Women and Leadership, Part Two
As 2024 winds down, another female presidential candidate's defeat brings reflection and even some hope!
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Some Reflections and Some Hope
Women and Leadership as 2024 Comes to an End
For the second part of the Women and Leadership series, I had another topic entirely about what I refer to as “the authority effect” - the very real and underutilized impact of a leader’s authority when used to promote predictability, clarity and boundaries and the specific ways this manifests for women leaders because I think it is a foundational. However, given the result of the 2024 election and how for many women, it was demoralizing to see a male candidate weighed down by so much baggage definitively defeat a qualified woman, this deserves some analysis and although there is a lot of hard truth to be swallowed as to our culture and society and the headwinds against women wielding national power, it is far from all grim out there.
I mostly worry that people take away the wrong message from the candidates in this election. It was incredibly close, even if ended in a definitive defeat for VP Harris. This was an election where, yet again, as we proceed through another time of uncertainty, a majority of the electorate wanted change with a familiar face. In 2020, they chose Biden. In 2024, they chose Trump, remembering a time not that long ago when groceries were 20% less. Months ago, I read a piece saying that Trump and Biden were the last two internationally known American leaders as they came from the “three global TV networks” era. This strikes me as correct.
For this article, I’m going to dispense with any throat clearing in terms of gender stereotypes, man bashing etc but I encourage you to read either for the first time or as a refresher, part one
First, the bad news.
“Strong and Wrong”
Twenty two years ago, referring to Democrats’ losses in the 2002 election, Bill Clinton remarked that Americans prefer “strong and wrong to weak and right.” This fall, I saw a sequence on CNN where a group of male undecided voters told the correspondent they wouldn’t vote for a woman because a woman, any woman, is “too emotional” to be president. So can a woman be seen as “strong”?
People have to take an extra step, and it’s a pretty big one, and reconfigure their basic conception of a leader, to see if a woman can fit within the frame of the default picture they have of a male leader. While that step is possible, it’s also an effort and there are plenty of circumstances where a person can get knocked off course, mid-step, and retreat to their original conception. It’s not an advantage to a woman leader, that’s for sure. The bar is higher and it’s inflexible.
If the picture of a leader is default male and a person’s concept of “charisma” is default male as well, then that’s two very big steps. Charisma can take many forms. We’ve all been in the presence of women who possess it. It can include warmth. It can be a contagious sense of possibility, positive energy, fun. Often it entails demonstrating a sense of humor and although we have come very far as women to not be considered a borderline freak for making a funny remark (in graduate school, I was part of a satiric surprise takeover of our student reading series and at the after party, one dude could not stop saying to me, with obnoxious wonder, “You were actually funny. Like, I really laughed.”). Historically, our female politicians were not generally known for their quips.
This concept of charisma posits an extroverted personality, verbal dexterity and a way of sometimes surfing the edge between funny and pointed that is much more dangerous for women and can easily get labelled “nasty.” And there seems to be a certain connection where “strong” women for some are “off-putting” for others. And I do think it’s harder for women than men, because of how we’re socialized, to accept that a large group of people may find them off-putting, no matter what they do, and go about their business. I would hazard a guess from recent studies around teenage girls and social media, this concern and dismay over being disliked is not going to go away anytime soon.
So projecting strength may be necessary but for women to get this right at the top of the presidential ticket, is it likely going to take the right woman with the right temperament. And developing that temperament may well be a personal sacrifice fewer women than men are willing to make.
The False Promise of Perfectionism
The other night I watched the Martha Stewart documentary on Netflix and if you’re reading this article, I would suggest giving it a watch. At the time of her rise, fall and subsequent reinvention, she was pretty much background noise to me and a symbol of the sanctification of the stereotypical womanly arts that felt retrograde, establishing goals for women’s roles that were damaging and unattainable at worst and ridiculous at best.
