Gender at Work: Why We’re Still Struggling to Get It Right

Personal Catalyst and Historical Context

• In 1990, the speaker (then a graduate student) identified a thesis on women in financial services after reading Judy Rosner's seminal HBR piece, "Ways Women Lead."
• The speaker observed senior women in the 1990s adopting masculinized personas (boxy suits, ties, aggressive language) to navigate command-and-control, military-style corporate structures.
• In 1990, diversity was rarely a business imperative; it was confined to HR departments under a framework of "tolerance" rather than inclusion.
• A specific incident occurred at a bank reorganization meeting where the speaker was chastised by HR for asking for gender demographics on an org chart, noting that senior management did not expect such inquiries.

Evolution of Diversity Strategy

• The speaker later advocated for diversity as a CEO of a private bank at Citi, driven by a specific business rationale: the influx of wealth among women and same-sex couples required dedicated management strategies.
• Corporate language evolved over three decades from "tolerance" (enduring differences) to "diversity" (including communities) to "inclusion" (expecting full participation).
• Structural barriers persisted well into the 1990s and 2000s; for example, the US Senate building lacked a women's restroom until 1992, and the House of Representatives did not install one until 2011 (ordered by John Boehner).

Strategic Goals for Normative Change

• Ruth Bader Ginsburg's 1993 comment was cited: the goal is to end the era where women appear in senior roles "one at a time."
• The speaker argues that societal norms shift only after the "second and third person" break through, making the presence of women standard rather than exceptional.
• The long-term objective is to reach a state where a dedicated "women's session" is unnecessary, as the cultural default would no longer assume a male leadership presence.
• Change is deemed most effective when directed at men and boys, teaching them to normalize women as colleagues, leaders, and customers, rather than solely focusing on women's capabilities.

Workplace Perception Gaps

• Gendered double standards exist regarding family participation; men taking leave for children's events (e.g., baseball practice) are praised, whereas women are stigmatized and feel compelled to suppress their parental roles to be viewed as serious professionals.
• The speaker asserts that organizations cannot solve problems without explicitly naming them, as ignorance of the specific nature of the barrier prevents creative solution generation.

Actionable Agenda for Participants

• Attendees were tasked with identifying three key takeaways from the day to inform future Milken Institute programming.
• Participants were directed to identify specific workplace perceptions that create challenges for women, requiring them to distinguish how female employees must navigate expectations differently than male counterparts.
• The session concluded with a 10–15 minute group discussion followed by a feedback loop via a digital app to aggregate these insights.