Outthinkers

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180

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Oct 2026

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About the show

The Outthinkers podcast is a growth strategy podcast hosted by Kaihan Krippendorff. Each week, Kaihan talks with forward-looking strategists and innovators that are challenging the status quo, leading the future of business, and shaping our world. Chief strategy officers and executives can learn more and join the Outthinker community at https://outthinkernetwork.com/.

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October 20, 202651 min

#177 –Challenge Your Assumptions: The Power of Questioning What You Think You Know: Naveen Jain

Naveen Jain is a serial entrepreneur, philanthropist, and founder of multiple billion-dollar companies, including Infospace, Moon Express, and the health company Viome, where he is founder and CEO. His new book, Counterintuitive: Unconventional Principles for Success in Life and Business, lays out the way of thinking behind all of it. His argument is that breakthrough results don’t come from being smarter or better connected. They come from asking better questions and refusing to accept the limits everyone else takes for granted. What if the reason you can’t solve a problem is that you’re asking the wrong question? Ask “how do we grow more food?” and you’ll get better farming. Ask “why do we eat food?” and a completely different set of solutions opens up. Naveen argues that solutions arrive when you change the problem, not when you dream up a cleverer answer to the old one. In this episode, we dive into why big goals are easier to achieve than small ones, how a three-level “then what” exercise turns a modest starting point into a moonshot people believe in, and why knowing nothing about an industry can be your greatest asset. In this episode we cover: • Why asking “why” three times gets you to the root cause, and why the label you put on a problem limits the solutions you’ll find • Why big goals are easier to achieve than small ones, and how the three-level “then what” exercise builds a moonshot • The three-question test for any venture (why this, why now, why me), and why Naveen believes a for-profit can do more good than a non-profit • Why knowing nothing about an industry can be your greatest asset • How losing his father to pancreatic cancer led him to a biodefense lab at Los Alamos and, a decade later, to Viome’s early cancer detection tests Additional resources: Counterintuitive: Unconventional Principles for Success in Life and Business: https://www.porchlightbooks.com/products/counterintuitive-naveen-jain-9781804093870 Viome: https://www.viome.com Naveen Jain on LinkedIn - https://www.linkedin.com/in/naveenjainintelius/?isSelfProfile=false This episode is sponsored by LHH. A beautiful working world starts with leaders who inspire and elevate others. Learn more about LHH Executive Solutions at lhh.com.

October 6, 202656 min

#176 – Algorithm Is Strategy: The Hidden Power Inside the AI You Deploy: Hamilton Mann

Hamilton Mann is an AI researcher, technology executive, and award-winning author. He is Executive Chairman and President of the Artificial Integrity Institute, lectures at INSEAD and HEC Paris, and mentors at MIT's Priscilla King Gray Center. In 2025 he received the Thinkers50 Distinguished Achievement Award for Digital Thinking. He is the author of the acclaimed Artificial Integrity: The Paths to Leading AI Toward a Human-Centered Future , and his new book, Trias Algorithmica: What Code Rules , argues that algorithms have quietly fused the three powers democracies have spent centuries keeping apart — the legislative, the executive, and the judicial. What if the AI tools your organisation is adopting aren't just technology, but a new form of power — quietly writing the rules, enforcing them, and judging the outcomes, all without a single vote or a moment of debate? That's the provocation at the heart of Hamilton's work. He argues that every company is a "mini polity" with its own checks and balances, and that the AI we deploy is steadily reshaping them without anyone ever deciding it should. In this episode, we dive into why strategy was always about leadership rather than planning, the six phases that carry an organisation from resisting an algorithm to being unable to decide without it, and what strategy leaders need to do about it now. In this episode we cover: Why "strategy" originally meant leadership, not planning — and why that distinction matters more under AI The difference between an answer and a decision, and why algorithms blur the two How algorithms quietly fuse the three powers democracies keep apart: legislative, executive, and judicial The six phases of algorithmic dependence, from early resistance to the point where leaders can't decide without the machine Why every company is a "mini polity" whose checks and balances are being reshaped by the AI it deploys Episode timeline: 00:00 — Welcome and today's highlight 01:30 — Introducing Hamilton Mann and the episode 03:20 — "If you really know me…" and the idea of "algorithmic romanticism" 06:00 — "What gets measured gets managed," and why culture can't be put on a dashboard 09:30 — Hamilton's definition of strategy: leadership, not planning 15:00 — The difference between an answer and a decision 22:00 — The three algorithmic powers: legislative, executive, and judicial 28:00 — Why we hand over power without noticing 29:00 — The six phases of algorithmic dependence, from resistance onward 40:00 — Phase six: dependency, and the reversal of control 42:00 — Why every company is a "mini polity" — and the governance risk 50:00 — What's really at stake as companies deploy agentic AI at scale 52:00 — Advice for strategy leaders: "algorithm is strategy" 55:00 — Where to find Hamilton Additional resources: Trias Algorithmica: What Code Rules (Wiley, 2026): https://www.amazon.com/Trias-Algorithmica-What-Code-Rules/dp/1394449283 Artificial Integrity: The Paths to Leading AI Toward a Human-Centered Future (Wiley, 2024): https://www.amazon.com/Artificial-Integrity-Leading-Toward-Human-Centered/dp/139429798X Hamilton Mann's website: https://www.hamiltonmannconversation.com Hamilton Mann on LinkedIn: https://www.linkedin.com/in/hamiltonmann