Watching it now, Martha Stewart was amazing! Her downfall, engineered by James “but Hillary’s emails” Comey (which does make you wonder if powerful women get under his skin…) and subsequent reinvention are worth reflecting on in this moment, and it is particularly interesting to compare her road to that of her peer, fellow business tycoon, TV star and very public figure, one Donald J. Trump. Stewart no longer possesses a billion dollar media empire but she does have a successful career that in part depends on parodying her former self. She is a survivor and she came from nothing. But compared to the gentleman, well…yep. It’s an interesting contrast.
Much of the first third of the documentary is about her perfectionism. Her first career was on Wall Street and she rose quickly up the ranks until a financial crisis in the mid seventies pushed her out of a job. She took that same intense dedication and put it into renovating her new home in Westport as well as entertaining. This led to starting a catering company which in short order became a million dollar business. Her husband’s career as a publishing executive gave her opportunities but it was Martha’s talent that got her hired and rehired. She accepted nothing but the best from herself or her employees. She was most certainly not easy to work for. There is one “behind the scenes” sequence of her correcting an assistant about how to cut an orange and she definitely would have made me cry.
But her formula for success was simple: you become the best at something - the best concept, the best attention to detail, the most magic delivered - you are rewarded. You sacrifice everything, and you are rewarded. You sweat the small stuff, day in and day out, and you are rewarded.
Does this sound familiar? I recognize it myself and see this all the time with aspiring women leaders when we interact. They are good in school and they get rewarded and then they go on up the chain in schools. There is such dedication and focus and drive towards serving the kids. And there is much taking over tasks ourselves when it takes too long to teach the assistant to cut the orange the way we need (or prefer it) to be cut. And it’s not incorrect to say these talented women can both effectively lead teams and execute on large initiatives - and they would get the details done better than anyone else, too.
But do these kinds of patterns contribute to our leadership capabilities or do they reinforce a sense that there are immutable rules that someone, somewhere created? Where do we land when someone else upends the rules? And what happens when we are in a position to make the rules and do we feel we have the power to amend them, change them or make them our own in a time of such change?
I understand the irresistible pull towards putting my mark on that orange. And even if you are really nice when you take the time to instruct your team members as to exactly how you want that orange cut, is this how you should be spending your time? All of the fears about leadership seem to manifest - what if people don’t know I’m involved? Will they think I’m not doing my job? How do they know I’m in charge unless it’s clear that I decide everything?
And how do you decide everything, even when you’re not an expert in everything, which then leads to a pressure to try and become the expert in everything (rather than working on being unafraid to ask the questions)?
Believe me, I lament people’s lack of focus and consistent discipline every damn day. I talk about how it’s easy to complain and much harder to do. But at the end of the day, as I watch younger women leaders, I worry that they have put too much faith in perfectionism, in there being a “right” answer, and not enough into establishing confidence that they have built up a track record of excellent judgment, have taken calculated risks and succeeded and that they can navigate the unknown.
Sometimes it is impossible to ascertain what the right answer is - and when that is unknown, you can’t do it perfectly, because there is no perfect.
Get comfortable with the fact someone will think you’re a nasty woman
In the end, Martha went to jail, it seems largely because of the testimony of one EA who went on at length about her rudeness. There was undoubtedly pleasure the public took in seeing a woman who seemed like something of an ice queen be revealed to be just exactly that.
But other times, criticism is background noise. There are times as a leader you can’t be “a nice woman.” You have to make decisions people will think are terrible, even if you know they are necessary..
Any leader can do her best and be as empathetic and generous as possible and some people will still paint her as a villain. The same goes for a man. You can’t control for the fact you’re a projection screen. In general, many people are not very happy right now and that malaise will get projected onto you, your personality and your decision making. If you go into headship today with the plan to become a beloved community figure, good luck with that goal in 2024. Probably good luck with that goal at any time, but many people became beloved through long tenure, learning on the job through many ups and downs and finally becoming the status quo. You can do amazing things for your school. You can be an inspired problem solver. You can be an inspirational speaker. You can be an outstanding mentor. “Beloved” may follow. It may not. And if head tenure keeps averaging under ten years, the chance of reaching “great beloved” status shrinks accordingly.
