Winning Through Culture

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 reflections on identity beyond titles, the power of presence and storytelling, the importance of recovery and sustainability, and how leaders can thoughtfully integrate AI while keeping people at the center of their organizations. Whether you’re revisiting these conversations or hearing them for the first time, this episode offers timeless reminders for leaders committed to building cultures where people can truly thrive. Featured Highlights Kelsey O’Connor (3:00) on identity, resilience, and seeing people beyond their roles Ross Kimball (8:44) on improv, storytelling, and presence as leadership skills Dr. Aaron Goodson (16:58) on burnout, recovery, and sustainable high performance AI in the Workplace (24:43) on embracing innovation without losing the human element ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group     The post Best of 2025: Human-Centered Leadership, Wellbeing, and Innovation appeared first on Winning Through Culture.

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 sets the stage for leaders who want to enter the new year aligned, energized, and better — not bitter. Key Topics: Why year-end feels overwhelming—and how to reframe “I’m busy” Choosing presence over pressure during the holidays Replacing the to-do list with a “to-be” list How to decide if 2025 was a winning year or a learning year The one question every leader should ask before January 1 Building your Personal Board of Directors: challenger, encourager, protector, integrator Creating small wins that build real momentum Using reflection, clarity breaks, and intention to enter 2026 strong Related Content: Living Your Core Values to Drive Growth: A Vision for 2025 | How to Build and Fuel a Healthy Company Culture ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group   CRN202812-9994828 The post Finishing With Intention: Building Culture and Momentum as You Enter 2026 appeared first on Winning Through Culture.

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 meaning behind his book Any Dumb-Ass Can Do It to his “Maniac Pledge” for accountability, he emphasizes that effective leaders balance courage with care and toughness with tenderness. His approach to leadership centers on trust, curiosity, and continual learning—what he calls “learning moments.” Through engaging stories and practical wisdom, Garry outlines the four cultural pillars every organization needs: care, candor, accountability, and responsibility. He reminds us that when leaders build cultures of trust and openness, people not only perform better—they go home happy, and that happiness ripples out into families and communities. Key Topics: The real meaning behind Any Dumb-Ass Can Do It and lessons from the humble donkey Leading with both toughness and tenderness: the heart of gold and backbone of steel The “Maniac Pledge” and how to empower accountability in organizations Why “learning moments” turn mistakes into growth The four pillars of a thriving culture: care, candor, accountability, responsibility Creating clarity through hierarchical core values How leaders can coach, not manage—and why it matters for culture The ripple effect of happy workplaces on families and communities About Garry Ridge: Garry Ridge is the Chairman Emeritus of WD-40 Company and recipient of an Honorary Doctor of Humane Letters from National University, recognized for his lifetime contribution to leadership, organizational culture, and workplace transformation. He also holds a Master of Science in Executive Leadership from the University of San Diego. Known globally as The Culture Coach, Garry helps leaders design workplaces where people feel safe, valued, and inspired to do their best work. Through his firm, The Learning Moment, he partners with executives to create cultures of trust, collaboration, and purpose-driven performance. He also serves on the boards of The Gorilla Glue Company and Eastridge Workforce Solutions, where he brings decades of global leadership expertise. A sought-after speaker and bestselling author, Garry co-authored Helping People Win at Work with Ken Blanchard and contributed to Work is Love Made Visible. His most recent book, the USA Today bestseller Any Dumb-Ass Can Do It, reinforces his belief that great leadership is simple—but never easy. Affectionately known as The Dean of Dumbassery, Garry champions the idea of “learning moments,” encouraging leaders to turn mistakes into opportunities for growth. His core philosophy is clear: when people feel safe, valued, and connected, they do their best work—and go home happy. That ripple effect strengthens families, communities, and ultimately, the world. Related Content: Braving the Workplace: Building Belonging and Leadership with Dr. Beth Kaplan | How to Build and Fuel a Healthy Company Culture ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Garry Ridge: LinkedIn Important Links The Pelora Group The Learning Moment Inc   CRN202811-9868393 The post Leading with Care and Candor with Garry Ridge appeared first on Winning Through Culture.