September 22, 202644 min

#175 – Apple Store Architect: Why Most Companies Confuse Different With Better: Ron Johnson

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Ron Johnson - the retail visionary behind the Apple Store and Target's design revolution about what it really takes to permanently change the trajectory of a business, not just improve it. During the conversation they unpack why being different isn't enough and why the only winning strategy is one that makes you preferred, how Ron identified unmet needs that customers couldn't even articulate, and the thinking behind some of the most iconic retail decisions ever made. Ron reflects on how he brought design to the masses at Target, why he put the thing every other technology store tried to hide right at the centre of the Apple Store floor, and how a single email to Steve Jobs quietly became the foundation of Apple's strategy for the next decade. The conversation covers: Why different is not the same as better — and why the only strategy worth pursuing is one that makes you preferred over every alternative, not just distinct from it How to find the unmet need your customers can't articulate — and build the conviction to act on it inside an organisation that wants to play it safe The story behind the Genius Bar, the digital hub insight, and why the Apple Store was completely rebuilt six months before it opened The conversation covers: - Why different is not the same as better - and why the only strategy worth pursuing is one that makes you preferred over every alternative, not just distinct from it - How to find the unmet need your customers can't articulate — and build the conviction to act on it inside an organisation that wants to play it safe - The story behind the Genius Bar, the digital hub insight, and why the Apple Store was completely rebuilt six months before it opened 00:00 — Highlight from today's episode 01:00 — Introducing Ron + the topic of today's episode 03:20 — If you really know me, you know that... 06:40 — What's your definition of strategy? 08:15 — Target in 1990: how do you compete with Walmart? 09:00 — Different vs preferred — Ron's pushback on Porter 11:00 — Redesigning Target Kids: the Gap Kids insight 14:30 — The entanglements: vendors, buyers, and six months of change 15:05 — Moving to home goods: design as a new category 17:30 — Meeting Michael Graves — "Ron, you didn't bring enough post-its" 21:00 — The unmet need: good design at a low price 22:30 — Making the bet: how Ron did the maths on Michael Graves 26:00 — Steve Jobs calls: why Ron left Target for Apple 28:20 — The strategic rationale behind the Apple Store 29:20 — Going after non-consumption: the other half of America 30:40 — Overcoming fear of technology — the North Star 31:15 — Why the Apple Store had to be in a mall 32:30 — Why the store had to be the size of the Gap 35:00 — The Genius Bar: turning the problem into the soul of the store 37:00 — The digital hub insight — and the email that changed Apple's strategy 39:00 — Delaying the store six months and rebuilding around the digital hub 40:30 — Who Ron hired — and why he refused to pay commission 43:00 — Where to find Ron and the book Additional Resources: Book: Shop Different — ronjohnsonshopsdifferent.com LHH: lhh.com Thank you again to our sponsor, LHH. Thank you to our executive producer Zach Ness, our producer Nazanin Homayoun Jam and our editor James Pearce. If you enjoyed this episode, please follow, download, and subscribe. I'm your host, Kaihan Krippendorff — thank you for listening. Follow us at outthinker.com/podcast

