Inside the Labyrinth: The Effects of Feminization on Women Assistant Heads’ Well-Being

Abstract

This qualitative study examines the organizational structures shaping the experience of 18 women assistant heads working at K-12 independent, co-educational, day schools serving students of 700 students or more. Specifically, we were interested in better understanding the disproportionate representation of women in the assistant headship and whether, and to what degree, this may be a function of the role. We wondered if gendered structural elements shaping the role and specifically feminization (e.g., gendered expectations, role elasticity, diminished professional autonomy, and compensation structures that devalue care work) may hamper these women’s overall success and well-being. We found that the structures shaping their role did appear to be feminized, such that while many participants felt a sense of purpose in their work, the expansive and seemingly endless nature of their responsibilities; the emotional labor the role necessitated; the limited guidance, autonomy, and feedback they received; and their frequent perception that their efforts were under-compensated contributed to diminished well-being. The implications of this study include the need for training in, and implementation of, best practices for evaluation, mentorship, and mitigating gender bias and discrimination in all aspects of school operations.

1. Introduction

Eagly and Carli (2007) liken women’s leadership trajectories to moving through a labyrinth with difficult and often circuitous paths to advancement. This metaphor reflects the research showing how gender discrimination and gendered racism shape women’s experiences and well-being across the leadership pipeline generally (Eagly & Karau, 2002; Rosette et al., 2016) and in educational leadership specifically (Weiner & Higgins, 2023). Women remain underrepresented in the highest status educational leadership positions—fewer than 30% of high school principals identify as women (National Center for Education Statistics, 2023) and only 28% of superintendents (White, 2023). Women of Color are even less well represented, with available numbers suggesting less than 9% of principals (Lomotey, 2019) and 1.5% of superintendents identify as Black women, and only 1% identify as Latinas (Miles Nash & Grogan, 2022). Data on other intersecting racial/ethnic identities and/or marginalized identities remains sparse—something that we should all be concerned with if we are to create equity-driven schools in which everyone can thrive.

We find a similar phenomenon in independent schools, and specifically, large, coeducational, independent, day schools, the setting of this study. While an understudied context, approximately 4.7 million children in the United States attend independent schools (National Center for Education Statistics, 2023), and hence this felt an important context in which to consider women’s educational leadership experiences. According to the National Association of Independent Schools (Rowe & Torres, 2024), in the nation’s largest coeducational independent schools (i.e., those serving more than 700 students), White women occupy just 30% of headships, and Women of Color, just 2%. And yet, when we go to the second tier of leadership in these schools, we find a different scenario—in 2024, women comprised a majority (56%) of assistant heads1 school positions. Additionally, although we were unable to find data on assistant heads disaggregated by race, we do know that the numbers remain low—though potentially better than for heads of school (only 5.3% of heads identifying as Black and only 2.6% identifying as Latinx/Hispanic (Rowe, 2021).

Looking at these numbers, we became curious about why women were substantially better represented in these “second in command” roles and their well-being therein—particularly as they could be considered stepping-stone positions to the headship. In fact, the 2021 NAIS survey on the state of independent school leadership indicated that over 40% of sitting heads of school had previously been an assistant head (Rowe, 2021). On one hand, it is possible that the concentration of women in these roles is a positive step towards equity and access. Evidence of this may be increased numbers of women moving on to the headship and/or thriving in these roles.

On the other hand, it may be the case that the same discriminatory structures keeping women out of the highest levels of leadership are the same ones funneling them into particular positions (e.g., the assistant headship). This orientation is aligned with longstanding work in other fields, including higher education, regarding the gendered nature of organizations (Acker, 1990, 1992) and how organizational structures tend to reproduce gender inequality (Britton, 2017). Given this prior work, it seems possible that women leaders in large, coeducational, independent, day schools would face organizational structures that serve to create ongoing challenges in accessing the headship (i.e., getting stuck in the labyrinth) and cultures that, as true for other women leaders (e.g., Machín-Rincón et al., 2020), would negatively impact their well-being.

Wanting to know more about how to make sense of this phenomenon and taking an institutional perspective grounded in Acker’s (1990, 1992) work on gendered organizations, we use the theory of feminization (Akorsu, 2016) to guide our inquiry. Specifically, feminized professions, beyond being those in which women are concentrated, are characterized by structures including cultural expectations that these workers exhibit stereotyped feminine characteristics (e.g., caring, nurturing, warmth). These professions or roles are also structurally devalued via policies (i.e., see the recent Trump administration Department of Education’s efforts to exclude female-dominated work, including teaching, from professions), lesser autonomy, and lower levels of compensation than other professional roles (Basten, 1997; Busch, 2018; Fondas, 1997). As a result, those working in these professions often face multiple organizational threats to their well-being and career progression.

Using feminization to help guide our inquiry, we asked the following research questions:

• To what degree do women leaders in secondary leadership positions describe the structures shaping their role as feminized?
• What impact, if any, do these structures have on their well-being?

2. Literature Review

Women and Leadership in Independent Schools

To begin, it is worth mentioning that the literature on women leaders in independent day schools, including large, coeducational ones, is somewhat sparse. When race and/or gender are considered in this setting, it tends to be oriented towards the student experience (e.g., Gonzalez, 2023; Hill et al., 2023) and how best to address gaps to create more equitable spaces and student experiences (Kallio et al., 2023). Beyond a recent Special Issue of Teachers College Record (August 2023), we could find few peer-reviewed studies, and only slightly more dissertations, on women in leadership in this space or their well-being. We mention this to explain the somewhat abbreviated nature of this section and to highlight the need to elevate these stories and women’s experiences in these roles.

In 2023, women comprised nearly 70% of the independent schoolteacher workforce (National Association of Independent Schools, 2024). However, within that same network of schools, women continue to lag men at the highest level of these organizations (i.e., the headship). This gap is nowhere more pronounced than in the nation’s K-12, co-educational, independent day schools serving more than 700 students (i.e., the context of this study). In 2024, women (81% also identifying as White) were less than 30% of the current cohort of those leading these schools but represented approximately 54% of assistant heads (National Association of Independent Schools, 2024). These divergent numbers bring up some questions of why and how this came to be the case—and hence this study.

