One of the first things that struck me on the night I was named 2023 National Principal of the Year was the reaction of the women in the room. As they shook my hand or, more commonly, embraced me, many remarked how glad they were that a woman would represent them. I remember thinking, “Oh my God, it’s 2023—this still matters?!” It shouldn’t still matter, but it does.

I would like to offer some insight into what it’s like to be a woman in charge. I’m passionate about this subject, and I am committed to supporting young women coming up through the school leadership ranks. I want them to know that they’re not alone and that they’re in for an interesting journey. What follows are seven lessons I’ve learned—several of them the hard way—over the last three decades.

Lesson 1: Say what you need to say but realize some people will hate you for it.

Principal Donna Hayward with students at Haddam Killingworth High School. PHOTO COURTESY OF DONNA HAYWARD

I became an administrator in 1998 when I was hired as the assistant principal of a suburban high school of about 700 students. To my knowledge, I was the youngest administrator in Connecticut and one of the only female leaders I knew at the high school level. In fact, for the first several months, I encountered only one other woman in high school leadership. Meeting after meeting with leaders from around the state, I would enter the room to encounter what I referred to as “the sea of gray suits.” As the only woman in the room, my natural inclination was not to draw attention to myself.

I distinctly remember telling myself to just keep my mouth shut at my first meeting, which happened to be about athletics in my school’s conference. That plan lasted about seven minutes. To be fair, the question at hand was whether to let a gifted swimmer from another school use my school’s pool to compete. If I blocked her, she wouldn’t be in top form to compete; if I allowed her to use my facility, she would likely defeat all our athletes. The vocal members of the group heavily favored the block, which seemed ridiculous to me. We are, after all, “in it” for all kids. Withholding the use of my school’s pool to blunt an Olympic-level athlete’s competitive edge was wrong. So, I said that, welcomed the swimmer to our facility, and made several enemies in my very first meeting.

Over the years, I have regularly found it impossible to just stay quiet. Typically, my message is stronger when encountering adversity or division and, in that way, some react to the messenger more than the message. Many years later, a friend in the mental health profession actually told me that I should consider making it easier on myself by acting more “traditionally female,” speaking softer, deferring to others, and being less outspoken. She acknowledged that this was “infuriating,” but that I had a choice to make. For better or worse, I made my choice long ago.

Lesson 2: It’s an entirely different thing to be a woman in a position of leadership than it is to be a man.

The reasonable reader probably wonders why this wasn’t the first thing I learned. Perhaps it should have been but, in my defense, I spent the first years trying to deny it because it shouldn’t be true. The bigger surprise was how different it is, especially given that I started in the 1990s, not the 1940s. How we are received as women as we go about our daily tasks and fulfill our leadership roles is markedly different from how men are received. How our voices are heard (or not heard) by men in a meeting, how a young woman’s career advancement is sometimes attributed to her “proximity” to men in power, and how, as women, we are often regarded first by gender and second (if at all) by our work itself. I’d like to think the path has gotten a little smoother for women since I started out, but Taylor Swift is singing to the next generation that “I’m so sick of them coming at me again ‘cause, if I was a man, then I’d be the man.”

Lesson 3: How “This isn’t supposed to be happening to me” happens.

It’s not as if I wasn’t aware of what can happen to women in the workplace. On the contrary, I thought I was well-schooled in dodging the common pitfalls of women in nontraditional roles like high school administration. I went to Smith College, come on! Having always been regarded as smart and strong, I fancied myself immune to the textbook speedbumps experienced by my unlucky female colleagues. I regret how shockingly naive I was to the dynamics at play that fuel harassment in the workplace. The target is often embarrassed that it’s happening, is afraid of not being believed and/or “blackballed,” and needs her job to support a family so cannot risk “telling.” Some of us mistakenly believe “it can’t happen to me.” But it can. It does. It did.

Lesson 4: We are teaching our own children how to be in this world when they watch us.

Part of the advice I offer my seniors in almost every graduation address is to live their lives in such a way that they can be honest with their children about it. I believe I walk the walk on this one. As she often attended evening school events with me, my daughter has observed how I interact with my colleagues, my students, and the parent community. She has watched me grapple with the tougher leadership decisions, show emotion when my school community has been hurt or suffered loss, and—some days—just put one foot in front of the other. Our children learn through watching us—our values, beliefs, and non-negotiables. They also learn how to treat others and how to allow themselves to be treated.

