In this episode, Jeff Benjamin, Global CCO of Tombras, shares how AI helps him get unstuck, build confidence, and push bold ideas forward—even when self-doubt creeps in. From romcom scripts to Arby’s pitches, he shows how AI acts as a sparring partner: sharpening thinking, stress-testing ideas, and keeping momentum alive.

We get into what separates distinct from generic, why affirmation can be a trap, and how the urge to share is still at the heart of creativity. If you're chasing big ideas—or just trying to beat the blank page—this one hits home.

Key Takeaways:

• Affirmation builds momentum—but can also blind you — One of AI’s biggest features is how confidently it backs you up. That “glazing” energy feels great—but if you don’t challenge it, you risk falling in love with something average. Confidence needs a counterbalance: taste.
• The best prompt is a person—not a question — Jeff gets better output by asking AI to role-play voices he respects—like Don Draper or a cold war-era Olympic judge. The magic isn’t in better instructions. It’s in asking from a more interesting perspective.
• Your idea is ready when it bubbles over — Jeff doesn’t go to his team with half-baked concepts. He waits until the idea is bubbling—when he can’t not share it. That moment is emotional, not procedural. AI helps him reach it faster—but the instinct to share is still deeply human.
• Big ideas have width—AI helps him see the shape — For Jeff, a great idea isn’t a line—it’s a landscape. If it’s a real “big idea,” it spawns more ideas: social angles, activations, scripts. AI helps him test whether a concept has legs—or if it’s just a clever line with no room to run.

Jeff's LinkedIn: Jeff Benjamin | LinkedIn
Tombras: Tombras | Full-Service Independent Advertising Agency

00:00 Overcoming Self-Doubt in Business
00:37 Meet Jeff Benjamin: Creative Leader at Tombras
00:56 The Role of AI in Creative Processes
02:24 Using AI as a Sparring Partner
04:34 Practical Examples of AI in Action
09:31 The Impact of AI on Team Dynamics
11:37 Balancing AI and Human Creativity
14:13 The Future of AI in Creative Industries
21:06 Exploring Human Skills for AI Mastery
22:09 The Art of Asking Better Questions
22:40 AI as a Creative Partner
24:41 The Excitement of Sharing Ideas
30:09 Generational Differences in AI Interaction
32:35 The Risk of AI Dehumanization
38:19 Concluding Thoughts

📜 Read the transcript for this episode: Transcript of How the Chief Creative Officer of an Award-Winning Ad Agency Prompts the Perfect Pitch

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.

In this episode, Joshua To, VP of Product Design at Meta, shares how AI is reshaping how—and where—we interact with technology. He walks us through Meta’s evolving approach to AR and wearables, why notifications are still the killer use case, and how AI is becoming the “brain behind empathy.”

We dig into what it means to build interfaces that understand you, why audio might be the future’s most underrated platform, and how designing for emotion changes everything—from form factor to function. Joshua also reflects on his path from launching a clothing brand to leading design at Google and Meta, and what those worlds taught him about craft, context, and human-centered systems.

This one’s for anyone designing AI into the real world—where every interface choice carries weight, and intelligence starts with listening.

Key takeaways:

• Empathy Is the Real Intelligence — Joshua flips the definition of smart tech. It’s not just about outputs—it’s about understanding you. Context, tone, emotion—that’s what great AI will sense and respond to.
• Design for the Moment, Not the Feed — AR’s killer use case isn’t games—it’s restraint. Joshua shares why the best AI product might just be the one that knows not to ping you. Context-aware computing is the real unlock.
• Audio Is the Interface to Watch — Forget screens. The most powerful interface might be your ears. From wearables to ambient signals, Joshua explains why audio design is the next big frontier for human-centered AI.
• AR Isn’t a Feature—It’s a System of Consideration — Joshua reframes augmented reality as quiet, ambient infrastructure. The real power of AR isn’t spectacle—it’s subtlety. It helps you move through the world with less friction, not more.

LinkedIn: Joshua To | LinkedIn
Website: Home - Joshua To
Meta: Meta Careers

00:00 Intro: Fixing Notifications With AI
00:54 Meet Josh: VP of Product Design at Meta
02:06 From Hoodies to Hardware: Josh's Journey
03:53 The Google Experience: From Ads to Product Management
10:37 The Evolution of Google Glass and AR
19:12 The Role of AI in Josh's Career
22:25 Designing the Future: AR, VR, and Attention Management
32:49 Contextually Aware Suggestions
33:38 Leveraging Generative AI in Design
34:52 AI's Role in Concept Art and Storyboarding
41:24 AI Tools and Model Capabilities
45:54 The Future of AI and Wearables
51:58 Reflections and Takeaways

📜 Read the transcript for this episode: Transcript of Chief of Staff for the Masses: How Meta’s Joshua To Designs Wearables with AI

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.

In this episode, Greg Shove, CEO of Section and founder of Machine and Partners, joins us for a "where are they now" follow-up—and doesn’t hold back. Greg walks through the rise of Pro AI, his new AI-powered coach, and why traditional upskilling is already obsolete.

We explore the overlooked friction points in AI adoption, from cultural taboos (“it feels like cheating”) to failed enterprise rollouts. Greg challenges the prevailing mental models and warns that the real upheaval is still ahead: business model disruption, not product disruption.

From royalty-based agents to outcome-based pricing, Greg lays out why service-heavy industries—from law firms to SaaS—are heading for a margin-crushing future. Plus: the moral responsibility of CEOs, the fallacy of lifelong learners, and why working with AI means holding onto your own judgment.

A sharp, honest look at what it really means to work smarter—not just faster—in the age of AI.

Key takeaways:

• AI use is no longer optional—it's the new baseline.
  Proficiency with AI tools isn’t a competitive edge anymore—it’s a basic requirement. Greg argues that “being in the AI class” is now table stakes, and organizations must rapidly close the gap between aspiration and actual adoption.
• Business model disruption will hit harder than tech disruption.
  Greg makes a compelling case that AI’s biggest impact won’t come from the tools themselves, but from entirely new ways of charging for value—like outcome-based pricing and AI-native service models that undercut human capital costs.
• Leaders must shift from AI policies to AI manifestos.
  Adoption is stalling because organizations lead with fear. Instead, Greg urges leaders to clearly message that using AI is smart, encouraged, and expected—and to model that behavior themselves.
• Most people won't be lifelong learners—so give them outputs, not courses.
  With Pro AI, Greg confronts a hard truth: most users don’t want to learn; they want results. AI-powered coaching that delivers outcomes—not just education—is the future of upskilling.

Linkedin: Greg Shove | LinkedIn
Website: Greg Shove | AI Strategist & Keynote Speaker for Enterprise Leaders
Section: Section | AI workforce transformation for real ROI
Machine & Partners: AI Consulting Services | Machine and Partners

00:00 Embracing AI: Changing Work Culture
00:29 Introduction: Meet Greg Shove
01:10 AI in Daily Work: Tools and Changes
03:59 Business Model Disruption: The Next Big Shift
12:45 Training and Adoption Challenges
19:14 The Future of Work: AI's Impact on Jobs
32:02 Leadership and AI: Strategies for Success
35:20 Embracing AI in the Workplace
36:51 Workflow Redesign with AI
39:39 The Role of AI Agents
40:12 Challenges in AI Adoption
45:14 Pro AI: The AI-Powered Coach
51:03 Disrupting Business Models with AI
57:52 Cognitive Offloading and AI
01:03:02 Final Thoughts and Reflections

📜 Read the transcript for this episode: Transcript of The AI Implementation Audit: What Section’s CEO Learned in 18 Months

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.