Podcast Summary: "You’re Using AI Wrong (Do This Instead)"

Unemployable with Jeff Dudan, Ep. #226 (November 11, 2025)

Guests: Host Jeff Dudan (Founder, Homefront Brands) and Jeff Woods (Author – The AI Driven Leader, CEO of AI Leadership)

Episode Overview

This episode dives deep into the strategic use of AI for business leaders and entrepreneurs, disrupting the common view of AI as a tactical assistant. Jeff Woods challenges listeners to stop “majoring in the minors” by misusing generative AI for menial tasks and instead leverages it as a high-level thought partner for strategic growth, transformation, and competitive advantage. He introduces actionable frameworks for deploying AI, shares client examples, and discusses the broader implications for leadership, organizations, and even personal development.

Main Themes & Purpose

• Strategic Leadership in the AI Era: How AI, when harnessed as a thought partner (not a replacement), can elevate leadership and business strategy.
• Rethinking AI Adoption: Why learning every tool or feature is a distraction—focus instead on the “20%” of use cases that create 80% of results.
• The CRIT Prompt Framework: A practical, repeatable way to unlock AI’s full potential for executives and teams.
• Cultural & Organizational Shifts: Why C-suite buy-in and modeling AI usage sets psychological safety and precedent throughout organizations.
• The Human Side: Reinforcing that distinctly human skills like creativity, strategic thinking, and communication will only become more vital as AI evolves.

Key Discussion Points & Insights

1. Are Today’s AI Skills Already Obsolete?

• Woods asserts that while much current AI “how-to” will become obsolete, what endures is using AI to enhance strategic thinking, not just tactical tasks.
• Quote: “Right now, people are using AI... for 80% use cases that only bring 20% of the value... The real game changer is using AI as your thought partner.” (Jeff Woods, 02:35)

2. Major vs. Minor – The 80/20 Rule

• Dudan and Woods agree most professionals remain stuck in unimportant work, a pattern now repeated with AI as they use it for low-value tasks like email or scheduling.
• Woods advocates identifying the “one big problem” whose solution offers disproportionate value, focusing AI efforts there.

3. CRIT: The Prompting Framework

• Context, Role, Interview, Task – CRIT transforms generic prompting into a collaborative, context-rich process where AI acts as a strategic advisor.
  • Example Prompt:
    • Context: (e.g., “Attached are my financial statements…”)
    • Role: (“Act as a strategic CFO…”)
    • Interview: (“Ask me up to five questions to gain deeper insight…”)
    • Task: (“Tell me the top five things I might not see in my business.”)
• Quote: “The interview part is the real game changer. I don’t ask AI questions. I make AI turn the tables and ask me the right questions to unlock deeper context.” (Jeff Woods, 06:38)

4. From Peripheral Brain to Boardroom Partner

• Dudan describes his IT partner as a “peripheral brain”; Woods parallels this with AI used for thought, research, and especially strategy, not just automation.
  • Memorable analogy: “It’s tough to read the label when you’re inside the box.” (Jeff Woods, 05:05)

5. Real-World Transformation Examples

• Woods shares a story of using AI to help restructure debt for a manufacturing CEO facing bankruptcy:
  • AI identified novel solutions based on deep contextual interviewing.
  • CEO: “In less than 10 minutes, I got hope.” (Story near 24:30)
• Woods’ “AI board” (including personalities of Steve Jobs, Warren Buffet, and his future self) to analyze his keynote talks—leading to a doubling in conversion rate. (48:00)
  • Quote: "Now, you tell me, did that replace my creativity or did that enhance my creativity?" (Jeff Woods, 50:49)

6. The New Model for Meetings & Strategy Sessions

• Old offsite, sticky-note brainstorming sessions are “dead.” Instead, teams use a pre-built prompt, each team member is interviewed by AI, and results are aggregated instantly, surfacing true alignment (or lack thereof), focusing subsequent discussion.
  • “The CEO stood up and goes, ‘That would have normally taken us three months. We did it in one hour. Every voice was heard, and we are actually aligned.’” (Jeff Woods, 32:15)

7. Overcoming Barriers – Why Leaders Resist AI

• Less than 5% of executives had adopted AI despite universal belief in its future importance.
• Main barrier: Not knowing where to start.
• Woods says showing AI as a tool for strategy rather than pure productivity “turns the lights on” for executive teams and breaks old adoption bottlenecks.
  • Quote: “If you show them how to use it for that [strategy], they realize they've been living their whole life in black and white and you just showed them color for the first time and they're never going back.” (27:19)

8. Bias, Collaboration, and Human Judgment

• Be explicit about assumptions and use AI to challenge not just confirm your thinking.
• Woods demonstrates he uses the CRIT methodology to have AI both create ideas and then play “challenger” or take on the persona of a skeptical customer.
  • “I’m recognizing I’m no longer the player of an instrument... I’m now the conductor.” (Jeff Woods, 36:57)

9. AI Will Not Replace Artistry – But It Will Democratize It

• In response to the question about the “last author or screenwriter,” Woods believes AI will create new categories of creators: “It's probably going to be the person you never heard of who's sitting at a computer at home, knowing how to wield AI to create something truly remarkable.” (54:00)
• Predicts future movies and content created bespoke for individual viewers.

