Boston’s Superintendent Finalists

Guadalupe Guerrero is on a mission to turn things around

Challenges as a principal inspired Guadalupe Guerrero to focus on school improvement.
Challenges as a principal inspired Guadalupe Guerrero to focus on school improvement.David L Ryan/Globe Staff

After a week of interviews with the School Committee, Boston has 4 choices for superintendent, Dana Bedden, Tommy Chang, Guadalupe Guerrero, and Pedro Martinez.

Boston Superintendent Thomas Payzant handed Guadalupe Guerrero the toughest assignment for a freshly minted principal: Orchestrating the turnaround of one of the worst-performing schools in the system.

With a little coaxing, Guerrero, who was in his early 30s at the time, agreed. What he walked into at Dever Elementary in Dorchester in fall 2002 was a school in crisis. Chronically low test scores. Parents who distrusted the school system. Instructional programs in dire need of overhauls.


Despite efforts to steer the school in the right direction, MCAS scores would rise only to fall again, and performance in the fourth grade was down notably by the time Guerrero left the school in 2008. Two years later, the state designated Dever as “underperforming” — based largely on the MCAS scores generated under Guerrero’s watch — and the school is now in state receivership.

His six years at the helm of the school now hang over his candidacy as a finalist for the Boston superintendent job. In public interviews last week, he faced questions about his leadership there, while some education advocates, teachers, and parents wonder how he could accelerate achievement across an entire system when he could not save Dever.

Guerrero, 45, has countered that he learned many lessons as Dever’s principal that have helped inform his work in San Francisco, where he says he has found success in helping to turn around low-achieving schools, first as an assistant superintendent and now as a deputy superintendent.

“I spent a lot of time reflecting on my time there,” Guerrero said of Dever Elementary. “It pains me to see the school went into receivership, because I feel those situations are preventable.”


Guerrero, who also worked as a teacher and paraprofessional, initially made headway as Dever’s principal.

He rolled out a new math curriculum, causing Dever to become a training site for the program for other Boston schools. He instituted MCAS boot camps, expanded outreach to parents. He brought more special education students into mainstream classrooms.

Everything seemed to be coming together in 2004, just two years into his tenure. A review by the state Department of Elementary and Secondary Education found the Dever had the makings of a “sound” academic improvement plan, and appeared to be on the track to implement it successfully.

The review also gave Guerrero high marks for his leadership, noting that “stakeholders expressed consistent belief in the principal’s ability to communicate effectively, nurture a positive school climate, set high expectations, and lead with confidence and purpose,” according to a copy of the report.

“It took a lot of blood, sweat, and tears,” Guerrero said of his work at Dever, during interviews last week. “Together with a group of dedicated teachers . . . I think we made a lot of inroads.”

But troubles emerged. He hired an assistant principal who proved unpopular with the staff. In June 2005 about three dozen teachers sent Guerrero a letter saying the “growing spirit of cooperation” the previous year had been replaced by the administration with an “us against them” mentality.

Kathleen Edwards, who taught at Dever at the time and signed the letter, said she got the sense that Guerrero was receiving directives from the superintendent’s office to be more tough on teachers, and he in turn delegated the task to his assistants.


“He was a nice guy, but he was painfully shy,” Edwards said. “He was not the kind of person who would run a meeting or rally the troops. He would give dictums by e-mail from his office.”

By the time he left, MCAS scores had slid. In spring 2008, Guerrero’s last year at Dever, only 10 percent of fourth-graders scored proficient or higher in English, and only 8 percent in the grade attained those results in math.

In spring 2002, just before Guerrero took the job, 21 percent of fourth-graders scored proficient or higher in English, and 13 percent did in math.

Michael Contompasis, who served as the Boston system’s superintendent after Payzant retired in 2006, said he believes Guerrero would have found more success at Dever if he had the tools now available to principals. A change in state law in 2010 gave them to authority to replace teaching staffs, extend the school day, and make other changes with little input from the teachers union.

“He had a struggle to convince that staff he wanted to do things differently,” Contompasis said, adding Guerrero did move out some staff. “He did yeoman’s work.”

Guerrero said the challenges he faced at Dever sparked his interest in 2008to pursue a doctorate at Harvard University’s Graduate School of Education, where he wanted to learn how to guide turnaround efforts across an entire system. Guerrero never completed his dissertation for the degree, and Harvard consequently terminated him from the program last fall.


Nevertheless, Guerrero got his chance to oversee school turnarounds in San Francisco. In 2010, then-Superintendent Carlos Garcia tapped Guerrero to work with low-achieving schools in the city’s Mission District, having been impressed with the dedication Guerrero showed as an administrative intern in his office as part of his doctoral studies.

“Right away, I knew he was a sharp, workhorse guy,” Garcia said.

Guerrero dug himself into the work. Instead of working out of the school district’s headquarters, he set up an office at Mission High School so he could work more intimately with the schools in his target area. He also wrote proposals for school-turnaround grants that secured $45 million.

San Francisco’s improvement effort has made big strides, according to a recent report by the Council of the Great City Schools, an advocacy and policy organization for large urban systems. The report examined test scores at schools that received federal school-improvement grants.

In the San Francisco schools, 39 percent of students scored proficient or higher in reading in the 2012-13 school year, up from 27 percent in the 2009-10 school year. Similarly, 55 percent of students scored proficient or higher in math in 2012-13, compared with 28 percent three years earlier.

The city’s current superintendent, Richard Carranza, who promoted Guerrero to deputy superintendent two years ago, said he believes Guerrero is ready to lead Boston’s system, even though he would like him to stay in San Francisco.


“He’s my right-hand man,” Carranza said. “I’ve seen him in very difficult emotional community meetings. I’ve seen him interact with parents traumatized over losing a child. I’ve seen him in every conceivable situation. He’s been unflappable. He operates from the core of who he is, the son of single mother — those are life experiences you can’t fake.”

James Vaznis can be reached at jvaznis@ globe.com. Follow him on Twitter @globevaznis.