Leadership lessons: How success is never a straight line

What does winning actually look like?

It’s a simple question, but one that often receives surprisingly superficial answers. Wins are celebrated. Trophies are polished. Careers are summarised through titles and accolades. The difficult parts, the setbacks, doubts and failures that made success possible, are often left out of the story altogether.

That is precisely what makes the third series of Rosenblatt Law’s Winning podcast so compelling. Hosted by Ian Rosenblatt OBE and, once again, produced by SEC Newgate, the third series continues to explore the mindset behind exceptional achievement. But rather than treating success as a destination, Winning focuses on the often-messy journey required to get there. In doing so, it manages to be both engaging and genuinely insightful.

The strength of the format lies in its guests and its host. On paper, there is little that connects music producer, Sir Robin Millar; Rabbi Baroness Julia Neuberger; banker, Matthew Westerman CBE; 55/Redefined founder, Lyndsey Simpson; and Sir Ian Blatchford. They come from entirely different worlds.

And yet a common theme quickly emerges, with Ian Rosenblatt often able to extract personal and insightful details through his hosting style – which for me offers a good reminder of the importance of listening.

Whether discussing leadership, entrepreneurship, faith, creativity or resilience, each guest reveals that success is rarely the result of a flawless masterplan. More often, it stems from adaptability, persistence and a willingness to embrace uncertainty. One word I’ve noticed guests often use is “serendipity”. That’s not a word I hear often in everyday life. But the truth is that most successful people, in addition to their talents, also need some luck and good fortune.

Sir Robin Millar’s reflections on the music industry are particularly fascinating, revealing that he once turned down Michael Jackson. Meanwhile, Rabbi Julia Neuberger tells the story of her family’s escape from Nazi Germany and her later career challenging convention. Matthew Westerman provides valuable lessons from the world of high-level finance, including when markets go drastically wrong, while Lyndsey Simpson’s entrepreneurial journey demonstrates how challenging accepted wisdom can create entirely new markets. Sir Ian Blatchford rounds out the series with insights drawn from leading some of Britain’s most respected cultural institutions.

The result is a collection of conversations that feel completely authentic.

Having filmed some of the episodes, I was also able to see first-hand why the interviews work so well. There is a natural curiosity from Ian Rosenblatt, which encourages guests to move beyond the polished anecdotes and into the experiences that genuinely shaped them.

The podcast landscape is increasingly crowded, with countless programmes competing for attention. What distinguishes Winning is its ability to draw lessons from remarkable people without becoming self-congratulatory or formulaic.

The growing recognition received by the podcast, through industry awards and nominations such as the Corporate Content Awards, is therefore well deserved. More importantly, it reflects the fact that Winning has developed into something larger than a corporate podcast. It has become a genuinely interesting exploration of what achievement, leadership and fulfilment look like across different professions and different stages of life.

The truth is that there is no single blueprint for success.

The third series of Winning demonstrates exactly why.