Why New Haven’s ambitious new education strategy might actually succeed.

As the recent Chicago teacher strike demonstrated, public school systems are phenomenally difficult institutions to change. The array of competing forces—unions, politicians, parents, principals, charter schools, state and national bureaucrats—gums up many reform efforts and frustrates all but the most persistent reformers. But what’s happening in the historically troubled New Haven, Conn., public school system suggests there may be ways around this, ways that all sides can support.

In 2009, New Haven’s school district and teachers’ union signed a groundbreaking contract for the 21,000-student system. The four-year deal included a small annual pay hike—and allowed the district to give merit bonuses, close failing schools, and evaluate teachers based in part on student performance. The contract’s reform-minded provisions brought praise to a struggling urban district, from admirers including Obama’s Secretary of Education Arne Duncan, American Federation of Teachers president Randi Weingarten, and New York Times columnists David Brooks and Nicholas Kristof. Three years later, there are signs that cultural change is coming, too, in fits and starts. It’s especially evident in the district’s unusual effort to groom future leaders by handing them over to a local charter network that it used to view as an upstart threat.

A little history so you can see how big a change this represents: In 1998, a group led by two Yale Law students, Dacia Toll, who’d previously worked as a student teacher in New Haven, and Stefan Pryor, who’d been a policy adviser for the city’s mayor, John DeStefano, opened Amistad Academy, a charter school. (Pryor is now the state commissioner of education for Connecticut.) Amistad soon posted test scores for its students that far outstripped New Haven’s. Charters like this one are often accused of creaming students off the top, but the Amistad kids were chosen by lottery and resembled New Haven’s student population demographically: heavily low income and almost entirely African-American and Hispanic.

DeStefano has been in office for nearly 20 years, along with school superintendent Reginald Mayo, and for much of that time, the New Haven schools has suffered from nepotism and low achievement and graduation rates. In 2003, Toll formed an umbrella organization, Achievement First, and opened a second school in New Haven. A couple of years later, DeStefano and Mayo felt attacked by a friend of Toll’s, former Rhodes Scholar Alex Johnston, who’d launched a pro-reform group called Connecticut Coalition for Achievement Now, or ConnCAN, with a board that included heavy hitters like Yale President Richard Levin. The mayor and superintendent accused ConnCAN of denigrating the New Haven schools. Toll expanded her charter efforts elsewhere, in Brooklyn, Hartford, and Bridgeport. Achievement First now runs 22 schools with 7,000 students; only five are in New Haven.

But a funny thing happened on the way to explaining away Achievement First’s success. Mayor DeStefano forced his way onto AF’s board (via a Connecticut law to requiring the charter to appoint a city official), and then as he sat through meetings, he found himself thinking that he had something to learn. “He sat and listened for a year, and then he and the superintendent started asking, ‘What do we need to do differently?’ ” assistant superintendent Garth Harries says. DeStefano began declaring that school reform would be his legacy. He and Mayo called in David Cicarella, the president of the New Haven teachers’ union. “Pre-reform, I’d almost never talked to the mayor,” Cicarella says. “Now he was saying, ‘What’s your input? What do you think?’ ”

The union and the district together hammered out a method for evaluating teachers based in part on state test scores and in part on factors like classroom management, use of data, and parent outreach. The goal was to help as many teachers as possible improve—and to drum out the ones who wouldn’t. Over the next two years, 70 teachers failed to lift themselves out of the bottom of the pack, and the union went along with removing them. The terminations were only about 4 percent of the total workforce of about 1,700 but far more than in previous years, and they sent an unmistakable signal. “The people who were let go had been fairly evaluated by a system we helped to create and shown no improvement,” Cicarella says. “I don’t see how we can defend that. Frankly, we shouldn’t.”

Connecticut students in the fourth through eighth grades take a state test every year, and in New Haven, their scores rose a bit in 2011. So did the graduation rate and the number of ninth through 11^th graders who are on track to graduate. Other news is mixed: Yale University and a local foundation started awarding scholarships to in-state public schools for New Haven high-school graduates with a B average and good attendance. Among the first group of 115 freshmen, only 62 percent made it to sophomore year. This fall, the principal of one of the city’s high schools is embroiled in a cheating scandal.

