Why management feels impossible today

In today’s technology landscape, management as a skill is becoming more complex as teams become larger & managers must navigate the balance between relationships and strategic execution. So how can AI tools help managers level up their game? Jonathan Raymond (Founder & CEO @ Ren) shares insights that can help managers navigate their modern-day invisible cognitive loads. We cover how AI can be used to enhance – not replace – inherently human skillsets, the three components that make up an effective manager / employee relationship, product-building principles for building relational systems, and using AI to guide rather than provide concrete answers.

ABOUT JONATHAN RAYMOND

Jonathan Raymond is the Founder and CEO of Ren, an AI agent for managers and teams that helps them give and receive feedback, have meaningful 1:1s, and access real-time personalized coaching. He is also the author of the award-winning book Good Authority and was named one of Inc. Magazine’s Top 100 Leadership Speakers. Previously the CEO of EMyth, Jonathan has led transformation projects across technology, renewable energy, and coaching. He’s a half-decent barista, a mediocre-but-enthusiastic surfer, and will never give up on the New York Knicks.

SHOW NOTES:

• Jonathan’s perspective on the impossible cognitive load & colliding pressures of modern managers (2:31)
• The complicated workflow it takes to be a great manager (6:05)
• “Field Intelligence” and the need to ingest non-technical data such as (mood, sentiment, and alignment) to make better leadership decisions (9:52)
• The managerial matrix: high/low performers and the 10-person team that feels like 50 (12:46)
• The cost of mismanaging your team & why it’s so easy to get it wrong (16:02)
• What’s uniquely human vs. where AI provides leverage (18:01)
• AI’s role: detecting signal and prompting human reflection (21:04)
• The “Growth Loop”: a 3-part system for effective leadership (27:20)
• Incorporating AI tools to enhance the manager / employee relationship (31:20)
• The future vision: an “in-ear” AI coach that closes the gap between learning and applying (33:09)
• Closing the gap between learning a new skill & it becoming an unconscious habit (35:59)
• Product Principle: Building a “Relational System,” not just a task manager (37:49)
• Product Principle: Why an AI coach must ask questions, not provide answers (40:50)
• How to harness AI tools for better emotional articulation / processing (45:11)
• A simple behavioral change to try this week (47:58)
• Rapid fire questions (49:57)

LINKS AND RESOURCES

• Good Authority: How to Become the Leader Your Team is Waiting For - Jonathan’s book in which he brings together what he has learned over a twenty-year journey as an executive, entrepreneur, team leader and leadership trainer.
• Entangled Life: How Fungi Make Our Worlds, Change Our Minds & Shape Our Futures - Merlin Sheldrake explores the spectacular and neglected world of fungi: endlessly surprising organisms that sustain nearly all living systems.
• Jonathan’s session at ELC Annual 2025

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

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