For decades since fully entering the workforce, women have navigated a labyrinth of expectations that can undermine their achievements and aspirations. For many high-achieving women, the journey through leadership roles is fraught with challenges that arise from the complex interplay of gender, leadership identity, and societal perceptions of success. When stepping into a new leadership role, many women must confront the unspoken rules that govern workplace dynamics, such as the expectation to be assertive without being labeled as aggressive, or to serve others' needs and vision without expecting reciprocity. Like a decoder ring to decipher the nuances of organizational culture, understanding these hidden expectations is vital. Unfortunately, many women enter their careers without being provided the decoder ring, leading to missteps and frustrations.

Adapting Is a Double-Edged Sword

As women rise in their careers, they are often faced with two choices when faced with challenges: they can strive to meet others' expectations or resist conforming to these norms. Many women, socialized to be attuned to others' needs, find success in the former approach—meeting the expectations of colleagues and superiors. This alignment can lead to positive recognition and promotional opportunities. However, this success often comes with a caveat. Once a woman begins to succeed, the very rules that brought her that success can shift dramatically.

After years of conditioning to be supportive, quiet, and accommodating, women are suddenly critiqued for not being assertive enough, taking risks, or expressing their opinions. The expectations surrounding leadership change, leaving many women grappling with their identity and how to navigate the new landscape. The lack of support during this transition can create a harsh reality, where the judgment women face from peers and superiors is often more stringent than that faced by male counterparts.

As some women attempt to adapt by becoming more "assertive," speaking up more often, stating their opinion more often, and making decisions more quickly—following all the general recommendations they receive to improve their leadership skills—they begin encountering backlash that these same behaviors are "off-putting" or "unbecoming."

This attempt to adapt creates a complex paradox: to succeed, they must demonstrate qualities based on traits established as traditionally "masculine," even though leadership competencies have no gender. When women try to exhibit these traits, they experience criticism. This dilemma can be demoralizing.

It reflects broader cultural beliefs about what constitutes an "acceptable leader." In many organizations, particularly within the United States, leadership archetypes are heavily skewed towards individualism and traditionally-labeled masculine traits such as emotional stoicism, assertive communication, and quick decision-making. This narrow view leaves little room for those who express collaborative, reflective, and measured communication styles. These latter traits are essential for any current leader, regardless of gender, and yet, they are more often socialized in women and also less valued. Consequently, women must work significantly harder to prove their capabilities, leading to compensatory hyper-achievement.

The Price of Success

The cognitive dissonance and compensatory hyper-achievement not only hamper progress but can also trigger feelings of burnout, impostor syndrome, and decision anxiety. Instead of being rewarded for their resilience and adaptability, high-achieving women often grapple with a reinforcing cycle of negative feedback.

The narrative becomes circular, as their strengths—previously seen as assets—are now misattributed as weaknesses. Such perceptions can lead to damaging statements like, "You aren't ready for the next level" or "You lack confidence." Ironically, these judgments lead to more compensatory behavior as women try to overcome these new barriers. Frustratingly, this is where most leadership development programs and coaching interventions fail women: they focus on the lack of confidence, decisiveness, and imposterism instead of the cognitive dissonance experienced and the root cause of those experiences.

An added layer of complexity comes from the fears that high-achieving women often harbor. They fear losing their value to the organization, becoming obsolete, or missing out on opportunities. These fears come from the negative message they receive about their value and it drives them to take on more responsibilities, even when such efforts yield diminishing returns in terms of career advancement.

Ironically, this can lead to further burnout, exacerbating the vicious cycle of struggle and self-doubt. Women endure both subtle and overt messages that often question their accomplishments. They receive skepticism regarding their success, with a prevailing narrative suggesting they could not have achieved their positions without external help. This scrutiny persists even amidst demonstrably high achievement levels, making many women feel their hard work is undervalued and misunderstood.

Escaping or Breaking the Cycle

At this critical juncture, women typically face three stark choices:

They can opt out of leadership roles altogether.
They leave the workforce, burned out and fed up.
They persist in pushing forward while feeling trapped, frustrated, and ambivalent about their leadership future, repeating this vicious cycle.

To break this vicious cycle, organizations and individuals must challenge the prevailing narrative about leadership. Here are three ways to start.

Broaden the definition of what a leader looks like. Recognizing and valuing diverse leadership styles is not just beneficial, it's necessary. It can cultivate an environment where women and others can thrive without compromising their identities. Training initiatives can educate organizations about the implicit biases that shape perceptions of leadership.
Create a support system that decodes career navigation within organizations. Mentorship opportunities can provide invaluable guidance, while organizational leaders can evaluate whether problematic messages are being inadvertently sent to women through trainings, leadership and coaching programs, and managers. Problematic messages must be replaced with structured, strength-building opportunities supported by mentors, managers, and sponsors across the organization.
Include identity development in leadership and coaching programs. Women should be offered an opportunity to learn about their unique leadership skills and identity that adds value to the organization and to unlearn compensatory hyper-achievement habits that can lead to burnout and frustration. By recognizing their strengths and reframing self-doubt, women can redefine success on their terms, allowing space for growth and authenticity. (This third recommendation can only occur if the other two are solidly in place.)

Women's ability to adapt to constantly changing rules of success first needs to be appreciated as a significant strength. However, ultimately top leaders in organizations who want to retain their most resilient, high-achieving women will need to create an environment where it's worth the journey.

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Note: The contents of the post were adapted from (1) a talk on "Redefining Leadership in 2025" delivered at the ATHENA of the Triangle 2025 Leadership Conference, (2) my upcoming book, Enough of Never Enough, and (3) a global training co-designed with Michael Grube of AIIR Consulting for one of their clients that included the topic of weakness misattribution.

Mira Brancu is co-author of the Millennials’ Guide to Workplace Politics, which includes tips like those above and more.