Bad Boss Confessional
Bad Boss Confessional
Speakeasy Podcast Network
48: Two Million Reasons to Ask More Questions
59 minutes Posted Jun 24, 2026 at 9:00 am.
Introduction to Dan Wallace02:50 Career Shift to Turnarounds07:39 Joining EOS and Growth11:25 The Niche Lending Company Challenge15:05 The $2 Million Software Mistake24:50 Visionary-Integrator and Empathy33:32 Lessons: Do Ask, Don’t Tell40:09 Preparing for Departure43:02 The Need for Operating Systems50:47 Walmart Missionary Mix-Up53:11 Humility and Kindness
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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
 
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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/@BethFaheyWant 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/orderDownload free Rollout resources at https://www.rolloutbook.com
Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events