554: Microsoft’s Dean Carignan on Using AI to Boost Joy, Focus, and Productivity at Work

554: Microsoft’s Dean Carignan on Using AI to Boost Joy, Focus, and Productivity at Work

What if the key to innovation isn’t a process, but a mindset that travels across boundaries, disciplines, and decades?

From international development to McKinsey to leading AI strategy at Microsoft, Dean Carignan has built his career at the intersection of systems, people, and impact. Now, as co-author of The Insider’s Guide to Innovation at Microsoft, he’s helping organizations rethink how real innovation happens, not just in startups or labs, but in legacy institutions and global companies.

In this episode, Dean shares lessons from two decades at Microsoft, where he’s worked across Xbox, Office, cognitive services, and AI research. He also reflects on why innovation is ultimately about people, not products, and how leaders can create space for meaningful change, even inside complex organizations.

We explore:

  • How Dean moved from solving global problems at the World Bank to driving change inside one of the world’s largest tech companies

  • The power of being a “boundary crosser” and why innovation happens in the in-between

  • Why mission often outperforms money as a motivator, especially in hiring for impact

  • The overlooked value of storytelling in innovation (and how case studies bring ideas to life)

  • How AI is transforming not only productivity, but the very nature of scientific discovery

  • Why learning to build with agents may be the most valuable skill of the next decade

Dean also shares practical examples of how he uses AI today, from research to writing to daily decision-making, and why “thinking about thinking” is the leadership advantage most people overlook.

Whether you're guiding a team through change, building a new product, or trying to stay ahead of the AI curve, this conversation offers a grounded, human-centered approach to innovation in a time of exponential possibility.

Dean Carignan’s career spans international economic development, startup ventures, and strategic roles in technology. He is an alumnus of Georgetown University and INSEAD, he was a charter member of McKinsey & Company's advanced technology practice.

During his 20 years at Microsoft, he has guided new businesses, including the early internet division, Xbox, and multiple Al efforts through the critical growth phases to their first billion dollars in revenue.

Most recently, Dean has focused on leading AI innovations within Microsoft Research and the Office of the Chief Scientist. His intrapreneurial spirit, deep institutional knowledge, and expansive internal network made the behind-the-scenes perspective of The Insider's Guide to Innovation at Microsoft

Get Dean’s book here: https://www.innovationatmicrosoft.com/

The Insider's Guide to Innovation at Microsoft

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Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach

McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf

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567: From Refugee to U.S. Marine pilot to NASDAQ-listed biotech CEO | Leadership & Fundraising Lessons (with Quang Pham)

567: From Refugee to U.S. Marine pilot to NASDAQ-listed biotech CEO | Leadership & Fundraising Lessons (with Quang Pham)

Quang Pham went from being a 10-year-old refugee airlifted out of Vietnam to becoming a Marine pilot, and the CEO of a NASDAQ-listed biotech company. In this conversation, he shares the exact lessons that guided each transition.   Key insight: On decision-making: “As a young officer, we were taught to make decisions… there’s not enough time to consult with everybody. You gotta make a decision to keep moving and then adjust along the way.” This became his foundational leadership principle across sectors. On capital discipline: “In the private sector and entrepreneurial world, resources are scarce… you have to treat it with the utmost respect and spend it wisely.” Military spending habits do not translate to startups. On performance and promotion: “You work hard, but you have to produce results.” Early in his corporate career, he assumed promotions would come automatically. They did not. On defining success: “You have to follow and pursue what makes you happy. Not what your family or your culture or society wants.” As a Vietnamese refugee, choosing the military was going against all cultural expectations. On raising capital without pedigree: “I lacked the skills to present to venture capitalists… so I spent a lot of time at Toastmasters picking up new speaking skills.” Within 90 days of leaving his corporate job, he secured venture funding as a first-time CEO. On pitch strategy: “You have to get to the key points… in the first seven or ten minutes, if not sooner.” Investors have limited attention. He focused his pitch on buyer, payment frequency, and execution, not theoretical market size. On cold outreach: “It was just three sentences. Who I was, what my company did, something about our common [background].” This approach led to two successful VC rounds. On leadership transitions: “I knew that I had the skills and the backing and that the baton had to be passed… the company flourished and I was then just a shareholder.” Founders must be willing to step aside to scale. On AI and decision-making: “There is somebody making decisions for AI, the decision to use AI, the decision to pay for AI… at the end of the day, we still need entrepreneurs and leaders.” This episode offers practical reflections for those navigating leadership transitions, capital formation, and decision-making in complex, resource-constrained settings.   Get Quang’s new book here: https://quangxpham.com/   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

9 Juli 39min

566: Silicon Valley’s CEO Whisperer on Why Most Startup Founders Fail (with Rich Hagberg)

