Navigating the Labyrinth

Summer 2014

By Tekakwitha M. Pernambuco-Wise

It was July 2013. While hot and humid outdoors, it was cool inside the Emory Conference Center in Atlanta. I looked around the room at the NAIS Institute for New Heads and wondered if anything had changed since I completed my leadership study 18 months earlier. It appeared not. Of the 59 brand new heads attending the 2013 institute, only 34 percent were female. My hunch was confirmed when I received the statistics from the National Association of Independent Schools (NAIS). The world of independent schools remains a female-dominated field — except at the topmost level.

At the time of my research, 72 percent of heads had been senior administrators in schools prior to attaining headship.1 This suggests that most heads rise from these ranks. Most teachers are women — 66 percent in coeducational schools and 81 percent in all-girls schools2 — and the majority of administrators on the traditional path to headship are female. Yet women comprise only 31 percent of independent school headships, with 50 percent of those women leading K - 8 schools. These numbers have remained static since 2002. Even though women fill most senior administrator positions, the percentage of applicants for headship also remains predominantly male (66 percent) and European American (86 percent).3

Curious about this phenomenon, I embarked on a journey to answer the following research question: “What factors are related to women attaining headships in NAIS schools and what sustained them in the job?” Performing a qualitative, grounded theory study, which sought to develop rather than test an existing theory, I interviewed 19 female heads of school and 12 search consultants. 

Besides curiosity, the impetus for undertaking this study was my assumption that, by understanding how some women attained and were sustained in the position, other women may be encouraged to seek headship as a natural progression of their careers. Additionally, I assumed that the results would prove informative for boards of trustees and search firms, two predominant gatekeepers for headship ascension, thus providing a significant resource from a potentially rich applicant pool for filling the predicted shortage.

Navigating a Labyrinth

In a grounded theory study, a theory can be generated when a core category emerges from the data. In my study, an apt metaphor emerged. One female head of school I interviewed described her experience of attaining headship not as some variation of the traditional trajectory that most males took (teacher to department chair, department chair to dean, dean to assistant head, assistant head to head of school), but rather as negotiating a labyrinth. The core category that then emerged from the data in my study was what I call Navigating a Labyrinth — and I used this metaphor to frame the characteristics that helped women attain and be sustained in the position.

The denotation of the labyrinth in the study was that of a maze with headship being the treasure. This meant that if 10 men entered the labyrinth, seven emerged with the treasure; however, when 10 women entered, only three attained the treasure. When the women were asked about their experience of the labyrinth, they stated that numerous paths took them either to the core, away from the core, or to different treasures, or that, at some point, the way was blocked. When questioned about how they were able to negotiate the labyrinth and attain the treasure, each produced “master keys” that she had acquired or made that helped unlock huge, iron-girded doors to paths that led to the labyrinth’s core. The women did not all pass through the same doors. The keys, however, used singly or in combination, helped them to get through any door they faced. 

For all the women candidates, four doors, some more powerful than others, blocked the path to headship: Unspoken Biases, Risky Candidate, Lifestyle vs. Job, and Loneliness. The six keys that opened the doors were: Foundation; Skills; Support; Opportunity; Voice; and Changing Times, Changing Position

Doors Blocking the Path

Unspoken Biases 

Unspoken biases about gender roles were primarily manifested in assumptions about how gender roles play out on the job. For instance, search committees tended to view the school-aged children of female candidates as a possible distraction for these candidates; whereas, for men, having school-aged children had no bearing on their desirability as candidates. 

Women, especially aspiring heads, had to be over-prepared in all aspects of running a school and excel far above male candidates to be given the same opportunity as men. They had to go to great lengths to prove that they were adept at handling school finances, for example; whereas, it was presumed that male applicants had the knowledge and/or could rely on the business manager for support. As one female head of school put it, “Like Ginger Rogers, [we] do the same thing that Fred Astaire is doing, but we’re dancing backwards and in heels….” 

This needing to be over-prepared had an adverse affect on the number of women when it came to making the decision to apply for headship. Search consultants noted that men tended to apply much earlier in their careers than women, even if they were under-qualified, while women typically did not apply until they had, as one consultant put it, “checked every box that you imagine a search committee is going to want to see.” Once committed to the idea, it took women an average of five or six years to attain their first headship, while their male counterparts obtained the position much sooner, and often at a younger age.

