In this episode, David sits down with John Holcombe from JH Leadership, https://jhleadership.com/ - a certified executive coach and author of Creating Value Faster: The Leadership Guide to Customer Insight-Driven Innovation who has spent decades watching what happens when leadership judgment fails to travel into rooms the leader is not in - to unpack what AI actually demands of the people who lead. Moving beyond the pressure of "just deploy AI," the conversation explores why AI is less a technology problem than a leadership one - exposing organizational fault lines, eroding trust, and forcing a reckoning with how deliberate leadership either extends the loop or exposes it.
Key topics covered:
AI as the fourth answer: Leaders have spent entire careers solving one question - how do you carry your judgment into rooms you are not in? Management layers, playbooks, and training were partial answers. AI is the fourth. It either extends the loop or exposes it. This episode frames why AI magnifies whatever is already broken beneath the surface of the organization.
The blurred North Star: AI does not move the North Star. It blurs it. Leaders inundated with information and forced to accelerate decision-making without a well-designed organization underneath them find that AI only magnifies the cracks. The C-suite can walk away from a congenial meeting thinking everyone understood the same picture - and be wrong.
The leadership arc of identity, altitude, and influence: John outlines the evolution from subject matter expert to conflicted doer-leader to architect and commercial operator. Each turn requires self-awareness, courage, commitment, and follow-through. Skipping the turns is what produces leaders who command instead of influence - and AI is exposing them faster than any prior technology cycle.
The influence gap where AI does the most damage: When AI surfaces problems teams were not aware of, untrained leaders attack the team instead of the problem. Copilot gets rolled out to everyone, governance is absent, and the gap between authority and influence widens. Command-and-control leaders are flushed out immediately - AI accelerates the discontent that was already there.
Delegating authorship to a machine: David shares a firsthand observation - functional leaders submitting AI-generated reports with polished visuals but uncorrelated data, telling the leader "you did a good job" without ever reading the output. The result: trust erodes from "trust and verify" to "trust and validate," and the leader becomes the inspector of work they should not have to inspect.
The magnifying glass and the loop: In a moment of parallel emergence between host and guest, John names what he calls "the cycle loop" - the connective tissue between leadership judgment, organizational execution, feedback, and adjustment. AI can either harness the loop or break it. Without maintaining what John calls "organizational integrity, for lack of a better term," AI accelerates the fracture faster than the leader can see the breakdown.
Job theory and the McDonald's milkshake: Borrowing from Clay Christensen, John reframes the AI question as a "job to be done" question. Before deploying AI, leaders must understand what the actual job is - for the customer, for the team, for the process. AI trained on meaningless data produces meaningless results. AI trained on real operational understanding becomes powerful.
Anthropic as a business coach: John shares the anecdote of a young executive using Anthropic as a business coach - a specific pattern showing how AI is already stepping into roles humans thought were uniquely theirs, and what it means for what leaders should actually be doing.
The dilution of authority: A leader's authority naturally dilutes over time as the organization watches their feet. When AI steps into that dilution without governance, breakage accelerates. David and John unpack where the breakage happens first - at the day-to-day task level, when tools are introduced without buy-in, guardrails, or clarity about how work changes.
Technical debt and stovepipes: Siloed functions that do not understand how they impact each other create conflict at every organizational layer. John argues that servant leadership - humility, cross-functional dialogue, and understanding how my function impacts yours - is the antidote to the stovepipes that AI makes even more dangerous.
The one decision for the next 90 days: When a leader feels the loop breaking, the answer is not strategy - it is one decision: go talk to your teams. Engage cross-functionally, find where things are breaking, empower people to bring concerns and solutions, and ask the null hypothesis question: what happens if we do this, and what happens if we do not? Set guardrails at the top, but make sure they extend all the way down to the individual.
You get what you walk by: The episode closes with John's core message - the best leaders are not sitting at their desks. They are walking the floor, talking to customers, understanding workarounds, and building the relationships that make AI an amplifier of good design rather than an amplifier of brokenness. Or as John puts it plainly: when your hammer, everything looks like a nail - and with AI, most systems do not need the hammer, they need the loop.
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