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 at the heart of effective leadership. The conversation uncovers practical ways for leaders to replace assumptions with invitations, meet people where they are, and build cultures rooted in authenticity and care. Key Topics: The difference between inclusion and belonging—and why both matter How to balance vulnerability, candor, and accountability as a leader Why psychological safety fuels courage and growth Practical ways to show genuine care and strengthen team connections How progress, not perfection, creates sustainable success Dr. Kaplan also shares findings from her ongoing research with the University of Pennsylvania and offers a reminder that leadership is never neutral—it’s either healing or harmful. About Dr. Beth Kaplan: Dr. Beth Kaplan is a researcher, writer, and thought leader on belonging and leadership development. Through her work with organizations like Salesforce, Georgetown University, and the Carnegie Foundation, she helps people and teams thrive through care, courage, and connection. Learn more at drbethkaplan.com Related Content: Winning Women Series | Kristen Eskew on Fostering Diversity, Equity, Inclusion & Belonging | How to Build and Fuel a Healthy Company Culture ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Dr. Beth Kaplan: Facebook | X | Instagram | LinkedIn Important Links The Pelora Group DrBethKaplan.com   CRN2028140-9763171 The post Braving the Workplace: Building Belonging and Leadership with Dr. Beth Kaplan appeared first on Winning Through Culture.

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 practical methods for uncovering purpose, including both conscious brainstorming and deeper subconscious approaches, and explains how leaders can test the strength of a purpose statement through measurable reactions. He also emphasizes the importance of regularly revisiting and refining purpose statements to keep them relevant and impactful. Drawing from his experience coaching executives, governments, and global organizations, Tim highlights why purpose is more than words on a wall—it’s the foundation for engagement, fulfillment, and lasting culture. Key Topics: Why many companies fail in crafting compelling purpose statements How to gather meaningful insights through “purpose-adjacent” questions Using strong reactions—positive or negative—as the best indicator of a powerful purpose Why bold and even “arrogant” purpose statements inspire action The role of unconscious methods in uncovering deeper purpose How purpose fuels employee engagement and cultural alignment Practical ways to apply purpose in daily decision-making About Tim Kelley: Tim Kelley is a global authority on purpose, an acclaimed speaker, and the author of True Purpose. He has trained more than 1,000 consultants, therapists, and coaches in his methods and worked with leaders from companies such as Alibaba, Oracle, and PwC, as well as government ministers and presidential candidates. A certified Conscious Capitalism consultant, Tim leads the Conscious Capitalism Consulting Certification Program. He holds a mathematics degree from MIT and previously served as a commanding officer in the U.S. Navy. Related Content: The Power of Storytelling with Danielle Krischik | How to Build and Fuel a Healthy Company Culture ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Tim Kelley: LinkedIn Important Links The Pelora Group True Purpose Institute   CRN202810-9682317 The post Crafting Purpose Statements That Inspire with Tim Kelley appeared first on Winning Through Culture.

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 explains how stories create trust, build alignment, and turn numbers into meaning, offering practical ways leaders can weave storytelling into everyday moments—whether in team meetings, one-on-ones, or company town halls. She also reflects on the importance of leaders understanding their own story and how storytelling will define the future of connection in the workplace. Key Topics: Why storytelling is a foundation of culture, not just communication The four areas leaders should connect people through story: company, work, leader, and team Turning “the grind” into purpose by giving the why behind the work The role of compassion, authenticity, and even failure in building trust Captivate, Relate, Motivate: Danielle’s framework for powerful storytelling How owning and reframing your personal story can strengthen your leadership About Danielle Krischik: Danielle Krischik is a master storyteller, executive advisor and Partner of Knight Agency, a marketing company based in Orlando, Florida, and Kansas City, Missouri, that builds business through human connection. With a background in story strategy and corporate communications, Danielle has worked with Fortune 500 companies and rising entrepreneurs alike. She is the creator of The Story Effect, an award-winning podcast and proven framework that transforms the way leaders communicate and connect. A former ballerina, Danielle still takes the stage as a speaker and leads storytelling workshops, helping people understand the power of stories to create connection and drive performance. Related Content: The Purpose Summit Insights | Michael Reddington: Unlocking Commitment Through Disciplined Listening ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Danielle Krischik: LinkedIn Important Links The Pelora Group The Knight Agency The Story Effect Podcast   CRN202810-9569217 The post The Power of Storytelling with Danielle Krischik appeared first on Winning Through Culture.

