How kid-rearing tips are helping Willa Bennett reignite legacy media brands

By Tony Case  •  April 18, 2025  •

Since taking charge last September, Bennett has brought her tech-savvy, generationally engagement from Highsnobiety, as well as the social team at Condé Nast’s GQ and Bustle Digital Group, to two of consumer publishing’s most iconic titles. Her secret weapon? Parenting books, of all things.

Here, Bennett reflects on infusing two legacy publishing powerhouses with fresh energy while using whole-brain parenting principles to nurture the next generation of media voices.

You shared in a recent podcast that you learned about managing people from parenting books. Which books most profoundly shaped your management philosophy, and what lessons did you extract from them that traditional business books might miss?

I’ve always been drawn to parenting books because they center emotional intelligence in a way that I’ve seen some traditional business literature skip over, yet it is quite valuable in leadership. “The Whole-Brain Child” by Daniel Siegel and Tina Payne Bryson really stuck with me. It taught me that people–regardless of level of experience — thrive when they feel safe, seen and understood. That’s shaped how I show up as a manager. I’m not here to micromanage someone into success — I’m here to help unlock whatever’s already there and inspire a team to work collaboratively to create and innovate. Another one I love is “How to Talk So Kids Will Listen and Listen So Kids Will Talk.” It’s a masterclass in communication, which is crucial when you’re navigating high-stakes editorial, creative tension or even just delivering day-to-day feedback.

Stepping in to lead two legendary legacy media brands, how have you balanced bringing fresh perspectives while respecting the foundation laid by those who came before you, and respecting the institutional knowledge and experience of existing staff?

I walked in aware that I was inheriting something iconic — not just brands with incredible histories but teams with workflows and muscle memory. My approach was to ask: “What is our brand mission? And what do we need to evolve immediately?” Respecting the legacy of a brand doesn’t mean you freeze time; it means you admire what came before you with care while also trusting your instinct to push that brand forward. 

How do you approach difficult conversations with team members when their work doesn’t meet expectations, and how might that approach have evolved since you took over this job?

I’ve learned that when you root feedback in care and clarity, it becomes less about conflict and more about growth. Directness is key. I’ll usually say, “Here’s what I’m seeing and here’s what I know you’re capable of.” I want people to feel challenged and energized.

Talk about the strategies you have developed to maintain authentic creative vision across the brands while also meeting the tough commercial demands of media properties today.

It’s a dance. And it’s about alignment. Are we partnering with brands that actually understand our audiences? Are we creating content that we would stop scrolling for? I push my teams to think audience-first and revenue-smart. Those aren’t opposing forces; they can actually strengthen each other when you are clear about what you stand for.

In which ways have you reimagined traditional editorial hierarchies to better engage with Gen Z audiences and creators?

The old model of top-down editorial control doesn’t reflect how this generation consumes, creates or shares media. At both Seventeen and Cosmo, I’ve tried to blur the line between “audience” and “contributor.” I love when readers reach out with ideas for stories they want to see on our platforms.

How do you approach cultivating talent, particularly when it comes to helping younger professionals develop their voices and confidence?

I see my role as helping creatives feel expansive and inspired. I try to reflect back the things I see in them before they fully see it in themselves. That might be calling out a sharp headline, or looping someone into a high-stakes conversation so they can see how their thinking matters firsthand. I also make space for experimentation. Not everything has to be perfect the first time. Voice and confidence are muscles — and they grow stronger when you’re trusted to stretch.

What about the work culture at Seventeen and Cosmopolitan do you value, and what are some things you’d still like to change up? 

There’s so much legacy. Both brands have this DNA of boldness, playfulness and rebellion that I really respect. I love how much institutional pride the staff has for both of these brands. But I also love how willing the teams have been to try new things and trust that good storytelling will find an audience.

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