The Angst in Affluent Communities

Leading a well-resourced school system carries its own distinct set of stressors and demands for superintendents

When Betty Sternberg was superintendent of the Greenwich, Conn., school district, her efforts to close the achievement gap between white and minority students caused controversy in the wealthy system.

Well-heeled parents who objected to her proposals pulled out all the stops — lawyers attended school board meetings on their behalf and full-page advertisements in the newspaper protested her plans. Powerful parents questioned her credentials — even with a Ph.D. from Stanford University. One parent wondered aloud why “anyone who has any brains wouldn’t just go into finance,” recalls Sternberg, who served as Greenwich superintendent from 2006 to 2009.

“It was clear to me there was a sense of, ‘Who are you to tell us what to do with our kids? We are highly educated and could buy and sell you 100 times over,’” she says. “They equated power and money with what was most important.”

Varying Manifestations

Leadership of any school system is a difficult enough job with trials that put superintendents to the test personally and professionally. The popular perception around districts with plenty of resources tends to run to the contrary. Wealthy districts carry the financial resources to keep class sizes low, can purchase the latest instructional devices, provide various enrichment activities — and may not need to worry about a measureable concentration of economically disadvantaged children. Directing such a system, the notion goes, is infinitely easier than another type of school community.

In highly resourced districts, the challenges may not be as immediately obvious. These school systems can and do provide a tough test of leadership skills, says James Harvey, executive director of the Seattle-based National Superintendents Roundtable, which has 97 current superintendents as members.

At gatherings he organizes of superintendents from all types of districts, Harvey says, “the sense you get from the discussion is that they all share similar problems, but they manifest themselves in different ways.”

Urban districts may grapple with students trying street drugs, while wealthier districts may be fighting student vaping or the use of prescription pain killers. Low-income districts may scramble for budget dollars, but a resource-rich district may experience opposition from parents when trying to budget for equity or shift funding priorities that they think may detract from their children’s education.

Those same parents, however, can be a huge asset to well-off districts — raising money for extras, being active and involved on school councils and committees, using expertise and connections and pushing schools to operate at the highest level. But there’s a darker side, says Harvey. “What you hear behind the scenes is that in upper-income communities with very well-educated parents who are professionals themselves … (some of) the parents feel entitled, in some sense, to bully the schools.”

Achievement Pressures

The 9,100-student Greenwich school system, located about 35 miles north of midtown Manhattan, may be the poster child for how wealthy school districts can present grueling challenges for superintendent leadership. The district has had 14 superintendents or interim superintendents over the last 20 years. Some outgoing superintendents have cited toxic school board relationships and a politically charged environment as reasons for their departure.

After one of Greenwich’s superintendents resigned following less than two years on the job, the Greenwich Times asked: “What’s wrong with us? Why can’t we keep a superintendent?”

The Greenwich district is filled with high-powered and highly paid executives in the corporate and not-for-profit arenas who commute to New York City. Earlier this year, Blooomberg ranked the town of Old Greenwich, which sits inside the school district’s boundaries, as the 12th richest place in the country, with an average household income of $336,692.

In fact, many of the school systems that show up on lists of the wealthiest districts in the country have median household incomes near or over $200,000, according to an analysis released in August by GoBankingRates.

But these types of districts present other challenges beyond the expected entitlements that some superintendents describe among parents.

Student Stressors

Randall Booker is the superintendent of the Piedmont Unified School District in the San Francisco Bay area of California. Per-pupil spending is close to $15,000 for each of the 2,500 students, whose parents are likely to be old-money doctors, lawyers and CEOs, with some new-money tech entrepreneurs mixed in. Local taxes and parent fundraising boost the district’s budget by nearly 40 percent.

But Piedmont is grappling with a significant teacher shortage. Skyrocketing housing costs make it difficult to lure educators to the district, especially those with degrees that could earn them lofty salaries in the sciences or technology fields. “The cost of living in the Bay Area is so ridiculous,” Booker says. “How can you live here and live off a $55,000 teacher salary?”

The district is trying to raise $2.6 million to supplement teacher’s salaries. Booker waits to see whether the community will support that.

Piedmont’s superintendent of four years also has to deal with the mental health ramifications of undue pressure and stress on his students from unrealistically high expectations around grades and college admissions. The district invested in a wellness center staffed with a clinical supervisor and therapeutic interns to work with students in need of support. Therapy dogs visit during exam time to relieve anxieties. The district’s high school counselors try to celebrate “the less-traveled college” as an alternative to the handful of brand-name universities that accept fewer than 10 percent of applicants. Still, Booker says, the stressors remain.

He admits he sometimes has been surprised by community reactions to his proposals to support apparent needs. Last year, Booker partnered with the local police chief on a grant for a school resource officer position. The proposal was unexpectedly met with strong opposition, particularly from community members of color who didn’t like the idea of a police officer on campus. After lengthy talks, the district reworked the grant request to adjust the amount of time the officer would spend in schools.

Superintendents in such districts must be prepared to explain the rationale for their program ideas — sometimes repeatedly. “You have to be able to articulate your vision and your plan and it can’t be half-baked,” Booker says. “The school board, the parent club, the education foundation are all going to be extremely involved.”