Female candidates were also held to a double standard. When they acted in identical fashion as a male candidate, they were viewed starkly differently. Those women who were authoritative were accused of wanting to be like men or were seen as difficult to work with, while commanding men were seen as powerful. Being too relational was viewed as a weakness in women, but a strength in men who, according to one search consultant, “get a lot of street credit” for acting in more traditionally female ways. Men could be either dominating or relational, while women walked a tightrope and had to exhibit both authoritative and nurturing qualities.

The composition of the search committee directly affected a woman’s candidacy, with women faring better with diverse committees, especially with respect to gender and employment in a variety of fields. These women, however, needed to be empowered. Even if women were initially in the applicant pool, conservative search committees tended to fill the position with sitting heads, which favored European-American men. Additionally homogeneous search committees tended to engage in similarity attraction — hiring candidates with similar attributes and values to theirs — and again this favored men since 88 percent of trustees are white men between the ages of 36 and 55.4 One search consultant stated that traditional hiring practices were disrupted only “if you have some strong women on the committee who are career women… used to speaking their minds.”

Risky Candidate

Boards and search firms perceived women as “out of the box” candidates and categorized them with persons of color applicants from noneducational fields (corporate or military). Boards tended to be conservative in their hiring practices, especially in secondary schools and if the outgoing head was a white male. According to one female search consultant, “There’s still this business of wanting to not be too far off the norm…. Boards worry about it because they think that if their head can’t be accepted in the social milieu, the school won’t be thought of as highly and they probably won’t raise as much money.” Curiously some of the women seeking headship self-labeled as being nontraditional. One female leader of a prestigious, K - 12, coeducational school, said, “I would not fall into what people would say is a traditional school head…. The idea of Mr. Chips or Frank Boyden… that still looms large. People expect… to see a guy who’s six feet tall, probably a white guy, and if he had a tweed jacket, that would be really good.”

During the interviewing process for headship, female candidates experienced either skepticism or paternalism, with many believing they were asked questions that were not asked of male applicants, such as invasive questions about childcare or family planning (one woman was asked if she were taking birth control pills and if she were happily married). Women stood better chances of being hired if the school was in economic crisis for two main reasons: (1) financially strapped schools can ill afford the higher salaries that more stable schools can afford and (2) sitting heads (the traditional candidates) were not attracted to struggling schools.

Lifestyle vs. Job

The vast hours heads committed to their school, including nights and weekends, affected their family time and obligations. This work-family conflict led some women who might otherwise seek headship to self-select out of this career track, while others waited until their children were older before they sought the position. Others subconsciously opted out of being candidates by being self-deprecating about not having expertise in all facets of headship, leading to, as one female head of school put it, “a mindset in which you walk into a room believing you’re at a disadvantage [and thus] you’ve already lost the job.”

Women heads, especially those heads with younger children, felt the added expectation of being the primary family caregiver. As such, according to the search consultants I interviewed, women had an additional burden of proving to search committees that they could fulfill the demands of headship and take care of their families. Search consultants surmised that the demands of headship sometimes led to divorce. However, they saw more of these separations when the head was a woman. Because of the highly social component to headship, the position was often viewed as a package deal of head and spouse (some schools provided stipends to head spouses to organize school social events). So single female heads faced an additional challenge of handling all social events without support — which leads to the next category.


The female heads of school I interviewed described the position as being extremely lonely. Particularly difficult was having no one else at school with whom to commiserate. According to the findings, women felt this more acutely than men, if only because women heads may have a penchant for (or have been socialized into) needing more relational supports than their male counterparts. In preparing for headship, incoming women heads were told about the tasks that needed to be done, but as one head stated, “They don’t tell you how you’re going to feel and that is the biggest challenge of the job. It’s feeling highly visible and feeling stressed out and feeling lonely.”

Keys to Opening the Doors


While not all of the female heads of school indicated that their upbringing was vital to the choices they made as adults, none of the male consultants indicated upbringing as a factor. Eight of the 19 females indicated that parents, teachers, and school leaders made a huge impact on their leadership choices. Being encouraged to be leaders from a young age helped the women to build self-confidence. Search consultants made a distinction between women who had a presence and women who were self-assured. It’s a challenging balance for women. One head cited the perceived differences between Hillary Clinton and Michelle Obama, stating that Clinton, when running for the presidency, was “in your face and relentless,” while Obama “grabs you with her presence but she doesn’t suffocate you.” Search consultants reported that this nuance of having presence was more important for female than male candidates because, to display authority, women had to exhibit assertiveness (self-confidence) and not aggressiveness; whereas, aggressive men were simply seen as powerful.


