How to Trust Yourself: Insights from 6 Top Women Leaders in Design & Tech

On April 19, 2016, Designer Fund hosted the fifth Women in Design event at Medium’s office in downtown San Francisco. Historic buildings painted a stunning background for the evening, during which top designers were treated to an intimate look at the inner worlds of six prominent female leaders in design and tech.

Maria Molfino, women’s leadership coach and host of the Heroine podcast, provided the wider context for the event’s theme on voice and risk. Female voices, she argued, are underrepresented in professional settings, from entry-level positions to the C-suite. But when women become more visible, they’re subject to extra criticism and backlash, whether they’re simply sharing their talents or pitching their voices into more charged discussions like negotiating salaries, raising venture capital, and speaking out against sexism.

Maria says that despite this reality, women should take risks and express themselves in order to find fulfilling careers and create a diverse and inclusive future.

Heather Phillips, Design Manager at Designer Fund, helps designers land roles at top companies that align with their values and career goals. She joined Maria to lead roundtable discussions with Anisha Jain (Dropbox), Tiffani Jones Brown (Pinterest), Jessica Hische (Independent), Julie Zhuo (Facebook), Leila Janah (Samasource), and Brit Morin (Brit + Co). They shared stories about internal self-doubt, criticism from the outside world, and how they found the right channels for their voices.


Each of these women comes from a unique personal background and sits in her own place along the introvert-extrovert spectrum. They each also manifest their leadership qualities differently, from the influential lettering artist working in near isolation to the tech executives managing dozens of employees. But one thing they all agree on is that a good dose of reality is the best way to set their critical inner voices straight.


Question your negative inner voices with data

Leila Janah, CEO and founder of Sama and Laxmi, has been working with her inner critic and impostor syndrome all her life. It was especially hard to feel like she “belonged” as a 25-year-old woman trying to start a business in Kenya. “I remember walking into meetings and people would be like, ‘Who the hell are you?’ I’d have to explain that I was the CEO of this company. And nobody took [my leadership] seriously.”

Tiffani Jones-Brown, Creative Director at Pinterest, described this as a screaming voice that says “I don’t fit here, I don’t fit here, I don’t fit here”—a little parachute on your back that makes it difficult to run fast, and discourages you from taking risks to avoid making mistakes. But our speakers noted that this calms down when they acknowledge real evidence that things are going well.

Insight: Collect data, look at results, and check whether reality matches your assumptions.

In Leila’s case, she couldn’t argue with the numbers: Samasource has moved over 7,600 workers and their families—about 35,000 people—out of poverty, from living on $2 per day to $8 per day. These reports, and Facebook messages from workers themselves, remind her she’s on the right path.

Brit Morin, CEO and founder of Brit + Co, was also 25 years old when she started her company and she didn’t always feel confident in her business decisions. As she put it, “You don’t have a ton of experience when you’re 25.” She sought advice from as many mentors and advisors as possible, until one day a coach told her to start going with her gut. So she did. When she looked back at her track record, she realized that most of her independent choices turned out to be right. It became easier and easier to trust her own leadership abilities as the company grew, and today Brit + Co attracts 80 million visitors per month.

Internal doubt can also sound like other people’s voices. You might worry about what they think of you and how they judge your abilities. Julie Zhuo, VP of Product Design at Facebook, has found that these voices are often wrong because they’re projections of her own fears, and that her imagination is always scarier than reality. One of Julie’s most important professional experiences in 10 years at Facebook was a 360-degree feedback evaluation: a 30-page report revealing what 20 of her closest colleagues thought of her. She took the report home, grabbed a cup of coffee, and cracked it open.

It turned out that for the most part, her worries were misguided. And when she did get negative feedback, her shortcomings didn’t seem so dramatic the moment they stepped into the light. She could now work on them openly with her team. “I refer to the report all the time,” she said. “It was like a source of truth that grounded everything, helping me recalibrate the voices in my head.”

Anisha Jain, Design Leader at Dropbox, pointed out that inner voices never really go away, they just change as you get older. But all of our speakers have found ways to express themselves and step into leadership anyway.


Find your medium

“I think we all have a vision for something,” Tiffani said. “If you believe in something deep in your gut and in your heart, it’s probably going to be inspiring to other people.” She acknowledged that finding the right way to articulate your worldview is difficult, but that this work is also important and worthwhile.

