The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving

Charles Steele reflects on "more than two decades in private equity, banking," combined with "public service roles, including advising Tony Blair," and how these experiences led him to a late but powerful discovery: "the best way to really find purpose in life is to be creative, to make stuff." He explains that "the things I'm writing about now I am only able to write about because of what I spent the last two decades doing," and how this realization became a turning point.
He describes how stepping outside traditional career paths creates "periods where you have perspective," and how "follow your curiosity" eventually brought him back to the ideas that mattered in his youth. He shares that "in the last five years, I feel like I've become a student again" and that this shift awakened a deeper understanding of work, mission, and meaning.
Charles discusses the discipline behind creative work: "writing is not writing. Writing is rewriting," and how the creative act is "one of making mistakes, learning from them, getting better." He also explains the importance of reframing difficulty, saying, "if it was an easy thing to do, then everyone would do it," and why maintaining "a sense of humor" matters when navigating the inevitable "peaks and troughs."
Turning to Elon Musk, Charles argues that Musk is "far more different than most people would imagine." He explains that Musk always says, "when I talk you don't need to read between the lines, just read the lines," and that understanding him requires stepping outside our assumptions: "you have to step out of your shoes and step into his shoes."
Charles outlines Musk's worldview, guided by what Musk calls "a philosophy of curiosity." Musk believes "the universe is the answer," and that progress comes from learning to "ask better questions" so we can "increase our consciousness" as a civilization. Charles describes how Musk's companies, from Tesla to SpaceX to XAI, are designed as "civilizationally positive" efforts to "increase the scope and scale of consciousness."
He explains Musk's use of first-principles thinking: "you need every time to go back to look at your assumptions," then "make a conjecture" and "try and prove that your theory is wrong." This mindset also shapes how Musk builds organizations: through mission, product obsession, and "the rate of innovation," a culture in which people "work extremely hard" because they believe deeply in the purpose.
Charles closes by stressing the importance of alignment and risk-taking: that leaders must understand "your risk tolerance," think in "a range of different outcomes," and recognize that this discipline "really helps you to think about how much risk you're willing to take on for what return."
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Lorraine Marchand, startup CEO, advisor to Johnson & Johnson, member of the Pharmaceutical Advisory Board at Columbia Business School, and faculty at Wharton, discusses how leaders can sustain growth through disciplined experimentation in an era shaped by AI and institutional risk aversion. 
Marchand's perspective is grounded in a career that spans large corporations and entrepreneurial ventures. Early in life, she learned to treat problem solving as an experiment rather than a test of personal worth. That principle later informed her approach to innovation in complex organizations.
Several practical themes emerge from the discussion:
1. Reframe failure as structured learning.
Marchand's operating principle is "try, fail, learn." The key is to set explicit learning objectives before undertaking a new initiative. When leaders define what they intend to learn, not just what they intend to achieve, they reduce fear and increase resilience. This mindset is particularly critical in startups and new ventures, where there is no playbook and early missteps are inevitable.
2. Innovation requires protected investment.
Drawing on research and executive interviews, Marchand highlights the value of disciplined portfolio allocation. A 70/20/10 model—70% core business, 20% adjacent opportunities, 10% new, exploratory ideas—creates room for experimentation without destabilizing the enterprise. The evidence she cites suggests that long-term growth frequently emerges from ideas that initially seemed peripheral.
3. Culture often suppresses experimentation.
Organizations frequently default to "playing it safe." Marchand argues that leaders must explicitly create space for candor and reflection. Her practice of "Fail Free Friday", a structured forum to discuss what is not working without defensiveness, illustrates how small rituals can normalize learning and surface risk before it compounds.
4. AI should assist thinking, not replace it.
Marchand observes both curiosity and fatigue around AI. Students and executives alike risk over-reliance, which can erode depth of analysis. Her discipline is simple: think independently first, then use AI as a research assistant to refine or challenge one's reasoning. Senior leaders remain relevant not by competing with automation, but by asking the right questions, an ability rooted in experience and judgment.
5. Integration of technology requires business judgment.
Technology cannot be bolted onto processes indiscriminately. Leaders must understand workflows deeply enough to decide where automation adds value, where human ingenuity remains essential, and where both are required. This integration demands clarity about the business, not just familiarity with the tool.
