Reflections from Sintelle Taylor

Meet Steppingstone’s First Executive Director

A 30th Anniversary Conversation with Sintelle Taylor

Sintelle Taylor still remembers being pitched on joining a new venture called Steppingstone. The then college counselor loved the idea of giving more underserved kids a path to higher education, but she couldn’t help but wonder if it was viable. Time would tell.

Three decades later, The Steppingstone Foundation’s first executive director gets emotional whenever she reflects on those early days. Making the idea a reality became one of the most all-consuming work experiences of her life. It took her across boundaries and into a space of challenging deeply rooted conceptions about race and class.

“The joy of my life has been working in this space we call diversity,” says Sintelle.

In the years since, she’s gone on to have a multifaceted career. When it comes to Steppingstone’s trajectory, “I’ve been overwhelmed by its success but not surprised,” she adds.

After its co-founders, Michael Danziger and John Simon, won her confidence, Sintelle signed on in 1990. While she originally had the title of director of programs, “we all wore different hats, and many of them,” she says with a laugh.

She dove almost immediately into helping recruit the first class of Scholars. Part of the challenge was “how to get families to buy into the notion.” She’d worked within communities of color in her days in college admission at UCLA, her alma mater. But she insisted to Mike that she was the right person to go into every corner of Boston, from Roxbury to Charlestown.

With Mike by her side, she helped families to see how the founding vision aligned with their own dreams for their children. By fall, an inaugural class of 14 Scholars had taken the leap, and she met weekly with each Scholar and every family.

As part of an early focus on measurable change, the team tested all Scholars upfront to have a baseline. In their elementary school, many had found success and motivation in earning top grades, but they lagged behind students in the schools for which Steppingstone aimed to prepare them. “There were so many things that they didn’t know yet,” Sintelle adds. Steppingstone teachers went to work instilling essential “how to” skills such as studying, writing papers, and asking for help.

Steppingstone Scholars, circa 1992

It’s a story that mirrored her own. Growing up in South Central Los Angeles, she’d attended struggling urban schools. Her grades masked the fact that she was being left behind. Attending an academically rigorous high school in suburban Carson opened a new world to her. “Straight A’s in South LA and straight A’s in Carson were night and day,” she notes. “When I walked into AP English class, my teacher was talking a whole other language.” It gave her a chance to “remediate myself,” but it took being very honest with her teachers–and with herself–about the challenges.

Through it all, she never forgot what her grandfather told her. “Getting an education is the most important thing you can do. No one can take that away from you.” He had a 4th grade education; her grandmother had made it through 9th grade. They proudly saw Sintelle go on to earn her bachelor’s and then her master’s in educational psychology at UCLA.

After studying and working there, she came east to Boston, lured by a job as director of college counseling at the Middlesex School. She was only its third employee of color. As the year unfolded, she realized how controversial her hiring had been. Amid the contentiousness, she found inspiration in working with students of color who “naturally gravitated” toward her.

As she focused on supporting students, her conversations with Randolph Carter, then director of multicultural services for the National Association of Independent Schools, provided her with wisdom and support. Fortuitously, he also introduced her to Mike and John. While they’d turned to him for guidance, he ended up uniting them with a powerful partner.

To Sintelle, they each had “absolute hearts of gold.” With his idealism and giving nature, Mike “became a brother to me,” she says. John was just as generous, committed, and compassionate. Like her, “they both wanted to be a presence in the children’s lives and to see equity in the world.”

She saw herself in so many of the kids. She felt that they deserved the same kind of opportunity that she had received. Her goal was “to provide them with the skills and resources that they needed to be successful,” she says. Ultimately, “that’s what builds true confidence.”

Sintelle and family enjoy youngest son’s graduation

From 1991 to 1994, Sintelle took on the role of executive director, helping to establish a solid base from which Steppingstone would grow. After deciding to return home to her native California, she shifted to doing multicultural assessment programs for companies, working largely with boards and C-suite executives. “Now they call it DEI,” she notes. Eventually, she reconnected with Randolph Carter and found herself on the East Coast again, working in diversity and inclusion.

For the past 15 years, she’s contributed her leadership as chair of the board of Legal Outreach, a New York City-based nonprofit that, similar to Steppingstone, “seeks to level the educational playing field for minority, low income, and first-generation students.”

Together with her husband, Sintelle also started investing in small community businesses, often making “emotional investments” in the ideas of friends. Along the way, she ended up starting a business of her own, a catering company. One of her favorite memories is of catering an event for then Senator Barack Obama. The encounter sparked a promise on which he followed through: catering an event at his presidential inauguration.

More recently, she’s watched her two sons graduate from college and begin pursuing their own career dreams. Her oldest has thought of devoting himself to DEI work. As she says knowingly, “the work can get a grip on you.”

All smiles for 2020 grad school honors

As she celebrates Steppingstone’s 30th anniversary, she says that she didn’t think of longevity as a goal in its first years. “As long as the needs existed, I thought we’d be there.” The pandemic has brought to light many of the ongoing inequities that students face today. It’s heartbreaking for her to see the entrenched nature of the challenges. “While we’ve come a long way, we still have a long way to go,” she says.

Pondering the course of her life, she cites a favorite line from Harper Lee: “She was powerful, not because she wasn’t scared but because she went on so strongly despite the fear.”

To Sintelle, “that describes my life journey.” She’s a survivor. At every place along the way, including her formative time at Steppingstone, “I did what I was called to do.”

Whatever the future holds, “I’m always that girl from South Central.”