What a transgender experience can teach us about leadership

I spent many years in technology leadership as a man. Now I lead as a woman. Through my transgender experience, I’ve gained a new perspective on many aspects of life, both personal and professional, and encountered surprises as well: In my transition to a woman, I’ve learned how to be a better leader. 

Over the course of my technology career, I’ve been an entrepreneur and held leadership roles in multiple startups, including several in Silicon Valley. I’ve also worked for Fortune 1000 companies and run international divisions of more than 500 employees. In each role, my specialty has been to be the translator, the bridge between the technology and the business. I figure out what our customers need and a way to deliver it.

Interpreting my own needs proved much more difficult. When I began my transition journey five years ago, it came with great personal costs. My marriage ended. I lost friends and have had significant challenges with my siblings. My 91-year-old mother still grieves and continually asks me to explain what “this transgender thing” is all about.

Physical changes lead to leadership changes

Professionally, my physical transition was eased by both the support of colleagues and the sudden shift to remote work. I shared the news with coworkers in January, which meant my appearance began to change as the shift to remote work was breaking established patterns. Our new shared experiences — struggling to take care of kids, losing someone to COVID — led to an environment of less formality and more human connection. And because we’re all just bits on a screen, it’s been easier for coworkers to absorb the changes in my appearance, the slow drift as I work out my new personal brand. 

My style of leadership is changing, as well. As a man, I’d been the leader everyone expected me to be. I crafted a communication style that was traditionally masculine. I could talk over people. I could barge into a conversation. I lived in a man’s world and experienced male privilege, and my career benefited from it.

Yet my natural management style is more intuitive and collaborative. I like to ask questions of others and cultivate their opinions, and that was often seen as weakness. I faced the choice of pretending to be someone I wasn’t or being seen as someone who didn’t fit in. For more than 20 years, I took the path of least resistance.

Now, both personally and professionally, I no longer have a default path. The beauty of being shattered into a million pieces is that I can decide how to put myself back together. I have the freedom to connect the dots for myself, and to think about what I bring to the workplace that’s valuable. My authenticity is a key part of that, as is my willingness to show up in a way that’s vulnerable.

Navigating my career in a new way

I now have a front-row seat on how rooted our ideas are in gender. I possess the same insights, talents and skills that I always have, yet people perceive me differently now that my gender presentation is as a woman. In meetings, they’re less apt to listen to what I say or pause so that I can speak. I could choose to interrupt conversations and aggressively insist on being heard, but that’s not my natural style. I’ve chosen to find a quieter and more authentic leadership approach.

When I led as a man, I’d felt pressure to primarily rely on logic. Being emotive was seen as anomalous, something “men didn’t do.” My transition has given me permission to not just feel more, but also to talk about feelings and allow others to do the same.

My thinking has always been that if someone expresses themselves emotionally, they’re probably on their way to getting to a logical place. Now I have the flexibility to ask a team member, “Why do you feel that way?” “You sound anxious. What’s your fear?” Or, “What does your intuition tell you?” It helps me understand as a leader where people are and where they need to go.

While I used to be afraid of expressing my vulnerability, I’ve learned it’s a gift you share with others. It allows me to connect with people in ways I’ve never experienced before.

Supporting a new leadership style

The professional cost of embracing this leadership style is as yet unknown. There’s often a competitive swirl that I’m not part of because I’m different, and while there could be a certain strength to that, I’m still tinkering around with what it means. Will my career advance with this leadership style? Or will I be seen as a person who’s nice but doesn’t have what it takes to get the job done?

The truth is that key leadership attributes transcend gender. The best leaders tap into their natural, authentic leadership style — and supportive organizations give them the flexibility to lead in the ways that make them most effective. They encourage diversity of style and welcome experimentation. They adopt agile ways of thinking that encourage new approaches. This can be as simple as supporting a team member’s rotation to another project or a different role. Creating a supportive community is also essential — without the friendship and emotional support I received through  Embrace, Cognizant’s community for LGBTQ+ associates and allies, I wouldn’t have been able to complete my transition.

I sometimes think of the leader I was as a man. I think of his struggle and his pain. If I had to do it again, I’d have followed my heart, and likely would have led more effectively.

For me, this perspective has been hard-won — and I’m still learning about the best way to lead. But of this I’m sure: By allowing yourself the freedom to embrace your true self, you might be surprised at what you find.