LeaderSips

Hosted by Karlynn Holbrook

Business Careers Education

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Episodes

229

Latest episode

Oct 2026

Language

EN-US

About the show

As a leader with more than 25 years of global leadership experience, I have seen firsthand how the best leaders can inspire people to fulfill their purpose and passion, while the worst leaders can quite literally ruin someone's potential. Join me for a few sips of leadership tips to help you become a better leader by first conquering the hardest person to lead: you. For more about me, visit www.karlynnholbrook.com

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60 recent

October 15, 2026Episode 5854 min

AI Is the Mirror: What Technology Reveals About Our Leadership with David Dean

Like or didn’t like what you heard? Share your sip with me! Is AI really changing leadership—or is it revealing things about our leadership that were already there? In this episode of LeaderSips, I sit down with author, speaker and Business AI Realist David Dean , author of An Inbox Between Us , for a fascinating conversation about artificial intelligence, organizational behavior and the very human side of how work actually gets done. David challenges us to look beyond the hype surrounding AI and consider something much more important: What is AI revealing about our organizations, and about leadership? We talk about the difference between the organization that exists on paper and the one that exists in real life—the workarounds, relationships, conversations, judgment calls and unwritten rules that keep work moving every day. And as AI becomes more embedded in the workplace, those hidden systems become increasingly important for leaders to understand. Our conversation explores human judgment, authenticity, trust, accountability and organizational self-awareness, along with why technology can amplify both what’s working in a culture and what isn’t. And perhaps most importantly, we talk about why the rise of AI doesn’t make human leadership less important. It makes good human leadership more important than ever. Whether you’re already using AI every day, cautiously figuring out where it belongs, or wondering what all of this means for the future of work, this conversation offers a refreshingly human perspective. Grab your favorite sip and join us for a conversation about AI, leadership and why the human behind the technology still matters. Connect with David Dean: LinkedIn: https://www.linkedin.com/in/davidchristopherdean/ Website: https://www.davidchristopherdean.com/ Learn more about David’s book, An Inbox Between Us : https://www.davidchristopherdean.com/book/ Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

October 8, 2026Episode 5748 min

Setting the Stage for Leadership with Carlo D’Amore

Like or didn’t like what you heard? Share your sip with me! What can theater teach us about leadership? A lot more than you might think. In this episode of LeaderSips, I sit down with actor, director, playwright, producer, experience designer and Live In Theater founder Carlo D’Amore for a fascinating conversation about storytelling, human connection, creativity—and the power of play. This conversation was an especially fun one for me. As a former theater kid who started my Disney career in Entertainment, I’ve always believed there’s something special about the connection between the stage, production, and leadership. Carlo and I found plenty of common ground in the lessons theater teaches us about listening, trust, collaboration, presence, storytelling and giving other people their moment in the spotlight. Carlo has spent decades creating experiences that invite people to step out of spectator mode and become part of the story. We explore how those same principles translate to leadership: truly listening, creating environments where people feel safe enough to participate, embracing curiosity, building connection and recognizing that the people around us aren’t simply an audience—they’re part of the experience. We also talk about Carlo’s unconventional journey, the power of our personal stories, resilience, and why adults may need permission to play more than we realize. Because great leadership isn’t just about directing people. It’s about setting the stage, creating trust and giving others the space to step into the spotlight. Grab your favorite sip and join us for a conversation about leadership, storytelling, play and the courage to participate. Connect with Carlo D’Amore: LinkedIn Live In Theater: https://www.liveintheater.com Carlo’s website: https://www.carlodamore.com Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

September 23, 2026Episode 5647 min

Pouring into Gen Z: Leadership Lessons with Anjan Kasi Sampath

Like or didn’t like what you heard? Share your sip with me! How do we pour into the next generation of leaders while also learning from them? In this episode of LeaderSips, I sit down with TEDx speaker, Gen Z leadership coach and John Maxwell certified coach Anjan Kasi Sampath for an insightful conversation about leading Gen Z, navigating a multigenerational workplace and becoming a stronger, more intentional leader ourselves. Anjan shares insights from his Pressure-Proof Promotion Method and explores how trust, communication and consistent leadership habits shape the way people experience our leadership—and prepare us for what’s next. We also dig into what leaders can learn from Gen Z, how different generations can better understand one another, and why great leadership isn’t about expecting the next generation to adapt to the way we’ve always done things. It’s about creating the trust, connection and opportunity that help people grow. Grab your favorite sip and join us as we talk about pouring into Gen Z—and building stronger leaders across every generation. Connect with Anjan on LinkedIn and watch his insightful TedX talk . Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

