Jessica Willis, candidate for school board

Part 5 in a hopefully-7-part series where I talk with every single school board candidate

[Note: I am traveling for work, so sorry for taking so long. I plan to send out Mike Zollicoffer’s interview by next week. I did an interview with Phillip Morris also, but he’s running unopposed so it seems less urgent.]

Part 1: Daniel Gugala, seat 6

Part 2: Lynne Woehrle, seat 6

Part 3: Liz Heimerl-Rolland, seat 5

Part 4: Chris Zirbes, seat 5.

Jessica Willis is running for seat #7 on the Wauwatosa School Board against Mike Zollicoffer. Her website is here. This is the fifth in a series of conversations I've had with school board candidates, and I hope to complete and publish the rest through February and March. I originally sat down to speak with Jessica on March 1st.

Sometimes it’s useful to ask each of the candidates the same questions so you can compare their responses. I think some groups are already doing something like this, so I didn’t. I have some topics I'm interested in, but I generally let the conversations go where they want. Perhaps through this, in combination with other candidate questionnaires, forums, and meet-and-greets, you can come to a slightly more complete understanding of these people.

Also, a note. Unless people are very polished public speakers, they tend to pepper their speech with things like sort of, kind of, like, not to mention err and uhh. They double back on themselves to revise the beginnings of their sentences and sometimes do all sorts of things that are seamless when spoken but sound clumsy when read. I tried to remove most of those.

Why run for school board?

Jessica and her family have always been active in the communities they’ve lived in, and Wauwatosa is no exception. Her husband, a former football player at Ohio State, enjoys coaching and likes to use “his love for athletics to connect with youth.” Even before leaving Columbus, Ohio, to move to Wauwatosa, Jessica tells me that she was “attending PTA meetings on Zoom […] just to get a feel for the community and the schools.” When she finally got here with her family just a few years ago, she immediately set about revitalizing the PTA’s flagging Equity Committee and created a welcoming committee for parents of students at Jefferson Elementary—where her sons attended—who might be new to the community or who lived outside the city limits.

Nevertheless, she says, it was a big change. In Columbus, “we shared an alley with my mom [,and] we had grandparents in Columbus. And my husband’s mom was five blocks away, and my dad was ten minutes away. We had the only grandkids, so childcare’s not something we ever had to deal with.” But she loved the “close-knit neighborhoods” in Wauwatosa, and—for better or worse—her family is not so far away anymore either. “My dad just moved in with us,” she says, laughing a little. “But we won’t talk about that. It comes with it’s challenges.”

What they really liked about Wauwatosa, in addition to it’s dense, walkable neighborhoods, were its schools and diverse community:

I’m biracial, my husband is black, so diversity was something that was really important to us. That our kids would go to a school where they had other children that looked like them and that didn’t look like them. That’s always been something that we’ve prioritized. And we found that specifically with Jefferson.

However, while she saw “great things happening in our schools every day” there were other things that concerned her. One was the “achievement gap” between black and white students that had only grown worse during the pandemic. Another was what she perceives to be a lack of engagement and belonging among some groups of students and the ways in which teachers might subtly reinforce those feelings. As a substitute teacher at Jefferson, she remembers, “One of the teachers that was out left sub notes saying to exclude a certain group of students because, They don’t do work anyway, so just let them put their head down in the back of the classroom. And they happened to be all black boys.”

She began to wonder why some students didn’t feel connected to their schools and how she might be able to help. When school board president, Steve Doman, resigned in 2022, some members of the Equity Committee suggested she apply. “Through a lot of conversations with parents and with community members, I thought why not apply for it? There had never been a black person of color on the school board,” and she thought it would be a good way to lend a “voice to some of the community members that didn’t have [one].”