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. They also discuss how leaders can measure culture with both tangible metrics and intangible impact, the role of compassion and radical candor in leadership, and how small, intentional daily choices shape resilient teams. This conversation sets the stage for upcoming episodes featuring guests and practical tools to help leaders strengthen their organizations from the inside out. Key Topics: Why culture determines how people show up and how businesses perform Practical ways to measure and evaluate culture beyond financial metrics Addressing loneliness, inclusion, and belonging in the workplace The role of purpose, compassion, and consistency in leadership Three focus areas to assess your culture: community, listening, and inclusion Why small daily choices—not grand gestures—create lasting cultural change Related Content: GRIT as the Cornerstone of Success: Passion, Perseverance, and Purpose with Amy Macari | Book Club: Exploring Learned Excellence Together ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group   CRN202809-9436474 The post How to Build and Fuel a Healthy Company Culture appeared first on Winning Through Culture.

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 hospice chaplain, pastor, and leadership coach, Steve highlights the importance of self-awareness, faith, and creating cultures where people feel safe to be fully themselves. Key Topics: How reactivity shows up in leaders and spreads within organizations Practical strategies for noticing, naming, and diffusing anxiety The role of faith and self-compassion in leadership well-being Why emotionally healthy teams grow faster and sustain long-term impact How leaders can create cultures where everyone is cared for, not just managed Steve’s message is clear: leadership growth begins with learning to manage your own anxiety, and in doing so, you open the door to healthier organizations and deeper human connection. About Steve Cuss Steve Cuss is the author of Managing Leadership Anxiety: Yours and Theirs and founder of Capable Life, an online community that equips leaders to lower anxiety, relieve pressure, and be more present. With over 25 years in pastoral leadership, Steve has served diverse organizations—from hospitals to Fortune 500 companies—and is known for his practical, compassionate approach to leadership development. Related Content: Behind the Mic: Leadership Lessons and Life with Tim Flanagan | Integrating Faith in the Workplace with David Wachter —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Steve Cuss: LinkedIn | Website Important Links The Pelora Group   CRN202809-9422790 The post Managing Leadership Anxiety with Steve Cuss appeared first on Winning Through Culture.

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 incremental growth builds resilience. They also explore how community, recovery, and intentional leadership play a role in creating a thriving culture. This conversation blends practical insights with personal reflection, offering listeners tools and perspectives for applying the principles of Learned Excellence in their own leadership journeys. Key Topics: Why excellence is learned, not innate The five mental disciplines from Learned Excellence Insights on growth mindset, resilience, and community Practical takeaways like the black box method and the 1% better principle How leaders can balance performance with recovery for long-term impact   Related Content: Michael Reddington: Unlocking Commitment Through Disciplined Listening | Core Value 5: Balance ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group   CRN202808-9324048 The post Book Club: Exploring Learned Excellence Together appeared first on Winning Through Culture.

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 character, heart, and impact. Kelsey shares how that transformation led to a viral graduation speech and a new calling to help others do the same. This episode explores how leaders and individuals alike can create cultures that see and celebrate people for who they truly are. Key Topics: The head injury that changed Kelsey’s life—and the self-work that followed What it means to live “beyond labels” and how to embrace identity shifts How journaling, volunteering, and faith supported her recovery Tools for leaders to cultivate a culture of recognition beyond job titles Why small moments of intentionality can have a lasting impact The power of describing people by their heart, not just their role Related Content: “Lead Like You Were Meant To” with Rob McKinnon | The Intentionality of Company Leaders —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Kelsey O’Connor: LinkedIn | Instagram | Website Important Links The Pelora Group   CRN202808-9232840 The post Life Beyond Labels with Kelsey O’Connor appeared first on Winning Through Culture.