DeStefano and Mayo get credit, though, for some adventurous hires. They brought in Harries, a former McKinsey consultant who came to New Haven in 2009 from New York, where he worked on special education reform for former schools chancellor Joel Klein. The district also tapped Gemma Joseph Lumpkin for the new position of executive manager of leadership development: She grew up in New Haven, had consulted for the district on using data collection to strengthen student performance, and had worked on a National Science Foundation initiative for urban schools. And DeStefano mended fences with Alex Johnston, appointing him to the school board.

For New Haven, Joseph Lumpkin oversees an unusual new partnership with Achievement First, the very charter school organization that once prompted such a defensive response from the city. Achievement First is now helping New Haven train its teachers and staff in school leadership, a relationship that may be the first of its kind in the country between a district and a charter. Here’s how it works: Last year, New Haven’s Joseph Lumpkin and Matt Taylor, the former principal of Amistad Academy, led a group who chose a handful of people from a pool of teachers and other staffers who wanted to move up the ranks to principal. The select few spent six months in residence at an Achievement First school. In many ways, they operated as administrators: running professional development days and lunch or bus duty, coaching teachers, handling discipline, meeting with parents. But they did this with Taylor’s intensive support. He was their coach and their teacher. They also had mentors in the district: principals at high-performing schools with whom they met weekly. And in a three-hour weekly seminar, they studied with outside experts, learning topics such as data collection and systems management, coming away with the credential they need to become an administrator anywhere in Connecticut.

“We concentrated a lot on school change and how you go about it,” Taylor said. “You don’t go in and start blowing things up. You have to be skilled at building relationships and credibility. You have to know how to build student motivation.”

I live in New Haven, and I know Taylor and several other people who work in education here.. But forget me—listen to Jamie Baker, a 31-year-old who worked for eight years in New Haven as a first-grade teacher and a literacy coach. Baker was part of the first crop of Achievement First “residents,” as they’re called. She told me:

I went over there, unprepared, as a novice. It was complete culture shock. It was all about systems—they have a systematic approach to everything from the way in which the students enter school, to how they sit at their desks, to turning in homework, to calling parents. And the way they use data is different. For example, I was working closely with the first grade, and we would look at the data, see where our kids were, and use it to determine actual objectives for students, which we’d plan out to the level of putting it in our calendars. We’d collaborate about what we were going to do for the kids struggling the most. At AF, they talk about “whatever it takes” moments: Get the kids during lunch and recess, whatever you have to do to make sure they’re getting it.

I asked Baker what she made of the whole experience, and she said, “It was amazing. I never in my life saw myself make so much progress in a short amount of time—in terms of leading people, understanding the curriculum, everything. It was just extremely rigorous.”

From AF’s perspective, the residency program, which costs about $1 million a year and is partly funded by the Buck Foundation, is a chance to reach outside the charter model and also address a need the network itself had noticed. “Finding principals is a big challenge for us—we don’t get a lot of the candidates we need, in terms of both quality and quantity,” Taylor said.

DeStefano said the same thing at a lunchtime panel during the Democratic National Convention: “The hardest thing” for the New Haven schools is “building leaders.” You can argue that in some of the choices of principals they’ve previously made, the mayor and superintendent created the problem they’re now turning to AF to help solve. And it’s not all transformed: Only three of the five residents from last year have been placed as assistant principals in the New Haven system. The other two are in intermediary positions, which isn’t the best advertisement for new recruits.

DeStefano and Mayo are sticking with the AF residency even though the teacher’s union bristles over it. AF’s teachers aren’t unionized, and Cicarella says comparisons between the charter’s results and the district’s are unfair because the city schools deal with far more student mobility and can’t ask students to leave if they pose a discipline problem. (In fact, AF has a high retention rate.) “They do well on coaching and lesson planning—we shouldn’t shirk from that,” Cicarella told me. “But I don’t like the idea that we validate them by sending our guys to Achievement First, as if they do it better than we do. Our people go there, and then they come back to us and they won’t be prepared to deal with stuff we deal with because they have a select group of students.”

That sounds like the old era of distrust between New Haven and its charter schools—a culture of suspicion that’s common across the country. (If you’ve seen the movie Waiting for Superman, you know what I’m talking about.) What’s striking about New Haven, though, is that the lines between district and charter are blurring. The new relationship with AF “is the district saying: We’re not going to be stuck in old fights,” Harries said. “We’re going to learn and grow from any source we can.” Baker says it feels that way on the ground, too. “The bottom line is that this opportunity shows that New Haven has a huge interest in developing talent,” she said. “They’re really investing in us.” The next step is for the union to recognize the value here, too—that’s when cultural change will have really taken root.