At one particularly dark time in my career, I remember detailing numerous ethical transgressions I observed at the district leadership level. I remember looking up at the dinner table and catching my daughter’s facial expression. At that moment, I realized that by staying in my position, I was inadvertently teaching her to accept this type of behavior from her future employers. Within three months, my assistant principal and I accepted new positions and chose to leave a school we had brought to the highest levels of performance in its history. I took my daughter to that last graduation, gave her a front row seat, and showed her how to speak her truth, never let herself be silenced, and find a dignified exit if she ever ends up in a place that conflicts with her core values. I got a standing ovation, and six months later there was a change in district leadership.

Lesson 5: Networking is key.

Throughout my career, one of my greatest resources has been a network of friends and colleagues I call on—and who call on me in return—for ideas, support, and to talk through any number of challenges. I cannot emphasize enough how grateful I am to have been taught and supported by masterful leaders over my career. I repeatedly mention my first superintendent, Cam Vautour, my first principal, Bob Pitocco, and my mentor principal, Mike Buckley, who guided me as I worked my way through my certification program. I am thankful to have taken Mike’s advice to join the Connecticut Association of Schools, my state’s NASSP affiliate. Through this network, I met and led alongside talented educational leaders, many of whom I count as my personal friends. Leadership can be a lonely business. Build your network. I promise you will need those in it, and they will need you.

Lesson 6: It IS possible to be a principal and a mom—and stick the landing on both.

Any administrator will tell you it is extremely difficult to find work-life balance in our positions. That’s even more true if you’re a parent. I was an administrator when my daughter was born. Throughout her infancy and childhood, she was brought along to sporting events, evening functions, even some school board meetings. Too many other times, she was left behind—and I missed tucking her in more nights than I can stand to think about. It seemed like leading and parenting were always in conflict, and I was faced with excruciating choices over where I was most needed each week. We can never know, I suppose, as we’re going through it, how we’re doing with the whole parenting gig. We can’t really know until later, through their words and life circumstances, whether we parented well.

“As more women attain leadership positions, it is important that we reach back and support younger women coming up through the ranks. Women must represent women.”

As my daughter and I were getting ready in our hotel room to attend the awards gala before I was named National Principal of the Year, she told me that she knew I always regretted not being able to spend more time with her when she was little. She told me that I needed to let that go—that, as far back as she can remember, whenever she needed me, I was there. She also told me how she couldn’t have had a stronger role model. When my name was called that night, nobody was happier than she was. My most important role in this life has been to be her mom. Guess I’m doing OK so far.

Lesson 7: It is critically important to represent and support other women in leadership.

I was certain I wouldn’t be the 2023 National Principal of the Year because, among other reasons, the 2022 one was also a woman. That winner was Principal Beth Houf, and we joked with each other that there couldn’t be two of us in a row! Women are finally becoming better represented in positions of school leadership. According to the National Center for Education Statistics, females made up a higher percentage of elementary and secondary school principals in 2020–21, the year for which most recent figures are available, than in 2011–12, for both public schools (56% compared to 52%) and private schools (63% compared to 55%). Although things have certainly gotten better over the course of the last 30 years, according to the ILO Group, 70% of superintendents are men.

I have been the first female principal in all three schools I have led. All my mentors were men—and I would like to point out that my seven lessons are in no way “man bashing.” Statistically, it was more likely that my mentors would be male since more males than females served in educational leadership when I began my career. That said, I would have loved to have female mentors in the mix, which brings up two things: First, as more women attain leadership positions, it is important that we reach back and support younger women coming up through the ranks. Women must represent women. Second, and I’ll tread lightly here, I have given a significant amount of thought to exactly how and when women support each other and how and when they do not. I encourage my female colleagues to reflect on how we support each other and why we sometimes don’t.

Landing on My Feet

One of my greatest hopes as I look back on my career is that I have helped make the path a bit easier for the next woman. For most folks, simply being aware of the issues that women in leadership encounter is a big first step in correcting them. It’s likely that any of us, looking back, might have made a few different choices knowing what we know now. But, of course, that’s not the way life works. Instead, I’m elated if some good comes to others from some hard lessons that I’ve learned. At the end of the day, I hope my journey encourages you. Although I encountered obstacles I should not have encountered, take heart. I seem to have landed on my feet.

Donna Hayward is the principal of Haddam Killingworth High School in Higganum, CT, and the 2023 National Principal of the Year.