Open Enrollment and Community

During our conversation, Jessica mentions belonging several times. If students in Wauwatosa schools felt like they belonged there, perhaps they would fight less. If black families had an easier time meeting and getting to know other parents in the community, perhaps they would be more likely to stay or maybe it would encourage others to join them. And so, she tells me, a lot of her initial efforts upon moving here have been oriented around, “how can I take my experience that was positive and translate that to some of our families that don’t feel connected to the Jefferson community?” She mentions some families she met through her involvement with the district’s Equity Committee as they partnered with several elementary schools to read books that “talk about social justice issues” to students there.

During that time I met a black mom who was really engaged, really committed, but she was taking her daughter out of Lincoln because of the micro-aggressions that she experienced, and she didn’t feel like her daughter was supported as a black girl at school. And during the summer my husband and I became friends with another black family who live in Tosa [and] pay Tosa taxes, but send their kids to private schools, because they don’t know that the Tosa schools are going to be a welcoming environment for their kids.

Jessica tells me that while she and her family have had a largely positive experience since moving here, she knows that others have not, possibly because—as in the anecdote above—they are new to the city, or in the case of families attending Wauwatosa schools through open enrollment (I previously wrote about open enrollment here¹), because they do not live in the city itself and simply have less time and fewer opportunities to meet other families. While she lives within walking distance of her children’s school and can easily spend time meeting and befriending other parents, she recognizes that not everyone can and wondered, “why aren’t we making those same connections with these families who are driving their kids, who don’t have the opportunity to stand on the playground and build relationships?”

And so many of her efforts since arriving here have been aimed at facilitating the types of connections she considers essential to building the diverse and welcoming community she would like to see, whether that’s through the creation of a mentorship program to “pair new families and even families that have been in Jefferson” with others more established in the community or a welcoming committee for the families of open enrollment students. Although she admits that the welcoming committee didn’t “necessarily capture the families that we want[ed] to capture” she continues to think about ways to “get parents not just to be committed to their kids education, but engaged in what’s happening in the district and feel like they’re a part of the community.”

Coming from Ohio, the peculiar dynamics created by the state’s open enrollment system were new to her and something she is still getting a handle on. “I remember sitting at Colectivo there on 68th and Wells right by our house” she says, “and thinking Where are all the people of color? Because all I see is white people, but Jefferson is 30% not-white. So where is the diversity of this community?”

She admits that the problems is complex and progress difficult to measure. Parents, nationwide and in general, are just less engaged with their children’s schools. She also worries that parents of open enrollment students might be more reluctant “to make waves.” “They just don’t have as much authority or power as the residents. Again,” she adds, “it’s a really complicated dynamic.”

Disproportionalities and Discipline

In describing some of her motivations for running, she mentions an experience where her son was waiting in the school office to be picked up after early dismissal one Wednesday, as she was running a little late to pick him up.

I drove and got them, and I got my boys and they got in the car. And I said, “Why did it take so long for them to call me?” And he goes, “Well there were a lot of kids in the office.” This is my now-11-year-old. He goes, “Mom, why are they all black?”

I mentioned concerns she had expressed during a recent board meeting about why so many more black students were getting in trouble or suspended and asked her what she thought the cause was.

It’s...so complex. I don’t think that there’s something I can point to. I know you read the book that was recommended to me, I don’t think you—[laughing]—I don’t think you appreciated it² in the same sense that I did.

I think there’s a lot of factors. I think as Wauwatosa evolves and changes, the demographics have changed significantly, even over the last 10-15 years. And as an educator I wonder, Are we creating inclusive environments for students? Are we welcoming them for who they are? Like understanding their cultural differences, understanding that they come from a community—especially with open enrollment—outside of Wauwatosa. And even the black residents that live in Wauwatosa—there’s just different cultural pieces.