Looking at job postings on the NAIS’ website, we find that assistant head titles and responsibilities range from “assistant head of school for enrollment management” to “assistant head of school for faculty and academics”. As such, assistant heads might manage departments or divisions; they may be charged with running day-to-day logistics, overseeing curriculum or professional development, and facilitating parent and community engagement. A determinant of how the role is conceived is the school structure. Some schools have more than one assistant head in addition to an associate head; others have only one or two assistant heads. In our study, most of the schools had multiple assistant-level heads, and the women’s work generally focused on faculty and academics. As we share in the findings, all the women described these roles as wide-reaching and amorphous—a reality research suggests is the norm (Flaxman, 2023a, 2023b). Critically, the varied elements of the job are key differences to note between independent and public school environments. In the latter, pay structures and job responsibilities are more likely to be explicit, publicly reported, and generally consistent across schools and districts. In contrast, in independent schools like those in our study, job expectations of similarly named roles vary from place to place, and compensation information is rarely made public or even readily accessible internally.

In addition to being a big job, for women in particular, the work of assistant heads seems to be shaped by some of the typical stereotyped gendered expectations for women leaders. For example, in Flaxman’s (2023b) study of 30 women heads of independent schools, 89% of whom served as an assistant head of school prior to assuming their first headship (p. 6), many of the women attributed their success in moving up the ranks to their willingness to take on unpaid labor and “say yes” to additional responsibilities others would not. Flaxman highlights these activities as a kind of “leadership literacy” that allowed these women leaders to navigate gendered organizations in which there was “bias at every step of their leadership journey and well into their headships” (Flaxman, 2023a, p. 10). This included negotiating the “double bind” in which women who take on the more stereotyped masculine characteristics associated with leadership (e.g., assertiveness, drive, ambition) are seen as unlikeable or a “b*tch”, while those who embrace more feminine stereotypes of care and emotionality are perceived as too weak to lead (Weiner & Burton, 2016).

The limited other research on women leading in independent schools expounds on the challenges they face, often due to discriminatory systems. For example, in their dissertation work, Scott (1997) provides an overview of survey findings identifying areas where men and women differ in their views and pursuit of the headship role to highlight “what is holding women back” (p. 5) from ascending to it. Women participants noted internal and external structural barriers as shaping their career trajectory, noting relocation issues and balancing work and family life as the most important in shaping their path and ability to thrive. Similarly, Hotchkiss (2019) and Gallagher (2017) both found that senior-level women administrators felt they were held back along the leadership pathway due to family responsibilities and gender bias in leadership. Finally, King (2021) found that underrepresentation of women on school boards of trustees, school search committees, and on executive search consultant teams made it more likely that these structures would remain intact and traditional norms of leadership as a masculine endeavor would be left unchallenged, making it also less likely that a woman would be hired as the head (p. 125). Inversely, Flaxman (2023a) found that shifting the structures to have women on boards and executive searches favorably impacted women leaders’ search experiences and outcomes.

As true for women aspiring to leadership in public schools (e.g., Liang & Peters-Hawkins, 2017; Muñoz et al., 2018), women in independent schools were also unlikely to receive the same level of mentorship as their male colleagues (Gallagher, 2017), affecting their access to leadership roles and their work and well-being therein. Alternatively, Hotchkiss (2019) posited that multiple levels of support from mentors, family, heads of school, and informal networks were powerful mechanisms to support women’s ability to move up and thrive. This finding was echoed in Otey’s (2024) study in which women heads of school said they were strongly influenced by women role models in their career journeys. Colmaire’s (2022) examination of the Womxn’s Leadership Alliance (WLA), an informal co-mentoring network of women independent school mid-level leaders in California, also highlights how participation in such networks can benefit women leaders, including providing them time to form their leadership identity outside the workplace and in the company of role models and peers. Taken together, we can understand the experience of many women assistant heads to be shaped by gendered structures in ways that may negatively impact their well-being. The question is, and the one we take up here, whether the role itself may be structured in ways that may serve to reify these stereotypes (i.e., whether it is “feminized”).

3. Feminization

“Feminization” can be understood as a process in which women become a larger proportion of the labor force or when a traditionally male-occupied profession becomes women-dominated (Akorsu, 2016). These shifts are coupled with the corresponding phenomenon of shifting structures that include diminished status, the implementation of compensation models undervaluing care work, and increases to oversight and control (Basten, 1997; Busch, 2018; Herd & Moynihan, 2025). Feminized professions are also framed through gendered expectation—that they necessitate traditional notions of feminine qualities, including “mothering” and thus pull-on stereotypes regarding women’s “natural” inclination towards service and self-sacrifice (De Boer, 2020) in how their work is structured. In these ways, Acker (1990) argues, gender bias is built into the workplace and operationalized and experienced by women in organizations through everyday structures and systems, including cultural norms. As Britton (2017) explains, in the context of higher education organizations,

Gender could become apparent to women faculty in their everyday interactions with sexist colleagues or administrators, or in rigid tenure clocks that leave little time for a life outside of work, or in practices like nominations for awards or allocations of service. Women might also feel its effects in culturally normative conceptions about their academic abilities in comparison to their male colleagues’.

(p. 11)

Such interactions, with some contextual differences based on occupational rules and structures, are also likely to occur in K-12 spaces as teaching has long been identified as a feminized profession. Moreover, scholars like Apple (2018) argue that policy efforts and other rules to control and inspect teachers’ work are directly related to the fact that most teachers are women. Feminization is also understood to be directly related to the “reduction of social prestige” (Brehmer, 1987, p. 56 as cited in Basten, 1997) that teaching holds. This point, that a feminized profession is not simply one in which more women work but one that is fundamentally culturally devalued because women do it, is a key element of feminization (Busch, 2018).

With that said, the negative associations of working within a feminized profession affect all those working within it, not just those who identify as women. As Fondas (1997) explains, a feminized profession does not necessarily relate to the intrinsic characteristics of actual men or women; it is, however, culturally associated with the categories male and female. Feminist theorists have argued that asymmetrical cultural evaluations of the categories male and female have created the idea that feminine traits are of lesser value, subordinate, and suppressed with respect to masculine qualities (p. 260).

As such, men inhabiting such roles may be viewed as “unnatural fits” and given elevated standing among their women counterparts (Simpson, 2004)—often leading to them more quickly moving into “more appropriate” management roles (i.e., the glass escalator) (Budig, 2002).

