The Leadership Lessons I Wish Someone Had Told Me (And Why We Need to Change the Conversation)

It was my first executive meeting. Having just been promoted, I walked in, head held high, ready to tackle the challenges ahead. As I spoke, I noticed the subtle glances, the raised eyebrows. Later, a colleague pulled me aside. “You need to soften your approach,” he said. It wasn't the first time I'd heard something like this. As a "masc" presenting woman in a leadership role, I constantly face a barrage of conflicting expectations. Am I too assertive? Too emotional? Not feminine enough? These experiences aren't unique to me. Women in leadership often find themselves navigating a labyrinth of double standards and systemic barriers.

Today, let's cut through the platitudes and take a realistic look at the landscape for women in leadership. We'll examine the persistent challenges, critique some conventional advice, and explore what it truly means for women to lead – beyond leaning in or shattering glass ceilings.

The Numbers Don't Lie: The State of Women in Leadership

While progress has been made, the numbers paint a clear picture: women remain underrepresented in top executive roles. A recent Pew Research Center survey found that 55% of Americans believe there are too few women in top business leadership positions. This isn't just a matter of perception; data from Checkr reveals that many young women lack confidence in the fairness of the system, with only 54% of Gen Z women believing they have the same chances as men to earn a management position.

The barriers women face are numerous and complex. Gender discrimination, unconscious bias, and the persistent pay gap are just a few of the systemic issues that hinder women's advancement. Moreover, women often face higher expectations and scrutiny than their male counterparts, being required to prove themselves time and again.

Beyond "Lean In": Rethinking Conventional Advice

Popular leadership advice, like Sheryl Sandberg's "Lean In" approach, has been both celebrated and criticized. While it encourages women to take charge of their careers, it can also place undue emphasis on individual action, overlooking the systemic barriers that many women face. It's not enough to tell women to "sit at the table" when the table itself may be tilted against them.

Mentorship is often touted as a solution, but access to mentorship isn't evenly distributed. Women from underrepresented backgrounds may struggle to find mentors who understand their unique challenges. We need to go beyond individual mentorship and create systemic change to ensure that all women have equal opportunities to rise.

Leading the Way: Women as Agents of Change

Women in leadership roles have a unique opportunity to drive change, both within their organizations and in the broader world. This goes beyond personal success; it's about advocating for policies that promote diversity and inclusion, mentoring and sponsoring other women, and creating a culture where all voices are heard and valued.

But let's be clear: the burden of change should not rest solely on the shoulders of women leaders. Men and organizations must also step up and actively work to dismantle the systemic barriers that hold women back.

Taking Action: Strategies for Women and Organizations

Success in leadership is a two-way street. Women need to advocate for themselves, while organizations must create environments where that advocacy is not only possible but rewarded. Here's how both sides can take action:

For aspiring women leaders: Your voice is your power.

Master the art of negotiation: This isn't just about salary. Negotiate for the resources you need to thrive, whether it's professional development training, flexible work arrangements, or access to mentorship programs. Don't underestimate your value; research industry standards and clearly articulate your contributions.

Build your skills strategically: Identify the skills that will propel you forward in your career and actively seek out opportunities to develop them. This could involve taking courses, attending workshops, or seeking out challenging assignments.

Network with intention: Building a strong network isn't just about collecting contacts. It's about cultivating genuine relationships with mentors, sponsors, and allies who can offer guidance, open doors, and champion your achievements.

Find your voice and use it: Don't be afraid to speak up against injustice, advocate for your ideas, and share your perspectives. Your voice matters, and it can inspire others to do the same.

For organizations: Invest in your female talent.

Recognize negotiation as a strength: When women advocate for themselves, see it as a positive sign of ambition and leadership potential. Foster a culture where negotiation is encouraged and rewarded.

Provide resources for growth: Offer comprehensive professional development programs that cater to the specific needs of women in your organization. This could include leadership training, mentorship initiatives, and sponsorship opportunities.

Make mentorship accessible: Don't leave mentorship to chance. Establish formal mentorship programs that pair aspiring women leaders with experienced mentors who can offer guidance and support.

Create a culture of inclusivity: Foster an environment where everyone feels safe to speak up, share their ideas, and challenge the status quo. Actively seek out and address any instances of discrimination or harassment.

By working together, women and organizations can break down the barriers that have long held women back. It's time to move beyond individual empowerment and create systemic change that benefits everyone.

A Personal Call to Action

The path to leadership is rarely a straight line, especially for women. But by challenging outdated norms, advocating for systemic change, and supporting one another, we can create a world where all women have the opportunity to reach their full potential.

I invite you to continue to share your own experiences and perspectives. What challenges have you faced as a woman in leadership? What strategies have helped you overcome them? Together, we can shatter the glass ceiling and build a more equitable future.