WHAT IF.......? with Stephen Bailey

The Connected Leadership Podcast

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.

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