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Taking on Tomorrow
Answering the Call of Leadership: Meet Cohort X Lead Cheryl Kaʻuhane Lupenui
June 11, 2025
Photo of Cheryl Ka‘uhane Lupenui, one of her mentors, Puanani Burgess, and Pua's daughters.

Cheryl (right) with Puanani Burgess (front), Pua’s daughter Pua‘ena, and Puni Jackson in 2018. Photo courtesy Cheryl Ka‘uhane Lupenui.

“When are you going to be Lehua?”

Cheryl Ka‘uhane Lupenui says that’s one of the many unforgettable questions that she was asked by one of her mentors, Puanani Burgess. As a part Native Hawaiian woman that grew up on the continent, Cheryl says she used to be embarrassed by her middle name—Lehua—which her parents picked out a book as a way of giving her a connection to her Hawaiian culture.

“When people asked if ‘L’ stood for ‘Lynn,’ I said yes.” she admits.

By the time Cheryl had moved to Hawai‘i Island to become president and CEO of The Kohala Center in 2017, Pua had gotten to hear Cheryl share the story of her name many times. But, as great mentors often are, Pua was curious to know more. And so, shortly after the move, Puanani asked Cheryl that unforgettable question.

“I think she knew that I was going to be able to unpack the story of ‘Lehua’ because of the relationship of ʻōhiʻa lehua [to Hawai‘i Island]” Cheryl reflects. “I have planted ʻōhiʻa lehua, I have seeded ʻōhiʻa lehua, I have a relationship with her. And I didn’t know that at the time when she asked me.”

“That’s the beauty of an unforgettable question,” Cheryl says. “It just lives with you, to be answered over and over as you learn from it. As a guiding question, that’s what’s leading me. I love that question because it reminds me who and where I come from.”

Photo of ‘ōhi‘a lehua on Hawai‘i island

A lehua blossom that “lives” up the stream from Cheryl on Hawai‘i Island. She says she continues to build relationships with this particular ‘ōhi‘a lehua.
Photo courtesy Cheryl Ka‘uhane Lupenui


"When someone expresses a value for Hawaiian culture, I get excited about what’s in store for them in this journey because I know from experience how magical that can be.”


A Transformative Conversation

In addition to providing her leadership to The Kohala Center, Cheryl has been the co-facilitator of Hawai‘i Leadership Forum’s Omidyar Fellows Cohort IX alongside Bill Coy. Cheryl also designed and facilitated leadership sessions for the first Cohorts of the Omidyar Fellows program. In fact, it was a series of conversations between Cheryl and Bill back in 2010 that helped forge a new path for her leadership career.

“Bill contacted me while he was doing his research to put together what has become this amazing Omidyar Fellows program and curriculum,” she remembers, “and I just appreciated the chance to dive deeper into the understanding of leadership with someone who is equally as passionate about the topic and also shares that same desire to make an impact in Hawai‘i.”

Through their exchange, she came “to the realization that I preferred being in the leadership development space.” She would ultimately leave her role as CEO of the YWCA to start her own indigenous leadership practice in 2011, The Leader Project.

Photo of Bill Coy and Cheryl Ka‘uhane Lupenui

Cheryl with Bill Coy, former director of the Omidyar Fellows program and creator of its model

“I remember someone once telling me that ‘what makes a lawyer is not their law degree, but their law practice,” she says. “And so, when I thought about that in the context of leadership, it resonated with me—that what makes the leader is the practice of leadership.”

Cheryl will also serve as lead for the upcoming Omidyar Fellows Cohort X.

“The Leader Project and Hawai‘i Leadership Forum have evolved over these past fourteen years, but our commitment to Hawai‘i as leaders remains a constant thread. And the Omidyar Fellows program is an important opportunity to lead from Hawai‘i for Hawai‘i.”


“It’s not about what I can do for Hawai‘i. It’s about what Hawai‘i can do for the world. Leading is a collective act, so we need strong relationship practices. Hawai‘i can teach us that.”


A Magical Journey

Being born and raised on the East Coast through high school, Cheryl says she was raised to be “very independent,” which then followed her into the field of leadership.

“It turns out that doesn’t actually make for a good leader!” she laughs.

“Hawaiian culture is very relationship based,” she explains. “It’s a relational culture and values interdependence,” while “my Western training and leadership was very focused on the individual.”

Until she was a teenager, her dad, Harry Denis Ka‘uhane, was the primary connection to her Hawaiian culture. She moved to Hawai‘i after high school and had to navigate being Hawaiian in a place where she was not born and raised.

“I quickly learned how little I knew about my culture,” she says, “so I understand how it feels to be uncomfortable and out-of-place here [in Hawai‘i].”

She immersed herself in Hawaiian culture. She joined a hālau hula. She built up her understanding and fluency in Hawaiian language. She cultivated a love for lei making. “These Hawaiian cultural practices were part of my every day, and there was a point where I realized that I was experiencing another approach to leadership through Hawaiian cultural practices.”

“As you start building and deepening your relationships with a place, you start taking on more responsibility for that place. And at some point, you’ll find that you’re part of a community.” She adds, “I think belonging to a community we learn to not just bring our own gifts, but as leaders, to also create the space where all the community’s gifts are generously given and received.”

Photo of Cheryl Ka‘uhane Lupenui and members of Omidyar Fellows Cohort IX at Hoʻoulu ʻĀina.

Cheryl with Fellows from Cohort IX at Hoʻoulu ʻĀina during their capstone.


“...what makes the leader is the practice of leadership.”


Because of her unique experiences, it has also become important for her to create ways for others to connect to Hawaiian culture. “When someone expresses a value for Hawaiian culture, I get excited about what’s in store for them in this journey because I know from experience how magical that can be,” she says.

“It’s not about what I can do for Hawai‘i,” she says. “It’s about what Hawai‘i can do for the world. Leading is a collective act, so we need strong relationship practices. Hawai‘i can teach us that.” She adds “the Omidyar Fellows program is one of those places where we are bringing multiple cultural approaches together. Each stands separately and can be interwoven for a stronger whole while not losing a culture’s identity. We can learn both and be more effective as leaders.”

“I appreciate others who want to learn from Hawai‘i, especially when they are committed to apply what they’ve learned in Hawai‘i,” she adds. “From a Hawaiian lens, leadership comes out of community. So, if you’re building that beloved community and you hear the call to lead from your community, then it’s your kuleana to step into that and answer the call.”


This story appears in the May & June 2025 issue of Taking on Tomorrow.


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