Litigation Challenges

Those same involved parents today have no qualms about pushing for the highest level of educational resources and support for their children and can be quick to threaten legal action. Researcher Elliot Weininger, a professor of sociology at SUNY’s College at Brockport near Rochester, N.Y., watched that play out. He documented parental actions in a 2018 study of a school boundary fight in a wealthy school district in the Northeast dubbed pseudonymously “Kingsley.”

“Parents didn’t hesitate to tell school officials, teachers, principals or district administrators if they felt that the school was not providing an absolutely first-rate education to their kids,” he says. “To some extent, that’s reasonable, but when these highly resourced parents start acting in concert, it can get a little crazy.”

In particular, wealthier parents were better positioned to file lawsuits when unsatisfied, Weininger says. “I suspect that very affluent school districts get sued more often than others.”

Many parents in Kingsley were attorneys, Weininger says, adding, “All they had to do was write up the relevant paperwork on the weekend.”

The use of litigation snarls district resources and sometimes does little to achieve the impact parents are seeking, says Fran Rabinowitz, executive director of the Connecticut Association of Public School Superintendents and a former superintendent.

“In a wealthy district, the families have the resources to hire legal assistance immediately,” she says. “It can often mean you have to let go of the personal relationship that develops with parents and you end up spending more time speaking to attorneys. You lose a great deal.”

The more desirable alternative from the perspective of educators channels that drive and those resources to benefit students and teachers, says Gary Plano, former superintendent of the Mercer Island School District in Washington, which sits a few miles off the coast of Seattle and serves some of the most prime real estate in the country. Plano led the school system for 10 years before retiring in 2017.

Mercer Island parents were incredibly generous, Plano says, raising more than $1 million annually for the district. “We had ample resources, but with ample resources comes a bundle of other challenges,” he adds.

Vocal parents demanded lower class sizes, the best educational programing and enrichment activities, while teachers called for higher pay. Even flush with money, not everything was doable for Mercer Island leaders. And sometimes the funds raised from well-to-do parents came with strings attached.

Some families with students in a class of 25, Plano says, “would be very annoyed, saying ‘I gave to my school’s foundation, but my neighbor’s kid is in a class of 21.’”

During his decadelong tenure, the district faced waning school enrollment, leading Mercer Island to open its schoolhouse doors to students in a nearby county, which had a less-affluent demographic. Some families referred to the new attendees as “off-island students” and objected to spending on new school buildings to accommodate them, he says.

Everyone’s an Expert

Superintendents in affluent districts must be ready to touch base continuously with the community and stakeholder groups. And be prepared, Plano advises, to have one’s ideas picked apart. He held community and parent gatherings and coffee events, met with civic groups such as the chamber of commerce and started advisory committees on diversity and equity.

“A superintendent in a high-resource community needs a great deal of emotional intelligence,” Plano says. “You need to always be assessing how your messages are being received, and whether you’re being understood.”

The reality of working as a superintendent in a high-resource district means dealing with many “experts” on pretty much any issue involving students, says Joshua Starr, former superintendent of the Montgomery County, Md., school district, which includes schools in some of the highest-income neighborhoods in the region, as well as low-income areas. “There are people who are in the tech industry so they think they should take a look at the algorithms you use because they might be able to do it better,” he says. “But they have no idea how public schools operate and their complexity.”

Dealing with demanding, well-educated parents can consume a lot of time, says Judith Ferguson, whose superintendencies included four years leading the prosperous Hopewell Valley Regional School District in New Jersey. Ferguson now works with the executive search firm Hazard, Young, Attea & Associates, where she shares her insights on all types of school communities when soliciting candidates for superintendent vacancies.

“It’s extremely time-consuming and stressful,” she says of leading well-funded school districts. “Many people choose not to work in affluent districts for that reason. It’s not for everyone.”

Holding Accountable

On the plus side, those high-powered parents also push superintendents, principals and teachers to do a better job, keeping them on notice through their attentiveness. Their advocacy, through phone calls, e-mails and presence at school board meetings and advisory committee sessions, raises the standards of school operations and requires continuous communication.

“But from a management side, you spend a lot of time with individuals,” Ferguson says.

Booker, of the Piedmont district near San Francisco, says he mostly views the picture as positive. “Everyone is Type A around here, and that’s okay,” he adds. But as superintendent “you have to have some humility. I might not be the smartest one in the room.”

Acknowledging that parents sometimes can become aggressive and demanding, he says “most of our parents are extremely caring, thoughtful and flexible.”

Sternberg, one of the string of superintendents to serve in Greenwich, Conn., says she often wonders what she might have done differently to help the community understand her aims around closing the achievement gap, which called for shifting some resources and creating a magnet school open to the entire district to boost racial diversity. Maybe she should have hosted more public meetings, moved slower and/or established more trust with the community before attempting anything bold.

“How could I have approached it so folks might not have felt as threatened?” she asks. “What I saw was people who felt highly threatened over losing the entitlement they had enjoyed for decades.