September 7, 2026Episode 551 hr 5 min

Grounded Leadership: Finding Clarity Beyond the Grind with Michelle Scott

Like or didn’t like what you heard? Share your sip with me! What if becoming a better leader isn't about adding another strategy, habit, or leadership tool, but about understanding yourself? On this episode, I'm joined by Michelle Scott, Executive & Intuitive Leadership Coach , for a conversation about the internal side of leadership we don't talk about enough. With more than 15 years of experience coaching C-suite executives, senior leaders, founders, and rising executives, Michelle helps high-achieving leaders move beyond the cycle of striving, stress, overthinking, and burnout to lead with greater clarity, presence, confidence, and ease. Together we explore why self-leadership matters, the blind spots that can hold even highly successful leaders back, how our internal state affects the way we show up for others, and why intuition deserves a seat alongside strategy and experience when making leadership decisions. Because sometimes the next level of leadership isn't about doing more—it's about becoming more aligned with who you already are. So grab your favorite sip and join us for a conversation about leading from the inside out. ☕️ Connect with Michelle Scott: Website: Michelle Scott Coaching LinkedIn: Michelle Scott MA-CHH, D.S.S. Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

July 11, 2026Episode 5457 min

An Affogato of Agility: Sipping with Robin Sims-Allen

Like or didn’t like what you heard? Share your sip with me! What if the biggest obstacle to growth isn't your strategy—it's your bottlenecks? In this episode of LeaderSips , I'm joined by entrepreneur, agile strategist, and Phoenix Marcus founder Robin Sims-Allen for a conversation on leading with purpose, building resilient organizations, and creating businesses where people can truly thrive. With more than 20 years of experience in technology and business leadership, Robin shares how great leaders identify what slows teams down, cultivate healthy cultures, and create environments where innovation can flourish. We also explore the lessons she learned from launching startups ahead of their time, why resilience is every business leader's superpower, and how her passion for empowering women inspired the creation of TotalHER , a global platform built on connection, collaboration, and opportunity. Whether you're leading a team, building a business, or navigating your own next chapter, this conversation is full of practical leadership wisdom and encouraging reminders that success starts with serving people well. In this episode, you'll discover: How to identify and eliminate the bottlenecks holding your team back. Why human connection and culture are your greatest competitive advantage. Lessons every entrepreneur can learn about resilience, timing, and growth. How agile leadership creates stronger organizations. The vision behind TotalHER and empowering women through authentic community. Why leading with both ambition and heart produces lasting impact. Connect with Robin Follow her on LinkedIn Discover more about TotalHER where women lead the feed Read her blog and learn more about how Phoenix Marcus can help you thrive in this fast-paced, constantly evolving world So, grab your favorite cup of coffee and join us for another inspiring conversation—because every great leader has a story worth sharing, and every great conversation starts with a sip. Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

June 15, 2026Episode 531 hr 5 min

Brew Bold: Leadership & Empowerment with Marie Lee

Like or didn’t like what you heard? Share your sip with me! Grab your favorite cup of coffee and join me for an inspiring conversation with Marie Lee , Chief Marketing Officer of Princess Cruises and a former Disney marketing executive, whose leadership journey is a masterclass in courage, empowerment, and intentional growth. After nearly 25 years building world-class brands at Disney, Marie made the bold leap to help transform Princess Cruises during one of the travel industry's most challenging moments. In this episode, she shares what it really means to empower teams through trust, clarity, accountability, and the courage to let others lead. Topics we discuss: Why empowerment is built on trust, vision, and guardrails How great leaders create cultures of continuous feedback and growth The importance of taking ownership of your own career instead of waiting for opportunities Why resilience and grit often matter more than having all the answers How intentional self-reflection can shape your leadership journey Whether you're leading a global organization, a small team, or simply trying to become a better version of yourself, this episode is filled with practical leadership wisdom and actionable insights. Connect with Marie Lee on LinkedIn to follow her leadership journey and insights, and be sure to subscribe to LeaderSips for more conversations that help you grow in your leadership with tips while we sip. Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