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, and what it really means to live them. Plus, Tim shares a timeless practice from a mentor—writing an “accomplishments letter”—that can help you reflect on the year ahead as if it’s already happened. Whether you’re a business owner, team leader, or someone striving for personal growth, this is your opportunity to pause, reflect, and re-align. Episode Highlights: Re‑center on your core values Ask: Are your actions and outcomes still aligned with those foundational values? Use structured tools—surveys, team check‑ins, scorecards—to assess alignment. Make values visible Reinforce your values in daily routines: meetings, performance reviews, peer shout‑outs. Celebrate specific behaviors that exemplify your values. Measure culture in action Track engagement, retention, and customer feedback metrics associated with values-led initiatives. Look for connections between lived values and impact—on performance, collaboration, and external results. Adapt‑and‑refine As Tim and Amanda reminded us, it’s not enough to simply define values; you must live them and evolve them as needed. Revisit your vision for 2025: are the values still relevant? Do they still point toward your goals? What You Can Do Today Step Action Pulse‑check Send out a quick values survey: How strongly do team members feel aligned? Recognize Gather examples of values-driven wins so far this year. Reflect Host a mid‑year session to revisit vision–values–action linkage for Q3/Q4. Amplify Replace or elevate one operational cadence (e.g., team meetings) with a values spotlight segment.   Related Episodes to ‘Mid‑Year 2025 Values Check‑In’:  Living Your Core Values to Drive Growth: A Vision for 2025 Our Core Values The Intentionality of Company Leaders ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group   CRN202801-7830605 The post Mid‑Year 2025 Values Check‑In appeared first on Winning Through 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 those same strategies. From journaling and self-awareness to intentionally creating recovery space for teams, Dr. Goodson shares powerful insights that bridge the gap between mental health and sustained leadership impact. Key Topics: Why recovery must be intentional, not optional How to spot early signs of burnout Why stress isn’t the enemy—and how to work with it The difference between evaluating and judging yourself What it looks like to lead by example, even imperfectly Related Content: Prioritizing Mental Health in Sports and Business with Lisa Bonta Sumii | Combating a Culture of Busyness —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Dr. Aaron Goodson: LinkedIn | Website Important Links The Pelora Group CRN202807-9018579 The post Leading Well: Prioritizing Health to Sustain Impact with Dr. Aaron Goodson appeared first on Winning Through Culture.

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 advisors who want to listen with intention and drive meaningful outcomes. With a focus on financial services, the discussion dives into how leaders can move conversations from resistance to commitment—without relying on persuasion. Key Topics: Why traditional active listening can fall short—and how disciplined listening goes deeper How fear and embarrassment show up in high-stakes conversations Techniques to uncover the real concerns beneath client hesitation The power of building curiosity and credibility at the start of a dialogue Why “certainty is the enemy of listening” Common traps leaders fall into when they focus too much on control or outcome How to revisit conversations that didn’t go as planned—and rebuild trust Related Content: Showing Up Better with Ross Kimball: Improv Principles for Presence, Connection & Culture | The Psychology of Sales with Nicole Cramer —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Michael Reddington: LinkedIn | Website Important Links The Pelora Group CRN202806-8924024 The post Michael Reddington: Unlocking Commitment Through Disciplined Listening appeared first on Winning Through Culture.

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 more deeply, think on their feet, and foster an environment where ideas—and people—are truly heard. Key Topics: Why presence is a learned skill, not a fixed trait—and how to develop it How improv teaches quick thinking, adaptability, and empathy The power of storytelling to make messages stick and create connection Using “Yes, And” to strengthen team culture and encourage innovation The link between active listening and psychological safety Simple mindset shifts to be more present in meetings and conversations Why the best leaders aim to make everyone around them look good Related Content: Client for Life – Mastering Culture and Connection with Richard Weylman | Fostering Innovation with Dan Roselli | Innovation Series —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Ross Kimball: LinkedIn | Website Important Links The Pelora Group CRN202806-8869957 The post Showing Up Better with Ross Kimball: Improv Principles for Presence, Connection & Culture appeared first on Winning Through Culture.