6. The "who" and the "how" matter more than the "what."
Late-career reflection led Marchand to conclude that outcomes achieved at the expense of people erode long-term value. Values alignment, integrity, and disciplined focus, often expressed through the willingness to say no, are strategic decisions, not personal preferences.
For senior professionals, the message is direct: sustained growth depends less on bold rhetoric and more on creating disciplined environments where experimentation is safe, technology is used thoughtfully, and people are encouraged to think independently. The capacity to ask better questions, protect time for reflection, and allocate resources to uncertain but promising ideas remains a defining leadership advantage.
Lorraine H. Marchand, an acclaimed author and innovator, is author of the new book NO FEAR, NO FAILURE and a leading consultant and educator on innovation with deep expertise in new product development. She has cofounded multiple start-ups, held senior roles at global companies including Bristol-Myers Squibb, Covance/LabCorp, and IBM, and advises top organizations while teaching at the Wharton School and Yeshiva University.
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Ashley Herd, former Head of HR North America at McKinsey, joins this episode to discuss what effective leadership looks like in practice, especially in environments defined by speed, pressure, and increasing expectations around AI.
Drawing on her experience training more than 250,000 managers, she introduces a simple but rigorous framework: pause, consider, act. In fast-moving organizations, leaders often default to speed over reflection. Herd argues that the brief pause before responding to a mistake, delivering feedback, or making a decision materially changes outcomes. It allows leaders to ask: What result am I trying to achieve? How would I want to be treated in this situation? What will the ripple effect of this action be?
Several practical insights stand out:
First, performance feedback remains one of the most persistent leadership failures. The issue is not usually saying the wrong thing, but saying nothing at all. Delayed or avoided feedback creates confusion, resentment, and surprises in annual reviews. Timely, specific recognition is equally important; a simple acknowledgment can shape engagement far beyond the moment.
Second, leadership style often oscillates between two extremes. Herd describes "tight jeans" leadership as micromanagement that restricts autonomy, and "oversized sweatpants" leadership as excessive hands-off behavior that leaves teams without direction. The effective middle ground is structured autonomy: clear expectations combined with room to operate.
Third, leaders underestimate the degree to which they influence their teams' well-being. Research shows a manager's effect on employee health rivals that of a spouse. Everyday behaviors whether following up, acknowledging effort, or setting realistic expectations, have consequences that extend beyond the workplace.
Fourth, organizations face a growing gap between executive narratives about AI and what teams are actually doing. Leaders often declare proficiency while employees experiment quietly, sometimes without clarity on what is expected, allowed, or rewarded. Clear standards around AI usage, what good looks like, what is permitted, and how it will be evaluated, are now a management responsibility, not a technical one.
Finally, Herd emphasizes upstream problem solving. Instead of repeatedly "cleaning up" issues after they escalate, leaders should invest in conversations, manager training, and clear norms that prevent recurring failures. This requires time, but it reduces long-term friction.
For senior leaders, the message is direct: results and humanity are not opposing goals. Deliberate communication, consistent one-on-ones, and realistic workload expectations are operational disciplines, not soft considerations. For managers at any level, the framework is simple but demanding. Pause before reacting, consider the broader impact, then act with clarity.
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John McGinnis, law professor at Northwestern University and author of Why Democracy Needs the Rich, examines constitutional design, democratic stability, and the accelerating force of artificial intelligence. Drawing on the Federalist Papers, Tocqueville, and public choice theory, he argues that a realistic understanding of politics is essential to preserving both liberty and effective state capacity.
McGinnis traces his intellectual formation to a "hard-headed realism" learned early in life and later reinforced by the American founding. At the center of his thinking is a practical constitutional question: how to build sufficient state capacity while preventing its abuse. He emphasizes the importance of an entrenched constitution that is difficult to amend, arguing that stability enables long-term planning and protects society from short-term political passions.
Several themes shape the discussion:
Public choice and political incentives. Politics does not operate in a purely public-spirited way; concentrated interests often organize more effectively than diffuse ones. Understanding this dynamic is essential for evaluating policy debates.

