Dot to Dot Life Connected™

From football boots to Dr Martens with CEO Kenny Wilson

Episode Summary

Some of the topics we explore this week - How a school boy en route to becoming a professional footballer ended up as CEO of Dr Marten’s, why a belief that ‘the harder you work the luckier you get’ can only get you so far, how important it is to love what you do and why no matter how senior or successful you are you still learn from other people. Kenny Wilson who describes himself as ‘a 52 year old Scottish bloke’ has been Chief Executive at the iconic brand Dr Martens for the past 2 years having previously spent 6 years as the Chief Executive of Cath Kidston. When I heard that Kenny was moving to Dr Martens it felt like a natural fit. The brand is about rebellious self-expression, independent thinkers and people who stand up for what they believe in – all things that reflect the depth and character of Kenny as person and a leader.

Episode Notes

Kenny spent the majority of his career working for another symbolic brand - Levi’s in roles spanning the globe, which he describes as being hugely informative in his development as a leader. He began working with a coach 20 years ago and has never stopped seeing it as essential to his growth saying that “As a leader the first step is being able to lead yourself” going on to say being a leader is about asking the right questions “You don’t need to have the right answers or to be the smartest person in the room”. Although having worked with Kenny I would wager a bet that he often is. He also describes how he prepares for each day as a leader by thinking “Not what needs to be done but how to be.” Because people will remember how you make them feel. 

In this episode Kenny describes growing up on a council estate in Aberdeen and how that didn’t make him “hard done by” but did focus his drive. He also explains how the form that his drive has taken has changed over the years. We discuss bringing up girls and how he wants his daughter who is now at university, to grow up as a strong independent woman able to make her own decisions about how to live her life. Also, how hard that is to do, far harder than any leadership role. Despite giving up a career in football Kenny has remained an avid supporter of Aberdeen and has been going to matches with his daughter since she was 7 years old. He shares how football is about his roots, where he grew up, unwinding and spending time with mates who couldn’t care less that he’s a CEO. Kenny also shares how important it is to him that people are respectful, no matter who they are talking to or where they are from. I hope you find him as interesting and motivating to listen to as I do.