The Puzzle: Blog

We already introduced you to Nicole A. DuFauchard, Head of School at The Advent School in Boston, MA, and one of two keynote speakers at CS&A's third-annual Women's Institute on June 14. (Read her interview here if you haven't yet.)

Now we're excited to learn a bit more about our second keynote speaker, Dr. Karen E. Eshoo. Check out our chat with her below.

Dr. Karen E. Eshoo

-Current Head of School at King School in Stamford, CT
-Former Head of School at Vistamar School in El Segundo, CA
-Former Middle School Head and the Principal of Grades 1-8 at Sacred Heart Schools in Atherton, CA
-Former Assistant Head of School at Lick-Wilmerding High School in San Francisco, CA
-Faculty member of the National Association of Independent Schools Institute for New Heads

What do you think is the biggest challenge faced by women in the workplace?

I certainly think that women face multiple challenges no matter the sector. We sometimes still struggle to be taken seriously, to be heard, and to be recognized for our contributions — even in what seem to be progressive and “evolved” workplaces. (Remember the stories of women who worked in the Obama administration who had to take measures to get the men in the room to stop talking over them and dismissing their ideas?!) When it comes to education, women have been well represented in classrooms but often less well represented in leadership positions. Women are still quite outnumbered by men in head of school positions nationwide, especially in secondary schools. I do think that part of the reason we struggle is that women have to contend with stereotypes and gendered expectations that men usually do not. Friends of mine who have chosen to have children have had to walk a fine line between demonstrating commitment to their jobs while still prioritizing family, regardless of whether they have a partner, whereas others of us who have chosen not to have children have to deal with a different set of assumptions. Women often have to think more carefully about “calibrating” ourselves with our audiences so as not to come across as too aggressive, too strong, too confident. I've experienced all of that and more…and my male head counterparts themselves have told me they have experienced little to none of it. That said, I also think that in many ways, the biggest challenge women face is…OURSELVES. We tend to look at job descriptions and, when we see we can't check every single bullet point on the list of experiences, we just don't apply. We start declarative statements with “I'm sorry, but…” And most of all, we look at heads of school and think “Wow, I could never do that.” That's the kind of thinking I'm hoping to help disrupt at the Women's Institute and in my own school.

What advice would you give a woman who is trying to advance her career in education?

First, make sure to get out there and get to know other women in leadership positions. As the saying goes, “If you see it, you know you can be it!” The more that we see each other taking on the challenges of leadership and succeeding, the more likely we are to give it our own shot. Second, take every opportunity to learn the things you don't know yet. Ask to sit in on a finance committee meetings or take a summer online course through NBOA to get better acquainted with budgets and operations. Ask to shadow a leader for a day or two, and take note of how she spends her time and with whom for which purposes. Take the advancement person to lunch to ask her what it's like to cultivate and solicit donors and possibly even enjoy it. Build a network of other female professionals who can be your empathy club by going to conferences, joining a leadership round, or showing up at your alma mater's local event. Ask another female leaders to be your mentor for a year, and set up meetings for the two of you to meet during the school year to talk about your hopes, dreams, and fears. Then ask her to introduce you to two other female leaders. Start to cultivate male allies as well; they often understand the game at a gut level since it was designed for them, and they can serve as advocates down the road. Make a deal with yourself — and the others on the team you work closely with — that you will actively work to stop apologizing for everything all the time. And then, before you're 100% ready, apply for the next leadership role you'd like to try. I think I've usually been about 80% ready for any new position I've held, and trust me, that's enough! Again, men don't wait to be 100% ready, so why should we?

Describe a key moment, person, or event that was critical in getting you to where you are now.

I starting teaching history at Sacred Heart Schools in Atherton, CA when I was finishing my master's degrees at Stanford in 1996. I had spent my entire childhood at the school, from preschool-12, and I absolutely loved teaching there. I had an amazing group of colleagues (all of whom are still some of my closest friends) who really cared about teaching and learning, worked hard, and always remembered to have a ton of fun. My department chair was grooming me to become the history department chair when she would “graduate” with the class of 2000, and I saw myself doing that job for at least 10 years there, then hoped to become the dean of faculty after awhile…and then I would retire. I laugh now when I look back at how much I tried to control, and how narrow my perspective was. When my department chair decided not to retire, I went into a tailspin, not wanting to leave the school but realizing that I might have to do that if I wanted to get into a leadership position. When my principal told me that there was an opportunity to lead the Middle School, I was unenthusiastic because I didn't have any experience with those grade levels. His response still resonates: “So what?! You're smart. You'll learn. And if you don't like it you can come back here.” He was right, of course. That position led me to become principal of the 1-8 division three years later, then onto an assistant head position, and later to head of school. I have learned that I can, in fact, learn on the job. I have learned that it is okay not to be an expert in everything for which I am responsible. And I have learned both that I cannot be happy in every school, and that I can be happy in many different schools…the ones that share my values. What I have let go of is the over-planning and the “control enthusiast” approach to career building, and instead have embraced careful, thoughtful examination of opportunities that come my way that might be a great match for my experience and expertise. Above all, no fear!

Who is your female role model?

