Show cover of My Worst Leadership Moment

My Worst Leadership Moment

We love hearing about mistakes people have made, relating to them and then learning from these mistakes. The 'My Worst Leadership Moment' series is a Leadership podcast where guests share their worst leadership moment. The focus is self reflection and showing vulnerability through the stories they share.


My Worst Leadership Moment with Brendan Rogers
Unlock the secrets to effective leadership as Brendan Rogers takes you on his transformative journey from a 19-year-old in accounts payable to leading global teams and eventually transitioning to a role where he empowers business owners. You’ll gain invaluable insights as Brendan shares candid experiences of political challenges and strained relationships during his corporate climb, and the pivotal decision that led him to focus on developing leadership skills. This episode promises a deep dive into the realities of corporate life and the power of following one’s true passion. Imagine learning from someone who turned his worst leadership moment into a catalyst for self-improvement and growth. Brendan opens up about a poorly managed team roster that taught him critical lessons in competence, relationship management, and mentorship. His story illustrates the importance of character development, continuous learning, and building strong connections. Through real-life experiences and hard-earned wisdom, Brendan lays out a three-pillar system for leadership success that will help you build confidence, enhance relationships, and make a meaningful contribution to your community. Don’t miss this episode packed with leadership lessons and inspiring narratives. The episode is also available on YouTube at:
20:14 7/6/24
My Worst Leadership Moment with Michael Crutcher
The show producer has not yet provided a description for this episode.
20:55 5/16/24
My Worst Leadership Moment with Angela Johnson
Discover the unforeseen rewards of leadership missteps with Agile and Scrum educator, Angela Johnson, as she brings to light her tumultuous journey with bad hires. Our conversation peels back the layers of her professional challenges, revealing the consequences of enlisting a rival and the resultant workplace toxicity. Angela’s transparency is a treasure trove of insights, guiding us through the self-doubt and chaos that marked her worst leadership moments. By unearthing the valuable lessons hidden in these experiences, she equips us with the strategies to handle similar situations with grace and minimal collateral damage. In our dynamic exchange, we dissect the intricacies of team dynamics and the art of making sound leadership choices amid conflict. Angela illustrates the transformation that comes from involving the team in hiring decisions, showcasing how collective input can steer morale and performance. She candidly underscores the pitfalls of emotional reactions, advocating for a grounded approach based on facts and data. Her compelling stories serve as beacons for leaders navigating the murky waters of hiring, stressing the significance of vulnerability, swift action, and the continuous learning curve that leadership embodies. Join us for a revealing session that resonates with every leader’s quest for professional growth. The episode is also available on YouTube at:
20:06 5/9/24
My Worst Leadership Moment with Phill Agnew
Unlock the hidden connections between marketing blunders and leadership gold with Phill Agnew, whose journey from academia to the trenches of the marketing world reveals must-know insights for every professional. Through a candid discussion, we navigate the treacherous gap between the classroom and the boardroom, with Phill’s personal evolution providing a roadmap for navigating the challenges of real-world applications of marketing principles. His tale delves into the critical skills often missed in formal education but are crucial for success and leadership within the industry, serving as a guiding light for marketers and leaders alike. Immerse yourself in the psychology of the ‘labor illusion’ and learn how this simple yet powerful concept can transform the perception of your work. Drawing from personal anecdotes and historical figures like Julius Caesar, we illustrate how effort visibility can dramatically bolster credibility and trust, cementing your status as a leader who truly invests in their cause. This episode not only highlights the significance of showing your work but also connects the dots to the broader implications of authenticity and dedication in leadership roles. Finally, we wrap up with a poignant revisit to a past guest’s worst leadership moment, emphasizing the invaluable lessons that come from vulnerability and the capacity to rise from setbacks. Through the art of message framing, we dissect the subtle yet profound influence leaders wield with their words, shaping team dynamics and driving performance. This episode is a treasure trove of wisdom for anyone looking to refine their leadership voice, underscored by the importance of positive reinforcement and clear, high expectations. Join us for a conversation that bridges the realms of psychology, marketing, and leadership, and come away with actionable strategies to lead with impact. The episode is also available on YouTube at:
28:17 5/4/24
My Worst Leadership Moment with Elizabeth Rosenburg
