A Bold Experiment in Women’s Leadership

by Ann Green and Kathleen Calabro

Great leadership and personal growth have always been intertwined. Drawing from our distinct backgrounds—Kathleen as Managing Partner and former Product Officer, and Ann's as a mental health practitioner and life coach—we recognized how rare it was to find spaces that truly honored both dimensions. So we created one—a place where women leaders build deeper connections while pursuing their ambitions. In this space, professional challenges and personal aspirations aren't separate conversations—they're part of the same powerful journey.

So here’s our story…

In 2024, we set this experiment in motion—not just to create another professional development program, but to build something fundamentally different. A space where women could bring the full complexity of their professional and personal lives into the conversation, engaging in open, honest dialogue that fuels both personal and professional growth.

We combined our distinct yet complementary expertise: Kathleen’s extensive experience building and scaling high-performing organizations, and Ann’s deep understanding of human emotional development and group processes. Together, we convened a group of women who met bi-monthly, forming a community where accomplished professionals and emerging leaders alike could share vulnerable moments and co-create new ways of leading—at work, in their relationships, and in their lives.

What we’ve witnessed has been both inspiring and unexpected. We’ve seen members step into their confidence, make bold choices, and navigate workplace challenges with fresh perspectives. We’ve watched relationships shift—both at work and beyond—and a new kind of leadership take shape: one that isn’t confined to a title or hierarchy but extends in all directions, influencing teams, peers, and personal lives alike.

Lessons Learned: Insights From Women Across Industries

A key element of our experiment was bringing together women from diverse industries and career stages. This turned out to be one of the most surprising and impactful aspects of our group. By connecting women from fields as varied as technology, healthcare, education, the arts, and finance, alongside those at different points in their professional journeys, we created a uniquely rich environment for learning, connection, and growth.

This diversity fostered a dynamic exchange of ideas, exposing members to perspectives they might not encounter within their own industries. For example, a tech leader was able to learn from the patient-centered approach of a healthcare professional, just as a nonprofit grant writer gained fresh insights from a corporate strategist. These cross-industry dialogues sparked creativity, challenged assumptions, and expanded the range of possibilities for addressing individual member’s professional challenges.

Equally powerful was the mix of women at different career stages. Aspiring leaders benefited from the experience and wisdom of accomplished professionals, while those further along in their careers found renewed purpose and inspiration in the fresh perspectives of emerging talent. This mutual exchange created a feedback loop of learning and growth, where every member had something to give and gain.

By intentionally curating a group with this level of diversity, we saw how shared experiences can bridge differences and create a collective intelligence far greater than the sum of its parts.

From Competition to Collaboration

One of our earliest revelations was about competition. Through our members' stories, we gained a visceral understanding of how deeply ingrained the narrative of competing for limited seats truly is. A product manager in tech described the relentless pressure in her workplace, where promotions were dangled like carrots, fueling intense competition and unsustainable work hours. In an industry where women are underrepresented and constantly pressured to prove their value, the few women in her field often found themselves competing against one another—vying not just for advancement, but for validation of their worth.

This pattern surfaced again in the experience of a strategy and innovation executive at a regional bank, who described working with a female leader who struggled to manage other women effectively. The scarcity mindset—driven by the limited opportunities for women—can fuel competition rather than foster collaboration, reinforcing cycles that hold women back instead of lifting them up.

A breakthrough moment occurred in our group when a nurse took a risk and openly shared her doubts about her value in her role. The product manager, moved by this openness, found herself sharing her own struggles for the first time. This exchange sparked a deeper conversation about how women can sometimes undervalue their own contributions—and, in turn, what they have to offer. It underscored what’s possible when we create environments that foster openness over competition—where women can support each other, rewrite the narratives they’ve internalized, and find new ways to navigate challenges together.

Discovering New Ways of Leading

As our sessions progressed, we noticed a pattern that challenges traditional leadership narratives. While most professional development focuses on climbing the organizational ladder, we’re uncovering a more nuanced form of leadership—one that emerges in everyday interactions, in the way we show up in relationships and conversations, and in how we influence across all levels of an organization, regardless of title or position.

One member’s experience brought this insight into sharp focus. As a teacher in a test-score-driven environment, she initially felt her values clashed with her administration’s singular focus on standardized results. Through our group discussions, she began to see leadership as an alternative to frustration and silent opposition—recognizing that her stance not only affected her supervisor and peers but also shaped how they perceived her. With support, she made a shift: she stayed true to her values of helping students thrive while finding ways to engage more constructively with her administration’s priorities. This approach—understanding organizational context and aligning with stakeholders’ goals—has transformed her relationships and deepened her impact at work.

Reimagining Mentorship

Traditional mentorship often follows a top-down model, where a senior leader guides a junior colleague within the same industry. We’re building something more dynamic—where mentorship isn’t limited by hierarchy or field but instead thrives on cross-industry learning and shared experience.

For example, when a bank executive shared her story of navigating unexpected career turns, it sparked a discussion on embracing non-traditional paths and finding confidence in unique journeys. Likewise, a grant writer launching her own business while managing financial pressures has found this form of mentorship invaluable. Instead of generic advice, she’s gaining actionable strategies from women at different career stages and industries—insights on building credibility, sustaining momentum, and growing her business.

This kind of mentorship—rooted in collective wisdom rather than industry-specific assumptions—creates a shared knowledge base that benefits everyone, helping women lead, adapt, and grow in new ways.

The Power of Collective Growth: Creating New Possibilities Together

Perhaps our most striking discovery is how women transform when they begin viewing challenges through a collective lens rather than an individual one. Members often arrive questioning their worth, decisions, or right to ask for more. Through group support and collective wisdom, these doubts often transform into clarity and conviction.

What started as an experiment is evolving into something powerful: a space where authentic connection meets professional growth, where vulnerability becomes a strength, and where women find not just support but transformation.

If you’re curious about joining this evolving community, we meet via Zoom twice a month for facilitated sessions blending business leadership expertise with emotional growth. Each session is structured to ensure both immediate practical value and long-term development.

To learn more about joining our next cohort, we invite you to visit our registration page!