Within the Wexner Foundation’s professional mentoring program, which has paired over 300 seasoned alumni of Wexner fellowships with newer ones for a year-long mentoring relationship, a small but steadfast group of alumni have chosen to volunteer not once but repeatedly, returning year after year to guide emerging Jewish leaders. 

In conversations with our volunteers who have said yes to mentoring more than three times, we’ve found that their reasons differ but a throughline emerges: mentorship guides the mentee, but it also renews the mentor. This give and take is an act of gratitude, continuity and service, and it’s a way of ensuring that Jewish leadership remains grounded in reflection, empathy and purpose.

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Giving back and paying forward

Many mentors describe mentoring for other alumni as a natural continuation of their own leadership training fellowship experience. A Florida rabbi who has mentored multiple times says he sees it as a way of extending the same generosity and intellectual companionship that once shaped him in the active stages of his Wexner leadership training. His own leadership, he notes, was profoundly influenced by those who helped him think deeply, ask better questions and lead with authenticity and he wants to pay it forward.

For one Virginia federation professional, who has served as a mentor four times in a decade, the motivation is rooted in gratitude and community. Having benefited from Wexner’s network and values, she considers mentoring an opportunity to “give back forward.” She describes the work as “holy listening,” meeting mentees where they are and helping them find clarity and confidence. Participating in this program multiple times is her way of saying “thank you.”

This impulse to reciprocate has become a defining feature of Wexner’s alumni community. It is rooted in their deep appreciation for being part of the Wexner professional community, and the Wexner Foundation’s deep and ongoing investment in our most important asset: our alumni. It also reflects a shared understanding that leadership isn’t only about vision or execution; it’s about sustaining others on their journeys.

Coaching, not consulting

Several mentors emphasize that effective mentoring is not about giving advice but rather helping mentees find their own answers. They come in with a “coaching mindset” centered on inquiry, not instruction, asking open-ended powerful questions, helping mentees clarify goals and encouraging reflection.

One New York-based educational leader focuses on drawing insight from the mentee’s experience. She often begins sessions with “What’s working?” — a deceptively simple question that orients the conversation toward strengths and agency. Her approach reminds mentees that growth is nonlinear and that self-awareness often precedes strategic clarity.

In a similar vein, one Colorado rabbi frames mentoring as an act of listening, not leading; for her, the mentor’s task is to provide space for self-discovery rather than direction. She describes her role as “a guide who helps others navigate their own paths.” Initially hesitant to mentor, she came to see the practice as a form of relational leadership, one that values attentiveness, empathy and humility. Listening, in this view, is not passive: it’s a professional skill that can transform how leaders relate to their teams, boards and communities. Mentoring becomes a laboratory for that skill, offering a contained space to practice deep listening before applying it in the wider organizational world. 

One executive at a Jewish nonprofit in New York, who has mentored multiple times in the program, believes that reflection is what transforms mentoring from conversation into growth. He encourages mentees to engage in structured reflection, through writing or dialogue, at the end of a cycle. This, he argues, helps capture insights and sustain growth beyond the formal relationship. This aligns with a broader recognition that leadership development isn’t a one-time event but an ongoing discipline of awareness and adjustment.

A Michigan leadership consultant adds to this framework by emphasizing assessment and feedback, advocating for mentees to incorporate professional development tools — 360-degree evaluations, strengths assessments — into the mentoring process. These tools, she says, can help mentees identify blind spots and leverage their natural leadership capacities. 

These ideas reflect a broader cultural shift in leadership mentoring from transferring expertise to facilitating learning. Emphasizing curiosity and empowerment over advice-giving, these methods align with contemporary coaching frameworks and are nurtured by our mentoring and coaching expert Michelle Lynn-Sachs, who serves as a consultant for this program. 

Mentorship is a relationship

Across interviews, mentors consistently describe their relationships with mentees as deeply personal yet professionally grounded. These mentors highlight the importance of adaptation, knowing that each mentee requires a different rhythm, style and level of challenge. While a mentorship can include structural elements like goal setting and follow-up between meetings, the relationship should also be allowed to also evolve organically.

One mentor focuses on vulnerability as a prerequisite for growth, encouraging mentees to bring their full selves into the conversation. She notes that progress often depends on the mentee’s willingness to be honest about uncertainty, self-doubt, and ambition.

For another, a successful mentor-mentee match is one where “you can feel the growth in the room” — a dynamic that benefits both mentor and mentee. Mentors often report that the experience refines their own leadership, reminding them to slow down, listen better and lead with greater intention.

One of the program’s quiet strengths, several mentors observe, is its capacity to bridge divides across the Jewish professional ecosystem. Working in education, congregational life, college campuses, philanthropy and nonprofit management, mentors and mentees often come from different sectors, creating unexpected partnerships that generate fresh ideas and new perspectives. 

Several mentors interviewed note that these cross-sector relationships foster empathy and collaboration, reminding participants that Jewish leadership is collective rather than competitive. Additionally, they appreciate that they can stay current on the pulse of the Jewish world through the diverse experiences of their mentees. 

Renewal and commitment

When asked why they continue to mentor, the repeat participants also speak of renewal. Each new mentee brings new insights and perspectives. It allows mentors to stay connected to emerging voices and evolving workplace norms. Many mentors find that their mentees’ questions help them stay grounded in purpose.

Far from a one-sided act of giving, mentoring becomes a reciprocal exchange. Each generation sharpens the leadership skills of the other, and in doing so rediscovers its own relevance and hope.

The Wexner mentoring program’s success lies not only in its thoughtful structure, but in the generosity of alumni who continue to invest their time and wisdom. The Wexner Foundation invests deeply in its growing alumni community; and in turn, the alumni invest in the community as well. They demonstrate that leadership is not defined solely by vision, but by the willingness to walk alongside others as they find their own. Its core remains simple: one leader sitting with another, listening, questioning and helping light the path ahead.

For the mentors who keep saying yes, that act of accompaniment is not a duty but a joy. And in the process, they model the essence of enduring Jewish leadership: learning, guiding and growing together.

Or Mars is a vice president of the Wexner Foundation.