align with their school’s mission and culture. Participants of this workshop will learn how to

• Develop proactive recruitment systems that extend beyond traditional posting-and-waiting
  methods.
• Leverage your school’s unique value proposition to stand out in a competitive market.
• Create strategic partnerships with teacher preparation programs and professional
  networks.
• Implement innovative technologies and platforms to streamline the recruitment process.
• Design authentic candidate experiences that showcase your school community.

Speaker: Kerry Ann Masoner

This workshop reimagines teacher onboarding as a comprehensive, year-long journey rather than a brief orientation event. School leaders will explore an approach from Ensworth School to designing immersive experiences that accelerate new faculty integration, confidence, and effectiveness while establishing foundations for long-term retention.

The session examines

• Frameworks for mapping a strategic onboarding timeline that addresses practical, cultural, and pedagogical needs across the entire first year.
• Strategies for distributing onboarding responsibilities across various school stakeholders to create a “whole community” welcoming experience.
• Methods for gathering feedback and measuring onboarding effectiveness to drive continuous improvement.

Through discussion, interactive exercises, and collaborative problem-solving, participants will assess their current onboarding practices and identify strategic opportunities for enhancement. School leaders will leave with an onboarding blueprint and practical tools to transform their approach from basic orientation to comprehensive integration—creating the conditions for new teachers to quickly acclimate to a new role and school, develop meaningful connections, and fully contribute to the school’s mission.

Speaker: Meredith Monk Ford, Snails to Ducks

This workshop guides school leaders in developing a comprehensive “Portrait of a Teacher” framework that defines and cultivates the essential competencies, mindsets, and values that drive educational excellence in your unique school community. Participants will explore how a clearly articulated teacher portrait can transform recruitment, professional development, and retention practices.

The session addresses

• Methodologies for identifying and articulating the core competencies that align with your school’s mission and cultural context.
• Strategies for involving key stakeholders in creating a shared vision of teaching excellence.
• Practical approaches to embedding these competencies throughout the employee lifecycle—from job descriptions and interview protocols to evaluation and growth planning.
• Frameworks for designing differentiated professional learning experiences that nurture these competencies at various career stages.

School leaders will leave with practical meeting tools and sample agendas that can be readily implemented within their schools, a clear outline of a strategic process for initiating this work in their own context, as well as valuable resources designed to support productive conversations with both faculty members and school leaders.

Speaker: MaSheena Johnkins, Woodward Academy

This workshop empowers school leaders to transform their recruitment approach from passive posting to proactive marketing that attracts exceptional educators. Participants will explore how strategic branding, targeted messaging, and innovative outreach can position their school as the choice for top-tier teaching talent.

The session covers

• Developing a compelling school brand narrative that differentiates your school in the competitive talent market.
• Crafting authentic messaging that speaks to what exceptional educators truly value in their professional experience.
• Leveraging digital platforms, social media, and professional networks to expand your recruitment reach.
• Building strategic partnerships with universities, professional organizations, and alumni networks to access high-quality candidate pools.

Through discussion and collaborative strategizing,  school leaders will audit their current recruitment marketing efforts and understand targeted campaigns for priority hiring needs. Participants will leave with practical tools for elevating their school’s visibility and innovative strategies to attract candidates.

Speakers: Kristy Lundstrom, The Mount Vernon School, and Matt Neylon, The Mount Vernon School

As generational shifts reshape the expectations of today’s workforce, school leaders must evolve how they lead, support, and grow their teams. This interactive workshop explores what different generations value in the workplace and how those insights can inform more responsive, inclusive leadership practices. Participants will examine key trends impacting talent in education, learn how to craft a compelling and adaptive employee value proposition, and walk away with practical strategies to build leadership capacity that resonates across generations and sustains organizational vitality.

Speaker: Cara Gallagher, Cara Gallagher Consulting

Employee turnover in schools rarely happens overnight. Research shows it’s a process—one deeply tied to culture, leadership behaviors, and emotional workload. Drawing on the latest findings from the field of Organizational Psychology, this session will introduce school leaders to evidence-based tools for understanding the early warning signs of staff attrition.

We’ll explore how to move beyond basic engagement surveys toward a proactive strategy that combines better data, strategic workforce planning, and preventative measures available. Special attention will be given to creating an employee listening program—how schools can effectively track, measure, and assess “leaving signals” before they turn into departures. Participants will leave with practical ideas to strengthen culture, increase retention, and create healthier, more resilient schools.

Speaker: Dr. Kara Loftin, The Schenck School & ReadSource

This workshop explores how strategic mentorship programs can serve as powerful retention tools in independent schools. Participants will discover how thoughtfully designed mentorship initiatives not only support new teachers, but also create meaningful growth pathways for experienced educators seeking leadership opportunities.

The session examines

• Research-based mentorship models that foster teacher satisfaction and longevity.
• Frameworks for identifying and developing teacher-leaders within your existing faculty.
• Practical approaches to structuring mentor relationships that benefit both participants.
• Methods for integrating mentorship into professional development and career advancement.
• Strategies to measure mentorship impact on school culture and retention metrics.

Through case studies and discussion, school leaders will gain actionable insights for implementing or enhancing mentorship programs that strengthen faculty engagement and commitment.

Speakers: Dr. Tiffany Russell, The Galloway School, and David Peden, The Galloway School

This workshop explores how school leaders can cultivate a professional community where educators feel deeply connected to the school’s mission and valued as integral members of the community. Participants will examine research-backed approaches to building faculty engagement that extends beyond traditional retention strategies. Through interactive exercises, school case studies, and collaborative problem-solving, leaders will identify specific opportunities to strengthen their school’s culture of belonging by addressing

• Frameworks for developing inclusive decision-making processes that honor teacher expertise.
• Practical approaches to celebrating contribution and fostering professional fulfillment.
• Techniques for measuring and responding to engagement metrics to sustain positive culture.