May 23, 2026Episode 5228 min

50 Cups of Coffee & Counting

Like or didn’t like what you heard? Share your sip with me! In this special episode recorded on Siesta Key Beach, I’m inviting all of you to celebrate my 50th birthday with an honest conversation about life, leadership, gratitude, and the lessons that have shaped me over five decades. Pour yourself a cup, and take a beachside walk with me for an unplanned, unscripted, and unfiltered reflective episode about living fully, loving deeply, and leaving things a little better than you found them. Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

May 2, 2026Episode 5153 min

Lead Like a Fighter Pilot with Christian "Boo" Boucousis

Like or didn’t like what you heard? Share your sip with me! What happens when fighter pilot precision meets the complexity of modern leadership? In this episode of LeaderSips , I sit down with Christian “Boo” Boucousis —former Australian fighter pilot, CEO of Afterburner, and a global voice in high-performance leadership. For over 30 years, Afterburner has translated elite military execution into the business world, impacting more than 3,500 organizations and over 2 million leaders—including two NFL teams that went on to win the Super Bowl. Boo’s journey—from the cockpit to the boardroom—is grounded in a powerful truth: in high-stakes environments, success isn’t driven by motivation…it’s driven by mindset, method, and mission clarity. We explore what that looks like in practice, including: Why today’s leaders need iterative thinking , not instinctive reactions The principles behind Flawless Leadership —a next-generation model built for speed, alignment, and adaptability How to lead with precision without burning out your team We also dive into Boo’s latest book, The Afterburner Advantage —an Amazon bestseller in leadership—and enjoy a sneak peek of his new book, Flawless Leadership . Explore more from Boo: Website: https://callmeboo.com Interactive AI Agent: https://ai.afterburner.com So pour yourself a cup, lean in, and get ready to rethink how you lead, decide, and execute. In a world moving at full throttle, the leaders who win aren’t the busiest—they’re the clearest. ☕️✨ Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

April 25, 2026Episode 5051 min

Sipping on Sustainable Success with Shelley-Ann Pieterse | Leadership, Identity & Alignment

Like or didn’t like what you heard? Share your sip with me! I’m thrilled to welcome Shelley-Ann Pieterse—founder of Glimmer Coaching and an executive alignment coach supporting high-performing women and senior leaders navigating ambition, identity, and leadership transitions. A former Managing Director at Accenture, she built her career at the highest levels of global consulting before making a bold identity shift. Today, her work sits at the intersection of ambition and alignment—helping leaders redefine success in ways that are both human and commercially sound, without losing their drive or impact. Pour yourself a cup and settle in—I hope this conversation serves you as much as it did me. Connect with Shelley-Ann on LinkedIn and get to know more about Glimmer Coaching on her website Shelley-Ann created a special coaching guide just for podcast listeners that isn't available anywhere else, which includes: A reframed understanding of high-functioning burnout A clear introduction to the GLIMMER Framework™ A short self-check to assess where your success energises or drains you A structured next step if you want deeper clarity Take her FREE assessment as referenced on the episode. Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com

April 19, 2026Episode 491 hr 2 min

Sipping on the Leadership Skill We Don't Talk About Enough

Like or didn’t like what you heard? Share your sip with me! Pour yourself a cup and join me for a thoughtful conversation with Carissa Sechrist — a communications and content strategist who believes the best workplaces are built through trust, clarity, and genuine human connection. With experience across major global organizations in the food, beverage, and entertainment industries, Carissa has seen firsthand that communication is about far more than sending messages. It’s about helping people navigate change, creating healthier cultures, and supporting teams in high-pressure environments. In this episode, we dive into emotional regulation — a topic that inspired me to invite Carissa on after reading one of her powerful posts on LinkedIn. We discuss how the ability to manage your emotions during stressful moments can truly set you apart. In environments filled with pressure, tight timelines, competing priorities, and strong personalities, staying steady when tension rises is a leadership advantage. Emotional regulation isn’t about hiding your feelings. It’s about creating enough space between stimulus and response so you can choose wisely, respond thoughtfully, and lead with maturity. We talk a lot about leadership skills. We don’t talk enough about this one. This episode is full of practical wisdom for anyone learning to lead themselves well before leading others. Connect with Carissa on LinkedIn and visit CarissaSechrist.com Support the show For more sips and tips, connect with me on social and follow @LeaderSips @Leadspirations and @LifeisGrit on Instagram, Threads, X, Facebook, YouTube, and Pinterest. Learn more about me at karlynnholbrook.com