It was essential for the women heads, through targeted preparation for headship, to develop specific tangible and intangible skills. One head advised, “Prepare well… and understand all the unstated implications of the job description, not just the stated ones.” Essential skills included being able to manage the board, understand community politics, develop an inspirational vision, exhibit emotional intelligence, and have emotional resilience. Another woman head stated that it was imperative that women heads first display emotion prior to delivering a logical argument or difficult news. “In my experience, [I do] not have the option of not being emotional about the work that I’m doing. There are simply things that my male predecessor… could do and people would say, ‘Well, he’s in charge.’ And if I did the same thing in the same way, they’ll say, ‘You cold, heartless bitch….’ To stay in the room, to have credibility, to be heard and not written off, I have to have some emotional understanding about things… not just have it, but exhibit it.” A search consultant named three main distinct skillsets that heads were required to have: academic credential, financial expertise, and personal development.

When contemplating headship 20 - 30 years ago, the veteran female heads of school had no benefit of preparation programs, so had to gain much of their knowledge on the job. Generally they admit feeling unprepared for headship. However, they survived and learned because at the time schools were run more like family-owned businesses in which one learned from a mentor. In today’s fast-paced, results-oriented society, on-the-job training is no longer an adequate means of gaining the requisite skills, especially since schools are now viewed akin to small corporations, with the head as the CEO. Women heads and search consultants highlighted three programs as excellent preparation for headship: Columbia University’s Klingenstein Institute, the National Association of Principals of Schools for Girls (now called The Heads Network), and the NAIS Fellowship for Aspiring School Heads.

While it was not necessary to be a financial guru, heads are expected to speak intelligently on the topic. The National Business Officers Association’s programs help “teach you how to understand all of the ins and outs of school finance so that you don’t have to have an MBA,” according to one head, who also urged women heads and headship candidates to practice mindfulness about headship by partaking in personal development programs to help them be aware of “derailment factors — things that, if they don’t pay attention to, could really cause them to unwind.” Women heads also encouraged aspiring heads to join the board of another school or nonprofit organization, meet with the development and business officers at one’s current school, and keep abreast of current literature. These are avenues to gaining knowledge and exhibit fiscal capability. Being strategic about sitting on board subcommittees such as finance, fund-raising, strategic planning, and development helped aspiring heads to gain experience in the nonacademic aspects of running a school “so that when people look at your documents, they can say, ‘Gee, this person really put herself out there and is doing some things,’” says a search consultant.


The women heads made a distinction between having mentors and having advocates. The former could be intentional or unintentional role models, while the latter actively assisted the women specifically in pursuing headship. Advocates offered advice, promoted the women to search consultants, put them in positions of authority in their schools, and continually challenged them to pursue leadership opportunities. In essence, advocates pushed them onto the labyrinth’s path. 

Search consultants also felt a responsibility to be advocates for female candidates. They recounted tales of women being excluded from searches because of flimsy excuses, such as being too attractive or too young to be taken seriously. Since search consultants often confer with sitting heads to help them identify potential candidates, aspiring heads were advised to connect with sitting heads for assistance in their career path. One search consultant urged, “If I had to pick one thing, a piece of advice to give somebody, I think that would be it. Get a good mentor who is in [the head] position now.” 

Just as the Old Boys’ Network assisted male heads in obtaining headship, the women heads advocated starting a New Girls’ Club, believing that the trailblazers had a professional responsibility to develop networks that would mentor and advocate for aspiring heads, irrespective of gender. Search consultants spoke highly of these trailblazers who they believed openly and warmly mentored other women who sought leadership roles.

Some search consultants suggested that schools examine the leadership potential within their walls and have a succession plan that includes aspiring heads. With the majority of administrators being women, succession planning could increase their headship numbers. Boards, however, traditionally avoid hiring internal candidates since boards tend to focus on the deficiencies of the outgoing head and try to hire a different skillset. Done well, succession planning has the benefit of a successor who is already familiar with the school’s culture.

