Managing Humans and AI Agents at the Same Time
Tue Jan 27 2026
Overview
As AI agents become part of everyday work, organizations face new questions about ownership, visibility, and how work actually gets done. In this episode, Jacob Crockett sits down with Matt Wyman, CEO and co-founder of Okareo, to explore the parallels between managing people and managing AI agents. Drawing on experience from developer tools, product leadership, and automotive systems, Matt offers a thoughtful framework for thinking about tools, innovation, and alignment in an agent-augmented workplace.
What we cover
* Matt’s path from engineering to product leadership – How starting as a builder shaped his perspective on tools, systems, and decision-making.
* Why AI agents should be treated as tools, not coworkers – The risks of personifying agents and how trust can be misplaced.
* Ownership in an agent-driven workplace – Who should own AI agents: the individual employee or the organization?
* Lessons from the automotive industry – What mechanics owning their own tools reveals about modern knowledge work.
* The boundary between “bringing tools” and “receiving systems” – How companies typically control infrastructure while individuals control contribution tools—and where agents complicate this.
* Visibility and accountability with AI agents – Why agent participation in decisions must be transparent, even if humans make the final call.
* Innovation, experimentation, and perceived waste – Why effective innovation often looks inefficient and how managers misinterpret it.
* Strategic alignment vs. tactical control – The danger of over-managing at the task level and how it creates brittle organizations.
* AI and learning depth – How over-reliance on agents can short-circuit understanding, pattern recognition, and long-term growth.
* Stretching vs. leaning back – The emerging divide between people who use AI to explore new domains and those who use it to disengage.
* What managers must do differently – Setting expectations, creating space to stretch, and making opportunities visible in an AI-augmented team.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hirealigned.substack.com
More
Overview As AI agents become part of everyday work, organizations face new questions about ownership, visibility, and how work actually gets done. In this episode, Jacob Crockett sits down with Matt Wyman, CEO and co-founder of Okareo, to explore the parallels between managing people and managing AI agents. Drawing on experience from developer tools, product leadership, and automotive systems, Matt offers a thoughtful framework for thinking about tools, innovation, and alignment in an agent-augmented workplace. What we cover * Matt’s path from engineering to product leadership – How starting as a builder shaped his perspective on tools, systems, and decision-making. * Why AI agents should be treated as tools, not coworkers – The risks of personifying agents and how trust can be misplaced. * Ownership in an agent-driven workplace – Who should own AI agents: the individual employee or the organization? * Lessons from the automotive industry – What mechanics owning their own tools reveals about modern knowledge work. * The boundary between “bringing tools” and “receiving systems” – How companies typically control infrastructure while individuals control contribution tools—and where agents complicate this. * Visibility and accountability with AI agents – Why agent participation in decisions must be transparent, even if humans make the final call. * Innovation, experimentation, and perceived waste – Why effective innovation often looks inefficient and how managers misinterpret it. * Strategic alignment vs. tactical control – The danger of over-managing at the task level and how it creates brittle organizations. * AI and learning depth – How over-reliance on agents can short-circuit understanding, pattern recognition, and long-term growth. * Stretching vs. leaning back – The emerging divide between people who use AI to explore new domains and those who use it to disengage. * What managers must do differently – Setting expectations, creating space to stretch, and making opportunities visible in an AI-augmented team. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hirealigned.substack.com