10. The Human Skills That Matter More Now

• “The ability to think strategically, to solve problems, to communicate, to collaborate, to create…” are described as the skills that will skyrocket in value, even as ‘robotic’ work goes away. (Jeff Woods, 45:04)
• “Isn’t it ironic that it might actually be a machine that returns us to being human?”

Notable Quotes & Moments

• On Focusing AI Efforts:
  “Most of the tools, most of the information is a distraction. Your filter is: if I focus on this, is it going to unlock 80% of my results? If no, why are we talking about it?” — Jeff Woods (10:13)
• On Speed of Change:
  “People are grossly underestimating how seismic this is because they are failing so slowly, they think they're succeeding.” — Jeff Woods (18:41)
• On Strategy vs. Tactics:
  “AI adoption is not the goal of any leader. Building a better business and better lives is, but it is strategy first, technology second.” — Jeff Woods (15:41)
• On AI in Meetings:
  “We have completely disrupted how we even hold meetings now… No longer do we show up for a meeting where the person running the meeting asks a question and starts to drive the meeting.” — Jeff Woods (32:16)
• On Education’s Obsolescence:
  “The problem with our current education system is that it was literally manufactured by John D. Rockefeller to create industrial workers… Is memorizing all the information for a test a skill that's going to matter in the future? No, it is not.” — Jeff Woods (69:15, 70:06)
• On Leadership Adoption:
  “If you, as the leader, are using this and you're going to people saying… ‘Did you use AI to do this?’ and they go, ‘No.’ And you say, ‘Then this meeting's over. Go bring it to AI...’” — Jeff Woods (59:44)
• On What a Creative Can Do with AI:
  “This time I took the last five transcripts from speeches that I had done, put them to my AI board… asked it how to improve… It doubled our conversion rate.” — Jeff Woods (49:15)

Practical Framework: The CRIT Prompt

Context | Role | Interview | Task

• Use whenever prompting AI for complex, high-value work.
• Ensure AI interviews you (or your team), drawing out context that otherwise remains “inside the box.”
• Always clarify your assumptions and ask AI to challenge your thinking.

Sticky Notes Exercise:
Put two sticky notes on your desk:

1. “How can AI help me do this?”
2. “CRIT: Context, Role, Interview, Task”
   (Woods, 05:05–06:38)

Segment Timestamps

• [00:43] – Intro and 80/20 Rule on AI use
• [03:27] – “Peripheral brain” analogy and strategic AI adoption
• [06:38] – Introducing the CRIT framework for prompting
• [13:22] – Real-world example: AI identifies strategic cracks in a business plan for a steel conglomerate
• [24:30] – Manufacturing CEO bankruptcy case, solved with AI’s “outside the box” questioning
• [32:16] – How AI fundamentally transforms meetings and strategic alignment sessions
• [36:57] – Detecting and countering bias using AI as a “challenger”
• [45:04] – Why human skills gain in value as AI grows
• [48:00] – Jeff’s “AI board” (Steve Jobs, Warren Buffet, future self) critique his own speeches
• [53:14] – Future self generating end-game insights and implications for executives
• [59:44] – How the leader’s AI use shapes organizational adoption culture
• [65:23] – Example: Executive assistant using CRIT to 10x and 100x her value and create new systems

Actionable Takeaways

• Adopt CRIT Prompting: Make CRIT your default for any significant work you do with AI—unlocking strategic rather than tactical value.
• Start Small, Focus on the 20%: Ask, “What is the biggest problem in my business right now?” and aim AI at it.
• C-suite Must Lead: AI culture and adoption must start with the executive team modeling and requiring strategic use.
• Challenge, Don’t Just Confirm: Use AI to pressure-test, red-team, and question your assumptions—not just to generate outputs.
• Embrace Messiness: Don’t attach to perfect grammar or structure; stream-of-consciousness works best with AI.
• Create a ‘Peripheral Brain’: Treat AI as an extension of your leadership thinking, not just a robotic assistant.

Resource Links

• AI Leadership (Jeff Woods' company, software, collective, and services)
• Book: The AI Driven Leader
• Podcast & Newsletter: Found at AI Leadership website

Memorable Closing

On Growth and Possibility:
“We often set goals based on what we think we can achieve, but none of us actually know what we're capable of achieving… Set a goal that's so big, it makes you uncomfortable and requires you to rediscover who you are and, more importantly, who you can become.”
— Jeff Woods (71:43)

For leaders ready to “get unemployable” and build for the future, the episode offers both a mindset and a toolkit for integrating AI not as a threat, but as a multiplier for human creativity and strategic impact.