Participants will leave with a purpose and agency that can be implemented immediately to enhance faculty satisfaction and commitment.

Independent schools are in the ultimate people business, with up to 80% of operating budgets devoted to salaries and benefits for the faculty and staff who deliver your mission every day. For this reason, a compensation system capable of attracting and retaining mission-driven employees is critically important to the health and stability of your school. Each school is unique, and the challenges and opportunities they face based upon their size, demographics, and geography will all affect their compensation strategy. Join this session to understand NBOA’s recent analysis of compensation systems within independent schools and explore the innovative ways schools are aligning their compensation systems with their missions and strategic priorities. Discover essential factors that must be considered when making changes to your school’s compensation and begin to explore the possibilities available to your school based upon your unique needs.

Speaker: Sheri Burkeen, SAIS

You asked for more relevant, actionable data—we listened. Join us to explore how Meridian delivers regional insights, including exclusive findings from our 2025 Annual Benchmarking Survey on teacher compensation. Discover SAIS’ comprehensive roadmap for delivering the meaningful data you need for informed leadership and how these resources will support your school’s operational excellence in the years ahead.

This workshop provides independent school leaders with a comprehensive overview of recent and upcoming changes to employment law that directly impact independent school operations. Participants will gain clarity on legal developments and practical guidance for implementing compliant policies and practices.

The session covers

• Recent federal and state legislative changes affecting employee classification, compensation, and benefits.
• Evolving legal standards for hiring practices, including background checks and interview protocols.
• Updates to leave policies, including family and medical leave requirements.
• Emerging workplace accommodation considerations in independent school settings.
• Best practices for documentation and policy revision to mitigate legal risk.

This workshop translates complex legal developments into actionable steps for school leaders. Participants will leave with a clear understanding of priority compliance areas, practical tools for policy review, and strategies to balance legal requirements with school culture and mission. This session is designed to help schools protect their institutions while creating fair, transparent, and legally sound employment practices.

This workshop addresses one of the most pressing challenges facing independent schools today: providing competitive compensation packages that include meaningful benefits and housing solutions within realistic budget constraints. School leaders will explore innovative approaches that schools are successfully implementing to attract and retain quality faculty despite rising living costs.

The session examines

• Creative benefits packages that extend beyond traditional health insurance and retirement plans to address faculty priorities.
• Successful housing assistance models, from on-campus residences to community partnerships.
• Cost-effective strategies for schools of varying sizes and financial resources to enhance their total compensation offerings.
• Collaborative approaches with other schools, local organizations, and community partners to expand housing options.

Through case studies of successful programs, collaborative problem-solving, and discussion, participants will identify realistic opportunities to enhance their school’s benefits and housing support. School leaders will leave with a list of strategies, partnership models, and implementation frameworks that can be adapted to their unique community context and budget realities—enabling them to compete more effectively for exceptional educators while maintaining fiscal responsibility.

Speakers: Russ Connell, Bayside Academy, and Dr. Michael Neel, Vanderbilt University

In this session, we bring together key scholarly literature on teaching-learning and practical on-the-ground practitioner experience in teacher engagement. Drawing on extensive scholarship in teaching-learning and decades of experience in independent schools, this workshop offers a practically grounded and theoretically sound approach to analysis of classroom practice and instructional coaching conversations with teachers.

Speaker: John Allman, Carney, Sandoe & Associates

This workshop introduces school leaders to polarity management as a powerful framework for navigating the inherent tension between faculty autonomy and institutional coherence. Participants will learn how to move beyond viewing these forces as either/or priorities and instead harness their interdependent nature to strengthen school culture.

The session explores

• Understanding polarities versus problems and why traditional problem-solving approaches often fall short when addressing complex organizational dynamics.
• Exploring the specific benefits and limitations of both faculty independence and mission alignment.
• Identifying warning signs when your school culture has overemphasized one pole at the expense of the other.
• Creating structures that honor teacher agency while advancing shared institutional goals.
• Approaches that help faculty understand and navigate this polarity productively.

Through discussion and examination of case studies, school leaders will be invited to explore practical ways to address this and other tensions that impact teacher fulfillment and retention. Participants will leave with actionable strategies for achieving workable balances within this and other polarities.

Speaker: Julie Bianchi, The Out-of-Door Academy

This workshop challenges independent school leaders to reimagine their approach to hiring and evaluation by aligning both processes around core traits that define exceptional team members. Participants will explore how creating consistency between recruitment criteria and performance assessment leads to stronger faculty culture and improved retention.

The session will explore

Identifying and defining the specific character traits and competencies that make educators thrive in your unique school environment.
Designing interview questions and evaluation tools that effectively measure these crucial attributes.
Creating rubrics that provide clarity and transparency in both hiring and growth conversations.
Building assessment processes that reinforce your school’s values and mission.
Implementing feedback mechanisms that nurture development of these essential traits.

Participants will leave with actionable strategies to enhance faculty quality and engagement by maintaining a consistent focus on the attributes that matter most for their school community.

Speaker: Marsha Little, Carney, Sandoe & Associates

This workshop reimagines professional goal setting as a catalyst for authentic growth rather than an administrative requirement. School leaders will explore approaches to creating goals that energize educators and advance institutional excellence. In this session we will

• Explore frameworks for crafting individualized goals that balance personal passion, professional growth, and school priorities.
• Discuss strategies for shifting from evaluation to growth-oriented coaching conversations.
• Share methods for connecting individual objectives to broader departmental and school-wide initiatives.

Leaders will leave with conversation guides and implementation strategies that transform goal setting from a perfunctory process into meaningful conversations for continuous improvement that enhances both teacher retention and student learning.