Cultural Expert and Brand Strategist Jess Weiner on Helping Brands Walk the Walk in Diversity and Inclusion

The FQuestionnaire spotlights pioneering women across different industries and their unique perspectives on career building, as well as how they are advancing equality in their fields. Jess Weiner is a cultural expert and creative who has spent 27 years helping people feel seen, heard, and understood through her research and insights on cultural trends. She’s a bestselling author, podcast host, adjunct professor at USC, and a speaker who has connected with audiences from the White House to Wall Street. Weiner was recently named by Fast Company as one of the most creative people in business in the areas of diversity and education. She has been a strategic partner in culture-changing moments such as Dove’s campaign for “Real Beauty” and the evolution of Barbie. Through her consultancy, Talk to Jess, she and her team help Fortune 500 companies to become more inclusive and culturally fluent. Weiner is also the producer and creator of branded podcasts including the new American Girl Podcast Network and Dominant Stories, produced with Shonda Rhimes and iHeartRadio.

Here’s what Weiner had to say about leading with curiosity and courage, how companies can create systems that truly allow women to advance, and the bad advice she threw out the window early on in her career.

The Female Quotient: What’s one example of how you and your organization are moving the equality needle — at work or in life?

Jess Weiner: My entire entrepreneurial journey has been dedicated to moving the equality needle. As a cultural expert and brand strategist, my work has been centered on helping Fortune 500 companies better represent people in their media, marketing, and advertising. We know that to see yourself represented is an important part of feeling included and acknowledged as a human being. BUT equality doesn’t stop at representation. To create equality and ultimately equity, we must do both internal and external work within a business. So my team and I now embrace a holistic approach to working with our clients we work with all aspects of the team from HR, legal, marketing, C-Suite, product design and development, and content producers to ensure that how folks make decisions from hiring to campaigns to copywriting all share intentionality and a framework for creating equity and inclusion. 

FQ: What are the three most important character traits in modern leadership?

JW: Humility, courage, and curiosity. I think recognizing that as a leader you are also always on a growth trajectory like everyone else. I used to believe that if I was leading, I must know it all or have all of the answers. A few royal failures remedied that! Now, I embrace the humility to know that my leadership gets better the more I learn. Courage and curiosity go hand-in-hand for me. I find when I stay curious and open to new ideas, to really listen to others, and to being willing to have difficult conversations, I grow stronger as a leader. The inner work is truly never finished for leaders it’s a continuous path to learn more about yourself and others.

FQ: What do you think is the single biggest obstacle limiting women’s career growth today?

JW: We have a lot of rah-rah rhetoric in our culture when we talk about women and business. We love to cheerlead and champion the idea of women being more confident in their careers, but ultimately, I still find the world doesn’t like confident women. All of this rhetoric may feel good when we hear it, but it’s ultimately what I call SFSN: “Sounds Fabulous, Signifies Nothing.” Especially in business, there are still too many systemic barriers for real change (pay inequity, lack of family leave options, and of course now, the reversal of Roe v. Wade). So when a company or industry says they are prioritizing women’s growth and development in leadership, we need to look behind the scenes at their C-suite and board makeup, and ultimately their policies impacting women to really see if it’s true. I find there is an incredible barrier that still exists between the surface-level programs we put into place to talk about women and career growth and the real risk and courage required to create systems that truly allow career growth.

FQ: What is the worst advice you received from someone in your career, and how would you reframe it to someone today? 

JW: Early on in my career in Hollywood, I had one of my agents tell me that I had to choose to be one thing. I couldn’t be a multi-hyphenate a producer, a writer, and a speaker. I had to choose one because people wanted to be clear on where to “put me.” Obviously, that was terrible advice and likely not something they’d tell a man. 

I remember that advice knocking me back for a moment in my early career, but ultimately, I decided to persevere and follow all of the interests and talents I have. This has served me well as I’ve created a career that expresses the different parts of me. I think the world is set up better now for people to be and do multiple things throughout their careers. I’d advise someone to make sure they do excellent work in whatever they are interested in that will speak volumes for them more so than any label.

FQ: If you could rewrite one rule of the workplace, what would it be? 

JW: I believe that relationships are the currency of business, and today, since our work is remote and hybrid in many cases, it’s important to really connect with the folks on your team and build those relationships in a meaningful way (especially if you are not able to spend time together in the office). One of the rules I’d enhance is not to be afraid of having meaningful conversations about life with your co-workers. We all need to be able to bring our whole lives to work, and while healthy professional boundaries are important, I would love to see more connection within the workforce. 

FQ: What’s one career-related question you wish people would stop asking women? (AKA, is there a question that we’d never ask a man?) 

I’d like to ban the question: “How do you do it all?” because A. It assumes someone is doing it all and no person is. We are all doing our best to juggle life. And B. It also assumes that women especially bear the brunt of the labor in their home lives in addition to career. This is a question we’d never ask a man. That’s why I think it’s important to normalize men supporting domestic duties as well as working. 

FQ: What is one career-related question you wish people would start asking women and aren’t? 

I’d like to dig deeper and ask, “What is one area of support you still need but aren’t getting?” I think it’s important to continue to check in on the support needed be it more access to capital, introductions for networking, a champion at work, etc. Sometimes, when women reach a certain level of success, they may feel like they must stop asking for help or that maybe they shouldn’t ask for support. It’s important at every career stage we are identifying gaps in support and resources and finding ways to ask for them.

FQ: Describe a moment in your career when you realized your potential. What sparked this eureka moment?  

JW: I started my career as a playwright and theater director, and I started hosting “Talk Back” sessions after the social issue plays I’d written. So, I’d spend 30 minutes or so deconstructing the plays and the issues we addressed ranging from body image to addiction to hate crime, often with a young audience. I realized then that I was good at a few things: holding space to have a public, difficult, and nuanced conversation. I was good at creating a safe space for connection and conversation, and that I really had my finger on the pulse of how to translate what was happening in culture in a creative and approachable way for people to learn more and look within. 

I’ve taken those skills and really refined them over the course of my career. I use those abilities every day in my brand consulting and cultural fluency workshops with clients and that’s what’s helped me retain long-lasting relationships with the brands I work with and the audiences I’m connecting them to. 

FQ: What’s one strategy you have for boosting self-confidence during moments of doubt? 

JW: I wish it was as easy as one strategy. I often use a few tools from my toolbox for self-confidence. One is perspective. I’ve learned to ask myself “Is this as catastrophic as I’m making it out to be in my head?” Oftentimes, my worry is far out of balance with reality. The other tool I use is courage. Everyone has doubts, even the most successful people, but we move through it with courage and grace. If I look at my life and my experiences in business as a big opportunity to learn about myself, it takes the pressure off of needing to be perfect, and that’s often where my doubt comes from. Thoughts like: “Am I doing this perfectly?” When that’s off the table, I can be more in the moment, enjoy the process (even if it’s a rocky one), and know that everything I’m learning serves me in the end.

FQ: Name a woman whose mentorship has had a positive impact on your career and life. What made their approach unique and memorable? 

JW: My friend Diane Reichenberger was one of the most dynamic executives I have worked with and had the privilege of becoming friends with. At every stage of her career, whether she was a VP or a CEO, she was gracious in always giving back time to volunteer for things she cared about, mentoring up-and-coming talent in her industry, and always asking “What can I do to support you?” to women at all levels of their career. She never behaved as though there wasn’t enough for everyone. In her world, there was more than enough love, success, support, and accolades to go around. She really modeled the generosity I choose to have in my life today.

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