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One Day Magazine

Truth Hurts, and Helps a Veteran School Leader

Real talk about trying, and not always succeeding, as a school and systems turnaround leader.

By Ellen Winn

February 19, 2020

A woman sits in a basket chair by a window reading.

Not long ago, a member of the One Day staff heard from an alum who’s been working in schools for nearly 30 years. This alum had taken on the challenge of turning around a school—the kind of project that’s high stakes for students and families and high risk for the school leader’s reputation. He said that while he’s inspired by reading turnaround success stories, reading about how leaders handle the inevitable defeats and rough patches would make him feel “less lonely.”

Hearing that made me think of Tiffani Curtis (L.A. ’92), whom I met in a fellowship for aspiring school systems leaders. Curtis stood out during the fellowship for her candor. She was the one to say out loud the things other people were thinking. I knew she had experienced both great successes as a school leader and also some setbacks. I asked Curtis if she’d talk to One Day about how she gets through the setbacks (especially the public ones) and how she stays focused and resilient in her current role as a systems leader in a Massachusetts turnaround district.

Right away—when I asked what advice she’d offer aspiring systems leaders—Curtis got down to real talk. “Be willing to sit in mind-blowing, historically institutionalized craziness,” she said.

Curtis began her career 27 years ago teaching math at John Adams Middle School in Los Angeles. Then she led a preschool for a decade and helped write the universal preschool master plan for Los Angeles County. As a parent, she experienced the challenges and complexities of securing an equal education for a child with disabilities. So when she moved on to become the founding principal of a Las Vegas elementary, success felt especially satisfying. English language learners and students with disabilities at the school she founded achieved the same academic successes as general education students.

But as she watched that school fill with increasingly higher-income families (to the extent that it lost its Title I status), Curtis felt a conflict with her commitment to serve the most underserved students. She accepted the challenge of becoming a turnaround principal at an elementary school in Albany, New York, which is where she ran into those setbacks.

Today Curtis is a mother and grandmother who lives across the country from her kids and grandkids but still hand sews Halloween costumes. She’s working 13-hour days as a school supervisor for Holyoke Public Schools in a Western Massachusetts city of 40,000 people, where four in five students live in economic hardship. The only woman of color on the superintendent’s leadership cabinet, she manages five turnaround elementary and middle schools in a district that was placed in state receivership due to chronic underperformance. She spends long weekdays and evenings travelling from school to school. On weekends, she renews herself by occasionally flying to see family in Las Vegas, diving into a good read at home, or hosting game nights with friends and colleagues.

One Day: First question: Why do you think people take on jobs with huge risk attached to them, like leading a turnaround district?

Curtis: You are walking into an already tough situation. But it’s what matters. It’s what gives you the adrenaline. It’s why you’re gritty, because it’s the kind of work you want to do. But it’s hard work, and when you don’t do it well, you’re judged harshly. But nobody remembers that no one [in that district] has been able to do this work well before you, either.

Q: Tell me why you moved into systems leadership, and specifically to Holyoke?

A: It was the natural step to have a broader impact across multiple schools and to be able to really use what I believe are my natural skills, which are tied to my deep-rooted value system.

The scope of Holyoke’s turnaround, and the relative freedom implicit in the relationship with the state, were intriguing and translated well to my past six years of charter school leadership. Perhaps even more important was my connection and strategic alignment with the receiver/superintendent, Dr. Stephen Zrike Jr. As we spoke, I knew I believed in his theory of change that the school is at the nucleus; the school is the unit of change, not the district.

Finally, the majority of the students in Holyoke—84%—are students of color, while the majority of the teaching staff are not. This mismatch of who is in front of our kids and who is sitting in those seats—that struggle is critically important to me.

© Photo Megan Haley Tiffani Curtis has a district office but she’s almost never there. She’s typically on the move, traveling between the five schools where she works alongside staff members and their school communities.

Q: So we’re here to talk about coming back as a leader from what feels like a public setback. Tell me about your first experience as a turnaround leader, when you moved to Albany to lead a struggling charter school.

A: When the opportunity to go to New York came, I was just primed for it, ready for the challenge. But moving to New York, away from my family, to a different climate,
to a different time zone, and to work with the highest-need population I had ever served in my life—it was all very hard.