My mom, Anna Eshoo, is one of the greatest role models I've had, without question. She represents the 18th district of California in the U.S. House of Representatives, having first been elected in 1992 (the first Year of the Woman). Like many women in the late 1950s, she went to secretarial school after graduating high school, which meant that she could move out on her own and take care of herself. When my brother and I were really young and with the encouragement of my dad, she decided to start taking courses at Cañada College, our local community college. When I was in second grade, she had become frustrated with the decisions being made at Cañada and decided to run for a seat on the community college board, which she lost narrowly (to the father of one of my classmates!). At that point she was hooked, and she began building networks within the local political scene by volunteering for campaigns, working with the local Democratic central committee, and generally making a name for herself. She was elected to the San Mateo County Board of Supervisors in 1983, a seat she would hold for 10 years before heading to Congress to represent much of Silicon Valley and Stanford University. Since she has been a member, she has sponsored and helped pass important legislation, such as the law that requires insurance companies to cover the cost of reconstructive surgery for mastectomy patients, and she has been the leader of the fight for net neutrality. She also was the author of the bill to require advertisers to lower the volume on their ads — which had more bipartisan support than just about any other bill ever — and is now sponsoring another one to end robocalls. And, one of the things that makes me the proudest of her is that while she never lets go of her principles, she has earned a reputation as a woman who is more than willing to work across the aisle with Republicans to get things done — indeed, a reputation she earned long before she came to Washington. She's tougher and smarter than most, and she owns her power in ways that inspire me. Watching her grill Mark Zuckerberg, her own constituent, was a moment of greatness! #GoMom

Who was your favorite teacher in school and why?

My 11th grade Western Civilizations teacher, Donna Gilboa, remains an inspiration to me to this day. Here are a few reasons why I love her so much:

• I spent the first semester of 11th grade as an exchange student at Convent of the Sacred Heart in Greenwich, CT. I was placed in a 9th grade class because that was the grade at which they taught Western Civ, and honestly it was a bit of a cakewalk. My friends back in California, however, regaled me with tales of “The Gilboa Class” that they were taking, where Mrs. Gilboa proved on a daily basis that she knew just about everything about everything as she lectured without notes, and also had a razor wit and somewhat irreverent sense of humor about some of history's most famous players. Apparently just about everyone failed the first test, and while I was quite happy to be cruising along in my freshman version of the class in Connecticut, I was terrified of what would happen to me when I got back. It took me exactly one class period in January of 1986 to promptly fall in love with Mrs. Gilboa. She certainly was knowledgeable, but for the first time in my life I experienced history as an intriguing story of politics and intrigue that actually inspired debate and analysis rather than just memorization. For the first time in my life in a history class I listened intently, I took furious notes, I asked questions, and I openly (and sometimes loudly) reacted to the successes and disasters of the characters in her fascinating stories. And, for one of the very few times in any class, I really studied for that first test…and was elated when I got it back and saw a “B” at the top along with a note that read, “Come see me about some revisions — this is not at all bad for a first try.” (I still have that test, by the way.) Years later, after earning a master's in medieval history at Stanford, I had the amazing opportunity to teach World Civ, as it was now called, alongside Donna herself. As I like to tell people, I got to teach the history class with the woman who taught me the history class that made me want to be a history teacher — what a gift!
• Donna was also the dean of faculty when she was my teacher, and she actually worked with my best friend and I through a disciplinary incident in which we were involved. I'll spare you the details (which are pretty tame by today's standards!), but she knew how to hold us completely accountable for our stupid mistake without making us feel like we were failures. She actually called both of us over to her house, and as we sat in her kitchen silent with heads hanging, she talked for a few minutes and then said, “Look, there are some battles you can't win. So knock it off.” And we did just that. Adults don't always have a ton of credibility with teenagers, but Donna was an exception. She was always authentic with us, pushed us hard, and treated us with respect and care. Knowing that she was disappointed with us was all the motivation we needed to turn the corner.
• As a head of school myself now, I look back at the time I spent with Donna as a student and as an adult as formative in my own leadership around teaching and learning. While content knowledge obviously is important for any teacher, great teachers strive every day to engage their students by helping students make meaning of that content. Great teachers use their content to help students understand their world and their place in it. Great teachers know to prioritize analysis and synthesis of content for deeper understanding over rote-memorization of Google-able factoids. And most importantly, great teachers get to know their students well, and leverage those relationships to inspire their students to reach for more — academically, socially, and emotionally — than they every might have imagined. These are the qualities I learned about from Donna Gilboa, and these are the capacities that I seek to encourage and build in my colleagues and in myself.

For fun, what are a few of your favorite quotes from women?

I loved Tina Fey's “Bossypants” so much. Humor is extremely important to me personally and professionally, and her ability to describe being a woman in a leadership position in ways that cut to the core of it all while making me laugh out loud while reading it make her a goddess in my pantheon. Here are a couple of good quotes:

• “Some people say, ‘Never let them see you cry.' I say, if you’re so mad you could just cry, then cry. It terrifies everyone.”
• “So, my unsolicited advice to women in the workplace is this. When faced with sexism, or ageism, or lookism, or even really aggressive Buddhism, ask yourself the following question: ‘Is this person in between me and what I want to do?' If the answer is no, ignore it and move on. Your energy is better used doing your work and outpacing people that way. Then, when you’re in charge, don’t hire the people who were jerky to you.”
• “In most cases being a good boss means hiring talented people and then getting out of their way.”
• “You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.”

CS&A is proud to to be hosting our third-annual Women's Institute on June 14 in Boston, an event designed to support women and their allies in the education community. Learn more about this personal and professional development event.

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