On the Brink with Andi Simon Podcast By Andi Simon cover art

On the Brink with Andi Simon

On the Brink with Andi Simon

By: Andi Simon
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Are you navigating change—personally or professionally? On the Brink is your space for discovering new ways to see, feel, and think about your business, your work, and your life. Host Andi Simon, award-winning author, corporate anthropologist, and change expert, brings you inspiring conversations with entrepreneurs, innovators, and thought leaders who are reimagining what's possible. Explore how purpose, reinvention, and a human-centered approach can guide you through transitions and help you thrive. New episodes weekly. Economics Leadership Management & Leadership Social Sciences
Episodes
  • Rethink Retirement: Why Leaving Work Isn't Leaving Relationships Behind

    Rethink Retirement: Why Leaving Work Isn't Leaving Relationships Behind
    Apr 14 2026
    Summary Retirement is often framed as a personal milestone—a moment when we step away from work and into freedom. But what if retirement isn't just about leaving a job? What if it's about navigating the deep relationships, identity shifts, and responsibilities we carry with us into what comes next? In this episode of On the Brink with Andi Simon, Andi speaks with Katherine Crewe, a Tech/Vistage chair in Canada, whose thoughtful approach to retirement reveals a powerful truth: transitions are not events—they are processes. The Myth of the Clean Exit: Leaving Work Isn't Leaving Relationships Katherine's story challenges the idea that retirement is a simple, clean break. After decades in biomedical engineering and leadership, she moved into a role guiding CEOs and executives. Now, in her late sixties, she is not "done"—she is reflecting, recalibrating, and carefully designing her transition. What makes her journey so compelling is this: she is not just leaving a role—she is stepping away from a community. As a chair, Katherine has built deep, trusted relationships with the leaders she supports. When she began discussing retirement with them, the reactions were emotional and varied. Some encouraged her to stay. Others supported her decision. Many wanted one thing above all—a thoughtful, gradual transition. This wasn't about replacing a position. It was about preserving relationships, continuity, and trust. Retirement Is a Social Transition, Not Just a Personal One One of the most important insights from this conversation is that retirement impacts more than the individual. Katherine realized that stepping away from her role felt less like leaving a job—and more like leaving a network of meaningful human connections. The responsibility she feels is not just to herself, but to those who depend on her leadership. This is a critical lesson for organizations as well. As Andi notes, companies are facing a "senior tsunami"—a wave of experienced employees approaching retirement. Yet many organizations still treat retirement as an administrative process rather than a cultural transition. What Katherine is modeling is something different: Thoughtful succession planning Gradual transitions Honoring relationships and institutional knowledge This is where anthropology becomes powerful. It helps us see what is really happening beneath the surface. The Paradox of Choice in Retirement Unlike traditional roles, Katherine's position has no fixed retirement age. She could continue indefinitely. And that creates a new kind of challenge—the paradox of choice. If you can keep working… should you? Rather than choosing between "all or nothing," Katherine is exploring a more nuanced path: Reducing from three groups to one Staying engaged in meaningful work Creating more space for personal life and exploration This is a powerful reframe. Retirement doesn't have to be binary. It can be designed. Preparing Before You Retire Perhaps the most valuable insight Katherine offers is that she has already been preparing for retirement—without calling it that. She has: Structured her own time for years Built her identity around relationships, not titles Prioritized wellness as a daily practice Maintained independence in how she works and lives As a result, she does not fear the four common retirement pain points: Loss of identity Lack of daily structure Unclear purpose Disconnection from community Why? Because she has already built a life that isn't dependent on a job to provide those things. This is the real lesson: Retirement is not something you enter. It is something you prepare for—while you are still working. Couples, Conversations, and "Confetti Moments" Another powerful theme in this episode is how retirement impacts relationships at home. Katherine and her husband are both still active, both thinking about the future—but not always in structured ways. Instead, they have what she calls "confetti moments"—brief, scattered conversations about what retirement might look like. This is deeply relatable. Many couples don't sit down and design their future together. They talk in fragments. And yet, retirement will require alignment: How will we spend our time?Will we keep working?What does "being together" actually look like? Without intentional conversations, these differences can become points of tension. What This Means for You Katherine's journey reminds us that retirement is not an ending—it is a transition into a new stage of life that deserves as much thought and care as any career move. It is not about stopping. It is about redesigning. Key Takeaways Retirement is not a single event—it is a gradual, human transition. Leaving work often means leaving relationships, not just responsibilities. Organizations must treat retirement as a cultural and strategic issue, not just HR process.The best retirement transitions are designed, not abrupt. Preparing early—by building identity, structure, ...
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    26 mins
  • The Generous Leader: Why Modern Leadership Is About Giving, Not Taking