Q: Not everything went smoothly. What were the lessons you learned to strengthen your leadership?

A: Brass tacks: I failed to manage my board, whom I reported to directly. So at the end of year one, when the school’s test scores were much lower than the board expected, they were very angry with me, and I was dumbfounded. I cried in the board meeting out of frustration.

Was I shocked about the scores? Absolutely not. They came out exactly where I thought they would, because I knew it would take time to see the effects of our work, like focusing on the instructional core, really strengthening teaching, stopping practices that weren’t working. But I had failed to communicate my strategy and my timeline to the board, so they were shocked by the scores and angry with me. The teachers and instructional leaders were really enthusiastic about the changes I was leading. I did a far better job communicating my goals and the timeline to them versus the board.

Q: And you learned what?

A: Not only did I lack the skills to manage my board and to navigate multiple stakeholder groups, I didn’t even have the desire to do these things. Up until then, I thought I could avoid the politics and just be good at what I do: school leadership. And so that’s where the learning was: realizing that I didn’t get to choose the things I wanted to do as a leader, and also to go slower when implementing big changes.

Q: You spent another two years there. How did you come back from your initial challenges?

A: I got a mentor who could teach me how to manage my board! My mentor had 13 years of experience on a publicly elected school board. He coached me on how to make personal connections with board members, how to think through my ideas and get them into the sightline of the board, even down to how to prepare for board meetings.

Q: How do you withstand the high odds of not delivering big, fast wins while you work through turning around schools or districts?

A: The risk is real. The way I operate is be very, very true to my values so that I know, even when I make the wrong decision, that it came from the right place. I also know that I have to be connected to people who are doing the work at all levels. I have to be able to talk candidly to leaders, to teachers, to parents, to students. I have to stay connected to the people who are being affected and impacted by the decisions that I make.

How I lead now was deeply influenced by my first principalship. I only ever want to make 10% of the decisions on my own, and I want the other 90% to be made collectively. It keeps me in the role of having to serve people, understand people, and collaborate with people. I say to myself, “Is this my decision to make, or can there be more voices in on this decision?” That way, I have also learned, you get to share some of the failure. And then, through failure, people grow.

I feel at my core that I really want to serve people, and I cannot do that unless I know what they need, and I cannot know what they need unless I’m close to them, and I cannot be close to them unless I’m working side by side with them. I want to lead from the hip, or from behind.

“You have to be ready to do things that people have been unwilling to do for years, to have conversations that are difficult but necessary.”

Tiffani Curtis

Q: What keeps you going in this tough work?

A: What helps me most is having people in my life who are willing to be very, very honest with me. I have a hard time not being a leader, so I surround myself with people who are bold enough and firm enough to tell me what they really think.

Q: And for the benefit of anyone thinking of doing what you’ve done, is there anything you would change looking back?

A: I would stay [in my school leadership jobs] for longer. Three years in the job of founding principal was not long enough for me to get good triangulated data around what I was good at and where my gaps were. And then I went into a turnaround school, and three years was not enough to get good data; it just wasn’t. And so, coming into this job in Holyoke, I would be devastated if I couldn’t stay at least five years.

Q: What advice would you give someone taking on a systems leadership role?

A: First, be sure you are ready and have solid results. And then, if you are a well-rounded leader—meaning you have a strong instructional lens, know how to hire and develop people, understand professional development, etc.—and if you are gritty and thick-skinned, then go for it.

But I would also say, be ready to sit in mind-blowing, historically institutionalized craziness. You have to be ready to do things that people have been unwilling to do for years, to have conversations that are difficult but necessary.

Then I think you have to find a way to not have the work be all-consuming. You have to figure out how to maintain your own sanity so that you stay grounded and have the ability not to take it all personally, because it’s very personal work. The moment I start to feel disdain for the system and people and experiences, I lose sight of that kid that I’m working for, and I lose sight of the most direct path to get that kid what he or she needs. You have to maintain clarity.

Finally, make sure you are values-aligned with the role. Because when you are asked to work in a specific way, or to support a decision that does not align with your fundamental belief system, you will struggle. The work is hard—but not worth compromising the values that keep you showing up for kids every day. 

This interview has been edited and condensed for clarity.