566: Silicon Valley’s CEO Whisperer on Why Most Startup Founders Fail (with Rich Hagberg)

Rich Hagberg, often referred to as “Silicon Valley’s CEO Whisperer, psychologist and co-author of Founders Keepers, has advised over 1,000 executives and founders. In this conversation, he outlines why most startup leaders fail, and what the data reveals about those who succeed. Some key insights include: “Founders, overwhelmingly, are visionary evangelists… but they’re not particularly good at execution.” Hagberg’s research shows that unsuccessful founders often score low on execution and relationship-building. They resist structure, delay key hires, and react impulsively under stress. “You can change your behavior to some degree, but it’s very hard to change your fundamental personality.” Hagberg encourages founders to identify three to four behaviors they can realistically improve, such as delegation, feedback seeking, and stress management. “You need to go from being a doer to a facilitator of doing.” Scalable leadership requires building teams that complement the founder’s own gaps and letting go of tasks that dilute impact. “Startups are almost a Darwinian survival of the fittest… the unsuccessful ones are more impulsive and reactive.” Stress and poor self-regulation directly impact team trust and decision quality. Founders who succeed tend to manage energy deliberately and maintain self-awareness. “If we had to zero in on one thing that is the biggest differentiator, it’s adaptability. You never have permanent product-market fit.” Hagberg shares why openness to feedback and reflection is often more predictive of long-term success than IQ or charisma. “I realized I was creating a culture that reflected my strengths and weaknesses. If I was going to make the company better, I had to grow as a leader.” This conversation is for founders, investors, and operators who want to understand the behavioral patterns that quietly shape success or failure in startups. It delivers clear, evidence-based insights into what it takes to lead effectively as complexity scales.   Get Rich’s new book here: https://shorturl.at/YsQcl Founders, Keepers: Why Founders Are Built to Fail, and What it Takes to Succeed   Here are some free gifts for you: Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

7 Juli 56min

565: Founder and CEO of GK Training on Communicating Effectively to Live a Better Life

565: Founder and CEO of GK Training on Communicating Effectively to Live a Better Life

Michael Chad Hoeppner, CEO of GK Training and adjunct professor at Columbia Business School, brings a deeply practical lens to one of the most undervalued professional skills: spoken communication. With roots in professional acting and over two decades coaching executives, Hoeppner challenges conventional wisdom, arguing that most communication advice is either vague (“slow down”) or abstract (“just be confident”), and fails to address the real issue: communication is physical.   In this episode, he shares specific, kinesthetic methods that help clients speak more clearly under pressure. From using Lego blocks to build well-structured thoughts, to timing answers with a wiffle ball in political debate prep, Hoeppner demonstrates that improving communication is not about talent, it’s about training behavior.   “Speaking is movement. We put air into action—that’s what talking is. And you can learn to do it a lot, lot better.”   Key Insights: Delivery is Undervalued, but Often Drives Perception “Most coaching hyper-focuses on content and completely neglects delivery,” Hoeppner explains. Yet “delivery really, really determines much of the impression your audience makes about you.” Rambling, Fillers, and Anxiety Are Physical, Not Mental, Problems He critiques typical advice like “don’t say um” as “thought suppression” and instead teaches clients to physically anchor themselves. One client stopped chronic blushing mid-session by simply learning to ground her feet. Tools Like Lego Blocks Make Structure Tangible “Pick up a Lego block, say your first idea, and put it down in silence. That pause gives your brain time to think,” Hoeppner shares. These physical anchors help clients avoid word salad and clarify complex thinking. Founders with Growth Mindsets Improve Fast “They’re not held back by ego. They care deeply, they want to improve now, and that means they practice,” he says. In contrast, those with fixed mindsets (“I’m just a bad speaker”) often plateau. AI Will Make Delivery the Strategic Differentiator As language models democratize content, he argues, “delivery, how you say it, will matter more than ever.”   The episode closes with a powerful call to reframe communication not as a soft skill, but a trainable, high-leverage behavior, one that can transform not just boardrooms and keynotes, but daily leadership and presence.   Get Michael’s new book here: https://dontsayum.com/ Learn more about Michael here: https://gktraining.com/michael-chad-hoeppner/   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

