Retaining Women: A Problem Startups Don’t Have

By Lucy Drummond 

Two early twenty-somethings catch my eye as they step out of the elevator in suits. This is an unusual sight at WeWork, where most employees dress in business casual. Comfortable wear is especially important during New York City’s humid, sweltering summer months.

The two young gentlemen sit down with wide eyes. I can tell they are in disbelief at what is going on behind me–sangria is flowing, beer is on tap, and a company is giving away free t-shirts. Relaxed lounge music plays in the background. It is 5:45pm on a Wednesday.

Park South

WeWork Park South, courtesy WeWork

I smile and turn to read the Bain & Company report I have been assigned, entitled “Everyday Moments of Truth: Frontline managers are key to women’s career aspirations.” My smile fades. The subject is women’s career aspiration in corporate America–or how it gets sucked out of them due to uninspiring management at mid-levels.

The irony is great as I simultaneously read this report and listen in on the young suits in their conversation. They have been joined by a third, a man who works at WeWork, but he wears a collared shirt and jeans. He has to persuade the younger two that the drinks and snacks are not some sort of trick, and now with beers in hand, the younger two relax.

The man who works at a startup within WeWork is a former private equity banker, and is a few years older than the other two. He tells them about the freedom and flexibility of his current career situation: the hours, dress code, amenities, events, autonomy. The two suits listen intently, occasionally chiming in with statements such as: “Yeah! I hate leaving work at 9pm, leaving at 6 sounds awesome!” I suspect their current absence from work is quite an anomaly.

The palpable excitement of the two young corporate men provides an interesting backdrop to the material I read.

Women graduate college with confidence and “wind in their sails” because academia has made significant strides in gender parity. At college, female students are encouraged to raise their hands, participate, form groups, and develop as public speakers. For their first two years of corporate experience, females carry this character strength with them–43% aspire to rise to senior level management and C-suite positions. This is more than their male counterparts: only 34% of males in entry level positions aspire to rise in the same way.

Unfortunately, this is the only time in corporate careers that women’s aspirations to rise surpasses men’s. Mid-career, the desire to climb the corporate ladder for women shrinks in an inverse relationship with the more experience they get. Some of this aspiration is regained at the highest levels of management, but it neither recovers fully nor again outpaces men’s.


By the time women are considered “experienced” employees–over two years of working on the job–their aspirations to reach the top level of management have split in half. Only 16% of female employees at this stage want to rise in their corporations, compared to 34% of males. At more senior levels, this number improves, but it never fully recovers. 34% of mid to upper level female employees desire to rise. However, more than half of men at the same level (56%) want to continue to rise. This last set of numbers may even be skewed as some of the women who lost aspiration have probably left.

Bain’s reason for this drop? Being human.

Employees today–especially millennials–want to feel engaged and inspired in their work, and are more productive when these elements are present. The more an employee feels understood and supported, the more committed she or he becomes. Especially for women, so says Bain, relationships and communication are central.

It makes sense: corporations measure success using qualitative terms. Women have been barred from many powerful positions because of exactly that; they have been considered to be “too emotional” for rational, calculated, professional decisions. However, that sort of biased thinking is long out of fashion, and has been debunked by research that proves having more women in executive decision-making positions increases the bottom line. The neglect of the qualitative actually hurts profit.

Female employees are as competent and committed as males, but on the whole they need more human and authentic relationships at work.

What will help women keep their aspirations is for mid-level managers to develop more open, interpersonal relationships with junior female employees. Two thirds of senior male employees are hesitant to have a private meeting with a more junior woman, which I imagine comes out of a respectable intention. However, the effects are detrimental because it stymies honest conversation and the possibility of a mentor relationship.

To fix this problem, Bain suggests managers share their personal stories about balancing work and family life in the conference room. Yes, you read that right, the conference room. One of the top management consulting firms says that opening up about family and personal life in typically professional-only settings will increase commitment and help retain female employees.

The surprising–albeit very welcome–suggestions do not stop there. Bain says: “Visibly reward and outwardly champion employees who break the mold, offering public recognition for those who are successful using non-traditional schedules or career paths.”

Another suggestion is–of course–having more women serve as role models in higher level management. But this is a chicken and egg problem, and will be ameliorated as the the pipeline for mid-level professional women improves.

I can’t help but feel that startups already do a lot of what Bain calls for. Granted, it comes with the territory; being small and new offers an inherent opportunity to do what big, established companies cannot. But I still wonder why so many women would choose to stay in uninspiring career paths, hoping that their superiors will change.

As I finish reading the report, I glance up. The three gentlemen are still talking, swapping stories and laughing in camaraderie. As I gather my things to go, I wonder how long it will be until I see the two younger men in t-shirts happily strolling the halls of WeWork.


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