At Work with The Ready

Episode 41: Why Your AI Strategy Stalled and How To Get Moving with Greg Shove

Host: Rodney Evans
Guest: Greg Shove, CEO of Section
Date: January 12, 2026

Episode Overview

This episode explores the persistent challenges and hidden opportunities of adopting AI at scale within organizations. Rodney Evans interviews Greg Shove, a pioneering AI workforce transformation leader and CEO of Section, renowned for training thousands in practical AI adaptation. Together, they dissect why most enterprise AI strategies stumble, how workforce dynamics and organizational culture shape adoption, and what forward-thinking companies are doing to genuinely capture value from AI. They emphasize the necessity of a deeper, more honest conversation about work redesign in the intelligence age.

Key Discussion Points & Insights

1. The AI Hype Cycle and Industry Sincerity

AI Hype and Disillusionment: Greg critiques insincere calls for "slowing down" AI:

“I wish that AI CEOs…would stop saying we should slow down and really contemplate the impacts...because…they don’t have any intention of slowing down. So just be straight up with us, we’ll figure it out.” — Greg Shove (01:28)
Future Role of AI Influencers:

"When the bubble bursts, all the bozos will get cleared out. All those AI influencers in my LinkedIn feed every day—they're gonna be gone." — Greg Shove (00:01, 35:28)

2. Why Enterprise AI Adoption Stalls (04:00 – 11:46)

Wide Gap: Consumer vs. Enterprise AI Adoption
- Consumers are rapidly adopting AI in daily life, whereas enterprise adoption is still lingering around 10–14% ROI.
- Organizational deployment mistakes: treating AI as traditional software, ignoring psychological and existential workforce impacts.
Individual Gain vs. Organizational Value:
- Early adopters (employees) hoard productivity gains privately, fearing layoffs if they reveal efficiencies.
- “If I use AI and get 6, 8, 10 hours back…what’s going to happen to me? Will I go on to more interesting work or get laid off…?” — Greg (05:23)
Work Redesign Bottlenecks:
- Organizational debt and sluggish bureaucracy leave middle/upper management unprepared to leverage newfound capacity.
- AI exposes ("truth serum") the inefficiency, lack of coherence, and busywork embedded in many corporate workflows.

3. Key Ingredients for Successful AI Transformation (12:05 – 15:04)

Purpose & Manifesto:
- Explicit “why of AI”—a visible, authentic AI manifesto to guide adoption.
Universal Access:
- “Give your employees good AI and pay for it...Everybody needs to get a great AI…” — Greg (12:39)
Continuous Coaching, Not One-Off Training:
- AI capability is evolving, so upskilling requires persistent, ongoing support.
Rapid, Relevant Use Cases:
- Move employees from basic prompting to real job-aligned applications quickly.
Redesign of Work:
- Leaders must actively define and invest in new, meaningful tasks to fill freed time and drive value.

4. The Challenge of Strategic Imagination (15:04 – 18:46)

Lack of Prioritization:
- Most leadership teams can’t identify what to do with new capacity; strategic skills have atrophied.
Contrast with Startups:
- Startups naturally operate closer to strategy and value-creation levers; large companies' insulation breeds inertia.
Risk Aversion & Bureaucracy:
- Big organizations favor the performance of risk mitigation and resist experimentation, underestimating how AI will ignore legacy boundaries and org charts. (20:03 – 21:37)

5. What Actually Drives Change? (21:37 – 25:43)

External Risk & Competition:
- Companies only truly transform when competitive or existential risk materializes (e.g., Google’s Gemini awakening after OpenAI’s ChatGPT).
The Problem of Lip Service:
- CEOs may embrace AI rhetorically, but unless it’s woven into operating rhythm, strategy, and roles, organizational change stalls.
Empathy for Heads of AI:

“I have a lot of empathy right now for heads of AI…because they’re probably not getting a lot of love and it’s hard work. It’s a real slog.” — Greg (24:43)

6. AI as Both Tool and Disruptor: Strategies for the Future (28:27 – 34:00)

If You’re Leading AI Adoption:

First Principle: Don’t Just Chase Productivity
- Prioritize both “cut and create”:
  - Cut obsolete work to free resources.
  - Create new products, services, and eventually, jobs.
Dual Transformation:
- Simultaneously optimize the core business while building the disruptive, AI-native “new house,” even if it cannibalizes the old.
Challenges in Large Organizations:
- Difficulties in self-disruption ("pivoting" and "skunkworks"), incentive misalignment, and risk aversion often doom attempts.
- Most will prefer to buy disruption than build it, often unsuccessfully.