September 8, 202647 min

#174 – Why You Should Assume You're Partly Wrong: The Science of Seeing Clearly: Caroline Webb

Caroline Webb is an executive coach, economist, and former McKinsey partner. She is the author of the global bestseller How to Have a Good Day, published in more than 60 countries, and has been named one of the world's top 50 executive coaches by Thinkers50. Her new book, Leadership Intelligence, distills three decades of advising CEOs and senior leaders into a science-backed playbook for mastering 21 everyday leadership challenges — and draws praise from Amy Edmondson, Jonathan Haidt, Daniel Pink, and Marshall Goldsmith. What sets Caroline apart is that everything she teaches is rooted in neuroscience, psychology, and behavioral economics, not management folklore. Most leadership advice is folklore — someone's one good instinct generalised into a rule. Caroline takes the opposite approach: every tool she teaches is grounded in how the brain actually works. Rather than march through all 21 chapters of her new book, we ran this conversation as a live coaching session on the situations strategy and transformation leaders face most often — from diagnosing the real problem to getting a strategy to travel through an organisation. In this episode, we dive into why you should walk into any complex situation assuming you're partly wrong, how to surface the doubts your team won't say out loud, and how to make change actually stick. In this episode we cover: — Why you should walk into any complex situation assuming you're at least partly wrong — How "360-degree vision" helps you see what your brain is filtering out — Why the problem everyone expects you to fix often isn't the real problem — and how causal mapping reveals it — How hypothetical questions surface the half-formed doubts people won't say out loud — The CASE model for change, and the four "frequencies" that make a strategy actually travel Episode timeline: 00:00 — Welcome and today's highlight 01:30 — Introducing Caroline Webb and the episode 04:00 — "If you really know me…" 07:00 — Caroline's definition of strategy: clarity about what you don't do 09:00 — Diagnosing the right problem, and the "top of mind" trap 11:00 — Why you should assume you're at least partly wrong 16:00 — Michael Roberts, the opera singer turned "Chief Question Officer" 18:30 — The CMO who found the brand wasn't the problem: causal mapping 24:00 — When people nod in the meeting, then message the CEO to disagree 26:00 — Hypothetical questions: surfacing half-formed thoughts 30:00 — The GUIDE coaching model and the power of "tell me more" 35:30 — What culture really is, and the CASE model for change 41:00 — Influencing without authority: the fix-flex approach 45:00 — The four frequencies that make strategy travel 49:00 — Where to find Caroline Additional resources: Leadership Intelligence: https://www.penguinrandomhouse.com/books/801146/leadership-intelligence-by-caroline-webb/ Caroline Webb's website (newsletter + free resources): https://carolinewebb.co Caroline Webb on LinkedIn: https://www.linkedin.com/in/carolinewebbauthor/ Thank you to our guest, Caroline Webb.

August 25, 202640 min

#173 – Culture as Competitive Infrastructure: Why Transformation Isn't About Tech: Julie Averill

Julie Averill is a technology and transformation executive with nearly three decades of experience scaling global businesses. As Global CIO and EVP at Lululemon, she led an eight-year transformation that helped grow the company from $2 billion to over $10 billion in revenue and built its award-winning India Technology Hub. She previously served as CIO at REI and held senior technology leadership roles at Nordstrom, where she helped pioneer early omnichannel retail. Today she runs Gold Thread LLC, advising boards, CEOs and CIOs on leadership, culture and decision-making in moments of change. She is the author of Chief Impact Officer: Real Transformation Comes from Human — Not Just Artificial — Intelligence. Imagine starting a new job as global CIO and discovering, on your very first call, that every page of the company website returns nothing but an error — with no monitoring, no alerting, and no one who can even tell you who's responsible for fixing it. That was Julie's welcome to Lululemon, and she argues it turned out to be the making of her career. In an age where every company claims to be "doing AI," Julie makes the case that the winners won't be the ones with the flashiest technology — they'll be the ones with the strongest culture behind it. In this episode, we dive into why every transformation she's led actually started with a crisis, why she calls culture competitive infrastructure rather than a soft skill, and how to tell real AI progress apart from euphoric hype. In this episode we cover: - Why every transformation began with a crisis — and how to turn a "burning platform" into a mandate for change - Why culture is competitive infrastructure, not a soft skill - What a major-league catcher taught her about reading people and seeing the whole system - How to separate real AI progress from "euphoric confusion" and headline-driven hype - Why the best leaders never have to choose between technology and people Additional resources: Chief Impact Officer: https://www.simonandschuster.com/books/Chief-Impact-Officer/Julie-Averill/9798993755380 Julie Averill on LinkedIn: https://www.linkedin.com/in/julieaverill/ Gold Thread LLC: https://goldthreadllc.com/ Thank you to our guest, Julie Averill.

