Beyond Vibe Coding: Why Questioning AI Output Is the New Core Skill
The Vibe Socratic Method: Why Questioning AI Output Is the New Core Skill
The art of deliberate questioning—a cornerstone of the Socratic tradition—has never been more vital. Generative AI now gives us full-stack reach: not just technical prowess, but the means to shape narrative, brand, and business strategy in one sweep. That promise is real, but it requires a level of discernment many organizations haven’t yet cultivated. The future isn’t about AI doing the work for us but about elevating the corporate strategist’s craft—mastering the Vibe Socratic Method: asking the right questions of what AI produces, teaching teams to examine, not just accept, and training for judgment, not just output.
This approach sits right at the heart of the Aspen Institute’s Executive Compass—anchoring innovation with empathy, inquiry, and clarity of purpose.linkedin
A Career of Full-System Vision
At Apple (2001–2010), I was immersed in bringing software and hardware together in ways that made devices magical. That meant understanding every moving part—the OS, rendering engines, platforms, retail, media relations, and beyond. Seeing the whole system was essential.
Later, at Cisco, I worked as a product strategy leader, supporting internal product executives across UCaaS and CCaaS portfolios. I drove initiatives that ranged from uncovering new AI opportunities to reinventing go-to-market execution, including launching the company’s first AI-driven sales battle card systems—tools that changed how sales teams connected complex solutions to real customer needs.
Today, as founder of a new startup at the intersection of AI and corporate strategy, I’m focused on building the tools and frameworks that can help companies harness next-gen AI responsibly—where questioning systems becomes second nature, and expertise means knowing which answers to probe, not just which buttons to push.
Three Forces Guiding the Shift
AI has collapsed the wall between idea and execution. Now, anyone with vision can prototype, iterate, and produce faster than ever. But this speed often outpaces understanding—making the skill of questioning that much more valuable.
Edges are the opportunity spaces. Previously, business logic and economics pushed teams toward the median. Today, AI enables meaningful customization, letting us serve unique workflows, minority languages, and smaller markets that were once left behind.
Empathic values are competitive differentiators. Technical barriers may be vanishing, but what endures is the human choice: did someone care enough to get it right—for the customer, not just the persona? Judgment, not just output, is now the differentiator.
The Real Cost: Judgment as a Discipline
The narrative around generative AI is often about speed and scale. But what’s rarely discussed is the cognitive overhead required: the expertise to distinguish between plausible-sounding results and what actually works.
These systems are notorious for bypassing human judgment in subtle ways. Companies now need a new discipline—questioning AI output with the rigor and practicality that executive strategy demands.
This means creating space for:
Probing assumptions and surfacing missing context
Diagnosing confident-sounding but flawed reasoning
Bridging the gap between what works in theory and what works in your market reality
Institutionalizing this curiosity—making it part of the institutional memory
The Vibe Socratic Method, in Practice
The new focus is not “does it work,” but “why this answer, not another?” What context drove the AI’s choice? Where did it generalize, where did it interpolate patterns, and where were edge cases missed?
With the volume of AI-generated output now flooding organizations, we need systematic frameworks—not exhaustive audits, but rapid, lightweight questioning aligned to real business needs.
Much as the Aspen Executive Compass calls for navigating with values, questioning AI output is an act of organizational self-awareness and intent. It’s about having the clarity to know when to trust, and when to dig deeper.
Encouraging Discernment as Key for the Next Era
Generative AI makes creation accessible, but the critical expertise—knowing how to interrogate those creations—is scarce. Without it, organizations risk mistaking velocity for progress and accumulating “judgment debt.” The adaptation? Recognizing that expertise in questioning isn’t a nice-to-have—it’s the new professional edge.
As much as AI liberates us from technical constraints, thriving with these tools requires a learning culture built on Socratic curiosity: probing gaps, validating assumptions, and never just accepting what’s generated.
Moving Forward
The heart of my work now—at the new venture—is architecting frameworks that keep human discernment front and center. AI tools will keep advancing, but real strategic advantage comes from organizations that consistently question, probe, and teach this discipline at every level.
In the end, the Socratic mindset isn’t about slowing down innovation. It’s about making sure we’re building what matters—and that begins with a commitment to thoughtful questioning, every time.