Leslie Grandy, a seasoned executive with leadership roles at Apple, Amazon, Best Buy, and T-Mobile, discusses the underestimated nature of creative capability and how leaders can systematically cultivate it. Drawing from her early career in the film industry and later product leadership across Fortune 50 companies, she presents a grounded, practical perspective on how creativity functions in high-performance environments.

She outlines three foundational skills transferable across domains: enduring ambiguity with resilience, sustaining momentum in the absence of external validation, and solving unfamiliar problems with resourcefulness rather than prescribed playbooks. These competencies, shaped by years in unpredictable contexts, later enabled her to thrive in zero-to-one product environments at scale.

Grandy also offers insight into organizational enablers and constraints for creative velocity. She identifies cultures that treat creativity as the remit of all functions, not just design or strategy, as more adaptive and resilient. Conversely, she cautions against consensus-driven thinking and status quo bias, which she sees as systemic inhibitors. The most effective environments, she argues, reward structured risk-taking and integrate post-mortem learning with equal weight to successes.

Reflecting on her time reporting to Steve Jobs, Grandy explains the discipline of brand stewardship and decisiveness under uncertainty. Jobs' intolerance for diluted brand signals, whether in product UX or retail merchandising, was less a quirk and more an intentional design principle. She recounts how even small misalignments, such as offering engraving suggestions on iPods, were swiftly reversed to preserve narrative clarity.

The discussion also explores her recent book, Creative Velocity, and its guiding premise: creativity is not a fixed trait but a repeatable discipline. Through structured techniques like the generic parts technique and SCAMPER, she argues that anyone, including those outside “creative” job titles, can develop idea fluency and confidence. She emphasizes the role of generative AI as a tool for exploratory dialogue rather than one-shot answers, calling for greater patience and iterative engagement to unlock its full potential.

For senior leaders, this episode surfaces a precise question: Are you designing your organization to perform or to invent? And are you personally equipped to model the latter?

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

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

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