Episodes

As we kick off 2026, Tim Flanagan and Amanda Kramer look back on some of the most impactful moments from Winning Through Culture in 2025. This Best Of episode brings together four standout conversations that captured the heart of what it means to lead with intention in today’s world—where performance, wellbeing, identity, and innovation are deeply intertwined. Across these clips, a clear theme emerges: winning cultures are human-centered, purpose-driven, and built with care. You’ll hear refle...

As the year winds down, the pressure ramps up — deadlines, family events, holiday expectations, and the natural urge to “finish strong.” In this episode, Tim and Amanda wrap up their how-to series by breaking down what it really means to close out 2025 with intention and build momentum for 2026. They explore practical ways leaders can stay present, choose priorities deliberately, strengthen culture during a noisy season, and shift from a “doing” mindset to a “being” mindset. This conversation s...

In this episode of Winning Through Culture, hosts Tim Flanagan and Amanda Kramer sit down with Garry Ridge, Chairman Emeritus of WD-40 Company, bestselling author, and founder of The Learning Moment. Known globally as The Culture Coach and affectionately as The Dean of Dumbassery, Garry shares timeless lessons on leadership, learning, and creating workplaces where people feel safe, valued, and inspired to do their best work. Garry explores how great leadership is simple—but never easy. From the...

In this episode of Winning Through Culture, hosts Amanda Kramer and Tim Flanagan are joined by Dr. Beth Kaplan, author of Braving the Workplace and a leading expert in belonging and leadership development. Together, they explore how leaders can create brave spaces—environments where truth is told with care and vulnerability meets accountability. Dr. Kaplan discusses the difference between safe and brave spaces, the impact of belonging uncertainty on performance, and why care—not perfection—is a...

In this episode of Winning Through Culture, Amanda Kramer and Tim Flanagan speak with Tim Kelley, a global expert on purpose and author of True Purpose. Tim shares his insights on why most organizations struggle to define a meaningful purpose statement—and how to create one that sparks real inspiration and change. The conversation explores why strong purpose statements often provoke both positive and negative reactions, and why that tension is a sign of authenticity and boldness. Tim outlines p...

In this episode of Winning Through Culture, Tim Flanagan interviews Danielle Krischik, partner and chief strategy officer at the Knight Agency, to explore how storytelling shapes organizational culture. Danielle shares her journey from advertising copywriter to master storyteller, highlighting how stories connect people to their work, their leaders, and each other. The conversation unpacks why leaders must not only become better storytellers but also enablers of their team’s stories. Danielle e...

In this episode of Winning Through Culture, Tim Flanagan and Amanda Kramer introduce the new How To series, a step-by-step guide for building and sustaining a thriving company culture. They share why culture is one of the most overlooked drivers of business success and why it matters for organizations of every size—from startups to large enterprises. Tim and Amanda explore foundational truths about culture, including the importance of authentic values, trust, and connection in the workplace. Th...

In this episode of Winning Through Culture, Tim Flanagan speaks with Steve Cuss—author of Managing Leadership Anxiety: Yours and Theirs and founder of Capable Life—about how leaders can recognize, name, and address anxiety in themselves and their organizations. Steve explains the difference between stress and anxiety, introduces the concept of reactivity as a contagious form of anxiety, and shares practical steps leaders can take to diffuse it. Drawing from his experiences as a trauma and hospi...

In this episode of Winning Through Culture, Amanda Kramer and Tim Flanagan dive into Learned Excellence by Dr. Eric Potterat and Alan Eagle. The book outlines five mental disciplines—values and goals, mindset, process, adversity tolerance, and balance and recovery—that shape how we pursue excellence in work and life. Amanda and Tim share their personal “aha” moments from the book, including the value of focusing on process, the importance of the black box method for overcoming setbacks, and how...

In this episode of Winning Through Culture, hosts Amanda Kramer and Tim Flanagan sit down with Kelsey O’Connor, a former Division 1 athlete turned motivational speaker, to explore what it truly means to live beyond the labels we carry. After a life-altering injury ended her softball career, Kelsey was forced to confront the loss of identity and navigate the uncertainty that followed. Through resilience, faith, and community support, she redefined success—focusing not on titles or roles, but on c...

As we pass the halfway point of 2025, now is the perfect time to ask: are you still living your core values? In this special mid-year re-release, Tim Flanagan and Amanda Kramer revisit one of the most impactful conversations from earlier this year—centered around core values, vision, and a practical exercise to guide your growth. Originally shared in January, this episode is just as relevant today. You’ll hear why values are more than words on a wall, how they influence decisions and culture, ...

As leaders, it’s easy to prioritize performance, results, and responsibility—often at the expense of our own well-being. But true high performance is built on a foundation of health. In this special Men’s Health Month episode of Winning Through Culture, Tim Flanagan sits down with Dr. Aaron Goodson, Director of Mental Health and Performance at Duke University Athletics. Together, they explore how elite athletes manage stress, recovery, and resilience—and what leaders in business can learn from ...