August 11, 202647 min

#172 – Global by Design: How to Build Innovations That Work Everywhere: Vijay Govindarajan

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Vijay Govindarajan — VG — about why the next breakthrough American innovation may be discovered in a village in India before it ever reaches Silicon Valley. Fifteen years after introducing the world to reverse innovation, VG returns with a new book co-written with MIT mechanical engineer Amos Winter, Global by Design, and a sharper argument: the strategy is only half the story. Someone still has to engineer the $400 ECG machine that replaces the $20,000 one. VG walks through what he calls problem merit — the discipline of finding a problem worth solving before anyone is allowed to propose a solution — and why most innovation teams fail at exactly this step. He explains why you should never define a problem in terms of its solution, why "raid the parts bin" beats reinventing from scratch, and why the affordability crisis now dominating American politics may already have its answer sitting in a market that had no choice but to solve it cheaply first. The conversation covers: • Why innovation never actually fails — and what does: design requirements nobody took the time to define • What six months of watching people shave in the dark gave Gillette — a two-cent blade, after the $7 Mach3 reached only 1% of Indiae • How Uber, the iPhone and the $400 ECG were built largely from technology that already existed, and why you innovate only for the part nobody has solved yet • Where the answer to America's affordability crisis may already be sitting — and why it isn't about importing the product, but bringing back the core value and making it here Additional Resources: Global by Design: How to Create Innovations That Scale, Travel, and Transform (Amos Winter & Vijay Govindarajan) VG at Tuck: https://tuck.dartmouth.edu/faculty/faculty-directory/vijay-govindarajan LinkedIn: https://www.linkedin.com/in/vg-govindarajan/ Thank you again to our sponsor, LHH.

July 21, 202640 min

#171 – Everyone's Blaming AI for Layoffs. Here's What's Actually Happening: Philipp Muelbert

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Philipp Muelbert about the three loops every company falls into when their talent needs shift — and why the cheapest-looking option on paper is usually the most expensive one in practice. During the conversation they unpack why AI has become a convenient excuse for restructuring decisions that were coming anyway, and why almost no organisation has a head of redeployment or a budget for one. Philipp Muelbert reflects on the hidden cultural costs of the "churn loop" — the survivor syndrome that hits the employees left behind, the institutional knowledge that walks out the door, and why new-hire retention is often harder than companies expect. He makes the financial case for redeployment over rehiring, and explains why building an alumni network of well-treated former employees can become a genuine strategic asset. The conversation covers: The three loops companies fall into when talent needs change: churn, exit well, or redeploy 75% look for a like-for-like role after layoff, but 60% end up in a full career pivot Redeployment saves $140,000 per person, yet no single function owns the process Additional Resources: LHH: lhh.com LinkedIn: https://www.linkedin.com/in/philippmuelbert Thank you again to our sponsor, LHH.

