This episode is a little different.

Instead of talking with a Chief Creative Officer or a Chief Strategy Officer about a recent ad campaign, I sit down with Rebecca Winthrop, senior fellow at The Brookings Institution and co-author of The Disengaged Teen.

Together, we dive into the insights that emerged from her research with over 60,000 students, 25,000 teachers, and 6,000 parents, and we explore what it takes to really engage young people in today’s tech-driven world.

Rebecca’s findings around engagement are fascinating and we talk about different modes of learning (passenger mode vs. resistor mode vs. explorer mode) and the surprising overlaps between the world of branding and the world of education.

In both worlds, you’re dealing with a rich combination of attention, inertia, distraction, and indifference. And in both cases, real engagement only happens when the people you’re talking to connect the experience you’ve created to something meaningful in their own lives.

Some of my favorite aha moments from our conversation include:

• What kids are neurobiologically primed to do in adolescence and the implications for designing more engaging experiences
• The Mattel-OpenAI partnership and why Rebecca is both excited and concerned about its implications
• How repetition and nagging can often shut down executive function in teens (and how brands might accidentally be doing the same thing with their messaging)
• What Minecraft can teach us about learning, rewards, motivation, and flow
• How working for the Fish and Wildlife Department in her 20s led Rebecca to some valuable life lessons about FIO (Figure It Out) jobs
• Why educational innovation starts with rethinking how we measure progress and what that also means for brand strategy

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

The Disengaged Teen by Rebecca Winthrop and Jenny Anderson

If I Built a School by Chris Van Dusen

Lies My Teacher Told Me by James W. Lowen

Six of Crows (Crooked Kingdom) by Leigh Bardug

Products

Lego

Clixo Toys

Innovative Alt Education Schools

Big Picture Learning

Templeton Academy

Alpha Schools

Most brands use surface level data to market to superficial stereotypes.

James Addlestone, on the other hand, uses data like a detective, reading between the lines of people’s survey responses and finding innovative ways to get to the truth behind their behaviors.

With a background in behavioral economics and a deep appreciation for detective fiction (we talk quite a bit about Agatha Christie), James brings an exciting approach to data-driven strategy: one that combines quant, qual, and creative curiosity.

During our conversation, James challenges the industry’s overreliance on survey panels, pre-loaded category drivers, and overly-tidy narratives that tend to collapse under real-world scrutiny.

By contrast, James makes the case for embracing those moments when the data doesn’t quite make sense and treating that ambiguity as an invitation to look closer.

In this episode, we explore how James uses data triangulation, not silver bullets, to connect the dots between data points, which leads not only to new campaign directions, but can also result in subtle shifts in operations and product innovation.

Some of my favorite aha moments from our conversation include:

• The “qual sandwich” framework James uses for insight generation
• Why it’s important to challenge company myths every so often with fresh data
• How a surprising spike in tomato sales led to a deeper investigation and a new campaign direction for a major grocer
• How the pet brand, Chewy, focuses on “moments that matter” and why moments-based segmentation matters even more than traditional demographics
• Three reasons why AI won’t replace good analysts anytime soon
• Advice for junior analysts and how to use different AI tools to help with big data projects

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

Factfulness: 10 Reasons why You’re Wrong About the World–and Why Things are Better than you Think by Hans Roling

Everybody Lies: Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are by Steph-Stephens Davidowitz

Algorithms to Live By: The Computer Science of Human Decisions by Tom Griffiths

Stolen Focus: Why You Can’t Pay Attention–and How to Think Deeply Again by Johann Hari

Blueprints: How Mathematics Shapes Creativity by Marcus du Sautoy

Companies

System 1: The World’s Most Predictive Ad Test

Meet the 85: Ethnographic Research Consultancy

Podcasts:

Thinking Inside the Box More Creatively with Dan Cohen, Creative Director at Saatchi New York

Katie Dreke has always been a rough and tumble explorer, ever since she was a kid.

From early childhood days, she wanted to do all the things the boys in her neighborhood were doing - jumping bikes off of ramps, playing in treehouses, reading science fiction - but she quickly realized that the world was always trying to steer her in another direction.

Those childhood experiences led to a lifelong fascination with social constructs and gender norms, which has shaped her groundbreaking work with sports brands, from Arc’teryx to New Balance to Nike’s historic maternity collection.

Katie’s work history has spanned the globe, from Amsterdam to Japan to Australia, and she’s worked at a wide variety of award-winning shops, including Wieden + Kennedy, the Wexley School for Girls, Droga5, and IDEO.

No matter what she’s working on, though, whether it’s a new DTC business model or product innovation, Katie always brings a distinct perspective to every project, one that blends cultural insight and deep empathy for the consumer’s lived experience.

Some of my favorite aha moments from our conversation include:

• How social norms and coded systems still shape women’s experience in sport
• Why many women over 40 were turning to Lululemon and not shopping for themselves at Nike
• How the Nike maternity collection uncovered a blindspot in how athletic potential is defined
• The techniques and strategic questions Katie uses to kick start almost any project
• How working the front desk at a software company in Seattle led her to a global career in strategy

Show Notes:

Below are links to inspiring ideas that came up during our conversation.

Books:

The Mountain in the Sea by Ray Nayler

Brands & Campagins:

Nike Maternity Collection

The Toughest Athletes - Nike Ad

Houdini Sportswear

Benim Denim - A Start-up Designed to Shut Down