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:

Related Content: “Lead Like You Were Meant To” with Rob McKinnon | The Intentionality of Company Leaders

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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!

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.

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.

—— 

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!

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:

Related Content: Prioritizing Mental Health in Sports and Business with Lisa Bonta Sumii | Combating a Culture of Busyness

——

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!

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:

Related Content: Showing Up Better with Ross Kimball: Improv Principles for Presence, Connection & Culture | The Psychology of Sales with Nicole Cramer

——

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!

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:

Related Content: Client for Life – Mastering Culture and Connection with Richard Weylman | Fostering Innovation with Dan Roselli | Innovation Series

——

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!

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:

Related Content: High-Growth Strategies in Volatile Times with Dr. Rebecca Homkes | Being Intentional About Culture with Rob McKinnon

——

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!

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.

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

—— 

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!

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:

Related Content: Core Value 5: Balance | Aligning Your Brand and Culture with Chelsea Pawlowski

——

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!

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.

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

—— 

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!

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:

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.

——

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!

CRN202803-8307423

The post The Psychology of Sales with Nicole Cramer appeared first on Winning Through Culture.