562: Steve Jobs' Former Colleague on How...

Leslie Grandy, a seasoned executive who has led global product teams at Apple, Amazon, Best Buy, and T-Mobile, shares a deeply practical perspective on how leaders can activate creativity across functions, not just in design or strategy.

Drawing from her early years in the film industry and later executive roles in technology, Grandy explains how she developed three capabilities that proved critical in high-performance product environments:

“You’ve got to grind it out… and you have to have that intrinsic motivation to continue, even when it looks like failure is obvious.”

“You have to be resilient and flexible… because you have so many people depending on the outcome.”

“If I haven’t seen the problem before, it doesn’t seem daunting to me… It seems fun.”

These capabilities (grit, adaptability, and creative problem solving) formed the foundation of her success in ambiguous, fast-moving, and high-stakes environments.

Grandy also speaks directly to what supports and undermines creative velocity inside organizations. She notes that the most adaptive cultures don’t reserve creativity for a few select teams:

“They expect every role is going to show up with that same creative intention… that the status quo doesn’t seep into the lower ranks.”

But she also warns:

“Status quo as a cultural norm is dangerous.”
“Consensus-driven thinking is equally problematic for creative velocity.”

Her insights on Steve Jobs provide a rare look inside Apple’s leadership culture. When asked about her interview with him, she explains:

“Your interview will be five minutes or it’ll be 60 minutes. It’s up to Steve.”
“I didn’t come in there acting like I was an equal… I just came in there with a confidence that I could answer whatever he asked.”

When her team added preset engraving suggestions to iPods to help customers complete purchases, Jobs reacted immediately:

“He saw it, and within a day, it was pulled down.”
“He had such a finite view of his brand… there were no blurry edges around the brand.”

Grandy’s new book, Creative Velocity, argues that creativity is not a fixed trait, but a capability that can be developed with intention. 

She addresses how leaders should approach generative AI, not just as an efficiency tool, but as a creative partner:

“What’s really transformative… is doing the exact opposite of prompt engineering.”
“It’s not about speed to answer. It’s about using that time to evolve a thought into different tributaries of thought.”

This episode raises a critical question for senior leaders:

“Are you designing your organization to perform or to invent?”

Get Leslie’s book here: https://rb.gy/d5zr69

Creative Velocity: Propelling Breakthrough Ideas in the Age of Generative AI

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