This fast-tracking of men to management while simultaneously structurally limiting women’s access has created a pattern of vertical stratification in which women are often clustered in roles that are deemed professionally “lesser” than those typically occupied by men (e.g., teachers vs. administrators, nurses vs. doctors) (Doshi et al., 2023). When women are given access to better-paid and higher-tiered jobs, they often experience “horizontal segmentation” and are funneled into specific specializations that are still tiered lower than those that remain male-dominated (Charles, 2003). An example of this might be in medicine, where women are often disproportionately represented in pediatrics while men tend to be clustered in better-paying and more prestigious surgical roles (Pelley & Carnes, 2020). Here, we note that despite the potential applicability of this same structuring of work within K-12 systems, we could find no studies applying feminization to educational leadership roles nor linking it to women’s well-being in these roles. Thus, we see the current study as creating an opportunity to both offer a new contextual application of the framework and to begin to integrate it into the well-being scholarship to better understand women leaders’ experiences and hopefully work to make schools more equitable and just.

The Link Between Feminization and Women Leaders’s Well Being at Work

Research on education leaders’ well-being, including within the so far understudied space of independent schools (Rowe, 2021), presents a grim picture of an overwhelming job that often leaves those inhabiting it physically and mentally depleted (see Fosco, 2022, for a review). If anything, the way the role is currently structured negatively impacts leaders’ sense of efficacy, satisfaction, stress, and overall health and only seems to be worsening over time (Riley, 2019; Wang, 2024). This includes an ever-expanding workload with greater levels of complexity (Fosco, 2022) and emotional strain (Drago-Severson et al., 2018; Walker, 2019). This complexity was undoubtedly accelerated by the COVID-19 pandemic and racial reckoning and the subsequent impacts on educators, students, and communities (Wang, 2024). Those in independent schools are no exception, as 28% of women faculty reported serious levels of burnout following the COVID-19 pandemic (Bernate, 2021).

While all education leaders are facing tremendous strain, women leaders and those in potentially feminized leadership roles may be particularly vulnerable to challenges to their well-being. As already highlighted, women leaders face several distinct challenges associated with gender discrimination (Heilman et al., 2024) and when identifying as women of color, gendered racism (Essed, 2020). These challenges include, but are not limited to, harsher evaluation standards and less mentoring support (Weiner & Burton, 2016; Weiner & Higgins, 2023), higher expectations for engaging in emotional labor and care work (Filippi et al., 2025), gendered and/or gendered racial microaggressions (Weiner, 2025), and pay inequity (Fox et al., 2019). As a result of these structural and cultural elements, women leaders often experience higher levels of stress and illness relative to their male counterparts (Rogers et al., 2025; Yildirim & Sait Dinc, 2019).

Structural features of feminization, including horizontal and vertical segregation, may further negatively impact women leaders’ well-being. For example, given the small number of women leaders in education, when promoted, they are likely to find themselves one of the few, if not the sole, woman on a larger leadership team, potentially leading to feelings of isolation (Eagly & Karau, 2002; O’Neill & Glasson, 2019). It is also the case that lower-tiered leaders (e.g., assistant head vs. heads) tend to face more ambiguity in their roles and, with it, a higher likelihood of feeling overwhelmed and resultantly incurring negative health results (Hu et al., 2023).

We also know demands for emotional labor in educational leadership can negatively impact job satisfaction (Maxwell & Riley, 2017; Zoro et al., 2021). Here, we define emotional labor as Vial and Cowgill (2022) do, “as the act of self-regulating one’s emotions to respond and attend to others’ needs and emotions in a manner that advances organizational goals” (p. 2). In this way, emotional labor asks individuals to sublimate their own emotions in favor of organizational needs. While all working environments require some degree of emotional labor, women are often expected to be more adept at it and are asked to do far more of this work than their male colleagues (Vial & Cowgill, 2022). Beyond constricting women’s ability to express their full selves at work in ways men do not experience, given that women’s, and particularly Women of Color’s emotions are often weaponized in working environments (J. S. Smith et al., 2016), and that care is systematically devalued in organizations (Busch, 2018), we can see the potent harms these unchecked expectations may cause to women’s ability to thrive at work.

We also know that women leaders are given less autonomy over decision-making and greater oversight (R. A. Smith, 2005). These constant and embedded challenges to their authority and autonomy may then diminish their sense of accomplishment and sense of purpose, feelings each found to influence well-being (e.g., Dicke et al., 2018). When pay inequity is also present, it can further exacerbate these negative feelings (and real economic opportunities), leaving women feeling undervalued (Filippi et al., 2025). Negotiating discriminatory systems is exhausting and has negative physical consequences to women leaders’ well-being (Burton et al., 2020; Hu et al., 2023).

Finally, we would be remiss if we did not mention women’s disproportionate role in home-based care work (Craig, 2007) and its impact on their well-being at work. Women often leave work only to engage in a “second shift” (Blair-Loy et al., 2015), serving as the primary caregiver to young children and/or aging parents. This double duty can create feelings of role conflict (Hu et al., 2023), a reality that can further drain women’s already heavily utilized psychic and physical resources (Machín-Rincón et al., 2020). Therefore, we can understand that women leaders are (1) more susceptible to experiencing structural features of their work that challenge their well-being, and (2) this may be particularly true in feminized roles where gender stereotypes powerfully shape these structures and hence women’ s experiences. It is with this framing that we examined the nature of these roles and the well-being of 18 women serving as independent school assistant heads.

4. Methods

As we were interested in exploring how feminization may be operating relative to women’s roles and thus experiences as assistant heads of independent schools, and needed detailed data to do so, we took a qualitative thematic analysis approach informed by phenomenological interviewing (Seidman, 2006). This allowed us to uplift participants’ narratives (Moustakas, 1994) and build a description of their experiences (i.e., phenomenon) (Creswell & Poth, 2018). Thematic coding (Boyatzis, 1998) allowed us to connect feminization to participant experiences and develop empirical support.

Note that we adhered to all standards for ethics indicated by our Institutional Research Board (IRB) regarding research with human subjects. These include expectations for participation, signed consent, and voluntary withdrawal, as well as confidentiality and data handling procedures. All data was de-identified as part of the coding process and stored in a secure manner aligned with our institution’s IRB standards. As indicated elsewhere, IRB approval was provided by The University of Connecticut.

