Ep 107 — Keeping Good Teachers is Simple with co-authors Jessica Holloway and Carrie Bishop

Summary of Ep 107 — Keeping Good Teachers is Simple with co-authors Jessica Holloway and Carrie Bishop

by Tammy Musiowsky

25m•May 5, 2026
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Overview of Minimalist Educator Podcast — Ep. 107: Keeping Good Teachers is Simple

In this episode, Tammy Musiowsky speaks with co-authors Jessica Holloway and Carrie Bishop about their book Make Your School Irresistible: The Secret to Attracting and Retaining Great Teachers. The conversation focuses on teacher retention, school culture, and practical leadership moves that help schools attract the right people and keep them engaged. Their central message: retaining great teachers is less about expensive initiatives and more about trust, relationships, clarity, and strong systems.

Key Themes and Main Takeaways

  • Teachers stay when they feel seen, heard, and valued

    • The guests emphasized that retention is strongly tied to whether teachers feel respected, trusted, and connected to their school community.
    • A sense of belonging and shared purpose matters more than perks or superficial incentives.

  • Teachers leave when they lose voice or growth opportunities

    • Common reasons for leaving included:
      • feeling powerless or unheard
      • lack of trust
      • no clear path for professional growth
      • a disconnect between the school’s promises and reality

  • Culture is the real driver of retention

    • School culture—not just strategy—determines whether teachers choose to join, stay, or leave.
    • Leadership and staff all contribute to shaping that culture.

  • Retention should be actionable and affordable

    • The book is designed to help leaders make meaningful changes that do not require extra funding or outside control.
    • The focus is on what school leaders can influence directly.

The Book’s Framework: Invite, Invest, Inspire

Jessica and Carrie explained that their three-part framework reflects the life cycle of a teacher’s experience at a school:

Invite

How schools attract people in the first place:

  • communicate clearly who you are as a school
  • build visibility through events, recruitment efforts, and social media
  • make sure your identity matches what you actually offer

Invest

How schools support teachers once they arrive:

  • provide onboarding and mentoring
  • create clear systems and structures
  • ensure teachers have the resources and support they need
  • listen carefully to feedback and adjust when needed

Inspire

How schools encourage people to keep going, even if they move on:

  • affirm their contribution
  • leave them with a positive, growth-oriented experience
  • support ongoing purpose and professional momentum

Systems, Identity, and School Fit

Systems Matter

The guests stressed that strong systems help schools:

  • create consistency
  • reduce person-dependence
  • make good practices repeatable
  • support smoother onboarding and collaboration

When systems are missing, leadership feels it quickly.

School Identity Attracts the Right People

A major part of retention starts with being honest and clear about:

  • your mission
  • your values
  • your priorities
  • what kind of school you really are

They shared examples of teachers choosing schools because the school’s identity aligned with their passions, such as English language learners or performing arts. They also noted that some teachers leave when they discover the school is not what they were led to expect.

Fit Matters More Than Selling

A recurring point was that schools should not over-promise to attract candidates.

  • It is better to be transparent and attract the right fit.
  • If a school misrepresents itself, it may create early turnover and damage reputation.

Leadership Advice: Listen Carefully and Build Shared Ownership

Carrie, now serving as a head of school, emphasized the importance of slowing down and listening:

  • really listen when teachers come to you
  • pay attention to what is said and what is not said
  • respect that teachers often use their limited time to bring concerns forward
  • follow up consistently

The guests also noted that when school leaders involve the right people in problem-solving:

  • the best solutions are often already in the building
  • people feel trusted and valued
  • solutions become more sustainable because they are created collaboratively

Pare Down Pointers

Jessica’s Pointer

Prioritize the people who help solve problems.

  • The right voices in the room often lead to the best solutions.
  • Shared problem-solving builds ownership and sustainability.
  • Many solutions cost nothing; they simply require restructuring or rethinking processes.

Carrie’s Pointer

Culture is everything.

  • “Culture eats strategy for breakfast.”
  • Everyone contributes to culture, not just formal leaders.
  • The way teammates show up affects whether others want to join and stay.

Notable Insights

  • “When teachers feel seen and heard and valued, they stay.”
  • “We’re all better collectively than anybody in isolation.”
  • “The solution to your problems is already in your building.”
  • “It’s not something that someone with a certain leadership role does — it’s something we build together.”

Bottom Line

This episode makes a clear case that keeping great teachers is not mysterious: it comes down to trust, clarity, belonging, and thoughtful systems. Jessica Holloway and Carrie Bishop argue that schools become “irresistible” when they know who they are, support their people well, and intentionally build a culture where teachers want to do their best work.