Most women I know are dedicated to being servant leaders. We want to serve and perhaps what’s underneath that is that we want to be needed and feel necessary. And perhaps what’s under that, is that it helps us feel loved and relevant. It’s complicated to do that servant leader work and then feel resented in return, even if an institution is better off in the long run for what was accomplished.
But to remind you of one of my three rules of administration, People Lead Complicated Lives.
4. Let your ambition show… but not too much!
In 2016, Hillary was running for president for the second time and had been defeated the first time around, so she was punished for her ambition. In 2024, Kamala was the accidental nominee. I wonder if their road to the nomination in some ways cut down on the criticism that either has too much ambition, because this still seems to be a thing for women it never has been for men.
Women who are ambitious are seen applauded but women who are too ambitious are seen as suspect. I find it totally fascinating how two women have recently ridiculed Jill Biden. One, Nellie Bowles, author of the satiric TGIF column in The Free Press on Substack, consistently mocks the First Lady’s use of her title as “doctor” since it came from an Ed.D which is apparently mockable (and I like Nellie Bowles’s other work!). I heard Tina Brown, former New Yorker editor among other publications, recently discussing the First Lady as Lady Macbeth.
Honestly, I have no insight into Jill Biden or feelings about her one way or another other than the fact I admire she still teaches. Given there have been no terrible stories coming from any of her decades of students who could surely find fifteen minutes of fame or a bit of cash for a tell-all as to her incompetence or unkindness, I find this both mean spirited and deeply puzzling. And Jill Biden has never run for office. Apparently getting the highest degree in your field in your fifties and appearing to enjoy being in the position of First Lady marks you as nasty.
Martha Stewart made no bones about being an ambitious workaholic and she ended up going to jail for five months, convicted of a crime of lying to the FBI about a crime they established she did not commit. Square that circle!
And I think that’s why it’s especially complicated to run an independent school as a woman. It’s a social risk for a woman to admit she wants power whereas it's a social risk for a man to admit he doesn’t. There’s an assumption that men go up the ladder and often a few unspoken questions if they don’t choose to do so. While it is natural for women to be “good students” of leadership and move up the ladder from teacher to department head to admin to head, I feel as if you also encounter questions as to why you want it, all along the way.
Now the good news…and it’s pretty significant!
There is more than hope - progress is apparent and the change train keeps moving forward
Leadership always comes with a big load of junk and part of the good news is, women’s load of junk is still woman-shaped but also becoming more and more like a man’s. The novelty of women in leadership is gone, absolutely. There are still more male heads than female heads but the gap is smaller. And I think the gender balance has flipped for many senior admin roles today. These are all milestones.
We’ve had two presidential candidates. In another CNN interview with undecided voters, several people who were on the fence about economic issues expressed what sounded like sincere, somewhat awestruck, admiration for how Kamala performed in a town hall and how they felt she uniquely and authentically tried to connect with their questions and concerns. It was quite moving!
It is hard to authentically navigate the space as a public figure, making genuine connections and empathizing with people, with being that servant leader as well as finding a certain centered looseness people gravitate towards and follow that is part of confidence or charm or charisma or whatever you want to call it.
And although I think leadership is tough on everyone right now, I think there are many men who start out with thicker skin, who are wired not to be as sensitive to social nuance, who didn’t grow up taking the emotional temperature of every room they’re in, and the background junk rolls off their backs more easily.
I worry the biggest long term risk to women’s continued success and momentum in climbing high will be that more women are going to decide at a certain point, the enormous effort, the extra accommodations and additional junk, is not worth it. But I do think numbers matter and as more women become leaders, baggage will shift during flight.
And seriously, watch the Martha documentary and put her story side by side with that of her old Apprentice colleague, the once and future President. It’s an instructive exercise for us all.
Have a wonderful December weekend - winter break is almost here!
And next Friday - it’s the Helpful Resources post for Winter, 2025 - largely AI and demographic/enrollment related links!
Julie
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