4.1. Site and Sample

Once we received IRB approval, we moved to form our participant pool. First, we consulted the Independent School Data Exchange (INDEX) directory to search for co-educational day schools with no religious affiliation and student enrollments of 700 or more. Once we determined schools meeting these criteria, we cross-checked school websites to verify enrollment numbers. We then used a purposeful, criterion-based sampling technique (Patton, 1990) to identify women who were working as assistant heads serving at these co-educational, non-religious independent day schools. As we stated above, these institutions are most traditionally led by men. Once we determined potential candidates for the study, we sent them emails inviting them to participate. A total of 18 agreed to join our study. To be sensitive to the privacy of our participants, we use pseudonyms throughout, do not include specific information related to race or ethnicity, nor do we include references to their location. After we received signed consent waivers from participants, we turned our focus to data collection.

4.2. Data Collection

Interviews were conducted virtually during three months in the fall of 2024 and transcribed verbatim. We modeled our interview process via Seidman’s (2006) phenomenological interviewing framework. Each participant was interviewed three times for approximately one hour each time. The first interview focused on participants’ work histories, including their path to their current role. The second interview focused on their experiences in their current position—with feminization guiding our inquiry (e.g., “To what degree do you feel you have autonomy in your role?”). The last interview, in keeping with Seidman’s suggestions, asked participants to reflect on how elements of their role might be gendered and/or impact their future goals and well-being.

4.3. Analysis

We analyzed the data thematically using a process that included both inductive and deductive coding (Boyatzis, 1998). Deductive codes came from the research on feminization and women leaders’ well-being at work. For our inductive coding, we followed Charmaz’s (2015) suggestions for a grounded coding process, including creating gerund-based phrases, aggregating and then interpreting these phrases to create our codes. This process was collaborative in that the authors simultaneously and separately engaged with the three randomly selected interviews from the first round. We then came together to ensure alignment and discuss disparities in coding. Upon reaching consensus and following this conversation, we completed the coding of the first round of interviews. This same process was repeated for each round of interviews. Additionally, we returned frequently to the data to ensure coherence and a grounding in participants’ experiences. Finally, we used member checks and sent transcripts and drafts of all written work stemming from the data to participants for feedback.

Positionality

The first author identifies as a white, cis-gendered, Jewish woman. Much of my work is dedicated to creating platforms for women education leaders’ stories, while simultaneously challenging conceptualizations of leadership steeped in whiteness and maleness. I know that I have the privilege of engaging in this work because of my whiteness and other dominant identities, and I am aware that these identities also shape my relationship to those who are willing to engage in this research and entrust their stories to me. As part of my embedded practice, I engage in reflexive practice (Erskine & Bilimoria, 2019) to attend to my subjectivities, including journaling, challenging common conceptions of truth and which knowledge is valuable, and engaging in dialogue to process my experiences relative to the analysis.

The second author identifies as a white, cisgender woman who has taught for 20 years in various public and independent school settings. Keenly aware of bringing my “insider/outsider” status as a white woman familiar with elite educational spaces (Dwyer & Buckle, 2009) to my work as a researcher in this study, I leaned into our prepared interview questions to guide my interactions with participants. Moreover, I worked to be reflexive throughout the entire research process to limit potential bias in my work at any stage (Ahern, 1999). At the time that we conducted this study, I was a doctoral student in educational leadership; therefore, I also looked to my advisor’s experience and perspective for support throughout this process (Castleberry & Nolen, 2018).

5. Findings

In the following sections, we share some of the gendered organizational structures that shaped these women’s roles and their well-being. These include, but are not limited to, (1) role elasticity, (2) normative demands regarding engagement in care work, (3) reinforcement of male dominance in organizational hierarchies through the devaluation of such care, and (4) pay structures that failed to honor the full scope of these women’s work. Together, though to differing degrees, these structures constituted and reconstituted the role of the assistant head as feminized, with repercussions for these women’s well-being.

5.1. Scope of Work

First, we focus on role elasticity and how women were expected to take on ever-increasing and expansive labor—often that which focused on care. When we asked the women about their scope of work, it quickly became clear that it was expansively defined, with somewhat porous boundaries (i.e., highly elastic), using terms like “nebulous” (Rachel), amorphous (Kathy), “always evolving” (Laura), or unclear (e.g., Vickie said, “I would say it wasn’t clear to me, because it just wasn’t clear to anybody”) to describe it. First, excluding two participants, whose primary responsibility was enrollment management, the formally recognized features of the other women’s positions were overseeing academics and teachers, teaching, and students’ behaviors and needs. This work included, but was not limited to, parent outreach, curriculum decisions, professional development, hiring, and evaluation. Additionally, the women participated in multiple other initiatives and committees at their schools (e.g., global initiatives, capital campaigns, AI task force, parent group liaison).

As relayed to us, many of these additional responsibilities, as well as the more informal ones discussed later, were requested without consideration for their overall workload or skill set. Rather, as Laura explained, it often felt that they were given more responsibility simply because the work needed to be done and no one else was able or willing to do it. She said,

Undefined things do come up that I’m like, “Whoa! That is so not in my lane, but I’ll help you try to get to where you need to be”. …It can be hard because people come to you for all sorts of things, and then I get assigned assignments that I’m like, “Is this really mine?”

On this issue of being asked to take on additional work due to gaps in the system, approximately a third of the participants told us that they held secondary formal leadership positions (e.g., math department chair, head of the lower division, DEI coordinator) as interims when the position could not be immediately filled. The most extreme case of this was for Mira, who, since entering the role, had always held multiple positions. On this point, she said

When I came here there was no director of Diversity, Equity and Inclusion, and so I was also doing that role for my first two years and my second year, in addition to being assistant head of school director of DEI for the second half of that year, I was also the head of the Upper School, because our head of Upper School left in February…last year I was supposed to just be the assistant head of school. And then our director of enrollment and financial assistance left and so I became the interim director of enrollment…So, this is my first year doing just my job as assistant head.

These additional responsibilities were often unpaid or minimally compensated and, as clear from Mira’s comments, failed to include a reduction in duties in their current position.

Adding to these more formal responsibilities, participants were often called to engage in informal forms of emotional labor. This included what some positively framed as “relationship building”, engaging in “tough conversations”, or “fighting the good fight”. For example, Joanne said a key part of her work was

Building relationships with not only the people I work with, but also the people that are within the community, parents, anybody that’s here…I’m wanting to welcome them to our community and offer that if they need anything. I will help them.

