When Jenna Howell, Owner and Senior Instructor at Contour Pilates, first sat down with Nanette Hill, 2024/25 Executive and Pilates Instructor, she didn’t start with small talk. She asked Nanette directly, “How can I show up for you in ways that matter this year?”
For Nanette, that question set the tone for a partnership defined by exactly what a leader like her needs: accountability, listening, and shared growth.
The Legacy Leadership Project brings together Executives, Upstanders, and Emerging Leaders to form a web of mutual support. Within this relationship, Executive Nanette Hill receives targeted guidance, different perspectives, and resources to strengthen her leadership journey from Upstander Jenna Sagraves, who brings valuable lived experiences and new ways of thinking about Nanette’s business into the relationship, things that Nanette’s Emerging Leader, Jenny Tham, Emory University, has expressed to be a guiding strength of their time this summer. After a summer of shared learning and real-world exchange, Nanette and Jenna embody the spirit of the Executive-Upstander relationship, where perspective, leadership, and growth are built together.
The Impact of a Meaningful Relationship
Nanette describes her relationships with both Jenna and her Emerging Leader, Jenny, as teaching her consistency and accountability. Having others walk alongside her keeps her grounded in follow-through, especially when her own travel schedule and responsibilities make structure difficult. She explains that these connections remind her that leadership is not about working in isolation but about cultivating collaboration and trust.
“Building a relationship with someone like Jenna is an example of the right person at the right time,” Nanette said, “Her experience owning her own mindful movement-oriented business provides me with valuable perspectives that I may not have had the chance to develop on my own.”
For Jenna, the experience has shifted her understanding of leadership itself. “I wanted to connect in deeper, more meaningful ways and expand my understanding while giving back more to my community,” she expressed as she reflected on the idea that leadership was not about her individual drive but about showing up for others. By learning to listen to Nanette’s experiences and priorities, she has sharpened her ability to support, rather than lead from the front. Her Pilates studio background prepared her to value different perspectives, but the Upstander relationship has required even more “intentional listening and accountability,” allowing her to develop the “empathy and collaborative skills that are essential for effective leadership.”
Nanette has already witnessed an uptick in her leadership qualities within the Pilates studio and the entrepreneurial space. “These relationships have significantly enhanced my leadership experience by teaching me how to effectively delegate responsibilities and manage different types of working relationships,” she said. With Jenna and Jenny by her side, Nanette’s leadership style has positively impacted her interactions with clients, partners, and students through the refined flexibility and collaborative approach that she has incorporated into her practice.
Jenny, the Emerging Leader in this trio, highlights the one-on-one nature of her internship with Nanette as a unique strength. She notes that working so closely has given her deeper insight into what it takes to balance entrepreneurship, wellness education, and community leadership. From Nanette, she is learning the mechanics of classical Pilates and the importance of grounding work in history and culture. Jenny says, “I’ve become more business-savvy, more organized, and more aware of how leadership is both flexible and rooted in values.”
With Nanette’s travel and many responsibilities that whisk her away from her work, making space for chances to reflect on her relationship with her Upstander and her Emerging Leader is vital. Yet, Nanette views the flexibility it requires as a strength, and Jenny sees it as a chance to deepen trust. Both agree that navigating these challenges strengthens the foundation of their work together.
The Upstander Perspective
Jenna stepped into the Upstander program with a clear motivation: she wanted to build deeper, more meaningful connections and “give back to her community in a way that felt tangible.” Her respect for Nanette was a major driver, as she was eager to understand Nanette’s life experiences and Pilates journey more fully and support the important work she leads. Like Nanette, the timing felt right for Jenna. In a moment where authentic connection is needed more than ever, this opportunity allowed her to expand her own understanding while standing alongside someone she admires.
This experience is reshaping Jenna’s leadership in profound ways. She has learned that leadership is less about her own direction and more about being present for others. Listening more intentionally and creating space for Nanette’s priorities has helped her step back from her own agenda and lean into collaboration. Running her Pilates studio gave her early lessons in valuing different perspectives, but the Upstander role is teaching her to stretch those skills even further.
Her prior work in the Seeing Whiteness program helped her examine blind spots and habits she had carried since childhood, making her more aware of what it takes to listen fully and respond with empathy. Those lessons, combined with her day-to-day leadership of a team with varied experiences and backgrounds, gave her a strong foundation to show up for this partnership.
For Jenna, the strength of this work is in its reciprocity. She and Nanette are not approaching each other as mentor and mentee, but as partners committed to mutual aid and growth.
“Leadership isn’t about one person standing at the front,” she reflects, “it’s about making space for others to succeed.”
Mentorship in Action with Unwavering Support
Nanette describes Jenna as someone who brings both encouragement and practicality to the partnership. “She helps me think through ideas and offers tools that make running my business feel more manageable,” Nanette shared. “It feels good to know that someone is invested in my growth, not just in what I produce.”
The opportunity to walk alongside Nanette has been equally impactful for Jenna. “I admire Nanette’s vision and her commitment to her work,” Jenna reflected. “Being part of her journey has helped me reexamine my own leadership style. I’m learning that sometimes the most important role is simply to listen, give space, and trust the process.”
This mutual exchange has created a rhythm of support where Nanette gains clarity and resources, while Jenna strengthens her ability to step back and create room for another leader’s growth.
The Ripple Effect of Mutual Aid
“This isn’t a one-way street,” Jenna explained. “I’m gaining just as much as I’m giving. Supporting Nanette challenges me to grow in ways I wouldn’t have expected.”
The two continue to invest in their relationship with consistency and intention. Whether tackling the everyday demands of running a business or reflecting on broader lessons of leadership, they have created a space where accountability, support, and learning are shared. Their connection embodies the ongoing ripple effect of mentorship: leadership strengthened, perspectives broadened, and a commitment to building together.
The LOLA is their space for Growth and Connection
Programs like Legacy Leadership thrive at The Lola, where leaders and their allies find community, resources, and intentional space for honest conversations. The relationships between Executives, Upstanders, and Emerging Leaders are strengthened by this environment, one designed to spark both personal and professional growth.
Support The Legacy Leadership Project
The partnership between Nanette, Jenna, and Jenny shows how leadership expands when rooted in authentic relationships. Each person grows because of the others, and their growth ripples outward into the communities they serve.
You can help sustain these powerful mentorship experiences for our mission-driven leaders. Donations to the Legacy Leadership Executive Membership provide resources, professional development, and the network necessary to keep this work alive.
Interview Conducted by Jenny Tham, 2025
