EPISODE · Oct 15, 2025 · 26 MIN
Jonathan Bennett: The #1 Job of a Leader is to Replace Yourself
from Start With A Win · host Adam Contos
In this episode of Start With a Win, Adam Contos sits down with Jonathan Bennett, a seasoned executive, advisor, and coach who has walked the path from building a thriving consulting firm to reinventing his career with deeper purpose. Together, they peel back the curtain on what most leaders avoid discussing - transitions, fulfillment, and the hidden weight of leadership. With candor and insight, Jonathan shares stories of growth, reinvention, and the art of truly listening - offering a rare window into the challenges and opportunities that come with leading at the highest levels. This is a conversation that will make you pause, reflect, and rethink how you define success and leadership in your own journey.Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies.00:00 Intro01:59 A single aha moment…03:56 Oh no who is leaving…do you have this in place?07:05 I spotted these core competencies and knew this person was the next CEO!10:55 Need to go on this journey to get unstuck.15:25 How can leaders benefit from listening however not just listening but this! 20:25 Are we wandering or focusing?24:25 Start not here but here for this management! https://clearlythen.com/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook ➡︎ https://facebook.com/AdamContosCEOTwitter ➡︎ https://twitter.com/AdamContosCEOInstagram ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory
What this episode covers
In this episode of Start With a Win, Adam Contos sits down with Jonathan Bennett, a seasoned executive, advisor, and coach who has walked the path from building a thriving consulting firm to reinventing his career with deeper purpose. Together, they peel back the curtain on what most leaders avoid discussing - transitions, fulfillment, and the hidden weight of leadership. With candor and insight, Jonathan shares stories of growth, reinvention, and the art of truly listening - offering a rare window into the challenges and opportunities that come with leading at the highest levels. This is a conversation that will make you pause, reflect, and rethink how you define success and leadership in your own journey.Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies.00:00 Intro01:59 A single aha moment…03:56 Oh no who is leaving…do you have this in place?07:05 I spotted these core competencies and knew this person was the next CEO!10:55 Need to go on this journey to get unstuck.15:25 How can leaders benefit from listening however not just listening but this! 20:25 Are we wandering or focusing?24:25 Start not here but here for this management! https://clearlythen.com/===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook ➡︎ https://facebook.com/AdamContosCEOTwitter ➡︎ https://twitter.com/AdamContosCEOInstagram ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory
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Jonathan Bennett: The #1 Job of a Leader is to Replace Yourself
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