Elizabeth Rosenberg, the mastermind behind the Good Advice Company, graces us with her presence, unraveling the complexity of leadership and the entrepreneurial spirit. With a rich tapestry of experience in communications and marketing, Elizabeth intertwines the artistry of personal branding with the rare gift of intuitive mediumship, offering us a glimpse into the infectious joy she derives from her craft. As we venture through her narrative, she lays bare her own “worst leadership moment,” serving as a poignant reminder that our blunders can often be the most powerful tutors, teaching resilience and the wisdom to seek expertise where we lack it. Her transparency in discussing the rigors of assembling the right team is like a beacon, guiding emerging entrepreneurs on their path to constructing a robust foundation for their ventures. Our conversational odyssey with Elizabeth doesn’t shy away from the gritty lessons carved out of business missteps—particularly when it comes to the thorny thicket of vendor selection and the essential trust in one’s own instincts. Together, we dissect the trials of donning multiple entrepreneurial hats, the strategic play of leveraging strengths, and the judicious act of passing the baton to more capable hands in areas that fall outside our wheelhouse. Elizabeth’s keen insights into the dangers of misplaced trust in referrals and the diligence needed in vetting such endorsements are invaluable to anyone at the helm of a growing business. This episode is not just a trove of wisdom for those leading the charge in business, but a vibrant tapestry woven with the threads of financial vigilance, perpetual learning, and the transformation into a more impactful leader. The episode is also available on YouTube at:
19:08 5/4/24
My Worst Leadership Moment with Matty Elliott
There’s a moment in every leader’s career when the armor cracks and the light of vulnerability shines through. That moment came crashing down on me when I lost touch with my team, leading to one of my darkest professional days. But just like a phoenix rises from the ashes, my conversation with Matty Elliott, former rugby league coach and the visionary behind The Change Room, served as a powerful reminder of the beauty and strength that vulnerability and human connection can bring to leadership. Matty bares his soul, recounting his journey from the sidelines of the NRL to the frontlines of empowering leaders and teams through well-being practices. He illuminates the simplicity of infusing high-performance habits into our daily lives and underscores the significance of maintaining a laser focus on our unique strengths amidst challenges. Our heart-to-heart traverses the landscape of leadership, from the peaks of personal triumphs to the valleys of tough lessons learned. The resonance of Matty’s stories sheds light on the quintessential lessons of leadership—acknowledging the individual contributions that each team member brings and the profound impact of crafting strong, trusting relationships. He shares how these core principles helped him navigate the complexities of coaching and business ownership, emphasizing that at the end of the day, success hinges on the human connections we foster. With Matty’s candidness, we peel back the layers of leadership, revealing that the true power lies in our ability to be authentic, to truly listen, and to engage with our teams on a level that transcends the day-to-day grind. The episode is also available on YouTube at:
21:18 4/19/24
My Worst Leadership Moment with Jodie Hill
Join us as Jodie Hill takes us on a profound exploration of her leadership journey, marked by triumphs and trials alike. From her early days coaching sports to her impactful role in professional leadership and change management, Jodie shares the intricate dance between personal struggles and professional responsibilities. Listen to her gripping account of a leadership crisis that hit close to home amidst the turmoil of 2020—a year that challenged us all. As Jodie recounts the emotional ordeal of supporting her helper through a family tragedy and the concurrent upheaval in her business due to the pandemic, you’ll be moved by her vulnerability and strength. In this episode, we also discuss the powerful lessons learned when facing adversity head-on. Embrace the concept of leadership as a reciprocal journey, where the support of a team can transform challenges into opportunities for growth. Discover how Jodie embraced the art of Imago facilitation to foster deeper communication and understanding within her team. You’ll come away with practical insights on navigating uncertainty, including the importance of reaching out for support and the creative strategies that can emerge from crisis. Don’t miss this candid conversation with Jodie Hill that will inspire you to reflect on your own leadership path and the resilience it takes to weather any storm. The episode is also available on YouTube at:
22:24 4/12/24
My Worst Leadership Moment with Karen Page
Embarking on a leadership path often conjures up visions of unwavering decisiveness and the glamour of influence. Yet for Karen “Kaz” Page, her ascent through the IT industry’s ranks to an executive level with an overwhelming 36 direct reports became a crucible moment, revealing the stark contrasts between idealized leadership and the realities of personal aptitude. In a candid conversation, Kaz lays bare the soul-searching realization that her analytical prowess and leadership style might be ill-fitted for the emotional demands and diverse personalities of a startup’s high-octane world. Her tale is a testament to the courage found in introspection and the liberating truth that success doesn’t obligate one to fit the traditional molds of management. Navigating the intricate dance of leadership styles, our discussion pivots to the ‘fixer’ archetype, valued in the breakneck pace of startup life for its quick reflexes and adaptability. Here, Kaz and I unpack the idea that effective leadership isn’t about a universal template but designing an approach that magnifies one’s unique strengths and aligns with each context’s distinct challenges. Her journey of vulnerability and growth offers a refreshing perspective on how embracing one’s individuality can chart a course for impactful leadership that uplifts a team without the need for conventional command. Join us for this profound exploration that cuts through the facade of leadership stereotypes, celebrating the many paths to making a lasting mark within an organization. The episode is also available on YouTube at:
