AI on Your Org Chart: Where Does AI Fit in Your Team?
Where does AI belong in your organization? Bert and Julianna tackle the critical question of positioning AI - from reporting structures to decision-making authority. Practical guidance for the new era of human-AI collaboration.
Episode Summary
What happens when a chatbot has a name and introduces itself as a team member? Bert and Julianna tackle the provocative question: Should AI agents appear on your organizational chart? From phone answering assistants named Jennifer to the "agentic era" where AI has access to company tools, this conversation explores the practical and philosophical implications of AI as a colleague.
They discuss how to position AI agents on teams, what happens to entry-level positions, interviewing for AI collaboration skills, and the critical importance of human judgment. Plus: why treating AI politely might actually get you better results, and the edge cases where human empathy can't be replaced.
Episode Timeline
Course Pre-Roll
Julianna announces the Automate to Accelerate course launch. Self-paced and live cohort options coming soon - sign up for early access and discounts.
The Named Chatbot
Julianna encounters a chatbot that introduces itself by name, as if it's a team member. This sparks the central question: Should AI be on your org chart?
Meet Jennifer & Dan's Assistant
Bert reveals he's already deployed named AI agents: Jennifer answers phones, and the CEO's digital assistant handles rejected calls. AI is already on the team.
The Agentic Era
Bert introduces the concept of the "agentic era" - where AI agents have access to company tools and can take actions independently, not just respond to queries.
Should AI Be on the Org Chart?
"The org chart probably should include the AI... but we're not gonna do it because that's not the way that people think." Bert on why this matters for organizational transparency.
Hiring for AI Collaboration
Will candidates be evaluated on how well they work with AI? Discussion of AI archetypes and whether employees can leverage AI to add value to the company.
Legacy vs Future-Focused Companies
Not every company needs AI. Bert notes 7-10% of Americans don't have smartphones and are fine. Some businesses don't need "all this crap" - it's about strategic fit.
Working with Your AI Coworker
Julianna asks: What does the relationship look like when AI is your coworker? Who's teaching whom, and how do workplace dynamics change?
The Politeness Paradox
Being polite to AI costs more (more tokens) but gets better results. Bert explains why humanizing AI with "please" and "thank you" improves prompt quality.
Positioning AI as Junior Staff
Bert's recommendation: Frame AI as a junior team member here to assist. Set clear expectations about what it can do and emphasize that humans still own the output.
The Intern + AI Experiment
"I'd actually get the intern in still and pair it with the AI and say, you guys knock yourselves out and see what I get." Human-AI collaboration at the entry level.
Managing 5 AI Customer Service Reps
The future: One human managing five AI agents answering customer calls. How do you track performance and attribution when AI is doing the work?
The Efficiency vs Productivity Trap
Bert's warning: Companies chasing efficiency now might harm productivity five years out. "They're eating their young" by replacing entry-level positions with AI.
Mixture of Experts (MOE)
AI agents specialized in different capabilities - like second-tier support. But they lack human sympathy and context for edge cases.
The Human Edge Case
Julianna's airline story: A customer service rep who stayed on hold and "thought outside the box" to solve a unique problem. Why human empathy and creative problem-solving can't be replaced.
AI Organizational Models
AI as Infrastructure
The Model
AI capabilities are treated like IT infrastructure - owned and managed centrally, accessed as needed by various departments.
- • Reports to CTO/CIO
- • Centralized governance
- • Shared services model
- • Standardized platforms
Best For
Established enterprises with existing IT governance, companies prioritizing security and compliance, organizations with multiple departments needing consistent AI capabilities.
AI as Strategic Function
The Model
Dedicated AI leadership (Chief AI Officer) with direct reports and budget, positioning AI as a strategic differentiator.
- • C-suite representation
- • Cross-functional authority
- • Strategic budget allocation
- • Innovation focused
Best For
AI-first companies, organizations where AI is core to competitive advantage, companies undergoing digital transformation, businesses with significant AI R&D investment.
Distributed AI
The Model
Each department owns its AI initiatives with central governance and standards. Combines autonomy with coordination.
- • Embedded AI roles
- • Department-level budgets
- • Central COE for standards
- • Federated governance
Best For
Large organizations with diverse business units, companies with mature departmental structures, organizations balancing innovation with governance.
AI-Native Organization
The Model
AI isn't a separate function - it's integrated into every role and process. The entire org chart is designed around human-AI collaboration.
- • AI-augmented roles
- • Hybrid teams (human + AI)
- • Continuous learning culture
- • Flat, agile structures
Best For
Startups and new ventures, companies building from scratch, organizations willing to reimagine traditional structures, highly technical teams.
Key Considerations
Strategic Importance
How central is AI to your competitive advantage? Core differentiators need dedicated leadership and resources, while supporting functions can be embedded.
Governance & Risk
Regulatory requirements, ethical considerations, and risk management needs often determine whether you need centralized oversight or can distribute AI capabilities.
Organizational Maturity
Your current organizational structure and culture matters. Don't force an AI-native model on a traditional hierarchy - evolve gradually.
Talent & Skills
Do you have AI expertise in-house, or do you need to build it? The right org structure depends on whether you're buying, building, or borrowing AI talent.
Your AI Org Chart Action Plan
📋 Assess Current State
- • Map existing AI initiatives and ownership
- • Identify gaps in governance and accountability
- • Evaluate current reporting structures
- • Survey stakeholder needs and pain points
🎯 Define AI Strategy
- • Clarify AI's role in competitive advantage
- • Set 3-5 year AI vision and goals
- • Determine build vs buy approach
- • Identify required capabilities and talent
🎯 Design Structure
- • Choose appropriate organizational model
- • Define roles, responsibilities, and authorities
- • Establish reporting relationships
- • Create governance frameworks
📋 Implement & Iterate
- • Start with pilot teams or departments
- • Measure outcomes and gather feedback
- • Adjust structure based on learnings
- • Scale what works across organization
Key Quotes
"The org chart probably should include the AI... but we're not gonna do it because that's not the way that people think. If you add the AI in there and they understand that there's an additional level of complexity, it might make it more real, more true."
— Bert Carroll
"I get better results working with it when I'm polite to it. If I'm humanizing it in the sense that I'm talking to it as if I were talking to a coworker, I'm able to frame my questions in a way that is less terse and is more in alignment with how I would talk to another person."
— Bert Carroll
"I think the relationship you wanna have with AI is you and an intern. I'm not asking AI to do anything that I can't do myself. It's just saving me 10 minutes of putting this together."
— Julianna Fricchione
"If I were to come in... now I have to be responsible for another pseudo employee. I think that's where I can see some pushback. That's where I can see, is this gonna be more work, more burdensome?"
— Julianna Fricchione
"This is a different side of the same coin. With the electricity example, for you to become an electrician, there's a whole journeyman process. Now imagine if there's no more journeyman's positions—that critical step was gone."
— Julianna Fricchione
"If AI needs to have a clearly defined place in the team as well as in the organizational structure, the teams themselves still know who's responsible for the output, and they can't just blame it on the AI going rogue."
— Bert Carroll
Episode Resources
📚 Further Reading
These recent publications validate and extend the themes discussed in this episode:
- • Fortune: "AI is already changing the corporate org chart" (2025)
- • McKinsey: "Building and managing an agentic AI workforce" (2025)
- • Harvard Business Review: "Agentic AI Is Already Changing the Workforce" (2025)
- • Salesforce: "AI's Human Impact" workforce research (2025)
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