While the help Joanne provided undoubtedly benefited the community, its weight, particularly when it came to more difficult or fraught issues (e.g., dismissals, student violations of policies, financial constraints), was substantive. Repeatedly, participants described their work as largely relational and oriented towards attending to the emotional needs of others, particularly when these emotions were bubbling over to administration or the topics were fraught.

Yin & Yang

Structural reinforcement of gendered expectations for leadership behaviors was consistently reported by participants, and this appeared to shape the experience of assistant headship. As participants dealt with many fraught issues, they also often positioned themselves as being expected to engage in more stereotypical feminine elements of leadership (e.g., care, empathy, listening) while their male heads were not. Kathy described her experience this way:

He [the head] hired me to be his external hard drive for emotional intelligence. He’s a good fundraiser, and he is a good budget person, and he is humanly incapable of relationships…I’m all relationships…And so it became this false binary between us, because I could do the finance stuff, too, but he could not do the people stuff.

Susan similarly described the cultural expectation that she would fill in the emotional gaps left by the head. She told us that her ability to effectively manage others’ emotions was part of why she was selected as the assistant head.

I see the nuances of things. He sees the bigger picture. He’s all positivity, and I’m all reality…people come to me. If they feel like they’re not being heard because I will sit with them, and I will sit in the mess, I will not be dismissive. I will listen; I’ll acknowledge and make sure they understand they matter and help them navigate that.

Genevieve expressed similar frustration regarding her disproportionate work engaging in emotional labor compared to her male head. She also saw her engagement in this work and the head’s lack of it as related to gender stereotypes, as well as how their jobs were structured. She said,

We see women in relation and fundamentally in a caretaking role for men. So naturally, the assistant head would be a woman…The same reason you want a female administrative assistant…I also think it lends itself to a lack of appreciation. Like those people become invisible really quickly. It becomes a thing where, like when I left [prior school], they replaced me with two people.

Taken together, we can understand these women’s roles as elastic, such that their work was expansive and shaped by gendered expectations regarding care work. As Genevieve put it succinctly, “It feels easier to ask a woman to sacrifice because it’s just part of the expectation”.

5.2. Work Valuation

Emotional labor and other forms of care work were devalued through normative structures and in ways that served to reify male dominance in their organizations. While the women saw themselves and their work as adding tremendous value to their schools, their experiences of external valuation were more mixed. While some experienced complimentary and appreciative comments from colleagues, others expressed feeling undervalued by those in governance (i.e., board members, other leaders at or above the women’s managerial status). In this way, the established hierarchy of the school tended to reinforce male dominance by positioning these women leaders more like staff than executives, whom board members might be more likely to position as colleagues.

5.2.1. Appreciative Colleagues

First, when we asked about whether they felt valued in their role, participants gave concrete examples of their accomplishments and the pride they felt as a result. Much of this pride was linked to feedback received from reports (i.e., teachers, department chairs, school counselors). For example, when asked to recall when she felt valued in her role, Diana said,

Someone was quoted in one of my annual reviews to say that I have moved the school further along than it ever has in over a decade of their time at the school…There’s a strong sense of trust in my leadership and the direction I move the school, and that is really important to me.

The positive perception of being trusted and respected by those whom they managed, and the fact that this care was captured and conveyed explicitly, in this case through their evaluation (i.e., a formal structure shaping their role), reverberated through other participant responses. Mira, for example, shared,

I hear a lot of verbal appreciation for the way I lead a meeting. Or I got an email last week from a colleague who said, “Every time I leave a meeting with you, I feel heard and understood…” And that feels really powerful. I feel appreciated and respected by a lot of my colleagues, which makes the other pieces much easier to navigate.

For these women, this positive feedback in the form of direct feedback on their performance provided a strong sense of being valued in their roles.

5.2.2. Undervalued by Those Above

As we will discuss later in our findings on professional autonomy, the women had mixed responses when it came to their views about whether and to what degree their heads viewed them as true professionals and valued their judgment in decision-making. In particular, and relevant here, some spoke to how they often felt devalued by others who were not necessarily the head but wielded equal or more power than them in the organization (e.g., Board members, other assistant heads, powerful parents). Indeed, the hierarchical structure of these organizations seemed to reinforce gender stereotypes in terms of positioning these female leaders more as staff than executive leaders. Vickie, for example, spoke about an interaction she had with the CFO in which he positioned her as working for him such that she felt both devalued and disrespected. She recalled,

He said, “I’m not used to having an assistant head push back at me and not execute my orders”. [I said] “Well, that’s interesting, because you’re never gonna get that with me. Ever. I’m your partner. I’m not your subordinate, and I’m going to call it like I see it”.

Though here Vickie was clearly able to speak up for herself, the interaction had deeply impacted her sense of self. She was visibly upset retelling this story and spoke about how it had rattled her.

Such feelings were common among the women after similar incidents, even as they attempted to remain calm when confronted. This was true for Debbie, who described being constantly challenged by her school’s board members in ways that left her feeling her expertise was devalued.

With our Board, I feel like a lot of times that my opinion’s not valued. They refer to a lot of us on the administrative team as “management or staff”, and it has that sense that you’re a tier down …A lot of times, I want to start conversations with the statement, “I’ve spent my whole life in education”…I know what I’m doing, but they don’t see it.

When asked about how her head dealt with similar feedback from the board, she said that the board never spoke to him that way—suggesting his role was normalized as being that of an executive. When we then asked what her head did to intervene when such comments occurred, she said that he had never said anything, and as a result, she had not broached the subject. In this way, while the head was not necessarily the perpetrator of the disrespect Debbie endured, one might argue that his silence was a form of collusion in this insult, thus reifying the existing hierarchy. In this way, and as we discuss next, while heads were not actively engaged in devaluing these women’s work, neither did they work to enhance how these women’s roles were structured and/or participants were treated within it.

5.3. Autonomy

Participants reported uneven levels of autonomy when it came to their roles, which could be reflective of gendered expectations for leadership. When we asked participants whether they felt they had autonomy in their roles, the results were mixed. Most suggested that while they were left on their own to make decisions, this was more of a function of incomplete information or disinterest rather than their heads’ trust in their capabilities. A smaller number of the participants (approximately ⅕) reported feeling positively empowered in their independence. They attributed this to the trust their head of school had in their leadership, skills, and knowledge. Diana described her relationship with her head, “I do feel like there’s a lot of trust, and I have a lot of autonomy to make decisions or move work forward in a way that I feel is in the best interest of the school”. Michelle echoed these sentiments by saying, “I think the support from my head of school feels like a trust that I can get the job done, and like a trust in my decisions, and a trust in my recommendations, and a trust in my perspective”. Laura also felt that she had “earned [my] head of school’s trust” as “a competent and thoughtful leader…by demonstrating to him that I understand what the needs of the schools are in the areas he’s charged me”.