Insight: Start sharing your voice. You just need to find the medium that works best for you.

Your voice can take many forms, from expressing your values through your job to publishing thoughts in writing, video, or audio. All of the panelists tinker with different media and have diverse online presences comprised of Medium posts, blogs, websites, guest articles, speaking gigs, guest spots on TV shows, and, recently, Facebook Live broadcasts.

The panelists also shared insights about how to make sure your voice is heard in collaborative settings at large companies.

The first key is to find the right communication vehicles for your style. For example, Julie tends to need alone time to properly process new information and come to a conclusion about next steps. This can be challenging in meeting-heavy environments, where groups of people try to hash out opinions in the moment. Julie found that it was helpful to set expectations with her colleagues about her preferred communication style, and she has found other ways to share her thoughts, including writing notes, sending follow-up emails, commenting on docs ahead of time, and staying active in internal communication channels.

The meetings issue resonated with several panelists and audience members. Fielding a question about this, Anisha shared her go-to tip: walk up to the whiteboard, grab a marker, and capture what people are saying in real time. This allows you to frame the conversation and make sure your viewpoints are seen. You can also summarize the discussion in docs and emails after the meeting is over.

Jessica Hische, an independent lettering artist, also strives for balance in conversations, but for her, it’s about using her voice and helping other people feel heard too. “I love talking and am very dominating in conversations. I have to keep it in check all the time.” Navigating meetings with her clients can be tricky, because they’re “basically phone calls with a whole bunch of alphas”—she’s the alpha of her company, her clients are the alphas of theirs—and often everyone is just waiting for their turn to speak. To make space for all voices, including hers, Jessica “whiteboards” what people are saying in her head while they talk, then verbally summarizes their viewpoints alongside her own.

For Leila, entrepreneurship itself was the best platform for her voice. In 2005, she was “a lonely researcher in the basement of the World Bank, the last place that a young woman without a PhD in economics can have a voice.” She knew she would never be recognized in such a big enterprise, so she took a big risk: she quit her job and started her own project. And it came full circle: by 2013, the World Bank had cited Samasource as an example in an Innovation for Job Creation report.

Brit’s entrepreneurship is also at the core of her self-expression. The Brit + Co brand is a direct extension of her identity and her dream to help women connect with their creativity. “We named the company after a person to keep it real and to make it accessible for women. I found my voice in all of that.”

Once you start getting your voice out there, your next hurdle is to deal with backlash, which our speakers confirmed is an inevitable reality of becoming a leader.


Keep an eye out for criticism—it means you’re doing big things

Leadership and career growth have an ugly underbelly. Peers, friends, family, and the internet peanut gallery hurl disappointment and criticism at female leaders. This hurts, but it’s no reason to hold back.

Insight: The bigger you go, the more negativity you may encounter from outer voices. Treat criticism as a sign that you’re onto something.

Tiffani explained that when you lead in a company, you need to be decisive, and the very nature of putting a stake in the ground means you’re going to anger or hurt someone. This is tricky if you’re a person who doesn’t like discord. “So, you have to figure how to create the right conditions to make good decisions, thoughtful decisions, and communicate them well. The worst thing you can do as a leader is to be frozen.”

Even your personal career growth can attract negative voices. “If you care about doing your best, every time you change course, you’re disappointing people—people on your team or people who believed in what you were doing,” Anisha said. This can be painful when you outgrow an old role, switch industries, or jump to a new organization.

Jessica shared that she transformed from a people-pleaser kid into a confident, outspoken woman and that it was “a long, hard journey to get there.” One thing she noticed was that socially successful people she went to high school with had something in common: they acted the way they wanted to, and didn’t apologize. “If you treat the things that you want to do in life, your actual desires, as your truth, people can’t argue with it.”

Brit acknowledged that criticism is an everyday reality for founders. But for her it’s worth it, because she serves a mission she believes in. Echoing Jessica’s sentiment, she said, “It’s your inner truth. If you’re doing your best work and you think it’s work that helps other people, who can tear you down?”


Women in Design: Voice and Risk is the fifth Women in Design event hosted by Designer Fund. This event was sponsored by Medium and Dropbox and supported by women-owned businesses including Voz, Picnic on Third, and Melanie Riccardi Photography. To hear about future events, get email updates here.

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