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

Headspace: Dr. Autumn Graves

June 6, 2024·40 min·1 clip

A mentor gives advice; a coach asks questions to help you figure it out yourself.

Rebecca Malachy-Meslin and Lynn Macheskey open with women in leadership. They bring confidence, imposter syndrome, new responsibilities, authentic leadership, and the work of reaching goals into the same conversation, which gives the episode its steady pace. The guest stays practical throughout. When mentoring comes up, the guest says clear expectations matter because they help each person understand what can be offered and what cannot, especially when the request is still undefined. That point lands cleanly. Rebecca and Lynn keep the back-and-forth focused on leadership that does not stay abstract, and the conversation stays anchored in the realities of headship and board meetings. Role models follow. Dorothy Hutchinson, who was the head of Nightingale Bamford in New York City, is the first name that comes to mind, and her example carries through the rest of the exchange. The setting matters. The guest recalls meeting Dorothy in 2002 at the Heads Network's Women's Leadership Center seminar at Miss Porter's, an event described as an incredible weekend and one the guest has been fortunate enough to join as faculty more than once. Lynn has attended too. What makes the seminar feel powerful is the evening session, when each head tells a piece of the road to headship and lets the room hear how that role arrived in real life. Dorothy's story stands out. She described her first year of headship, said she was exhausted after her first board meeting, and then let the room see that she was also pregnant with her first child. Both details stay present. The episode does not smooth those facts into polish, and that choice gives the story its weight, because the job appears as something physical, demanding, and shaped by ordinary limits. The tone stays warm. Rebecca and Lynn keep the conversation collegial as they move through mentoring, role models, confidence, and the ways women measure themselves against the example set by others. It never rushes. By the end, the show leaves confidence looking like something built through clear expectations, lived experience, and women who are willing to tell the truth about how a headship begins.

As heard by us

A practical leadership conversation on mentoring, expectations, and confidence in independent-school life.

Confidently You stays true to its mission with a focused discussion of women in leadership, imposter syndrome, new roles, authentic style, and confidence.

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Why you'd press play

You get a calm, candid look at leadership confidence shaped by mentorship, role models, and a first year of headship.

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