Learning from failure and timing pivots

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Are you making critical decisions without consulting AI? Greg argues it’s now irresponsible for any leader to make high-stakes decisions without talking to AI first.

In this episode, Greg Shove, CEO of Section and a multi-time founder with 30 years of entrepreneurial experience, shares how AI is fundamentally different from any previous technology wave. Unlike traditional software that makes us more productive within our existing boundaries, AI allows us to jump capability boundaries – enabling individuals and organizations to do things they simply couldn’t do before.

Greg explains why most enterprise AI rollouts are failing (hint: they’re treating AI like software when it’s actually co-intelligence), how to cultivate resilience through multiple startup failures, and the practical strategies for getting teams to adopt AI (from simple hacks like putting a post-it note on your monitor to creating an entire AI-dedicated screen).

This conversation goes beyond the hype to explore both the superpowers and limitations of AI, the real organizational outcomes you can expect (spoiler: it’s not just about layoffs), and why moving from efficiency to creation is the key to unlocking AI’s true potential in your organization.

Key topics discussed:

• Why AI breaks capability boundaries unlike any other tech
• Treating AI as a thought partner, not just a productivity tool
• Why most large organizations fail at AI deployment
• Managing workforce anxiety during AI transformation
• The four possible team outcomes when rolling out AI
• Moving from efficiency (cut) to growth (create) with AI
• The Post-it note hack that changed how teams use AI daily
• Walking the walk: leading authentically in AI adoption

Timestamps:

• (00:00:00) Trailer & Intro
• (00:02:44) Career Turning Points
• (00:06:03) Cultivating Entrepreneurial Resilience
• (00:07:49) Understanding the AI Wave: Scale and Transformation
• (00:12:29) Pivoting to AI: Section’s Transformation Journey
• (00:17:57) AI as a Thought Partner
• (00:22:57) Practical Tips for Leaders Using AI Daily
• (00:30:49) Rolling Out AI Organization-Wide: Managing Change and Anxiety
• (00:41:30) AI ROI: Beyond Efficiency to Creation
• (00:51:01) AI-Powered Education: The ProfAI Approach
• (00:57:53) 1 Tech Lead Wisdom

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Greg Shove’s Bio
Greg Shove is a seven-time CEO, all in on AI. After first using ChatGPT in February 2023, he pivoted his company Section to be AI-powered. Now he helps enterprise organizations move from AI-anxious to AI-proficient with a proven playbook, delivered through keynote speaking and executive workshops.
Greg is also the founder of Machine & Partners, an AI lab building custom enterprise AI applications, and co-author of Personal Math, a weekly newsletter sharing business insights for early-career leaders and founders.

Follow Greg:

• LinkedIn – linkedin.com/in/gregshove
• Newsletter – personalmath.substack.com
• Section AI – sectionai.com
• Prof AI – prof.ai

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Show notes & transcript: techleadjournal.dev/episodes/240.
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