We Ran an AI Leadership Audit Live. Here’s What It Showed | Christopher Skinner and Chris Wessling

What happens when you run an AI leadership audit live on a global engineering firm? Christopher Skinner and Chris Wessling join David Carr to show what leadership mindset, discipline, and systems thinking reveal about AI readiness, and what any business owner can learn from it. Both guests return after their first episode on how AI can make culture worse when we are not intentional. This time, Christopher Skinner of Stealth Dog Labs runs a live audit of a publicly traded architecture, engineering, and environmental consulting firm (AECOM), built from publicly available statements by more than 275 of its leaders. Important context: the scores shown are an AI simulation of how an organizational psychologist might read those public statements. They are a conversation starter, not a formal assessment. The audit points to strong discipline and planning, which fits work where the bridges have to stay up, and very little systems thinking. From there the conversation turns to what that could mean when AI changes the work. Chris Wessling of Solomon Group, the process guy and a Baldrige examiner, adds where large organizations lose time and knowledge: in coordination, communication, and a pile of disconnected apps. They close on retiring experts and why mentorship still matters. In this episode you'll learn: → How an AI leadership audit is built from public statements, and what its scores can and cannot tell you → Why a disciplined, planning heavy leadership team can be a strength today and a risk when the work changes → How coordination and communication loss drains large organizations → Why knowledge transfer from retiring experts is a leadership issue → How app sprawl hides time you could win back Key Insight An audit is not a verdict. It shows what you have put out into the world, and the useful question is whether that matches who you want to be. Chapters 00:00 Welcome back and today's live AI leadership audit 01:48 Christopher Skinner on creating new variables for a changing business reality 04:07 Chris Wessling, the process guy 05:40 Why an AEC firm, and how the audit was set up 07:00 What the audit measures: purpose and business philosophy 09:32 Screen share: business philosophy scores 12:31 Who was analyzed: public statements from 275 plus leaders 14:30 Discipline and planning: a strength with an AI risk 17:09 The leadership gap and readiness for change 20:47 Perception, reasoning, memory, and planning 24:53 Institutional memory and losing the people who did the work 26:19 Demographic shift and the knowledge transfer plan 29:15 Is this who you want to be? Audits for individuals 31:05 Chris Wessling on baselines, deployment, and coordination loss 38:40 The age of acceleration and being proactive 40:34 Mentorship: people and process 42:43 How to connect with Christopher and Chris About the guests Christopher Skinner is a business transformation executive, data scientist, and co-founder and chief architect of Stealth Dog Labs. A search engine veteran with four technology patents, he helps companies, and mostly people, get ready for the future with AI. Chris Wessling is co-founder and managing partner of Solomon Group, which runs your marketing and reports what it earned. He brings a Navy Nuclear background, 25 years in operations, and Baldrige examiner experience, and looks for the smallest, least painful intervention with the biggest impact. Resources Christopher Skinner on LinkedIn:   / christopherjskinner   Stealth Dog Labs: https://www.stealthdog.com Chris Wessling on LinkedIn:   / christopherwessling   Solomon Group: https://solomongroup.ai Watch the first episode with Christopher and Chris: [ADD LINK] Leadership Clarity Call – Steward Your Business If you're a business owner or leader navigating growth, team challenges, leadership overload, or succession planning, this is a place to start. This 30-minute Leadership Clarity Call is designed to help you: → Identify where friction or misalignment is showing up → Clarify what is actually holding your business back → Determine the next step forward with confidence This is not a sales pitch and not generic advice. It is a focused conversation to help you move forward with clarity. Schedule here: https://calendar.stewardyourbusiness.... Phone: +1 909-404-9865 About the Business Roundtable Podcast The Business Roundtable Podcast brings together founders, executives, and experts to explore leadership, growth, and building sustainable businesses. Hosted by David Carr, founder of Steward Your Business, the podcast helps leaders build aligned teams, stronger organizations, and businesses that can grow without constant pressure. Like the video. Subscribe for more leadership conversations. Comment: Does your leadership team lean more toward discipline or systems thinking, and is that where you want it to be?