Notably, participants who felt they had autonomy, given their head of school’s trust in them, often cited the importance of bringing people together to collaborate and make decisions. Stacy described “feeling empowered to make and execute on decisions” from her head of school as an opportunity to “gather perspectives from various persons…I love to engage other people”. Elise reported, “I feel like I often have as much autonomy as I want, like I’m trusted to do a lot on my own, but I prefer to do things as collaboratively as possible and to get different perspectives”. In a sense, autonomy gave assistant heads the power to activate community members and make collective decisions.

Other participants felt that while they did not have total autonomy, they did not expect it and thus were satisfied with their more controlled decision making. Susan, for example, remarked on the intersection of trust and authority in her position at the school this way:

I do defer to [the head], or will even say in a meeting, “Well, I’m going to check in with my head of school first before we make a final decision”. But I really like that relationship. It’s not in any way uncomfortable or what I feel is unjust or unequal. It’s just the nature of how we make decisions.

Similarly, Debbie said, “I always keep my head of school well informed, you know, like what I’m working on and what I’m doing…I’m like, “Here’s what I’d really like to do, and he will be like, “Go run with it for a while and see how it goes”. These examples demonstrate a sense among the women that the nature of their position as second in command made their deference to the head in decision-making logical and appropriate. In this way, it is possible that, even without perhaps intending to, these women were reinforcing the existing gender hierarchy that was shaping other, less preferred elements of their work.

5.3.1. Limited Guidance Brings Isolation

In contrast to these more positive viewpoints, many participants reported receiving limited guidance from their heads of school when it came to understanding and navigating their significant responsibilities. The result of this lack of clarity was that they felt, and indeed were, more on their own than positioned as experts in their work. As Genevieve explained,

I really struggled to get him [the head] to articulate publicly or to me anything he wanted me to do. He would tell me to do something and be like, “Yeah, never mind, here’s this other thing. Oh yeah, don’t do that”. It was very confusing…rather than him telling me, “Here are your priorities”, I’m like, “How about these?”…So, I feel I have too much autonomy.

Danielle similarly noted, “I don’t have a really defined job description…I think a solid org chart would really help me feel even more supported because the lines of authority over what I manage and influence would be clearer”. These participants did not feel effectively managed when it came to gaining a better understanding of the scope of their work; as a result, they could not earn or give the trust necessary for true professional autonomy.

5.3.2. A General Lack of Formal Evaluation

Perhaps one reason that many of the women felt their heads had limited knowledge of their work was the frequent absence of meaningful performance criteria and evaluation for their roles. While some participants described having standing, regular check-ins or one-on-ones with their heads of school at the end of the year, these events tended towards the informal. Most said they rarely received any real feedback on their performance and/or lacked the opportunity to go through a formal evaluation process. Danielle revealed, “I’m not really evaluated, just to be honest…I’m not used to having a formal write up at the end of the year. I’ve never experienced that before”. Laura had a similar experience:

I haven’t ever really been evaluated…But I certainly would appreciate a more formal kind of evaluation and goal setting and things like that…But it doesn’t seem to happen structurally or formally in my role here, or in my previous school, so, I don’t know if it happens in other schools.

Rachel echoed this desire for more opportunities for growth, saying,

I don’t get an evaluation or formal written feedback that says, “Hey, here’s what you’re doing really well. Here’s what I’d like you to work on”. But I don’t think anybody else is getting that either. But the fact that I stay in my role and I’m not getting a lot of formal negative feedback, and then I’m continuing to be given large responsibilities, I sort of interpret as, “Ok, things must be fine”.

While previously stated findings suggest the power of evaluation and direct feedback, these examples emphasize that participants who did not receive regular feedback typically felt their potential was not fully utilized. It also added uncertainty to their already difficult role and made it challenging for them to self-advocate with either their head or others in the school.

5.4. Pay

Pay is an important structure to consider as it relates to the feminized experience of assistant headship and how the devaluation of women’s work gets manifested in their compensation. While not all the women felt their compensation was inequitable, it was clear that they were often making less money than other executive-level leaders in school and, in all cases, substantively less than their male heads. Of course, the general lack of transparency regarding how individuals are compensated and for how much limits the nature of these comparisons while also being a potential factor in the maintenance of potential inequities.

With that said, it is worth mentioning again that, during their tenures as assistant heads, many of the women also fulfilled additional administrative roles (e.g., department chair, DEI coordinator, HR director), often without additional compensation. When compensation was offered, it was often minimal (e.g., “I’ve gotten stipends for the work, but they’ve been like, one-tenth of the salary that the person that they were saving in salary”—Mira). In some cases, as true for Debbie, women refused even these small stipends, saying that they felt “bad” or “guilty” for doing so. “I was offered…a little bit over $3,000. And I felt really bad about taking that money from the school because I was already being paid so much money”. This feeling that, because they were making so much more than they had as teachers, they did not “deserve” the extra compensation for doing more is tightly linked with the normalization of women’s overwork in schools and brings up additional questions about how such orientations may impact their willingness and ability to effectively negotiate for fair compensation at the outset.

Shifting now to their core salaries and specifically whether they were compensated at the same level as their other leadership level colleagues, it was clear that few were suggesting that the compensation model itself devalued the components of their work. In some cases, like for Jane, these differentials were accepted as appropriate and fair. She explained that her Head of School had provided her with the following explanation for existing differences,

[He] has explained to me that his way of thinking about it is, he’s the highest paid employee. The CFO makes 50% of the head of school salary, and then the assistant head makes ⅔ of what the CFO makes. I don’t know if that’s a common metric. I have not questioned it. Right now, I feel appropriately compensated.