17:06 4/4/24
My Worst Leadership Moment with Barnaby Howarth
The resilience and warmth of Barnaby Howarth is nothing short of a beacon of hope, and our latest conversation with him is a testament to the human spirit’s tenacity. Barnaby, a stroke survivor who reinvented himself as an entrepreneur and resilience keynote speaker, took us on a journey through his life’s seismic shifts, from the devastating stroke at 25 to finding his footing again, both personally and professionally. He opens up about creating his podcast ‘Everyday Greatness’, where he uncovers the often overlooked splendor in the lives of ordinary people — proving that being a decent person is at the heart of true success. We also take a peek at Barnaby’s own podcast episodes, where he converses with an array of individuals, from sports stars to the humblest carrot farmers, drawing out their stories to show how kindness and goodness are the real cornerstones of achievement. Our dialogue then steers towards the subtle yet profound leadership lessons Barnaby has gleaned through his experiences. He shares anecdotes of connectivity and the ripple effect of consistent, incremental actions — wisdom he picked up both from his ABC days and while leading his own ventures. Through his eyes, we see how qualities like kindness, which some might mistake for a business liability, actually fortify the foundation of successful leadership. Barnaby has lived through challenges that test the soul, including scaling the heights of Kilimanjaro, and it’s through these narratives that we understand how everyday actions and genuine authenticity can contribute to a leadership style that not only inspires but resonates on a deeply human level. Join us as we explore the essence of what it means to lead with heart, and discover how you too can embody the greatness in the everyday. The episode is also available on YouTube at:
19:02 3/28/24
My Worst Leadership Moment with Ben Law (The Financial Bloke)
Discover the pivotal moments that shape effective leadership as Ben Law, affectionately known as the Financial Bloke, opens up about the trials and triumphs of his career. This episode serves as your gateway to understanding the nuanced art of hiring and the critical importance of aligning values within a team. Ben, with his wealth of experience as a financial advisor and podcaster, shares a powerful narrative of his worst leadership blunder, delving into the repercussions of compromising on hiring principles. His tale is a stark reminder that the decisions we delay may define our professional landscape more than the ones we eagerly embrace. The conversation then shifts towards the often-overlooked practice of values-based decision-making, where Ben and I dissect the complex dance of handling discordant client relationships. Drawing on the profound insights of thinkers like Jordan Peterson, we discuss the perilous cost of shirking tough dialogues in business. You’re invited to absorb Ben’s seasoned perspective on assembling a team that resonates with your company’s ethos, fostering a culture steeped in honesty, and mastering time management. Join us for an enriching session that promises to leave you with actionable lessons for cultivating leadership that is as resilient as it is empathetic.
16:02 3/21/24
My Worst Leadership Moment: A Heart-to-Heart with Andrew Stotz
Walking through Bangkok’s vibrant streets, inspiration struck Andrew Stotz like a bolt of lightning. The result? The “My Worst Investment Ever” podcast, a project that not only opened up a wellspring of shared wisdom on financial mishaps but also sparked the creation of our leadership-focused series. Join us in an intimate discussion with Andrew as we uncover the roots of his transformative show. We reminisce about my own experiences as a guest on his platform, where lessons in leadership are distilled from the bitter brew of past errors. This episode is a tale of innovation, adaptation, and the sweet victory that awaits when one dares to tread the untrodden path. Every leader carries a mosaic of memories, a collection of triumphs and trials that shape their journey. Andrew’s canvas is rich with the colors of resilience: from the challenges of the Asian financial crisis to the heartache of personal loss, his rise to the presidency of the CFA Society Thailand is a stirring anthem to perseverance. Listen closely as we peel back the layers of Andrew’s inspiring climb and the indelible lessons on harnessing the strength of diverse opinions. His narrative is a beacon for all who seek to understand how confronting and embracing adversity can sculpt a more empathetic, robust leader. Closing our conversation, we turn the focus inward, reflecting on the transformative power of communication and the grace found in redemption. I share a chapter from my own book of leadership, where challenging a client’s ire led to a mutual breakthrough in understanding and respect. We also trace the path of extending a hand to those in need, illustrating how past missteps can be reformed into guiding lights for others. As our laughter intertwines over the quirks and quips of being podcast hosts, we seal this episode with a commitment to learning and staying vulnerable—a promise to keep mining the depths of leadership, one story at a time. The episode is also available on YouTube at:
28:27 3/15/24