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 why emotional connection, not just features, wins clients and how advisors can stand out in a commoditized industry. This episode is a roadmap to creating meaningful relationships and thriving practices. Weylman’s stories, from Freddy’s Steakburger’s $2.7 billion sale to his work with orphans, underscore the power of purpose and persistence in business and life. Key Topics: Why intentional culture is the foundation for client trust and business growth The Power of Why: Connecting with clients’ emotional needs, not just financial ones Underrated client acquisition tactics, like leveraging clients’ networks and associations Simple touchpoints—using preferred names, avoiding “follow up”—to boost loyalty Personal habits like daily devotions and positive affirmations for staying purpose-driven Related Content: High-Growth Strategies in Volatile Times with Dr. Rebecca Homkes | Being Intentional About Culture with Rob McKinnon —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Richard Weylman: LinkedIn | Website Important Links The Pelora Group CRN202805-8777409 The post Client for Life – Mastering Culture and Connection with Richard Weylman appeared first on Winning Through Culture.

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 blend of nostalgia, humor, and actionable insights, revealing how Tim’s Colorado roots and family legacy fuel his drive to build thriving, people-first cultures. Whether you’re an aspiring leader or a seasoned pro, Tim’s journey underscores the power of showing up and inspiring others. Key Takeaways: Childhood aspirations: From cowboy dreams to racing cars and beyond Early jobs and lessons in hard work, showing up, and relating to people Influential books like Managing Oneself and their impact on self-aware leadership The role of faith, family, and mentors in shaping a legacy-driven career Debunking the myth that leadership is easy—especially in today’s complex world Related episodes to “Behind the Mic: Leadership Lessons and Life with Tim Flanagan”:  Behind the Mic: Amanda Kramer’s Journey, Values, and the Power of Vulnerability  |  Coaching Tomorrow’s Leaders: Confidence, Growth, and the Power of Mentorship ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Rebekah Miller: LinkedIn Important Links The Pelora Group   CRN202805-8712399   The post Behind the Mic: Leadership Lessons and Life with Tim Flanagan appeared first on Winning Through Culture.

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 organizations can empower people to pursue their passions. Chelsea’s story highlights the power of community and curiosity, offering leaders and parents alike a roadmap for fostering inclusivity and impact. This conversation blends raw vulnerability with practical wisdom—showing how storytelling, kindness, and organizational support can create environments where everyone thrives. From educating kids to choosing words that uplift, Chelsea and Amanda reveal why living your values starts with listening and acting with intention. Key Topics: Launching The Fearfully Made to raise limb difference awareness and support moms Balancing family, work, and passion projects by prioritizing what matters most How organizations can foster stewardship by championing employees’ personal causes Educating kids on inclusivity with books like Different is Awesome and open curiosity The power of words in leadership to build kind, inclusive cultures Related Content: Core Value 5: Balance | Aligning Your Brand and Culture with Chelsea Pawlowski —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Chelsea Pawlowski: LinkedIn Important Links The Pelora Group CRN202804-8558779 The post Living Core Values: A Child’s Limb Difference Diagnosis to Advocacy with Chelsea Pawlowski appeared first on Winning Through Culture.