Susan presented a similar argument in that she knew that she made less money than her colleagues and the prior assistant head, but that this “made sense, because that person had been at [School] for 20 plus years. So, there was some loyalty there. I think I make probably in the 75th percentile of what other assistant heads of school make in the independent school world”. In neither of these cases did these women wonder about the overarching compensation model and its fairness relative to the valuation of different and often gendered forms of labor, but only focused on their compensation relative to others in the same industry. In other words, it can be both true that they are paid like others in this role and that this role is systematically underpaid in a way that reflects its gendered positioning.

In most other cases, participants expressed frustration about their often-lower compensation than their similarly positioned peers, whose work was also often better defined with fewer expectations for care work. As Diana put it,

I’m pretty certain that I am underpaid for the work that I do, and at the same time comparatively to other individuals who hold a similar title…I’ve had small, incremental raises but I consider those pennies on the dollar as it relates to the scope of my work, the experience that I brought into this role.

Similarly, when asked about her relative salary to other senior administrators, Joanne told us, “When I took on the role [assistant head], I didn’t receive a significant increase…I know that I’m not compensated at the same level”. These differentials were, as Kathy highlighted, far smaller than the gaps between the women’s compensation and that of their heads. She explained,

My starting salary as assistant head was less than a third of his salary when I came to [school name]. My starting salary…The only person who we have hired. who makes more than me is the CFO—$30,000 more than me…That was like a sticking point to me. I was like, “What?”

Finally, it is worth pointing out that even if the gap in compensation between their role and that of the head was smaller, there was evidence that inequities would remain. As participants described it, the headship also came with a host of non-salary benefits that were significant (e.g., cars, housing, tuition remission, retirement bonuses) though often hidden. As such, we can imagine the differentials in their compensation and that of their head to be larger than their salary differences would suggest.

5.5. Challenges to Well-Being

While many participants said they felt a deep sense of purpose and personal satisfaction from their work, as apparent in the prior findings, the structures shaping their positions had negative implications for their well-being. First, the somewhat porous boundaries of their work and ever-growing workload, many experienced feelings of deep exhaustion and diminished self-efficacy. For example, Diana told us, “When you have some years that are harder, where that just seems to be, like, the consistent experience, it does chip away at your sense of self efficacy”. As Mira explained, similar feelings were moving her to consider leaving for another position.

I’m still experiencing burnout…When I’m here, the feeling I have most days is this feeling of being rushed and, like, the to-do list has increased and I’m working against time…I’m just becoming more attuned to, like, what is my ideal work environment? I’ve been used to this, but is this what I want?

Mira was far from the only participant to suggest that her job had become unmanageable or to indicate that she was considering exiting her role. In the following, for example, we hear Susan speak not simply to the relentless pace of her work but also to the physical toll it took on her.

It’s hard work, right, no matter what… [and it’s] forcing people like me who are committed and really hardworking to consider if they’re in the right place…it’s like, “I’ve got to get out. I can’t do this anymore”. We [she and her brother] were talking about how our health is being affected. I’ll just tell you this week I have a cracked tooth, and it’s because I’m grinding my teeth. So, I mean, it’s just affecting our overall health, mental and physical health. And I think being a woman and being responsible for all of the relational pieces of the job magnifies all of that.

Here, Susan highlights how stress associated with how the role is structured can go from mental load to negative physical manifestations. She also sees the source of this stress as attributable to expectations for emotional labor—labor she understood as mandatory because she is a woman. Such statements highlight how a culture of benevolent sexism (e.g., expectations that women are naturally “caring”) can be experienced as oppressive.

Genevieve similarly called this expectation of care work “soul wearying” and described how constant cultural demands for her to “care more” were seriously and negatively impacting her ability to thrive. She said,

…the message I got when we had some faculty members who were absolutely refusing to follow all of our processes and it was just, “Well, have you really developed a relationship with them? Do they really understand the reasons? Have you observed them teach and really celebrated their success?” It was essentially, “Do you care enough? Are you caring enough?” …And I’m like, “These are people not following the basic rules… And we’re not doing anything about it”. Like, it’s not really about me caring. But that was the way my work was framed.

Finally, at some point in their interviews, virtually all the women spoke about how the lack of flexibility built into the role made it so they had to negotiate their family and work goals in ways that created deep role conflict. Elise summed up how the role expectations shaped these feelings, as well as why her experiences as an assistant head had made the headship a less desirable position.

I’m not alone in factoring the responsibilities I have with my own children into what feels manageable to me…it’s just hard for me to imagine balancing, balancing having two lower schoolers…with the responsibility that a headship involves…I could do it, but I would be sacrificing a lot with them that I just don’t want to.

These feelings that simultaneously doing the work of the headship as constructed and being an effective mother were unsustainable were reiterated across the interviews, regardless of the woman’s phase of life. In this way, the women presented inflexible roles that frequently forced hard and seemingly unwinnable choices about their professional/personal choices and goals. And yet, about a quarter continued to actively pursue the headship—often, as they told us, because of their children being much older and/or their status as a single woman.

6. Discussion and Implications

The purpose of this study was to better understand the higher representation of women in the assistant head position in independent schools in the context of limited representation in the headship and particularly in schools considered the most prestigious (i.e., coeducational day schools with 700 or more students). We wondered if gendered structures may help to explain this outcome and, if so, whether women holding these roles experience organizational conditions hampering their overall success and well-being. Our findings suggest that both elements seem to be true: the assistant head role appeared feminized, and participants experienced challenges to their well-being as a function of their roles.

Before jumping into a more nuanced discussion of our findings, we take a moment to consider the potential contribution of feminization to the field of educational leadership and leader well-being. While Acker’s (1990, 1992) argument that gender is deeply embedded in all aspects of organizations has been used expansively in the organizational and management literature, neither her work nor that of feminization has been meaningfully applied to educational leadership and/or women’s experiences therein. In this way, our study offers both a new context in which to consider the applicability of the framework as well as to integrate it with our understanding of well-being.

As this study shows, feminization does appear to offer opportunities to consider not simply how discrimination shapes organizational structures in ways that subsequently limit women’s access to/experiences in the highest positions of educational leadership, but also how these same discriminatory structures keep them concentrated in others (i.e., horizontal segregation). We say “keep” as gender is constantly being constituted and reconstituted in organizations through its structures, rites, and rituals (i.e., culture) (Acker, 1990, 1992)—in this case, in the way the assistant headship role is constituted, and the negative relationship such structures have with women leaders’ well-being.