The women heads of school believed that it was essential to join local, regional, and national professional networks of other school heads who served as sounding boards. Some consultants suggested joining groups that were for all heads and others separated by gender since the issues of leadership were, at times, different for men than women. The NAIS Institute for New Heads was lauded as essential for novice heads for learning about the nuances of headship and, more importantly, for its networking opportunities.

On the home front, having the support of and equal partnership with spouses was vital to the success of the female heads. The search consultants noted that in recent years for couples in a husband-wife relationship traditional gender roles were switched. Often when relocation occurred, the male spouse gave up his career to follow his wife’s or worked in a less demanding job. He also became the family’s main caregiver.

For single heads of school, the challenge is to build a support system that works for them.


Schools have different needs at various stages of their development and thus need heads with specific skills best suited for those times. Some may need a skilled fund-raiser, for example, while others need a curriculum expert or a head who is astute at promoting the school in a highly competitive environment. Above all, however, being the correct match for a school was essential to flourishing in the position. Many expressed love for their schools and compared the search process with dating and the headship with marriage. One head said, “I always say I can’t imagine working this hard for a school that I wasn’t in love with. So when you’re ready to do the job, do it in the right venue, do it in the right place. The match is everything.”

Search consultants urged aspiring heads to understand that they and boards are gatekeepers for headship and so candidates needed to seek opportunities to exhibit their leadership prowess to these groups. Aspirants were encouraged to pave their own paths by serving on the boards of their own or other schools, entering multiple searches in order to obtain experience of the process, and volunteering to run school-wide committees. Female candidates, in addition, were advised to listen to the stories of women heads to obtain clues about how to successfully navigate the labyrinth. However, they were cautioned against seeing themselves as female candidates lest, as one head put it, “we let that define us as opposed to our interests, our skills, our intellect, our wisdom, our experiences.”


Not only was Voice a master key in helping women heads navigate the labyrinth, it also emerged as a means to their self-actualization. Being able to have influence at the highest level of the organization — through policy-making, shaping the institution, and ensuring that diverse perspectives were presented in decision-making — was seen as promoting social justice. The women heads described the power of Voice as not singlehandedly accomplishing every school task, but rather as a matter of influencing every facet of the school — if not in-depth, then in breadth. This influence was both a blessing and a curse, so the women heads had to be careful with how they presented themselves. “What comes out of your mouth, how it comes out, how energetic you are about it, really will have an impact on how people perceive the school,” cautioned one head.

Headship afforded the women heads opportunities to effect social action and they were fervent in their condemnation of social injustice, believing that if one did not actively denounce social injustice, then one was tacitly permitting it to occur. They stated that a powerful way to dispel assumptions based on ascription is to belong to diverse social groups. They advocated for gender equity in memberships on the national committees on which they served, were persistent in implementing anti-harassment educational programs at their schools, and dogged about initiating systems that would protect the underrepresented. Some were purposeful in hiring persons of color in positions of authority because, as one head put it, “the children of color are never going to see themselves as [equally] valuable if they don’t see powerful people of color.”

Having gravitas, or being presidential in one’s deportment, was touted as essential to building political clout and gaining credibility, especially with other schools and external constituents. Now a highly influential head, one female head of color described a moment early in her career when she immediately realized that she needed to both extend her hand in greeting and assert her presence. Attending a social function at a conference where she was surrounded by white heads, she was surprised when one of them, presuming she was a waitress, turned and gave her his empty plate for her to dispose.

Self-actualization was described as a matter of living a life of integrity and authenticity, despite the numerous challenges that headship presents. The women heads were unanimous in expressing their love for their jobs. Many described it as a vocation that fed their soul and fulfilled their destiny. Taking time to engage in daily solitude, reading, and cultivating their spiritual lives helped the women heads to become more self-aware. This was valuable in offering to others what they saw as their true selves. “I think if you know yourself, it’s like a coach,” stated one head. “Do I really want to recruit the players to my plan or am I willing to switch my plan based on the players I have? There’s not a right or wrong. You just have to know yourself well enough to know which you fall into.”

The women heads said it was imperative to not only merit the position but also be perceived as having deserved it. They did not desire accommodations to fulfill the duties of the position based on society’s perceptions of their needs as women, for that would reinforce the stereotype that they were not at least as qualified as their male counterparts. Additionally if they were internal candidates, they were emphatic about not wanting it by default. In such cases they insisted that their boards do a national search that included their candidacy.