2 Juli 56min

564: Yale’s James Kimmel Jr. on the Science of Revenge

564: Yale’s James Kimmel Jr. on the Science of Revenge

James Kimmel, Jr., lawyer, Yale psychiatry lecturer, and author of The Science of Revenge, joins us in the Strategy Skills podcast to explore the neuroscience and behavioral dynamics of revenge. Drawing on law, psychiatry, and over two decades of research, Kimmel offers a sobering view: revenge is not a form of justice, it’s a “pleasure-seeking behavior” that operates like an addiction, fueled by unresolved pain.   He opens the conversation with a deeply personal story: as a teenager, after years of bullying, he chased down his aggressors with a loaded revolver. In a pivotal moment, he recalls, “The cost of getting the revenge I wanted was far more than I was willing to pay.” That flash of insight redirected his life and seeded a lifelong investigation into how grievance, retribution, and healing operate in the human mind.   Key insights from the discussion include: Revenge Mimics Addiction in the Brain Kimmel explains that “your brain on revenge looks like your brain on drugs.” The cycle begins when a grievance activates the brain’s pain network, followed by a surge of dopamine in the reward system. Over time, the craving for retaliation can become compulsive, forming habits akin to substance abuse. Grievance Retention Impairs Judgment Unchecked rumination can degrade executive function. “If that prefrontal cortex does not stop you,” Kimmel warns, “and you really crave it… it doesn’t matter how many laws there are.” This impaired self-control is what allows otherwise rational individuals to commit extreme acts of violence. Social Exclusion Can Be a Form of Revenge “If you’re ending a relationship not for present harm, but to punish someone for a past wrong, that’s retaliation,” he explains. Even subtle acts like ghosting or ostracism can activate the same pain circuitry in the brain as physical harm. Forgiveness Interrupts the Revenge Cycle Neuroscience shows that imagining forgiveness “shuts down the brain’s pain network, silences addiction circuits, and reactivates executive control.” Kimmel calls forgiveness a “human superpower… It doesn’t just cover up the pain like revenge does, it takes the pain away altogether.” Revenge Can Be Prevented, Like a Heart Attack Kimmel proposes a new public health framework: treat revenge attacks like cardiac events. “There are warning signs,” he says, grievance fixation, revenge fantasies, acquiring weapons, and they demand the same level of emergency attention. Legal Systems Often Deliver Revenge, Not Justice Kimmel reflects on his time as a litigator: “Lawyers get paid to sell revenge under the brand name ‘justice.’” He urges professionals to be aware of how sanctioned systems can enable and normalize compulsive retribution.   For leaders in high-stakes environments, the message is clear: understanding the mechanics of grievance and retaliation isn’t just psychological, it’s strategic. Kimmel’s work offers actionable frameworks to recognize revenge-seeking before it becomes destructive, and calls for a deeper integration of neuroscience into how we define justice, manage risk, and lead with compassion.   Get The Science of Revenge here: https://www.jameskimmeljr.com/   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

30 Juni 57min

563: Brand Global, Adapt Local: Executive Lessons from Nike, Louis Vuitton, and HubSpot

563: Brand Global, Adapt Local: Executive Lessons from Nike, Louis Vuitton, and HubSpot

In this episode, I spoke with two highly respected global brand leaders, Katherine Melchior Ray and Nataly Kelly, whose experience spans executive roles at Nike, Louis Vuitton, HubSpot, Zappi, and more. Our discussion centered on their latest book, Brand Global, Adapt Local, but more broadly, we explored the evolving demands of building and sustaining global brands in a world defined by cultural complexity, rapid technological change, and shifting consumer expectations. A few themes stood out: 1. Consistency is not enough. Nataly Kelly shared: “I used to believe that branding required absolute consistency and very little flexibility. But when I began to work in global marketing, I realized that there is adaptability that’s required to really succeed.” Successful global brands, in her view, hold tightly to a clear core while flexibly adapting how they show up across markets. 2. Cultural blind spots have real consequences. Katherine Melchior Ray reflected on an early leadership experience at Nike: “The common refrain was, for women’s shoes… ‘shrink it and pink it.’” She underscored the importance of cultural sensitivity, noting: “Listen with your eyes. Because in many cultures, people communicate with nonverbal forms of communication.” 3. Strategy and judgment cannot be delegated to machines. As the use of AI accelerates, Nataly cautioned: “You can’t outsource your strategy… Judgment and strategy are the two things that I think humans will start to realize [must stay human].” 4. Trust is built over time, not through messaging alone. Katherine observed: “At the end of the day, a brand is all about a promise. People support brands that they trust.” 5. Human connection remains central. As Katherine succinctly put it: “The more we rely on technology, the more we must double down on our humanity.” If you're involved in shaping brand strategy, whether globally or locally, this discussion offers valuable perspective.   Get Brand Global, Adapt Local here: https://shorturl.at/f4EnF   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

25 Juni 52min

562: Steve Jobs' Former Colleague on How to Achieve Creative Velocity in the Age of Gen AI

562: Steve Jobs' Former Colleague on How to Achieve Creative Velocity in the Age of Gen AI

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   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

