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Four years ago, Jenna Monley鈥檚 work took her inside a maximum-security prison near Philadelphia.

A recently incarcerated father had met with Monley, the deputy chief of family and community engagement for the Philadelphia school district, to tell her how badly some of the men he鈥檇 met in detention wanted to share in their children鈥檚 school experiences.

Undaunted by challenges like ensuring student privacy, securing parental permission, and acquiring the funding, Monley cleared every hurdle, bringing a busload of children and their custodial caregivers to the prison to do art and literacy projects with their fathers, an experience many of the men had never had before.

鈥淭hey are not their circumstances,鈥� Monley said. 鈥淭hese were fathers who were fully committed to their children and their education, but their circumstances prevented their ability to be present in their children鈥檚 lives every day.鈥�

The program exemplifies Monley鈥檚 work building partnerships between families and schools, which has continued even as the pandemic has changed the contours of her job, her peers say. It has led her to say 鈥測es鈥� to some bold proposals, unafraid to deal with the uncharted territory of logistical issues and potential complications that cause other educational leaders to recoil.

And it offers a window into her approach, her colleagues say: Try new things, ground everything in a game plan that gets educators on the same page, and constantly evaluate to see what鈥檚 working and what needs to be improved.

鈥淛enna is an example of what can happen when a leader brings a lot of her own skills and background to the situation, spends some time learning from best practices around the country, and then creatively applies them,鈥� said Kwesi Rollins, the director of leadership programs at the Institute for 91制片厂视频al 91制片厂视频, a nonprofit organization that promotes stronger relationships between educational leaders and communities.

Monley has been a member of the organization鈥檚 collaborative for family and community engagement, where Rollins saw her start as a young administrator learning from peers in other districts and eventually grow into the kind of high-energy, innovative leader others draw inspiration from.

Grounding innovative ideas in a comprehensive strategy

It started with vision.

鈥淪he was willing to take on a lot of bits and pieces of work in the district and make it into a big whole,鈥� Rollins said of Monley. 鈥淪he really got people on board at the district level for a systemic vision. She moved away from isolated and random acts to a strategic approach.鈥�

A case in point: The prison visit evolved into an ongoing program, which served about 20 incarcerated fathers before it was paused during the COVID-19 pandemic. Monley鈥檚 team also worked to arrange phone calls between the men and their children鈥檚 teachers, and they are exploring ways to involve them remotely in parent-teacher conferences.

鈥淢y commitment to this work is truly grounded in the belief that families want to help their children be successful,鈥� Monley said. 鈥淏ut sometimes that path forward isn鈥檛 always clear.鈥�

Monley, 40, started her current position in March 2016, taking leadership of an office that had lacked a permanent director or vision for years as the district tended to other priorities. She faced a daunting challenge in a district where, for nearly two decades, school board members were appointed, not elected. Waves of school closings in 2012 and 2013 had all but shattered parents鈥� faith in the school system.

She quickly organized the office鈥檚 mission around a list of easy-to-understand 鈥減ower principles鈥� that would guide the work of everyone from teachers to administrators in building stronger connections with families. She arranged those principles, like increasing communication and developing strategies, in a framework and identified ways to measure the success of each priority.

Under Monley鈥檚 watch, the district reassigned engagement staff to oversee a new team of liaisons between schools and the central office. Monley nearly doubled the number of bilingual aides to 98. They are tasked with providing interpretation services in schools, a key to engagement for many parents in the diverse school system where students speak 130 languages at home. She worked with refugee advocates and the Mexican consulate to attract candidates and inform her work.

鈥淲e want our parents to really feel as though they can engage, and, frequently, cultural norms and language differences can be barriers,鈥� said Karyn Lynch, the Philadelphia schools鈥� chief of student-support services, who hired Monley for the family-partnership role. 鈥淎 good deal of [Monley鈥檚] work involves eliminating barriers for families to engage.鈥�

Monley鈥檚 team sought to empower teachers in their own outreach: It developed a family-engagement onboarding session for new teachers and refreshers that could be incorporated into ongoing professional development. Those sessions helped teachers role-play strategies like how to conduct difficult or emotional conversations with parents and how to discuss complicated education data in a digestible way.

Her team helped develop 鈥渇amily academy鈥� courses at 11 locations throughout the district, including public libraries, which are more accessible to some families. Those workshops offer lessons on how to engage with the school system, advocate policy changes as a parent, and support children鈥檚 well-being.

In another program that has attracted about 1,500 total participants, parents and teachers meet in teams to dissect data and learn about classroom instruction. The effort helps families learn more about how the district works and what happens in their children鈥檚 classrooms, and it helps educators understand how to strengthen their offerings and to better communicate their results.

Monley also helped draft formal policies about school advisory councils, addressing constituent concerns, pregnant and parenting students, and seeking parent and community input on plans for such federal programs as Title I, which supports the needs of disadvantaged students.

