#24—Why AI Adoption Is a People Problem, Not a Technology Problem: Joanne Sheppard

#24—Why AI Adoption Is a People Problem, Not a Technology Problem: Joanne Sheppard

Joanne Sheppard is a strategic advisor to the Holzbrinck Group — the German family holding company behind Macmillan Publishers, Springer Nature, and Die Zeit — and a board member across several of its owned and invested companies. Her career spans publishing, M&A, and corporate strategy, and she brings an unusually wide lens to her work: graduate study in English literature, executive education in AI and innovation at MIT, positive psychology from Penn, and board governance through INSEAD. In this conversation, we explore why AI adoption stalls inside large organisations — and why the answer has far less to do with technology than most leaders assume. Things we will cover: * Why AI adoption is fundamentally a change management problem, not a technology problem * How to build the psychological safety that makes experimentation and upskilling possible * What IKEA and JP Morgan can teach us about bringing employees along on the journey * How to think about reinvesting the productivity AI frees up — and why that decision deserves a quarterly board conversation * The architects, bridgers, and catalysts framework for understanding the role of leadership in driving adoption From employee resistance to board-level strategy, Joanne draws on real experience inside a complex, decentralised organisation to offer one of the most grounded and human-centred perspectives on AI adoption you'll hear. * Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/ [https://outthinker.com/] * Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks [https://www.linkedin.com/company/outthinker-networks]

#23—AI, Infrastructure, and the New Battlegrounds of Value : Insights from Shantnu Sharma

Today’s guest is Shantnu Sharma, a senior public-company executive who has led enterprise strategy, transformation, and corporate development across the semiconductor and digital infrastructure ecosystem. Shantnu’s career spans leadership roles at Western Digital, Arrow Electronics, AMD, and McKinsey, giving him a rare perspective on how technology strategy, capital allocation, and competitive advantage are being reshaped by AI from the infrastructure layer up. In this conversation, we explore the forces shaping AI’s next phase and unpack what strategy leaders need to understand about the bottlenecks, value shifts, and strategic tradeoffs emerging across the semiconductor and digital infrastructure landscape.  Things we will cover:  • How semiconductor capacity, talent, and execution constraints are shaping the pace of AI growth  • Why the distinction between AI training and inference matters for infrastructure strategy and economics  • How advanced packaging and supply chain choke points are becoming new sources of strategic advantage  • What the “convergence frontier” could mean as AI moves into physical industries like manufacturing, logistics, energy, and healthcare  • The bull and bear cases for AI’s future, including regulation, power constraints, and the difficulty of scaling into messy real-world environments  From semiconductor strategy to AI infrastructure and long-term value capture, Shantnu brings a highly informed perspective on where AI is going and what Chief Strategy Officers should be paying attention to now.    * Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/ [https://outthinker.com/] * Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks [https://www.linkedin.com/company/outthinker-networks]

#22—Google’s Chief Strategist Neil Hoyne: How Great CSOs Build Decision Systems That Scale

Neil Hoyne joins Kaihan Krippendorff to unpack why most strategy failures aren’t caused by a lack of data — they’re caused by organizations asking the wrong questions, setting the wrong standards, and rewarding the wrong behaviors. Neil is Google’s Chief Strategist and the bestselling author of Converted. In this conversation, he shares how he thinks about strategy as an incremental discipline: keeping the business alive today while moving it into a stronger position tomorrow. They explore how leaders unintentionally turn metrics into theatre, why “more measurement” often becomes a coping mechanism, and how to set decision standards that match the speed of your competitive environment. The conversation also examines where AI can amplify strategic confusion, and how CSOs can keep strategy anchored in what customers actually value. Things we’ll cover: How Neil defines strategy as survival + positioning Product-led vs customer-led models (and the role marketing plays in each) Customer lifetime value and what it changes in enterprise strategy Why common metrics aren’t comparable (even when they share the same name) The “manipulation test” to reveal weak KPIs How leaders override data — and how to design better decision standards Why AI adoption fails when strategy is unclear Learn more about Outthinker’s community of chief strategy officers - https://outthinker.com/ Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks * Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/ [https://outthinker.com/] * Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks [https://www.linkedin.com/company/outthinker-networks]

#21—The Four Problems Strategy Leaders Are Really Hired to Solve

Today’s guest is Adam Zalisk, Chief Strategy Officer at Amplify — a pioneer in K–12 education since 2000. Today, Amplify serves more than 10 million students across all 50 U.S. states, delivering next-generation curriculum and formative assessment in ELA, math, and science.  In this conversation, Adam reflects on what changes when strategy becomes a formal role inside a growing organization. Rather than treating strategy as a static plan, he frames it as a set of clear commitments tied to an explicit end state — and explains why ambiguity around those commitments is often what causes companies to struggle as they scale. He also introduces a practical framework for understanding why strategy offices emerge in the first place, helping leaders distinguish between different strategic needs and translate strategic thinking into real organizational traction.  Things we’ll cover:  * How Adam defines strategy in growth-stage companies  * The four distinct reasons organizations create a strategy office  * What leaders are actually looking for when they say, “we need strategy”  * How a strategy office avoids becoming an internal order-taker  * Where strategy functions most often lose — or earn — credibility  This episode is a practical guide for CSOs navigating growth, ambiguity, and rising organizational complexity. If you’re wrestling with focus, alignment, or execution as your organization scales, this conversation will sharpen how you think about the role — and the impact — of strategy. * Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/ [https://outthinker.com/] * Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks [https://www.linkedin.com/company/outthinker-networks]

#20—From Founder-Led to Function-Led: Scaling Strategy with Michael Drexler

Today’s guest is Michael Drexler, Chief Strategy Officer at Brightstar Capital Partners, a private equity firm that invests in closely held, middle-market businesses and helps them scale into professional, process-driven organizations. Michael’s career spans leadership roles across investment banking, global strategy, and private equity—from Barclays to the World Economic Forum, and Brightstar Capital Partners—giving him a rare perspective on how strategy functions evolve as companies mature from founder-led to institutional scale.  In this conversation, we unpack lessons from Michael’s career leading strategy functions  and explore how the head of strategy role transforms along a company’s growth journey.  Things we will cover:  * How strategy evolves from a “chief of staff” role in founder-led companies to a full-fledged internal consulting function  * The mindset shift from advising a single CEO to influencing a broader leadership team  * How to build and sustain an effective strategy team—including Michael’s “2-to-4-year rotation” and “no bad news for two weeks” rules  * Why private equity firms view internal strategy functions differently—and how to reposition your team in a PE environment  * Michael’s four-step framework for prioritizing projects that’s “never failed him once”  From developing consulting-style skillsets inside corporations to balancing neutrality among competing executives, Michael brings clarity and practicality to what it means to be an effective CSO. * Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/ [https://outthinker.com/] * Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks [https://www.linkedin.com/company/outthinker-networks]