EPISODE · Jun 24, 2026 · 59 MIN
48: Two Million Reasons to Ask More Questions
from Bad Boss Confessional · host Speakeasy Podcast Network
In this episode of Bad Boss Confessional, Beth Fahey sits down with Dan Wallace, one of the first EOS implementers and a former turnaround operator with a background spanning Harvard Business School, investment banking, and strategy consulting. Dan's confession is a good one: six weeks into a new role, he green-lit a $2 million software build that the company never launched. The conversation explores what happens when a high quick start moves before they've truly understood the problem, why buying is almost always better than building, and what it costs a team when the person at the top has no one to slow them down. Dan also reflects on the two leadership lessons he stumbled into by accident, both of which still shape how he coaches teams today. Timestamps 00:00 Introduction to Dan Wallace 02:50 Career Shift to Turnarounds 07:39 Joining EOS and Growth 11:25 The Niche Lending Company Challenge 15:05 The $2 Million Software Mistake 24:50 Visionary-Integrator and Empathy 33:32 Lessons: Do Ask, Don’t Tell 40:09 Preparing for Departure 43:02 The Need for Operating Systems 50:47 Walmart Missionary Mix-Up 53:11 Humility and Kindness Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces. Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events
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48: Two Million Reasons to Ask More Questions
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