And I recognize this as being bi-racial, especially coming from a multi-cultural family, where my dad’s side of the family is vastly different from my mom’s side. I mean with their cultural differences and their life experiences. I think there’s something to be said about having a system—I think public education in general is a system that’s been designed to educate a certain group of students and not taking in necessarily those cultural differences. Even when we look at our LGBTQIA students—and I talked to the GSA group—and they don’t always feel seen and heard. So I think that we have systems in place that don’t recognize the uniqueness of all students, and I think that’s not just specific to black students.

Referring to some of the measures the school district has implemented over the past year to curb violence and misbehavior in schools, Jessica says that she’s “hopeful that the things we’re putting in place are going to be effective” but mentions that the board is fairly new and that there is and will continue to be a lot of turnover—“Dr. Hoag has been on less than a year, I’ve been on eight months, we’re now having three folks who have been on the board leave.” She also says that many in the administration, including the superintendent, are relatively new (Dr. Demond Means was hired in April, 2021, as superintendent) and that they’ve “had literally months to put things in place.” Some problems, as well, are just hard to handle through school policy:

When we see these outlier, extreme behaviors, like these fights involving parents—these are outlier students. No disciplinary framework, no policy the board creates, no resolution is going to magically make those things go away. I think that we’re dealing with—again—complex issues. But as far as the behaviors in the classroom, having these expectations stated through our disciplinary framework. Our policy committee is working on a discipline policy that outlines where every stakeholder has some accountability and what their role is.

Boys and Girls

Jessica continues:

I think there are also differences in the behavior of—and I think research supports—that some of our black and brown boys need to [get rid?] of some of that energy. They can become more fidgety. But again, are those behaviors, to your point, looked at as being insubordinate? And where their white peers might do the same thing, but [a teacher] doesn’t observe it in the same way? Like I said, it’s complex, but I think a lot of these things are at play.

I suggest maybe we should try to get more male teachers. She is sympathetic to the idea that kids “can make a connection with different teachers for different reasons” but doesn’t seem too optimistic. “How do we get them in—people aren’t entering college for education. How do we incentivize these high schoolers to go into education? I don’t know.”

I ask her what she makes of the fact that a majority of the most serious disciplinary problems involve girls. While acknowledging that she is “hugely concerned about it as a woman of color,” she thinks that we’re facing some unique challenges today, particularly around social media. “At the root,” she says, “I think most of these occurrences, they start somewhere on social media and then they morph into this in-person thing” and while some might disagree with schools putting resources toward “social emotional learning,” she believes it is necessary and helpful. But she also thinks that the pandemic and the policies imposed as a response to it have played a role, that many students are still overcoming the unique challenges presented by at-home learning, and that this is exacerbated by the student’s circumstances and home life.

I worked in a very urban district, actually the high school I worked at was 98% black students. They faced issues that other students didn’t. They came from very low SES. Lots of trauma and crime in their neighborhood. And I saw as a result of that, just this increase in violence. And I think we’re seeing that with some of our black students.

She concludes, “Students that don’t have that support in their home life, they come to school looking for that consistency, that structure, that adult that they can rely on. And I think that they lost a lot of that during Covid. And we’re still dealing with some of those implications.”

Teacher Compensation

Jessica wants to give teachers more money. She would also like to increase the proportion of black teachers in the district but notes that there’s a supply problem. “They’re so limited” she says, and “we can’t just go and pay black teachers $20,000 more.” But she does think more black teachers would do a lot to help black students “feel represented, and feel heard, and feel valued.”

While she doesn’t have a particular dollar figure in mind for average teacher salaries (I asked), she does note that public education funding in Wisconsin is tricky and complicated and much lower than she thinks it should be. “We have a constitutional duty to fund our public education system adequately, and I don’t believe that we are.” I point out that it’s hard for a school board to have much of an effect on state education funding and ask her what she thinks we could do in the absence of such changes. She says she’s not entirely sure but suggests there might be ways to get more creative with our budgeting.

I think that Wauwatosa has always prided itself on being a fiscally conservative district. And talking to [CFO] Keith Brightman and even attending some of these sessions at the convention I went to for the Wisconsin School Board Association, I think we need to be creative. We’ve always had a lot of money in reserve as a district, and we always have above the percentage of the operating costs we want to have.