Historical perspective as stabilizer. Many contemporary political phenomena appear unprecedented but are not. From Andrew Jackson to the present, democratic politics has repeatedly unsettled elites while preserving constitutional continuity.

Technology as the dominant variable. McGinnis argues that AI will overshadow most current political disputes. As a general cognitive tool, it will be embedded across sectors, reshaping law, education, national security, and economic organization.

Comparative advantage in an AI world. As machines assume cognitive tasks, human value will shift toward persuasion, judgment, and relational skills. Professionals must rethink where they add distinctive value.

Education under acceleration. The coexistence of AI-enabled and AI-restricted learning may become necessary to preserve independent thinking while leveraging technological capability.

The civic role of the wealthy. In Why Democracy Needs the Rich, McGinnis contends that wealthy individuals diversify democratic discourse, counterbalance concentrated interests, support minority rights movements, and fund public goods such as universities and museums. Their independence allows them to take risks others cannot.

The episode also addresses rising student anxiety, the erosion of historical literacy, and the long-term question of meaning in a world where work may change substantially. McGinnis maintains that constitutional stability, plural centers of influence, and technological leadership remain central to American resilience.
This conversation offers a grounded framework for thinking about democracy, incentives, and technological acceleration. It situates current debates within a longer historical arc while identifying AI as the structural force most likely to define the next decade.
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Dr. Guy Winch explains why we must treat emotional injuries with the same urgency as physical ones. "We ruminate, we beat ourselves up, we criticize ourselves, we think we're weak… and we end up compounding the emotional injury." He introduces the idea of "emotional first aid" and why we need a psychological toolbox to stop that downward spiral.
Guy breaks down the difference between how we respond to physical pain versus emotional pain. "We go to the medicine cabinet for a physical injury, but we have no cabinet for emotional injuries." He explains why we must learn emotional hygiene: "The injuries don't just go away."
We also discuss how emotional neglect works and the long-term consequences of unacknowledged wounds. "The mind does not heal itself. The mind broods."
Finally, Guy offers a new model for how to respond when people open up to you emotionally. "Start with compassion. You can offer logic later."
Key Insights:
Insight 1:
"We ruminate, we beat ourselves up, we criticize ourselves, we think we're weak… and we end up compounding the emotional injury."
This explains why emotional pain often intensifies over time without care — because we engage in harmful self-dialogue instead of healing practices.
Insight 2:
"The mind does not heal itself. The mind broods."
Guy challenges the myth that emotional wounds naturally heal. Without intervention, the mind tends to replay and deepen the pain.
Insight 3:
"We go to the medicine cabinet for a physical injury, but we have no cabinet for emotional injuries."
He contrasts our well-established responses to physical pain with the absence of tools for emotional distress — and why this gap needs to be closed.
Insight 4:
"Emotional hygiene is about treating those injuries when they occur and trying to prevent them in the first place."
He introduces emotional hygiene as a proactive and reactive strategy, just like physical hygiene protects against illness and injury.
Insight 5:
"Start with compassion. You can offer logic later."
This is a clear framework for responding to others in distress — showing why empathy should precede problem-solving.
Action Items:
"Start with compassion. You can offer logic later."
Use this sequence when someone shares emotional pain.



"The first step is to recognize the injury for what it is."
Acknowledge when you've been emotionally hurt. Label it.



"Would I say this to a friend? If the answer is no, then don't say it to yourself."
A reframe technique to interrupt self-criticism.



"You don't take one antibiotic and stop. You have to do the course. It's the same with emotional first aid."
Practice emotional tools consistently, not just once.



"Rumination is like a psychological infection. And so what you need to do is stop the infection from spreading."
Interrupt rumination cycles early.

"You have to override your own instinct."
Emotionally healthy responses often require pushing against our natural urges to withdraw or self-blame.


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