In this episode of the Connected Leadership podcast, host Andy Lopata investigates the power of asking “what if?” with guest Stephen Bailey. Stephen is an entrepreneur, leadership and workforce expert, and co-founder of Exec Online the pioneer of online leadership development for enterprises. He oversees the organisation’s strategic vision and broader efforts to connect all leaders to their future potential through online learning and Coaching. Stephen graduated from Yale Law School, and is on the boards of the Truman Center for National Policy, Match Group, Ibotta, and Prospects Schools, a charter school network in New York City.

The discussion explores how Stephen’s journey from corporate lawyer to entrepreneur was fueled by a profound desire to make a meaningful impact on the world, a desire that led him to choose the path of risk and innovation over the perceived safety of a traditional career.

Stephen shares his experience of leaving the security of a Yale law degree and a lucrative law firm to join a startup. His decision was not driven by a fear of failure, but rather a fear of regret – a powerful insight that resonates with the podcast’s theme. He reflects on the importance of fostering a “what if?” mindset, not just within organisations but also among external partners. Stephen emphasises the need for leaders to create a culture of boldness, curiosity, and purpose, where individuals are encouraged to embrace discomfort and push boundaries, leading to innovation and continuous improvement.

Andy and Stephen examine how this mindset impacts Exec Online’s approach to leadership development, highlighting their transition from traditional in-person programmes to a more dynamic, online-centric model. Stephen shares the challenges and lessons learned during this evolution, emphasising the iterative process of experimentation, adaptation, and learning from failures.

The podcast concludes with Stephen reflecting on the impact of this “what if?” mindset on his personal and professional life. He acknowledges that while this approach can be stressful, it ultimately leads to a greater sense of fulfillment and the ability to make a positive difference in the world.

This episode of the Connected Leadership podcast offers valuable insights into the power of embracing a “what if?” mindset for leaders and entrepreneurs alike. It encourages listeners to consider their own desires to contribute and make an impact, and to embrace risk and innovation as essential components of personal and professional growth.

Connect with Andy Lopata: Website | Instagram | LinkedIn | X/Twitter | Youtube

Connect with Stephen Bailey: Website | X/Twitter | LinkedIn |

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Andy Lopata Author, Podcast Host and Speaker on Professional Relationships Strategy

Andy Lopata is a specialist speaker on professional relationships, mentoring, networking, and social media strategy. He is a firm believer that professional relationships underpin our success in business, our roles, and our careers. The right relationships with the right people can lead to new business opportunities, investment, collaborative working, innovation, and career progress. We just need to be comfortable approaching those relationships strategically, without making people feel ‘networked’ by us.

Andy has worked in the field of networking and professional relationships for 25 years, working with global giants such as Paypal, GSK, AstraZeneca, Wella, HSBC, Wembley Stadium, the BBC, and the Prime Minister’s Office of the UAE, among many others during that time. He has also worked with leading universities including NYU, Duke University, and Oxford University’s Said Business School.

A regular blogger for Psychology Today, Andy has been quoted in The Sunday Times, The Financial Times, and The Guardian, as well as many other national and regional newspapers and magazines worldwide. He has written or co-authored six books on networking and professional relationships, with his sixth book, "The Financial Times Guide to Mentoring," being published in Spring 2024. He is also the host of The Connected Leadership Podcast and has interviewed globally recognized names in business, academia, sports, and entertainment for the show.

Andy has been inducted into the PSAE Hall of Fame – the Professional Speaking Association Award of Excellence, which was held by only 21 other speakers at the time it was presented. He is a Fellow and a former President of the Fellows’ Community of the Professional Speaking Association (PSA), a Fellow of the Learning and Performance Institute (LPI), and a Member of the Association of Business Mentors and the Meetings Industry Association.