"Forever Cheerleader" Phyllis Glassman Retires from Ossining Superintendency

An Ossining resident for 20 years, she plans to stick around.

When Phyllis Glassman and Bob Roelle came to the Ossining school district in 1992, the community had an inferiority complex about everything from special education to college-attendance rates. 

The duo was ferocious about two things: upping student achievement and measuring results. They promoted rigorous curriculum and instruction and refused to protect programs—even their own—that could not be shown to be successful.

Their emphasis on equity shook up a community that, like many others, didn't realize the extent of the problem. Also like elsewhere, Ossining parents' concerns about slicing the pie focused on concerns about special education, elementary enrichment and college prep. Everyone was into tracking.

Roelle was the superintendent; Assistant Superintendent Glassman was expert at research-based teaching and learning.

And the district grew and changed, focusing on students whose performance lagged while creating more opportunities for students to excel, with programs such as the AP Academy, the Science Research Program and the First Steps/Primeros Pasos early literacy program. 

When Roelle retired in 2007, the Ossining Board of Education appointed Glassman as his successor. 

Five years later, she's retiring too. It's the end of an era.

Glassman's office suite on the second floor of the Roosevelt School, long the district's headquarters, is filled with boxes as she packs up. Her last day is Jan. 14. 

"I think I surprised everybody," she says of her announcement in July. "It just seemed as if I had had a wonderful career and many of the goals we set for the district had been attained. It was probably the hardest decision of my life. I love the Ossining school district."

Roelle brought Glassman with him from Long Island to take over the district in 1992. Right off the bat they decided to tackle a national, sensitive, intractable issue: the achievement gap between white students and students of color. 

Here is Glassman's description, from an article in the November 2007 edition of School Administrator magazine:

Well before No Child Left Behind Act required it of every school system, we boldly disaggregated achievement data by student groups. Shocked and amazed by what we were reporting, residents who filled the board meeting room one night in 1992 listened to our school report card presentation detail the wide gap in achievement test scores between black and white students locally. Residents expressed concerns. Hadn't the Ossining School District been recognized as one of the finest around? How could our school produce such inequitable outcomes?...

We committed ourselves to overcome the inequities...

In 1992 the district did not have a single principal or assistant principal of color. In 2006-07, nearly a third of our principals and assistant principals were people of color. In terms of classroom teachers, the representation of minorities has increased over the same period from 12 percent to nearly 25 percent....

The performance of Ossining's black students on the New York state graduation examinations, in terms of passing rates, increased by 16 percentage points in U.S. history and government and by 22 percentage points in biology/living environment since 2000. On mathematics Regents exams, scores improved by 49 percentage points over the same time. 

Here's more perspective on the changes in the past two decades.

  • In 1992, Ossining had about 3,000 students. This year, enrollment is upward of 4,700.
  • In 2003, 44 percent of Ossining's students were white, 32 percent were Hispanic and 18 percent were black. Compare that to 14 percent black, 33 percent white and 46 percent Hispanic in 2010-11, the last year for which state data is available.

Glassman plans to stay in the community she adopted (despite early hostility from some members of the community who didn't trust the new district leadership or its agenda).

"It was a deliberate decision—I decided since I was passionate and committed to the program I wanted to integrate my work life and my everyday life," she says.

One of the things that attracted her was diversity. She found the staff and parents absolutely open to the idea that equity and excellence were not mutually exclusive.

The results proved she was right.

"Years ago, no one would have believed we would be the Intel Star Innovator," she says, referring to the Innovator Award given to the school with the most successful and innovative math and science program in the country. Ossining won the award in 2012. (Just yesteday the district announced that it had again produced several semi-finalists in the annual Intel competition. This is rare.)

"Critics worried if the resources [we were spending] could be justified," she says about the start of the Science Research Program in 1997. "Thankfully the board and staff supported us."

They dotted their i's on that and every other initiative. "We instituted audits and program reviews," Glassman says. "We sought outside expert recommendations."

To make it happen—make sure there weren't just programs on paper—they instituted professional development for staff using research-based tools and strategic plans for education as well as buildings, so that everyone was "looking at the gestalt of the district," she says.

Continuous improvement was the mantra she and Roelle started preaching in 1992.

"It's always important to have long-range plans," she says. "We're on our third, which takes us through 2017."

Here are some of the innovations:

  • The First Steps program at Park School—because early literacy is a clear predictor of school success—for which staff and supporters recruited private money since pre-school programs may not be funded with taxpayer dollars.
  • Two middle- and high-school programs, Project Earthquake and High Hopes and Expectations, which targeted young black male students when the data showed how much that demographic was at risk.
  • The AP Academy—which offers Ossining High School students with potential who weren't on the college track a chance to practice the higher-order thinking skills and study disciplines and experience the rich knowledge base needed for success in Advanced Placement courses and exams.

Among the other things Glassman is really proud about was the decision to make the PSATs mandatory at OHS. Before, mostly the kids whose parents were pushing them toward college took The College Board's preliminary SAT test. 

"We recognized that some able students were not being given the opportunities that a good public school education should afford them," she says.

And the district's statistics showed that the number of students taking a more rigorous curriculum was increasing exponentially with no dimunition in performance. They proved that students who maybe wouldn't have tried could indeed achieve at high levels, while the highest continued to perform well.

"In addition to having a fantastic district, we have outstanding teachers and an exceptional staff," she says. "And parents. Everyone is so committed to the success of students."

Glassman's commitment has been so complete that she has no idea what she'll do starting next Tuesday.

"I am such a meticulous planner," she says, "yet I've been such a 24/7 person for the district. I have not yet thought past Jan. 14. First I'll sleep more than three-and-a-half hours a night!"

No matter what, she says, "I'll be the forever cheerleader of Ossining." 


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