229. Compressed Workweeks, Culture by Design, and Coaching Your Team Through AI Adoption — with Art Shectman

World's Greatest Boss

In this episode I’m joined by Art Shectman, founder and CEO of Elephant Ventures, a global innovation firm helping companies unlock the full potential of AI transformation. But we don’t just talk tech: we dive into the human side of building and leading a business.

Art shares how he intentionally designed a company culture built on dependability, psychological safety, and joyful work. We talk about how his team successfully adopted a compressed four-day workweek, and what it really takes to implement major organizational shifts like AI adoption without sparking panic or burnout.

You’ll walk away with a better understanding of how to structure your team for accountability (without toxicity), why empowering employees beats micromanaging every time, and how to lead transformation with honesty, clarity, and how to get buy-in from the ground up.

If you’re thinking about hiring across borders, piloting a 4-day week, or embracing AI in your business you don’t want to miss this one.

What you’ll hear in this episode:

[1:40] How Elephant Ventures helps companies get 20X results from AI - not just 20%

[3:29] Why Art started hiring internationally in 2008

[4:12] The early struggles of global hiring (and why EORs are game-changing now)

[7:17] Why founders must prioritize their “joyfulness battery”

[10:17] Building culture intentionally: dependability, kindness, and the value pyramid

[14:02] Holding people accountable without being toxic

[18:17] How Elephant Ventures rolled out a compressed 4-day workweek

[22:15] Lessons from testing and scaling flexible work

[24:10] Coaching teams through AI transformation without fear

[26:29] Creating psychological safety in practice

[30:06] Why vulnerability and consistency matter more than charisma

[32:19] Where to find Art’s thought leadership on AI and transformation

Resources and links:

• Connect with Art on LinkedIn: Art Shectman
• Explore Elephant Ventures’ AI resources: Elevate.ElephantVentures.com
• Connect with me on LinkedIn: Jackie Koch
• Download my free HR + Hiring Essentials Playbook: peopleprinciples.co