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.

"Trust the Experts" Failed. What Now? ft. Walter Kirn

The Charlie Kirk Show

Ad break

The AI-powered Podcast Player