Additionally, we might anticipate that as more women attempt to access traditionally male spaces of leadership (i.e., the headship), new rules will make it harder for them to do so while simultaneously favoring men (Mastracci & Arreola, 2016) (e.g., creating policy requirements of finance leadership experiences for the headship—a skillset and positions dominated by men). By naming these organizational structures, women and their allies are more able to recognize when such shifts occur and fight against them. Indeed, to our knowledge, our study is the first to explicitly name the clustering of women in the assistant headship in larger co-educational independent day schools as a form of horizontal segregation facilitated through gendered structures.

Moreover, by working to integrate feminization with the research on workplace well-being, it also creates opportunities to identify specific structural features of work that may shift, which can enhance the likelihood that women leaders can thrive (e.g., creating clear, bounded job descriptions from which women can self-advocate). It also should move those leading educator training programs to teach about gender discrimination, including feminization and how it is operationalized and reified through organizational structures. We know gender discrimination hurts women’s ability to thrive at work (Burton et al., 2020; Weiner & Higgins, 2023), and mitigating its effects should be everyone’s priority.

Thus, we call on researchers to continue to explore how gender is operationalized in educational leadership and feminization and the implications for women’s trajectories. This would include extending to other contexts and including men holding feminized roles to better understand their experiences. Here, it is important to note that while feminization may offer tools to disrupt gendered structures in schools, as we already highlighted, it does not consider how other forms of discrimination may also be shaping organizations (See Ray’s (2019) work on racialized organizations for an example) and the experiences of those within them. Given there is already a rich tradition of scholars using intersectionality to understand the lived experiences of Women of Color generally (e.g., Agosto & Roland, 2018) and Black women specifically (e.g., Jean-Marie et al., 2009), in educational leadership and their well-being (Burton et al., 2020; Reynolds Vassar, 2026), there are ripe opportunities to extend feminization in ways that attends to these experiences and better reflects organizational structures that impact Women of Color and the legacy of gendered racism in situ. We call on researchers to take up this issue and to more effectively capture how multiple forms of discrimination impact diverse women’s experiences in these roles.

Returning to the need for clear and bounded job criteria, we find these elements to be largely lacking amongst our participants. They instead reported expansive and seemingly ever-growing responsibilities. Simultaneously, this work was often emotionally intensive, and, like other women leaders (Vial & Cowgill, 2022), participants were expected via gendered norms to hold the emotional needs of others with what seemed to be little thought to their own well-being. As such demands are negatively correlated with job satisfaction (Maxwell & Riley, 2017; Zoro et al., 2021), and that school administration is often emotionally exhausting work (Drago-Severson et al., 2018), it is perhaps no surprise that these women, like many others in similar positions, seemed frustrated with these arrangements and/or overburdened (Biju & Pathak, 2021).

The broad and loosely bounded scope of their work also moved participants, like others in mid-level leadership (Hu et al., 2023), to describe their role as ambiguous, a situation that seemed exacerbated by a lack of meaningful evaluation. Additionally, while some of the women felt they had an appropriate level of autonomy in their roles, overall, it seemed that this was more grounded in benign neglect than professional respect, with few reporting feeling truly trusted to make independent decisions. In these cases, it seemed that feelings of trust towards and from their head undergird their feelings of professional autonomy. This brings up several questions regarding how such trust was facilitated and if there were other aligned structures that helped to produce these feelings of empowerment. Inversely, given research that women’s expertise is often less valued than men’s (Joshi, 2014), it may also be useful to further probe whether and to what degree these trusting relationships may also be framed through a gendered lens (e.g., women’s expertise being validated through a male superior rather than standing on its own merit). If so, it may be useful to trouble such conceptualizations of empowerment to center not just proximity to power but also liberation.

Participants also highlighted how, while they felt personal satisfaction and efficacy in their roles and were offered positive feedback from those they managed, they felt less valued by those at the top of the organization (e.g., board members, powerful alumni). Given that feeling appreciated by one’s employer (Stocker et al., 2014), autonomy (Fosco, 2022) and role clarity (Mazzola & Disselhorst, 2019) are major factors in well-being at work and clear goals and feedback are essential to employee motivation and success (Dwivedula & Bredillet, 2010), our findings indicate a need for independent schools to develop clear, fair, and transparent performance criteria for the assistant headship (hopefully in concert with those in the position) and to provide meaningful feedback based on these criteria to support growth.

In keeping with other feminized roles (Pelley & Carnes, 2020), women assistant heads experienced inequitable pay structures that appeared to devalue the gendered work they were expected to do and thus often earned less than other leaders at the same tier of the organization and far less (sometimes less than ⅓) than the head. It is worth noting that not all the women felt negatively about this discrepancy, often grounding their positive feelings in the fact that they were making much more money than they did when teaching. This finding brings up some larger questions about women leaders’ sensemaking about compensation and how it may shape their inclination and ability to effectively advocate for themselves during salary negotiations. Just because some women feel comfortable with an inequitable system does not mean we should simply accept it. To this point, there was also a group of women who felt harmed by their inequitable pay—feelings that can negatively impact their overall well-being and organizational commitment (Cheng & Zhang, 2024).

Finally, our findings can also help identify potentially high-leverage interventions to change organizational structures and disrupt, or at least buffer women from, existing gender hierarchies. For instance, and as already mentioned, the development and consistent referral back to well-articulated and bounded roles and responsibilities could help women assistant heads self-advocate over the nature and amount of their work. Clarifying roles would also help to facilitate the type of clear and evenly deployed evaluation systems we call for above. Such structures also create opportunities for developmental conversations with supervisors that can build capacity and trust—a key feature supporting participants’ feelings of empowerment within their roles. Additionally, evaluation tools should quantify emotional labor and other forms of care work so that they are adequately acknowledged and rewarded (Bass, 2009; Weiner & Higgins, 2023). It is also important that care work is more evenly distributed across roles and not perceived by decision-makers as being of less value compared to executive-level work. Finally, bringing greater transparency to current compensation models across all positions is an essential component in enhancing equity and women leaders’ well-being (Weiner, 2026).

7. Conclusions

Feminization provides the opportunity to illuminate how gendered organizational structures shape the experiences of female assistant heads of school and how these same discriminatory systems can shape women’s well-being at work. Addressing some of the issues associated with feminized roles through better articulated job descriptions and performance evaluations will likely improve their well-being, overall job satisfaction, and stress, as well as, we hope, increase the number of female assistant heads who subsequently pursue school headship.