7. Section’s Self-Disruption (35:28 – 37:24)

Pivoting with AI:
- Section shifted from an online business school to an AI workforce transformation platform (Prof.AI) after direct experience with ChatGPT.
- Success required shedding high-margin “old” revenue for riskier, new AI-driven offerings—a leap executives at larger, public companies are rarely willing to make.

8. Reimagining Stewardship and Leadership for the Intelligence Age (37:33 – 44:39)

From Leadership to Stewardship:
- Rodney: “We talk about this age, the intelligence age, as requiring a shift from leadership to stewardship…to steward its survival, steward its adaptation.”
Greg’s Take:
- Combination of stewardship (systemic, longer-term care) and decisive, old-fashioned leadership (“kick ass, take some names”).
Call for Systems Thinking:
- Leaders must look beyond quarterly results to understand environmental and societal impacts, engage in values led procurement (“pay for responsible AI”), and practice systems thinking.

9. Peak Capitalism & the Coming Shift (44:39 – 47:52)

“Peak Capitalism” & Peak Inefficiency:
- CEOs now openly brag about layoffs as means to keep stock prices up.
- Greg predicts growing resistance, especially from Gen Z, as knowledge work becomes more precarious and companies focus on leanness (“super companies”).
Rise of Super Companies:
- Smaller, high-impact organizations with “super leaders, super employees, and a giant cable…to a bunch of AI.”
- Most people will have to find meaningful work outside these “super companies,” potentially in entrepreneurship and small teams.

10. The Role of Companies in Society (49:39 – End)

Ongoing Human Purpose in the Intelligence Age:
- As AI takes over routine work, organizations might serve as the conveners of meaningful, community-impactful work.
- “We're short teachers…nurses…healthcare workers…we have labor shortages everywhere and expertise shortages everywhere…So maybe that is one role of an organization in the future, which is to organize us to go tackle some of these challenges.” — Greg (51:17)

Notable Quotes & Memorable Moments

On Organizational Anxiety:

"Most companies deploy [AI] like software and then they're shocked that no one's using it…because they haven't really answered the question…what am I going to be doing after?" — Greg (05:23)
On AI as Truth Serum:

“AI is truth serum for organizations and AI reveals a lot…You'll see the lack of growth mindset, you'll see the lack of organizational coherence, you'll see a lot of busy work, you'll see the undocumented workflows...” — Greg (10:09)
On Stewardship and Leadership:

“The stewardship doesn’t 100% land with me. It lands in part. But I would say it’s that combined with old-fashioned leadership…kick ass, take some names, make some tough calls…and own it...” — Greg (39:08)
On Strategic Skills in Organizations:

“As AI takes the more rote, easier, dopamine producing layer of work, those people don’t know what the fuck to do. And so…do we all actually want that space opened up?” — Rodney (09:24)
On Dual Transformation:

“In order to do real transformation, one has to do the transformation in their core business at the same time as they build the new business alongside—even understanding that the new business may ultimately cannibalize the core business.” — Rodney (30:19)
On AI Strategy:

“If you’re going to start with cut, do it fast. All the anxiety in AI is in that first phase, the cut phase…get through it…get to the fun part: reinvent your products and services and business model.” — Greg (28:54)
On The Future of Organizations:

“We are entering this next era of capitalism, which is super companies…inside they’re smaller, they have super leaders, they have super employees, and they have a whole bunch of agents and a giant cable going out the back to a bunch of AI. And I think CEOs want super companies…But so few of us can work in them.” — Greg (46:46)
On Systems Thinking:

“Systems thinking is the skill for leaders to learn…That is what allows you to know the levers of your business…understand the levers in the larger environment…” — Rodney (42:54)

Timestamps for Significant Segments

| Timestamp | Segment | |-------------|-----------------------------------------------------------------------| | 00:01 | Greg’s take on the coming AI “bubble burst” and influencer fatigue | | 01:28–03:20 | Opening reflections on AI hype, corporate insincerity, and uncertainty| | 03:44–08:58 | Why enterprise AI adoption is so poor; individual vs. org incentives | | 09:56–11:46 | Bureaucracy & “AI as truth serum” for ineffective organizational work | | 12:05–15:04 | Necessary ingredients for true AI transformation | | 15:04–18:46 | Challenges of strategic work design and comparison with startups | | 20:03–21:37 | Risk obsession and bureaucracy block AI progress in large orgs | | 21:37–25:43 | What really catalyzes organizational change (competition, fear, risk) | | 28:27–34:00 | “Cut and create” and the importance of dual transformation | | 35:28–37:24 | Section's pivot and self-disruption with AI | | 37:33–44:39 | Leadership vs. stewardship in the intelligence age | | 44:39–47:52 | “Peak capitalism” and the rise of “super companies” | | 49:39–51:17 | The evolving role for organizations: organizing meaningful human work |

Conclusion & Final Thoughts

This episode delivers an unflinching, often irreverent critique of why most enterprise AI strategies fail to deliver, and what a more honest, humane, and ambitious approach looks like. Greg Shove and Rodney Evans illustrate that meaningful progress demands more than software purchases and productivity hacks—it requires cultural reckoning, managerial courage, systems thinking, and above all, a vision for reshaping work itself in the intelligence age.

Further resources:

GregShove.com | “AI Truth Serum” podcast & newsletter
Section (AI workforce transformation platform): prof.ai

Produced by: The Ready
Contact: podcast@theready.com

At Work with The Ready

Episode 41: Why Your AI Strategy Stalled and How To Get Moving with Greg Shove

Host: Rodney Evans
Guest: Greg Shove, CEO of Section
Date: January 12, 2026

Episode Overview

Key Discussion Points & Insights

1. The AI Hype Cycle and Industry Sincerity

AI Hype and Disillusionment: Greg critiques insincere calls for "slowing down" AI:

“I wish that AI CEOs…would stop saying we should slow down and really contemplate the impacts...because…they don’t have any intention of slowing down. So just be straight up with us, we’ll figure it out.” — Greg Shove (01:28)
Future Role of AI Influencers:

"When the bubble bursts, all the bozos will get cleared out. All those AI influencers in my LinkedIn feed every day—they're gonna be gone." — Greg Shove (00:01, 35:28)

2. Why Enterprise AI Adoption Stalls (04:00 – 11:46)

Wide Gap: Consumer vs. Enterprise AI Adoption
- Consumers are rapidly adopting AI in daily life, whereas enterprise adoption is still lingering around 10–14% ROI.
- Organizational deployment mistakes: treating AI as traditional software, ignoring psychological and existential workforce impacts.
Individual Gain vs. Organizational Value:
- Early adopters (employees) hoard productivity gains privately, fearing layoffs if they reveal efficiencies.
- “If I use AI and get 6, 8, 10 hours back…what’s going to happen to me? Will I go on to more interesting work or get laid off…?” — Greg (05:23)
Work Redesign Bottlenecks:
- Organizational debt and sluggish bureaucracy leave middle/upper management unprepared to leverage newfound capacity.
- AI exposes ("truth serum") the inefficiency, lack of coherence, and busywork embedded in many corporate workflows.

3. Key Ingredients for Successful AI Transformation (12:05 – 15:04)

Purpose & Manifesto:
- Explicit “why of AI”—a visible, authentic AI manifesto to guide adoption.
Universal Access:
- “Give your employees good AI and pay for it...Everybody needs to get a great AI…” — Greg (12:39)
Continuous Coaching, Not One-Off Training:
- AI capability is evolving, so upskilling requires persistent, ongoing support.
Rapid, Relevant Use Cases:
- Move employees from basic prompting to real job-aligned applications quickly.
Redesign of Work:
- Leaders must actively define and invest in new, meaningful tasks to fill freed time and drive value.

