#0445  –  The Skills AI Can’t Replace with Katie O'Malley

#0445 – The Skills AI Can’t Replace with Katie O'Malley

Author: Jon S. Rennie August 23, 2026 Duration: 39:40
As AI continues to reshape the workplace, what will separate the people who thrive from those who get left behind? In this episode of Deep Leadership, I’m joined by Katie O’Malley, executive coach, leadership educator, and founder of Encourage Coaching. Katie has spent more than 20 years helping people build meaningful careers, become stronger leaders, and create more courageous workplace cultures. We discuss why the future of work may depend less on technical skills and more on the distinctly human skills that AI can’t replicate. Katie explains why critical thinking, learning agility, communication, empathy, and listening will become increasingly valuable as technology changes how work gets done. We also explore career pivots, finding work that aligns with your values, giving employees greater agency, building trust during times of rapid change, and why leaders need to become much better listeners. In this episode, you’ll learn: • Why human skills will become more valuable in the age of AI• The two skills employers are looking for most right now• Why your past career experiences are never wasted• How to build a “stack” of skills that makes you more valuable• Why employees are pushing back against workplace change• How trust and agency help organizations adapt faster• Why listening is one of the most underrated leadership skills• Katie’s AIR formula for becoming a better listener• Why “ready” is a choice, not a feeling If you’re thinking about the future of your career, leading people through constant change, or wondering how to remain valuable in an AI-driven workplace, this conversation will give you practical ideas you can put to work immediately. Connect with Katie O'Malley: LinkedIn: ⁠⁠https://www.linkedin.com/in/kateomalley/ Instagram: ⁠⁠https://www.instagram.com/encouragecoachchicago/?hl=en Website: ⁠⁠⁠https://encouragecoaching.org/ TED Talk: https://www.youtube.com/watch?v=HUNGPk978uE Subscribe to Deep Leadership: If you enjoyed this episode, make sure to subscribe and share it with someone who wants to become a better leader. Sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Cadre of Men⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Farrow Skin Care⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Salty Sailor Coffee Company⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Leader Connect⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Qualified Leadership Series⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠HERE⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

For anyone who’s ever felt that leadership advice can be too theoretical or disconnected from reality, Deep Leadership offers a grounded alternative. Host Jon S. Rennie operates from a simple, powerful belief: “Leadership is a People Business.” This isn’t about abstract concepts; it’s about the tangible, often messy work of guiding teams and organizations. Jon brings a unique perspective shaped by his time as a Cold War Submarine Officer and over two decades leading within Corporate America before founding his own manufacturing company. In each episode, he translates that extensive experience into practical, actionable insights you can apply immediately. The conversations here delve into the core of what makes leadership work-or fail-across business, culture, and society. You’ll hear from Jon and a variety of expert guests as they explore the philosophical and practical dimensions of guiding people, discussing everything from daily management challenges to broader cultural forces that shape how we work. This podcast is built on the conviction that leadership matters profoundly, and that getting it right requires depth, reflection, and a relentless focus on the human element. Tune in for thoughtful discussions that cut through the noise and get to the heart of leading well.
Author: Language: English Episodes: 50

Deep Leadership
Podcast Episodes
#0449  –  Too Many Ideas Are Killing Your Team with David Fung [not-audio_url] [/not-audio_url]

Duration: 38:23
Too many ideas can be just as dangerous as too few. In this episode of the Deep Leadership podcast, I talk with David Fung, a former senior director at Salesforce who spent more than 20 years in tech before founding Coac…