23 Juni 54min

561: Harvard’s Bill George on Leading Authentically in Today's Workplace

561: Harvard’s Bill George on Leading Authentically in Today's Workplace

In this wide-ranging and direct conversation, Bill George, former Medtronic CEO and Harvard Business School professor, offers a disciplined framework for leading in conditions of persistent volatility. Drawing from decades of leadership experience and research, George emphasizes that leadership today is no longer about managing processes, it is about confronting ambiguity, enabling experimentation, and sustaining purpose across shifting conditions.   Five themes stand out: Opportunity Must Be Created, Not Awaited. George argues that emerging leaders should not wait for promotions or formal permission. Instead, they should identify unaddressed problems, volunteer to lead, and deliver results without demanding titles. Career growth, he suggests, is a function of action, not seniority. Innovation Begins at the Front Lines. Whether referencing his early decision to cancel a Medtronic pacemaker program that lacked patient benefit, or urging leaders to spend less time in conference rooms and more with customers and staff, George insists that enduring breakthroughs stem from direct observation and empathy, not from internal data analysis alone. Risk Tolerance Determines Strategic Renewal. George contrasts firms that institutionalize risk such as Medtronic’s venture incubation model, with those that allow internal resistance to block change. Innovation, he asserts, must be structurally protected from corporate inertia, and leaders should be judged on the courage to champion unpopular ideas that later prove transformative. Culture Must Reward Learning Over Defensiveness. Drawing parallels between U.S., European, and Japanese innovation cultures, George critiques over-regulated, failure-averse systems that suppress experimentation. True progress, he says, requires the willingness to learn through trial, adaptation, and even initial failure. AI Is a Strategic Imperative, Not a Cost Play. Rather than using AI to drive out labor costs, George advocates for using it to rethink business models entirely, supporting frontline autonomy, enabling new services, and unlocking unmet needs. He cautions leaders against adopting a defensive posture and urges them to fund experiments that explore the true potential of the technology. Throughout, George offers a leadership mindset anchored in authenticity, courage, and customer-centric design. His advice is clear: future leaders must raise their hands, operate at the edge, and move fast before the window of relevance closes.   Get Bill’s book here: https://shorturl.at/3iHRb True North, Emerging Leader Edition: Leading Authentically in Today's Workplace   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

18 Juni 49min

560: American Economist and Professor, Steve Hanke, on Rewriting the Rules of Our Financial System

560: American Economist and Professor, Steve Hanke, on Rewriting the Rules of Our Financial System

Central banks in major economies have repeatedly misread inflation trends by relying on models that omit a fundamental economic lever: the money supply. In this episode, economist Steve Hanke offers a detailed critique of prevailing post-Keynesian frameworks and the policy missteps that have followed. Drawing on historical and current data, Hanke underscores the predictive power of the quantity theory of money, a model largely excluded from central bank thinking, and explains how ignoring this leads to erroneous inflation forecasts and misguided interventions.   The discussion outlines how inflation, often attributed to exogenous shocks such as supply chain disruptions or geopolitical events, is more reliably explained by changes in the money supply. Hanke presents evidence that inflation today is the result of decisions made one to two years prior, making it critical to focus on monetary trends rather than short-term data fluctuations. He further contrasts U.S. and Chinese monetary responses, highlighting how both under- and over-corrections in money supply growth have resulted in either recessionary pressures or deflation.   Key insights from the episode include: - The quantity theory of money remains one of the most reliable frameworks for anticipating inflation, yet is absent from mainstream economic models used by central banks. - Inflation is always a monetary phenomenon, rising or falling primarily in response to shifts in the money supply, not due to external shocks, which only affect relative prices. - U.S. monetary policy is currently on a path toward recession, not inflation, due to anemic money supply growth since 2022, a trend Hanke predicts will continue unless reversed. - Regime uncertainty, policy volatility that undermines business investment, amplifies economic stagnation. Drawing parallels to the New Deal era, Hanke warns that unclear or shifting fiscal and regulatory rules will delay recovery even further. - Most of the money in circulation is created by commercial banks, not central banks. Post-2008 regulations have constrained these institutions, diminishing their role in supporting economic growth.   Taken together, these points call for a recalibration of macroeconomic policy, placing money supply at the center of analysis and re-empowering commercial banks to function as essential components of the financial system. For senior leaders navigating strategic decisions, the episode provides a timely and data-grounded lens on the structural drivers shaping inflation, recession risks, and economic stability.   Get Steve’s book here: https://shorturl.at/t5uDw Making Money Work: How to Rewrite the Rules of Our Financial System   Here are some free gifts for you:   Overall Approach Used in Well-Managed Strategy Studies free download: www.firmsconsulting.com/OverallApproach   McKinsey & BCG winning resume free download: www.firmsconsulting.com/resumepdf   Enjoying this episode? Get access to sample advanced training episodes here: www.firmsconsulting.com/promo

16 Juni 39min

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