4. The Challenge of Strategic Imagination (15:04 – 18:46)

Lack of Prioritization:
- Most leadership teams can’t identify what to do with new capacity; strategic skills have atrophied.
Contrast with Startups:
- Startups naturally operate closer to strategy and value-creation levers; large companies' insulation breeds inertia.
Risk Aversion & Bureaucracy:
- Big organizations favor the performance of risk mitigation and resist experimentation, underestimating how AI will ignore legacy boundaries and org charts. (20:03 – 21:37)

5. What Actually Drives Change? (21:37 – 25:43)

External Risk & Competition:
- Companies only truly transform when competitive or existential risk materializes (e.g., Google’s Gemini awakening after OpenAI’s ChatGPT).
The Problem of Lip Service:
- CEOs may embrace AI rhetorically, but unless it’s woven into operating rhythm, strategy, and roles, organizational change stalls.
Empathy for Heads of AI:

“I have a lot of empathy right now for heads of AI…because they’re probably not getting a lot of love and it’s hard work. It’s a real slog.” — Greg (24:43)

6. AI as Both Tool and Disruptor: Strategies for the Future (28:27 – 34:00)

If You’re Leading AI Adoption:

First Principle: Don’t Just Chase Productivity
- Prioritize both “cut and create”:
  - Cut obsolete work to free resources.
  - Create new products, services, and eventually, jobs.
Dual Transformation:
- Simultaneously optimize the core business while building the disruptive, AI-native “new house,” even if it cannibalizes the old.
Challenges in Large Organizations:
- Difficulties in self-disruption ("pivoting" and "skunkworks"), incentive misalignment, and risk aversion often doom attempts.
- Most will prefer to buy disruption than build it, often unsuccessfully.

7. Section’s Self-Disruption (35:28 – 37:24)

Pivoting with AI:
- Section shifted from an online business school to an AI workforce transformation platform (Prof.AI) after direct experience with ChatGPT.
- Success required shedding high-margin “old” revenue for riskier, new AI-driven offerings—a leap executives at larger, public companies are rarely willing to make.

8. Reimagining Stewardship and Leadership for the Intelligence Age (37:33 – 44:39)

From Leadership to Stewardship:
- Rodney: “We talk about this age, the intelligence age, as requiring a shift from leadership to stewardship…to steward its survival, steward its adaptation.”
Greg’s Take:
- Combination of stewardship (systemic, longer-term care) and decisive, old-fashioned leadership (“kick ass, take some names”).
Call for Systems Thinking:
- Leaders must look beyond quarterly results to understand environmental and societal impacts, engage in values led procurement (“pay for responsible AI”), and practice systems thinking.

9. Peak Capitalism & the Coming Shift (44:39 – 47:52)

“Peak Capitalism” & Peak Inefficiency:
- CEOs now openly brag about layoffs as means to keep stock prices up.
- Greg predicts growing resistance, especially from Gen Z, as knowledge work becomes more precarious and companies focus on leanness (“super companies”).
Rise of Super Companies:
- Smaller, high-impact organizations with “super leaders, super employees, and a giant cable…to a bunch of AI.”
- Most people will have to find meaningful work outside these “super companies,” potentially in entrepreneurship and small teams.

