Answering Difficult Questions Can Create Breakthrough Brand Stories


November 14, 2016

gregory-diehl-on-brand

“You have to look beyond the color and logos with brand identity. They’re really the product of something deeper.” It’s this kind of brand introspection that Gregory Diehl excels at. As the author of two best-selling books including Brand Identity Breakthrough, Gregory has a unique, global, and modern perspective on how we build brands both online and off. We discussed all of this and more on this week’s episode of the On Brand podcast.

Enjoy This Episode Now

About Gregory Diehl

Raised in California, author Gregory Diehl embarked at age 18 on a global quest for learning, self-discovery, entrepreneurship, and inquiry. Since then, Gregory has lived and worked in 45 countries and continues to use his experiences to help others along the path of self-fulfillment through exploration. This year, he published two Amazon bestsellers in business, travel, and personal development. He helps entrepreneurs prepare complex value messages across many mediums, and offers unconventional lifestyle coaching and brand identity consultancy for impassioned individuals.

Episode Highlights

What’s the secret to brand identity today? Gregory’s answer was surprisingly classic. “Everybody talks about your unique selling proposition but few explore what it really means.” Look for ways to really be different as a brand. As Diehl says, “You should be just beyond the edges of your comfort zone.”

You have to look deeper, beyond the surface. “Things like color and logo are a symptom of something deeper. People try to bypass this introspection.” So how can brands go deeper?

Start by asking difficult questions. “There are 50 questions I use in the book (Brand Identity Breakthrough) but here are my top three. Who are you? What do you do? And why should I care?” Answering these introspective questions often short circuits scripts and elevator pitches and gets closer to true differentiation.

What’s the role of story in brand building today? “Story is your main differentiator. We have functional aspects of our brands like speed, price, and quality — but what does it really mean?”

What brand has made Gregory smile recently? “McDonald’s — They’re kind of my go-to mega brand.” Gregory shared some smile-worthy insights on the disconnect between their brand personality and product.

To learn more, check out Gregory’s books on Amazon and his website.

As We Wrap …

Before we go, I want to flip the microphone around to our community … Recently Irene Gil us a shout for our episode on being your brand’s editor in chief featuring Ann Handley. Thanks for listening Irene!

Did you hear something you liked on this episode or another? Do you have a question you’d like our guests to answer? Let me know on Twitter using the hashtag #OnBrandPodcast and you may just hear your thoughts here on the show.

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Until next week, I’ll see you on the Internet!


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is a strategist, speaker, educator, and author of Brand Now: How to Stand Out in a Crowded, Distracted World and Get Scrappy: Smarter Digital Marketing for Businesses Big and Small. He is the Chief Brand Strategist at Brand Driven Digital, an educator at the University of Iowa, and host of the On Brand podcast. More about Nick.