Good Employees Quit Bad Bosses | Brett Myles, Founder of LeadWell

Bad leadership isn't just a morale problem — it's costing U.S. companies $8.8 trillion a year in lost productivity. In this episode of Wall Street To Y'all Street, leadership expert Bret Myles breaks down why the most dangerous hire in any company is often your best individual contributor — promoted to manager with zero training.Brett has built a leadership operating system used by organizations including Chick-Fil-A. In this conversation, he gets real about what bad bosses actually cost, why one-off training workshops don't work, and what it takes to build leaders who make people want to stay.In this episode:- Why high performers get promoted into leadership roles they're not ready for- The "Pit of Despair" — and how leaders get stuck there without knowing it- Why disengaged employees are a leadership problem, not a people problem- The GIANT Framework: a repeatable leadership operating system- How to build trust fast as a leader — and the #1 thing that destroys it overnightTIMESTAMPS00:00 Why great employees get promoted before they’re ready to lead01:13 Intro: why most leadership training is a waste of time03:20 What in Brett’s background shaped how he thinks about leadership?04:10 When did Brett first realize he could lead other people?05:15 What did Brett learn from seeing both great leaders and bad leaders?08:05 Can bad leadership teach you as much as good leadership?08:55 What is the Support-Challenge Matrix — and why does it matter?10:05 Why do companies keep promoting people with no leadership training?12:20 How should companies prepare employees for leadership roles?12:55 Why does Brett say most leadership training is useless?14:10 Why do companies keep spending money on leadership training that doesn’t work?15:00 What do younger employees want from work that older generations didn’t ask for?15:35 Why execution problems usually start with trust and communication17:05 How much employee turnover is really caused by bad leadership?18:35 What is the most common leadership flaw Brett sees?19:15 What happens psychologically when someone gets promoted too fast?20:20 Brett’s “sharpen your axe” advice for overloaded leaders21:15 What is a leadership operating system?22:25 Why leadership development has to happen over time, not in one workshop24:20 Can leadership actually be measured?25:50 What is the biggest myth companies believe about leadership development?27:00 What leadership habit quietly destroys teams?27:35 Why “hire good people and leave them alone” is bad advice28:20 Why leadership has to be tailored to different personalities29:20 What is the fastest way for a leader to lose trust?30:20 What mistake do new managers make over and over?31:35 What separates great leaders from average ones?34:05 Can leadership systems work for companies of any size?35:05 Why leadership training should apply from CEO to first-year employee36:25 What happens to companies that never build a real leadership system?37:00 What does Brett’s 2.0 leadership rollout look like after the first year?Connect with Brett on LinkedIn at https://www.linkedin.com/in/brett-myles-leadwell/ or his company Leadwell at https://www.letsleadwell.com/⚖️ Need a corporate attorney who actually understands business and startups? Discover how Raetzer Law can help you scale and protect your company:🔗 https://raetzerlaw.com/📞 Call: (945) 221-6318✉️ Email: [email protected] Business Law, Mergers & Acquisitions and Securities Law (capital raising) ⚖️🎙️ABOUT THE HOST: Joseph J. Raetzer, MBA, JD is Corporate, Mergers & Acquisitions (M&A) and Securities Lawyer (capital raising). He started his career over 20 years ago on Wall Street and he has done over $100+ billion in transactions. He is also a serial entrepreneur with a successful 7-figure exit in under 3 years, and founder of his corporate M&A and securities law firm Raetzer PLLC. His podcast Wall Street to Y’all Street features real lessons from founders, operators, and executives who have built, scaled, lost, and rebuilt businesses. This is not legal advice - always consult with your attorney. Joseph J. Raetzer, MBA, JD is licensed in New York and Texas. 🎙️