Developing a whole-district approach to family engagement

Through all those efforts, Monley has made family engagement feel like a key strategy, rather than a diffuse set of well-intentioned ideas, Lynch said.

鈥淲e tend to have great ideas in public education, but we don鈥檛 always have great execution of those ideas and we don鈥檛 always have systemic execution of those ideas,鈥� she said, adding that Monley has managed to do both.

Lynch credits some of that success to Monley鈥檚 unconventional background: She earned a bachelor鈥檚 degree in communications from West Chester University and a master鈥檚 in business administration from Saint Joseph鈥檚 University in Philadelphia. She always saw herself working in public relations and did so in her first job out of college, at Special Olympics of Pennsylvania.

But she very quickly found herself drawn to working in schools.

鈥淚鈥檓 a Philly girl,鈥� Monley said. 鈥淚 was born and raised and educated in our schools from elementary to high school. I鈥檓 also the child of a teacher. Seeing my mother as an educator, working in collaboration with families and her peers to boost the educational advancement of her students, was really impactful for me.鈥�

The hometown connection helps Monley relate to families who may distrust the school system. And her background in business and public relations has helped her recognize that effective communication with families鈥攁bout everything from classroom lessons to districtwide policies鈥攃an rebuild trust in the school system or break it permanently.

In May 2004, Monley took a job with the Philadelphia schools, where she served as a grants officer. Concerned about whether a special program for pregnant and parenting students complied with grant requirements, Monley took over that initiative in 2010.

Under her leadership, the district improved, expanded, and elevated the program, which helps teenage parents and their young children through the use of case management. It connected them with social services and programs that provided free diapers and other supplies. Educators completed home visits to check up on the well-being of both the students and their young children.

The program, which remains part of Monley鈥檚 portfolio, also worked to bring consistency to the varying ways schools interpreted and applied the district鈥檚 policies on pregnant and parenting students. Monley created materials to communicate the rights and resources of students with children, and she reached out to employees, such as office staff and school nurses, who are more likely to interact with such students, to help share the materials. She also developed an online training module for teachers about working with pregnant students.

鈥淚 really understood families as a key lever of a child鈥檚 success. Seeing those young students strive to achieve their own success and continue in school and, at the same time, try to uplift their young children was really powerful for me,鈥� Monley said. 鈥淚 wanted to take the lessons learned from the work I did with our young families and move that into working with the district at large.鈥�

When the district listed her current position in 2016, Monley quickly shaped a pitch for how she would fill the role and how she would bring more intentionality to the office, said Lynch, who is now her supervisor. Administrators argue over whose idea it was to hire Monley, Lynch jokes.

鈥淚 was impressed with her initiative,鈥� she said. 鈥淪he saw something and she went after it. She said straight up, right upfront: 鈥業鈥檓 going to demonstrate that I can do this and I鈥檓 going to do it well.鈥欌��

Lynch said she鈥檚 fulfilled that promise, even taking on additional roles in helping to coordinate and communicate the district鈥檚 response to the COVID-19 pandemic. That鈥檚 critical because the crisis has strained parents鈥� relationships with schools in many parts of the country, said Rollins of the Institute for 91制片厂视频al 91制片厂视频, and it has made the work of family engagement more urgent.

When schools closed for in-person learning in March 2020, Monley鈥檚 office quickly set up tech-support hotlines, sent informational flyers in a variety of languages to break down policies for families, and held virtual events for parents to ask questions and provide feedback.

Parents met online to discuss the challenges of virtual learning, their strategies for keeping their children engaged, and some frustrations, too. Meanwhile, the parent-engagement staff participating in the video chats did something really bold: They stayed quiet.

While officials in some districts might have felt defensive after hearing parents鈥� complaints, Monley said her staff wanted parents to feel heard. At the end of the call, they would unmute themselves to answer any questions that came up: how to pick up a computer, where to pick up a free meal, how to contact a district program office.

鈥淎s opposed to myself, or one of my team members leading that conversation, we were there to make sure that the environment remained a safe space,鈥� she said. 鈥淲e wanted families to have that comfort that it wasn鈥檛 going to be us coming in and saying, 鈥楲et us explain why that happened.鈥欌��

The Philadelphia district continues to face some criticism from parent organizations about issues like the condition of facilities and communication with the school board. And Monley is quick to acknowledge that she is still learning, despite outside recognition for her work: The incarcerated fathers鈥� program and her support for teen parents have been featured in educational conferences around the country.

There are still more families who need outreach, more educators who need to feel equipped to do so, more strategies to be refined or improved, she says.

She鈥檚 also quick to credit her team鈥攚hich has grown from seven to 50 staff members during her tenure鈥攆or remaining true to the vision and consistent in carrying it out.

鈥淚 don鈥檛 do this on my own.鈥