July 7, 202640 min

#170 – Why Most Mergers Fail After the Deal Closes: David Fubini

David Fubini spent 34 years at McKinsey & Company, where he was a Senior Partner, Managing Director of the Boston office, and co-founder of the firm's Worldwide Merger Integration Practice — leading dozens of the world's largest M&A transactions. He's now a Senior Lecturer at Harvard Business School, where he co-leads the Mergers & Acquisitions and Leading Professional Services Firm programmes. He's the author of Post-Merger Integration: Building the Mindset, Skills, and Discipline Needed for Deal Success (Wiley, 2026), co-written with Patrick Sanguineti, and the earlier Hidden Truths: What Leaders Need to Hear but Are Rarely Told. Most leaders obsess over closing the deal — the strategy, the financing, the negotiation. But according to David, that's not where deals break down. They fail in the messy weeks and months after the ink is dry, when two organisations, two cultures and two workforces actually have to become one. Hundreds of billions in promised synergies are lost every year to integration that was treated as an afterthought rather than the engine of the whole transaction. In this episode, we dig into why so many companies under-resource the integration effort, why your most capable people — not your spare capacity — should be running it, and why David deliberately refuses to hand leaders a step-by-step playbook. In this episode we cover: Why the Integration Management Office is the real engine of a deal — and why companies staff it wrong The one question — "Why are you actually doing this deal?" — that should govern every integration decision How American Airlines and US Airways turned a hostile takeover into a functioning merger Why decision velocity matters more than perfect information when two companies combine Where AI genuinely helps integration — and the one thing it will never do: read the room Additional resources: Post-Merger Integration: hhttps://www.hbs.edu/faculty/Pages/item.aspx?num=69100 David Fubini on LinkedIn: https://www.linkedin.com/in/david-fubini-b0009bb/ David Fubini, HBS faculty: https://www.hbs.edu/faculty/Pages/profile.aspx?facId=102821 Thank you to our guest, David Fubini.

June 16, 202642 min

#169 — AI Is Doing the Junior Work. Who Becomes Your Next Senior Leader? | Carrol Chang

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Carrol Chang about why the unit of work is shifting from the full-time employee to the task itself — and what that means for every leader rethinking their workforce in the age of AI. During the conversation they unpack what happens when AI handles all the junior work today, and who develops the senior judgment your organisation will depend on tomorrow. Carrol Chang reflects on watching two of the biggest shifts in the history of work collide in real time at Andela, why the productivity dividend forces every leader to a strategic fork in the road, and why AI collapsing the cost of talent doesn't eliminate competitive advantage, it just moves it. The conversation covers: Why the unit of work is shifting from the full-time employee to the task — and what that means for how you hire, build teams, and plan headcount The "birthrate problem": if AI absorbs all the junior work today, who develops the judgment and governance your organisation will need in five years? What remains as your true competitive advantage when AI commoditises both capacity and expertise — and why human judgment, EQ, and relationship-building are the last real moat Additional Resources: Andela: andela.com CodeWars: codewars.com LHH: lhh.com LinkedIn: https://www.linkedin.com/in/carrolchang Thank you again to our sponsor, LHH. Thank you to our guest, Carrol Chang.

June 2, 202640 min

#168 — Why Good Companies Go Bad: Eric Ries

New on the Outthinkers Podcast, supported by LHH, host Kaihan Krippendorff speaks with Eric Ries — author of the landmark The Lean Startup — about his new book Incorruptible , and why the way we've run companies for the last fifty years may be fundamentally corrupt. Not in the dramatic, headline-grabbing sense, but in the older, quieter sense of the word: a slow corrosion of the bonds that make an organisation strong, trusted, and worth building in the first place. In this conversation they unpack how shareholder primacy — the idea that a company exists only to enrich its investors — took hold without a single vote ever being cast, and what it actually takes to build something that endures. Eric reflects on why this idea is far more recent and far more fragile than we assume, what the most enduring companies in the world have quietly been doing differently, and the practical mechanisms any founder or leader can use to protect a mission from the forces that will inevitably try to erode it. The conversation covers: Why shareholder primacy is a recent invention — and why the "citizens vs tourists" problem in corporate governance changes how you should think about who really owns a company What "human flourishing" really means, why mission-driven companies aren't sacrificing financial performance, and how the best operators treat trustworthiness as an asset to bank rather than spend The practical defences — mission guardians, multi-entity "constellations," and the paths of ethos and integrity — that leaders can use today to build a governance fortress, no revolution required Additional Resources: LinkedIn: https://www.linkedin.com/in/eries/ Book: Incorruptible — https://www.incorruptible.co/ LHH: lhh.com Thank you again to our sponsor, LHH.