10. The Role of Companies in Society (49:39 – End)

Ongoing Human Purpose in the Intelligence Age:
- As AI takes over routine work, organizations might serve as the conveners of meaningful, community-impactful work.
- “We're short teachers…nurses…healthcare workers…we have labor shortages everywhere and expertise shortages everywhere…So maybe that is one role of an organization in the future, which is to organize us to go tackle some of these challenges.” — Greg (51:17)

Notable Quotes & Memorable Moments

On Organizational Anxiety:

"Most companies deploy [AI] like software and then they're shocked that no one's using it…because they haven't really answered the question…what am I going to be doing after?" — Greg (05:23)
On AI as Truth Serum:

“AI is truth serum for organizations and AI reveals a lot…You'll see the lack of growth mindset, you'll see the lack of organizational coherence, you'll see a lot of busy work, you'll see the undocumented workflows...” — Greg (10:09)
On Stewardship and Leadership:

“The stewardship doesn’t 100% land with me. It lands in part. But I would say it’s that combined with old-fashioned leadership…kick ass, take some names, make some tough calls…and own it...” — Greg (39:08)
On Strategic Skills in Organizations:

“As AI takes the more rote, easier, dopamine producing layer of work, those people don’t know what the fuck to do. And so…do we all actually want that space opened up?” — Rodney (09:24)
On Dual Transformation:

“In order to do real transformation, one has to do the transformation in their core business at the same time as they build the new business alongside—even understanding that the new business may ultimately cannibalize the core business.” — Rodney (30:19)
On AI Strategy:

“If you’re going to start with cut, do it fast. All the anxiety in AI is in that first phase, the cut phase…get through it…get to the fun part: reinvent your products and services and business model.” — Greg (28:54)
On The Future of Organizations:

“We are entering this next era of capitalism, which is super companies…inside they’re smaller, they have super leaders, they have super employees, and they have a whole bunch of agents and a giant cable going out the back to a bunch of AI. And I think CEOs want super companies…But so few of us can work in them.” — Greg (46:46)
On Systems Thinking:

“Systems thinking is the skill for leaders to learn…That is what allows you to know the levers of your business…understand the levers in the larger environment…” — Rodney (42:54)

Timestamps for Significant Segments

Conclusion & Final Thoughts

Further resources:

GregShove.com | “AI Truth Serum” podcast & newsletter
Section (AI workforce transformation platform): prof.ai

Produced by: The Ready
Contact: podcast@theready.com

41. Why Your AI Strategy Stalled and How To Get Moving with Greg Shove

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Summary

At Work with The Ready

Episode 41: Why Your AI Strategy Stalled and How To Get Moving with Greg Shove

Episode Overview

Key Discussion Points & Insights

1. The AI Hype Cycle and Industry Sincerity

2. Why Enterprise AI Adoption Stalls (04:00 – 11:46)

3. Key Ingredients for Successful AI Transformation (12:05 – 15:04)

4. The Challenge of Strategic Imagination (15:04 – 18:46)

5. What Actually Drives Change? (21:37 – 25:43)

6. AI as Both Tool and Disruptor: Strategies for the Future (28:27 – 34:00)

If You’re Leading AI Adoption:

7. Section’s Self-Disruption (35:28 – 37:24)

8. Reimagining Stewardship and Leadership for the Intelligence Age (37:33 – 44:39)

9. Peak Capitalism & the Coming Shift (44:39 – 47:52)

10. The Role of Companies in Society (49:39 – End)

Notable Quotes & Memorable Moments

Timestamps for Significant Segments

Conclusion & Final Thoughts

Summary

At Work with The Ready

Episode 41: Why Your AI Strategy Stalled and How To Get Moving with Greg Shove

Episode Overview

Key Discussion Points & Insights

1. The AI Hype Cycle and Industry Sincerity

2. Why Enterprise AI Adoption Stalls (04:00 – 11:46)

3. Key Ingredients for Successful AI Transformation (12:05 – 15:04)

4. The Challenge of Strategic Imagination (15:04 – 18:46)

5. What Actually Drives Change? (21:37 – 25:43)

6. AI as Both Tool and Disruptor: Strategies for the Future (28:27 – 34:00)

If You’re Leading AI Adoption:

7. Section’s Self-Disruption (35:28 – 37:24)

8. Reimagining Stewardship and Leadership for the Intelligence Age (37:33 – 44:39)

9. Peak Capitalism & the Coming Shift (44:39 – 47:52)

10. The Role of Companies in Society (49:39 – End)

Notable Quotes & Memorable Moments

Timestamps for Significant Segments

Conclusion & Final Thoughts