Changing Times, Changing Position

As social norms change, educational systems evolve and so the women heads believed that the shape of the labyrinth and thus types of master keys needed to open the doors also needed modification. The veteran women heads saw the position alter, especially within the past decade, from one of chief academician to one in which they needed to be well-versed in subjects far removed from education, such as law, human resources, marketing, and financial planning. As such some suggested that, if the position were to be done well, it would be too much for a single person and that perhaps coheadships were preferable, with one head concentrating on the business aspects and the other on the academics. 

Search consultants corroborated this finding, stating that boards were now more interested in the applicant’s skillset in the business arena than in his or her values. Parents’ attitudes too have changed, with many of them seeing the schooling of their children as an investment and often questioning the return on investment. This is in contrast to past eras when parents partnered with the school to build community. With these modifications in the focus of headship, search consultants have seen many capable administrators of both genders express interest in educational leadership positions, but not headship, stating that the excessive demands of the position made it unattractive, especially if they had young children of their own. Search consultants suggested that perhaps headship could follow the university model of leadership in which the president manages the external affairs and the provost oversees the academic aspects.

Attaining the Treasure

According to the theory that emerged from the data, women, unlike men, who aspired to headship in independent schools need to prove beyond a doubt that they are highly proficient in all aspects of the position and must perfectly align preparation, opportunity, advocacy, and support. An analogy would be that to have a winning poker hand, women had to have four aces while men did not need to even have four cards. Search consultants and boards are gatekeepers for headship, so it is crucial for educators to understand the role they play in placing the right heads in a school at the right time in the school’s history.

According to the data strategic initiatives that are helpful to gatekeepers in enlisting more women to fill headships and helping them to be sustained in the position include:

  • Diversifying boards — an increase in diversity of age, experience, gender, ethnicity, profession, values, etc. tends to decrease similarity attraction.
  • Being ascription-blind in hiring practices — resist seeing women as nontraditional candidates or as female candidates.
  • Having a succession plan while the current head is in place — which could include looking within the walls of the institution to develop leadership.
  • Advocating for aspiring heads — this may include pushing some women on to the path of the labyrinth.
  • Creating a New Girls’ Club — similar in concept to the Old Boys’ Network.

All aspiring heads, especially females, would benefit from the following strategic initiatives:

  • Focus on targeted skills preparation for headship — academic (a terminal degree is a boon), duties of a head (e.g., financial, fund-raising, board management), and emotional intelligence.
  • Network with trustees and search consultants — to learn from these gatekeepers but also impress upon them one’s seriousness about pursuing headship.
  • Seek out mentors and advocates, especially sitting heads.
  • Sit on boards of other schools or organizations.
  • Listen to the stories of how other women attained and are sustained in the position.
  • Understand the importance of the right match and not just headship of any school.

I grew up in what was an acutely patriarchal society. As a member of the Wapishanna Indians of South America — a culture in which women walk behind the men, carry the load from the fields, and have no voice in their homes — I would have led a life of a subservient woman were I not born to maverick parents. So I undertake all this research with a deep sense of appreciation for the opportunities women have in the nation and in the field of independent education. However, I know we can do better. And anyone concerned about social justice and who understands the importance of diverse perspectives will want us to do better.

Using master keys to navigate the headship labyrinth is but the beginning of a social movement to attain a critical mass of women in the topmost leadership role in independent schools. The next step will be to transform the paradigm of leadership so that, as the 2009 White House Project Report put it, “we can move permanently beyond gender and on to agenda.”5


1. National Association of Independent Schools, The State of Independent School Leadership, 2009. Washington, D.C., February 2010. Retrieved from

2. National Association of Independent Schools (2004-2005), NAIS StatsOnline Data Analysis. Staff Statistics in NAIS Member Schools Executive Summary, 2004-2005 School Year. Retrieved from

3. National Association of Independent Schools (February, 2010).

4. National Association of Independent Schools, The State of Independent School Governance, 2006. Retrieved from

5. The White House Project The White House Project Report. Benchmarking Women’s Leadership, November, 2009. Retrieved from

Tekakwitha M. Pernambuco-Wise

Tekakwitha M. Pernambuco-Wise is in her first year of headship at Sea Crest School (California). The complete findings of her doctoral research, Private-Independent School Headship for Women: A Grounded Theory Study, can be obtained from