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 Pelora Group, Amanda has a unique perspective. But there’s more to Amanda than meets the eye—let’s dive in to learn more about her life, career, and what motivates her. Key Takeaways: Early Influences Matter: Amanda’s mom, a nurse, sparked her passion for caring—now channeled into leadership, not a stethoscope. Listening Over Fixing: A college peer mentoring gig taught her to ask, “Do they need advice, or just an ear?”—a skill she still uses daily. Travel Like a Local: With 30+ countries under her belt, Amanda swears by food tours and Airbnb neighborhoods over tourist traps. Stewardship in Action: Raising guide dogs with her family reflects her drive to leave the world better than she found it. Culture Myth Busted: It’s not just events and feel-goods—true culture builds trust, belonging, and tough conversations. Related episodes to “Behind the Mic: Amanda Kramer’s Journey, Values, and the Power of Vulnerability”:  Building a Purposeful Culture with Lila Ressler  |  “Lead Like You Were Meant To” with Rob McKinnon ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Rebekah Miller: LinkedIn Important Links The Pelora Group   CRN202804-8497087 The post Behind the Mic: Amanda Kramer’s Journey, Values, and the Power of Vulnerability appeared first on Winning Through Culture.

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 driving success. Nicole introduces her Five-Step Dance framework, a structured approach to sales conversations that focuses on curiosity and connection to guide better decision-making. Nicole also shares insights on how effective questioning, preparation, and active listening create stronger sales interactions. Slowing down, rather than rushing a deal, leads to deeper trust and more meaningful relationships.  Key Topics: The Psychology of Sales – Why sales isn’t about selling but helping people make buying decisions. Connection Over Transaction – How relationships and trust fuel sales success. The Power of Questions – How curiosity and asking the right questions drive influence and leadership. Self-Leadership & High-Performance Culture – Why personal accountability and motivation set the foundation for success. Slowing Down to Speed Up – Why taking a step back in sales conversations leads to better outcomes and stronger relationships. Leading Sales Teams Effectively – Frameworks for coaching and supporting high-performing teams in a competitive market. Related Content: Leading Your Team to a Winning Culture with Sherry Winn | Living Your Core Values to Drive Growth: A Vision for 2025 About Nicole Kramer: Nicole Cramer is a Sales Conversation Coach, Keynote Speaker, and Exactly What to Say Certified Guide who works with professionals to master their sales conversations through connection, psychology, and leadership. A former #1 Fortune 500 salesperson, she now teaches sales psychology, strategic communication, and human connection to help clients sell with integrity, influence with purpose, and lead themselves to bigger opportunities—all through the power of self-leadership. —— Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will take you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips on remaining impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide you with opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Nicole Cramer: LinkedIn | Website Important Links The Pelora Group   CRN202803-8307423 The post The Psychology of Sales with Nicole Cramer appeared first on Winning Through Culture.

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 as a tool for creativity and human interaction. This is an episode about balancing technological innovation with people-first leadership. Key Discussion Points from AI in the Workplace & Culture: Understanding AI’s Role in the Workplace: AI as a tool, not a replacement—enhancing productivity and saving time. Examples of AI integration: ChatGPT, Perplexity, and other AI tools. The importance of teaching teams how to use AI effectively to enhance—not hinder—human connection. AI’s Influence on Workplace Culture: The balance between efficiency and human connection. AI’s role in enhancing team dynamics and collaboration. Real-world examples of AI enhancing internal communications and leadership interactions. AI as a Tool for Professional Growth & Efficiency: Leveraging AI for leadership development, curriculum design, and strategic thinking. Using AI to refine communication, enhance productivity, and free up creative space. The importance of teaching employees how to ask the right questions to maximize AI’s potential. Balancing AI & Human Leadership: AI as a support tool to increase white space for human connection and strategic work. The importance of human intuition, empathy, and leadership in an AI-enhanced workplace. Maintaining human-centric values and culture while embracing technological advancement. Related episodes to “The Impact of AI in the Workplace & Culture”:  Innovating New Solutions with Catapult CEO, Dr. Cheryl Richards  |  Fostering Innovation with Dan Roselli ——  Tune into Winning Through Culture on your preferred Podcast platform Apple Podcasts Spotify YouTube Music About Winning Through Culture In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant. That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant. With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur. This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth. Let’s create a winning culture together! Connect with Us Tim Flanagan: LinkedIn | Instagram Amanda Kramer: LinkedIn Important Links The Pelora Group   CRN202802-8209869 The post The Impact of AI in the Workplace & Culture: Navigating Change & Embracing Innovation appeared first on Winning Through Culture.