In this episode of Winning Through Culture, Tim Flanagan and Amanda Kramer sit down with Michael Reddington, Certified Forensic Interviewer and author of The Disciplined Listening Method. Michael shares how techniques from forensic interviewing and cognitive psychology can transform leadership communication—especially in high-stakes business conversations. From understanding hidden resistance to building trust and uncovering unspoken concerns, Michael offers practical tools for leaders and advi...

What does it really mean to “show up” as a leader? Ross Kimball—actor, comedian, and executive communication coach—joins Tim Flanagan and Amanda Kramer to explore how the mindset and techniques of improv can reshape the way leaders connect, listen, and communicate. Drawing from his own journey on stage and screen, Ross breaks down how presence, adaptability, and storytelling translate into stronger relationships and better team culture. He also shares practical exercises to help leaders listen m...

Richard Weylman, bestselling author and Customer Experience Hall of Famer, joins Tim Flanagan to share battle-tested strategies for building a client-focused culture in financial services. Drawing from his remarkable journey—overcoming a childhood in 19 foster homes to leading sales for Rolls-Royce and The Robb Report—Weylman unpacks how intentional culture drives client acquisition and loyalty. From his books The Power of Why and 100 Proven Ways to Acquire and Keep Clients for Life, he reveals ...

In this Winning Through Culture episode, Rebekah Miller sits down with co-host Tim Flanagan for another “Ask Me Anything.” From childhood dreams of being a cowboy to leading The Pelora Group as a third-generation financial services veteran, Tim shares stories of hard work, self-awareness, and cultural impact. He opens up about the books, mentors, and philosophies that shaped him, offering young leaders practical wisdom for navigating today’s challenges with intention and grit. This episode is a...

Chelsea Pawlowski, marketing director at The Pelora Group, sits down with Amanda Kramer to unpack how core values like stewardship and purpose shape personal and professional lives. As a mom navigating her son’s limb difference diagnosis, Chelsea launched The Fearfully Made to support other families, turning a challenging moment into a beacon of hope during Limb Difference Awareness Month. Together, they explore the messy reality of balancing motherhood, career, and advocacy, and how organizatio...

Today’s episode is a special one where we’re stepping behind the scenes to get to know one of the hosts a little better. In this ‘Ask Me Anything’ episode, Amanda Kramer opens up about her personal journey, career, and values—letting our listeners in on who she is beyond the microphone. While Amanda is known for leading engaging discussions and interviews on the podcast, today’s the day we spotlight her. As one of the hosts of Winning Through Culture and Director of Advisor Experience at The Pe...

In this episode, hosts Tim Flanagan and Amanda Kramer welcome Nicole Cramer, a sales conversation coach, to discuss the connection between sales psychology, leadership, and high-performance culture. Nicole shares her journey into sales and how she discovered that selling is about building relationships rather than pushing a product. The conversation explores what makes a high-performance culture, the balance between performance and emotional well-being, and the role of self-leadership in drivin...

In this episode of Winning Through Culture, Tim Flanagan and Amanda Kramer dive into the rapidly evolving role of AI in the workplace and its impact on team collaboration, productivity, and leadership. They discuss the benefits and challenges of integrating AI into day-to-day operations while emphasizing the importance of maintaining human connection and a vibrant workplace culture. From enhancing efficiency to fostering professional growth, they explore how leaders can strategically leverage AI...

In this episode of Winning Through Culture, hosts Tim Flanagan and Amanda Kramer and sit down with sales performance coach Dave Resseguie to explore the power of control and influence in leadership and client relationships. Dave shares his philosophy: “Control 100% of the things that are in your control | Influence everything else.” With a background in leadership coaching and sales performance, Dave highlights how mindset, intentionality, and collaboration shape non-transactional relationships...

What does it take to grow the next generation of leaders? In this episode, Caitlin F. Cohoon, founder of Interdependent Leadership and an ICF Certified Professional Coach, shares insights on developing emerging leaders, building confidence, and leveraging mentorship. Key Topics: Redefining Growth for Emerging Leaders – What do young professionals truly want from their careers? How can organizations better align with their aspirations? The Confidence Factor – Why confidence is the bridge betwe...

In this episode of Winning Through Culture, Amanda Kramer and Amy Macari explore the concept of grit, emphasizing its importance in entrepreneurship and personal growth. They discuss how grit, defined as passion and perseverance, is crucial for success and how it can be cultivated through community support and a growth mindset. The conversation highlights the significance of having a clear purpose and the role of a supportive network in overcoming challenges. They also touch on the need for lead...

A strong company culture isn’t just about creating invested and engaged employees and clients—it drives revenue growth and business success. The core values that shape your business decisions, team dynamics, overall brand, and client experience are at the heart of this success. In this special New Year episode, Tim Flanagan and Amanda Kramer explore how living your company’s core values “at the top” (executive team, senior leaders, etc.) fosters client loyalty, strengthens team cohesion, and fue...