    The Generous Leader: Why Modern Leadership Is About Giving, Not Taking
    Apr 2 2026
    Podcast Summary In this episode of On the Brink with Andi Simon, Dr. Andi Simon speaks with Joe Davis, former senior partner at Boston Consulting Group and author of The Generous Leader. Their conversation explores how leadership has evolved in a fast-changing world—and why the most effective leaders today succeed by developing others, listening deeply, and embracing humility. The discussion offers practical insights on leadership, team development, and navigating uncertainty with confidence and compassion. Why Leadership Must Change in a World of Constant Disruption We are living through an era of continuous transformation—technological disruption, shifting workforce expectations, and evolving organizational cultures. As Dr. Andi Simon notes, the past is no longer a reliable guide for the future. Leaders must adapt, not by controlling change, but by learning how to move with it. Joe Davis's career journey reflects this reality. From Procter & Gamble to Harvard Business School and ultimately to leadership roles at BCG, his path was anything but linear. Instead of following a predictable trajectory, Davis embraced unexpected opportunities—often the ones others might avoid. Key takeaway: Great leaders don't follow a fixed path—they develop the agility to step into the unknown. What Is a Generous Leader? At the heart of the conversation is Davis's core idea: leadership is not about personal success—it's about enabling others to succeed. A "generous leader" gives of themselves freely to help others grow, without expecting immediate personal gain. This mindset transforms leadership from a position of authority into a platform for impact. Core Traits of Generous Leadership Generous Listening – Truly hearing others, not interrupting or assuming Generous Communication – Connecting with clarity and empathy Generous Inclusion – Bringing diverse voices into the conversation Generous Development – Actively coaching and growing others Generous Recognition – Celebrating contributions, big and small Small Acts, Big Impact – Simple gestures that build trust Authenticity & Vulnerability – Leading as a human, not a persona The Leadership Mistake Most People Make One of the most powerful moments in the podcast is when Davis reflects on a common leadership error: thinking you already know what others are going to say. He shares a story of interrupting a colleague mid-thought—only to be told bluntly to "let me finish." The lesson was clear: Listening is not waiting to speak—it's learning something you don't already know. This insight is critical in today's workplace, where collaboration and innovation depend on diverse perspectives. Leadership at Scale: Can You Lead 7,000 People? Davis once led over 7,000 people. His approach offers a valuable lesson for executives and emerging leaders alike: You don't scale leadership through control—you scale it through culture and systems. How to Lead at Scale Reinforce clear values consistently Build structured feedback and development processes Promote people who model the culture Communicate constantly—and check if your message is truly understood Create environments where people feel seen and heard When leaders align behaviors, values, and systems, leadership becomes self-reinforcing across the organization. Why Empathy Is a Strategic Advantage During the COVID-19 pandemic, Davis realized how disconnected leaders can be from employees' lived realities. While he had space and comfort at home, younger employees were working from cramped apartments, sharing limited resources. This realization changed how he led. Leadership insight: You cannot lead effectively if you don't understand the context in which your people are living and working. Empathy is no longer optional—it is a strategic necessity. The Future of Leadership: From Authority to Enablement One of the most important shifts discussed in the episode is this: The leader's job is not to have the best answer—but to get the best answer out of the room. This reflects a broader transformation: From command-and-control → to collaborate-and-enableFrom individual expertise → to collective intelligenceFrom certainty → to adaptability In a world shaped by rapid change and uncertainty, leaders must become facilitators of growth—not just decision-makers. Final Takeaway: Ask and Listen If there is one lesson to remember, it is simple but profound: Ask. And then listen. Great leadership begins with curiosity and humility. By understanding others' perspectives, leaders unlock innovation, trust, and performance. Why This Matters Now As organizations face talent shortages, generational shifts, and accelerating change, leadership is being redefined. The most successful leaders will not be those who know the most—but those who develop the most in others. Joe Davis's philosophy of generous leadership offers a powerful roadmap for navigating this new reality. From Observation to ...
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    40 mins
  • How AI Is Transforming Meetings Into Strategic Assets with Ramsey Pryor

