How the Chief Creative Officer of an Award-Winning Ad Agency Prompts the Perfect Pitch

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.