Jonathan Bennett: The #1 Job of a Leader is to Replace Yourself

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

Boost your productivity by prioritizing critical tasks and projects! Instead of merely checking boxes, focus on meaningful activities that make a real impact. Identify and prioritize tasks that contribute most to personal and organizational success. By concentrating on what truly matters, you'll achieve more and make a lasting difference. That's the key to a more productive day! #ProductivityHacks #TaskPrioritization #SuccessStrategies⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

Make today count by setting clear, achievable goals with specific actions and outcomes. Planning your day ensures you don't miss opportunities that come your way. Don't wander aimlessly—have a plan, execute it, and achieve your goals. #DailyGoals #ActionPlan #Productivity⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

This episode of Start With a Win brings together two of the most dynamic voices in leadership, Anne Morriss and Frances Frei, for a conversation that challenges outdated business mantras and replaces them with a powerful alternative. With wit, clarity, and decades of experience guiding organizations and leaders at the highest levels, they reveal how true impact is created - not by choosing between speed and care, but by mastering both. From Harvard classrooms to global boardrooms, their insights cut through the noise and inspire a fresh way of thinking about trust, momentum, and solving big problems. If you’ve ever wondered how great leaders accelerate results without sacrificing integrity, this conversation with host Adm Contos is one you won’t want to miss.Anne and Frances are best-selling authors, influential leadership experts, and the founders of The Leadership Consortium—a pioneering accelerator focused on building inclusive executive teams and preparing the next generation of senior leaders. Frances is a Harvard Business School professor and former SVP of Leadership and Strategy at Uber, where she led efforts during a time of massive transformation. Anne is a serial entrepreneur and sought-after leadership coach. Together, they advise top companies—from startups to Fortune 10s—on strategy, operations, and culture, helping leaders navigate complex change. They’ve co-authored three acclaimed books, including Move Fast & Fix Things, and co-host Fixable, a TED Audio Collective podcast. Their work and insights have been featured in viral TED Talks and recognized by Thinkers50 as among the world’s top management thinkers.00:00 Intro02:01 Moving fast gave this a bad name…05:20 Great leaders do this!08:20 Here is the secret sauce!12:25 What is Monday-Friday?17:01 Look at problem through this lense – 3 key words…22:30 Talk to stake people?...celebrity the uncommon. 34:16 Empower AND Delegate and two other Fridays…39:18 Always on the beach and the night before?    https://anneandfrances.com/https://anneandfrances.com/fixablehttps://anneandfrances.com/fix-things https://tlcleaders.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

Boost your productivity by prioritizing critical tasks and projects! Instead of merely checking boxes, focus on meaningful activities that make a real impact. Identify and prioritize tasks that contribute most to personal and organizational success. By concentrating on what truly matters, you'll achieve more and make a lasting difference. That's the key to a more productive day! #ProductivityHacks #TaskPrioritization #SuccessStrategies⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

One of the top skills every leader needs: constant learning. Trust me, it's a game-changer. Remember what my mentor once told me? Be a sponge. But here's the kicker: being a leader isn't just about soaking up knowledge, it's about giving back too. Soak up new insights, then share them with others. That's how you level up as a leader. Leaders learn, and learners lead. Don't miss out on today's quick win! #LeadershipSkills #ContinuousLearning #QuickWins⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