    How AI Is Transforming Meetings Into Strategic Assets with Ramsey Pryor
    Mar 24 2026
    Summary Meetings dominate our workdays—but what if they could become a source of intelligence rather than inefficiency? In this episode of On the Brink with Andi Simon, I speak with Ramsey Pryor, CEO and founder of Rumi, an AI‑powered meeting intelligence platform that is redefining how organizations capture knowledge, collaborate, and make decisions. Together, we explore how artificial intelligence is reshaping the future of work by transforming everyday conversations into actionable insights. The Problem with Meetings Today Let's start with a simple truth: most meetings underperform. Professionals spend 30% or more of their time in meetings, and much of that time is wasted repeating information, catching people up, or trying to recall what was previously discussed. As Ramsey noted, research suggests that two‑thirds of meeting time is spent rehashing prior conversations—a staggering drain on productivity and morale. Across industries—from banking to healthcare—I've seen meetings with no agenda, no clear outcomes, and no shared understanding of next steps. Attendance becomes the work, rather than progress. So the real question becomes: What if meetings could finally work for us instead of against us? The Hidden Value Inside Your Meetings—and How AI Unlocks It Ramsey Pryor founded Rumi during the pandemic, when virtual meetings exploded and attention became fragmented. His idea was deceptively simple: Capture everything that happens in meetings and turn it into usable knowledge. Using AI, Rumi: Automatically transcribes conversationsSummarizes key insightsIdentifies and tracks action itemsCreates a searchable "meeting memory" Instead of relying on human recollection—or scattered notes—teams gain access to a living, searchable database of institutional knowledge. This is where the transformation begins. From Note‑Taking to Knowledge Creation Traditional note‑taking is reactive. You jot things down and hope they make sense later. AI flips that model. With meeting intelligence, employees can: Ask: "Why did we make this decision?"Find: "Who has expertise in this area?"Track: "What actions were assigned—and to whom?" As Ramsey explained, this reduces interruptions, eliminates redundant conversations, and accelerates decision‑making. Instead of digging through emails or pinging colleagues, employees can query their organization's collective memory directly. The result is simple but powerful: Less redundancy. Faster decisions. Better alignment. Changing Habits—and Culture This shift is not just technological—it's behavioral. We are moving from: Listening and forgetting → capturing and retrievingIndividual memory → shared intelligenceMeetings as events → meetings as data assets Just as many of us instinctively turn to tools like ChatGPT for answers, organizations are beginning to turn inward—to their own data—for insights. This represents a profound cultural transformation. The Global Dimension: Culture Still Matters As an anthropologist, I find the global implications especially compelling. Meetings are deeply cultural: In some regions, hierarchy shapes who speaksIn others, open debate is expectedCommunication norms vary widely AI can help bridge gaps—especially in language, documentation, and clarity—but it cannot replace the need to understand how people interpret and act on information. Technology enables. Culture determines adoption. Measuring the Impact The value of AI‑powered meeting intelligence is not theoretical—it's measurable. Ramsey shared an example of a 300‑person sales team that saved 33,000 hours annually by reducing repetitive tasks and improving access to information. That's the equivalent of adding 15 full‑time employees—without hiring anyone. This is where AI shifts from "interesting" to indispensable. A New Way to Think About Meetings Here are three key insights to carry forward: Meetings are a hidden source of value They contain knowledge your organization is already paying for—but not fully using. AI turns conversations into assets What was once ephemeral becomes searchable, actionable, and scalable. Behavior change is the real transformation The technology matters, but the real shift is in how people think, ask questions, and access information. Final Thought We are at the beginning of a major shift. Just as the internet democratized access to global knowledge, AI‑powered meeting intelligence is democratizing access to organizational knowledge. The question is no longer: "What did we say in that meeting?" It is: "What can we do with everything we know?" From Observation to Innovation, Andi Simon, PhD CEO | Corporate Anthropologist | Author Simonassociates.net Info@simonassociates.net @simonandi LinkedIn
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    34 mins
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