I know I mentioned short-term borrowing. This was something that was actually brought up by a former school board member—she and I had a conversation. Her experience at Longfellow right now is that her kid has gone through three different teachers. Whether it’s maternity leave or retirement or teachers leaving. We need to attract and keep teachers. I’m not the CFO, I’m learning the complexity of our budget, but I do think we need to get creative on how we compensate teachers. [I’m] just not sure what that might be.

Obviously you’re right, we don’t influence—I can’t directly influence what’s happening at the state level. But I do think the community can rally behind talking to their legislators saying, “We need this to pass. We need more money at the state level.”

When I suggest that some of the demand for higher pay might reflect teachers’ perception that the job has gotten worse, she mentions that not only was Covid quite difficult for teachers, it also encouraged a greater acceptance of flexible work arrangements in other professions that have made many non-teaching jobs relatively more desirable. It’s not necessarily just that teaching has gotten worse since Covid but that many other jobs have gotten better, and that it might be worth considering some ways to bring that flexibility to teachers as well, whether it’s through the addition of more paraprofessionals, combined classrooms, or more counselors to remove some of the burden from teachers of dealing with disruptive students.

East vs West

Jessica tells me that the thing she’s been most surprised by since she became a school board member is “this division within the community.”

The two things she mentions specifically were the AVID scandal and the board’s revisions to the school district’s human growth and development curriculum. While she thought the district “did a good job of engaging various stakeholders,” she did feel that the community “had very valid points about the district communicating better with families before it was happening.”

Nevertheless, she expresses some optimism that underneath, “we all have the same values” and believes “that every single board member has the best interest of the whole community” as it makes decisions.

While she doesn’t necessarily think that living on one side of the community rather than other “make[s] you qualified to be a board member,” she does think people can overweight their own experiences and that it takes concerted effort to seek out disconfirming perspectives. She is proud of her efforts in this regard.

I’ve had coffee with some of my biggest critics. They send me a nasty email about not caring about them, and I offer to have coffee. Because I do think at the end of the day we all want the same thing. We all want great, safe schools that are inclusive and thriving and our kids are doing great things. I don’t think anyone can argue that. So I think it’s finding that common ground.

Final Thoughts

But most of all, Jessica said she wants to make sure students remain at the center of the community’s conversations. Referencing the candidate forum held at the senior center last month, she said that questions likes those tend to focus too much on the concerns of parents and community members and not enough on the desires of students. “Those questions we’re asking about teachers, and parents want this, and parents are concerned about this, and community members are concerned about money—but what about students?”

I say we might care a lot about what parents and residents think about the schools because they are the ones paying the taxes for them (I swear it all comes off less obnoxious in person). Jessica doesn’t disagree but still feels the preferences of students and various student groups are not given as much weight as they could be.

I think there’s value to get input from all stakeholders, but I think the one stakeholder that we don’t necessarily talk about enough are the students. Even as I meet with these different affinity groups, the gender sexuality alliance, and the black student union, I think it’s really important to honor their perspective and what their lens is of the school.

Again, that’s where I get to the base and essence of why I’m running, is because I believe all students should have a sense of belonging. And they should be in a welcoming environment where they can be their authentic self and get the supports that they need so that they can thrive. And I just feel like all too often that we’re missing kids from the conversation.

1. But the basic idea is: Wisconsin allows children to apply to attend school in any school district in the state subject of course to the availability of open seats. Wauwatosa is a popular destination for students from nearby Milwaukee Public Schools (MPS) and as Jessica says at one point in our conversation “many [open enrollment students] come from culturally diverse backgrounds.”

2. She’s referring to this review from December of last year. It was fair—I think—but pretty critical. It was also long, so I’m not sure how many people read it. It was kind of her to do so.