Confidently You: Women in Leadership · Rebecca Malotke-Meslin & Lynne Macziewski

Confidence & Career Pivots

February 3, 2026·39 min

The conversation starts in familiar school leadership territory. Rebecca Malotke-Messlin and Lynn Macheskey talk about confidence as something women build while stepping into new roles, finding an authentic leadership style, and taking on more responsibility. Erin Riel comes in through career pivots. The excerpt catches the hosts noticing how her winding path fits together, then moves back to her work as chief operating officer at OneSchoolHouse. Middle leaders sit at the center of the conversation. Erin describes the OneSchoolHouse academic program as a tool academic leaders can reach for when a school has a problem that needs a creative answer right away. One email makes that real. An assistant head has a senior who may not be able to finish the year on campus, and the question becomes how that student can still complete coursework. The answer is not flashy. It is a practical virtual option parents may not know to ask for, but a school leader may need to serve a student well. Teachers matter here too. Erin explains that OneSchoolHouse teachers come from independent schools around the country, so the partnership also creates room for professional growth. The development work feels current and specific. Generative AI comes up through classroom questions about assessment, students, and what it means to teach with these tools now. Structure helps the creative work hold together. The classes use backwards design, which gives school leaders and teachers a clear framework. The hosts keep the tone collegial. They let the story wander a little, then pull out the leadership lesson inside it. The close stays tied to community. Erin points listeners toward upcoming conferences and four forums this winter and spring in Philadelphia, LA, Nashville, and Chicago, with the invitations connected to association and professional relationships. It ends warmly, with practitioners comparing notes on how confidence grows when leaders solve real problems with help, clarity, and patience.

As heard by us

A practical leadership conversation centered on confidence, structure, and support.

Erin Riel's conversation with Rebecca Malotke-Messlin and Lynn Macheskey follows a leadership path shaped by early turns, education choices, and a return to purpose.

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Why you'd press play

If you lead in schools and want a steadier way to grow into new roles, start here.

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