This episode of Start With a Win dives deep into the heart of leadership and culture with Jim Stevenson, founder and CEO of The Bletchley Group. From global brands to scrappy startups, Jim has been in the trenches helping businesses transform, scale, and thrive. Adam and Jim uncover why culture is the true engine of growth, how leaders unknowingly sabotage their teams, and what it really takes to build organizations that win. Packed with candid stories, hard-earned lessons, and bold insights, this episode challenges leaders to rethink how they hire, trust, and empower their people. If you’re ready to sharpen your leadership edge and uncover what truly drives sustainable success, you won’t want to miss this one.Jim Stevenson is the founder and CEO of Bletchley Group, a renowned International Growth Consultancy with 23 years of expertise in strategy, transformation, and growth. He established Bletchley Group with a fundamental belief that while technology is powerful, it should always serve a meaningful purpose. Jim's unique value stems from his diverse background, having worked in numerous roles across a wide array of companies. This experience has provided him with a valuable bird's-eye view of business operations, enabling him to identify common mistakes made by businesses.00:00 Intro02:38 What is first to focus on, if you get it right everything else becomes easy? 06:01 Customer this is the key point!07:43 Great concept is…10:02 Follow special forces on this…14:30 Might need to check your HR process…17:02 Your job as a leader is to do this!  23:30 Common problems from leaders and stop doing them.26:02 I realized and I changed my routine…w: www.bletchleygroup.coml:  http://uk.linkedin.com/in/jimstevensont:  http://twitter.com/JimStevenson===========================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

Enhance your team's productivity through strategic resource management! Assess and allocate time, budget, and personnel effectively to maximize results. Beware of resource creep, which can lead to unnecessary spending and wasted time. Combat business waste by continually evaluating resource utilization, ensuring optimum efficiency, and identifying areas for cost savings. Achieve more by managing resources efficiently. That's your quick win for the day! #ResourceManagement #Efficiency #Productivity⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

Ever wondered about the real secret to success? Spoiler alert: it's not overnight. It's all about consistent effort, day in and day out. Trust me, there's no such thing as an overnight success story. Success is built on small, actionable steps taken every single day. So, roll up your sleeves, put in the work, and watch those small efforts compound into something incredible. That's your quick win for today! #SuccessMindset #ConsistencyIsKey #QuickWin⚡️FREE RESOURCE: 𝘞𝘩𝘢𝘵'𝘴 𝘞𝘳𝘰𝘯𝘨 𝘸𝘪𝘵𝘩 𝘠𝘰𝘶𝘳 𝘓𝘦𝘢𝘥𝘦𝘳𝘴𝘩𝘪𝘱?  ➡︎ https://adamcontos.com/myleadership===========================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

In this powerful episode of Start With a Win, Adam Contos is joined by Dr. Alexa Chilcutt - executive presence expert and faculty lead at Johns Hopkins Carey Business School - for an eye-opening conversation about what it really takes to lead with confidence, credibility, and authenticity. From navigating imposter syndrome to mastering the unspoken signals that define how others perceive you, this episode uncovers the often-overlooked elements that can elevate -or quietly undermine - your leadership. If you've ever wondered why some leaders inspire trust and authority the instant they enter a room, this is the episode you can’t afford to miss.Alexa Chilcutt, Ph.D. is a nationally recognized expert in executive presence, team communication, and professional public speaking. She is the Faculty Lead for the Business Communication Certificate at Johns Hopkins Carey Business School and co-leads the Academy for Women and Leadership. In addition to her work at Johns Hopkins, she designs custom corporate training programs and teaches executive education for Texas Christian University and The University of Alabama. A certified Executive Coach, Chilcutt specializes in leadership development for women and technical professionals. She is also the founder of Maestro CE LLC, delivering tailored communication coaching and programs for corporate clients. Previously, she directed The University of Alabama’s Public Speaking Program for over a decade and developed communication curricula for UAB’s Dental School and NSF-funded engineering research programs.00:00 Intro02:51 What is executive/leadership presence? 05:34 If you are not doing this that scares you then you are not taking this…09:08 How to deliver this without being egotistically?  10:44 Professional vs Personal Values  13:35 One of the biggest questions on executive presence?18:10 Action to take - What is your judgement of them as a leader? 22:50 How to own the space?   24:15 Difference between good and great leaders!26:36 Key piece of wisdom!29:12 Grounded? Https://www.linkedin.com/in/alexa-chilcutt-phd/===========================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