Every founder I talk to is asking the same question: “Should I be using AI to replace my assistant?”
Here’s what I’ve learned after working with 60+ executives and their EAs: You’re asking the wrong question.
The real question is: How do I give my EA superpowers?
Why AI Isn’t Making Founders More Productive (Yet)
I posted on LinkedIn last week asking who’s actually getting more productive with AI. The overwhelming answer? Software engineers.
Why? Because their work is:
- Black and white (code either works or it doesn’t)
- Deep and focused (they can lock themselves in a room)
- Pattern-based (tons of training data exists)
Compare that to a founder’s day:
- Constant context switching across sales, ops, product, and people
- Relationship-driven work (clients, team, investors)
- Nuanced decision-making with incomplete information
- Few patterns - every problem is unique
The exact opposite environment for AI to thrive.
That’s why every founder who tries to build their own AI workflows ends up spinning their wheels. The friction is massive. The fatigue of learning yet another tool when you’re already drowning? It’s too much.
What Actually Works: The EA Interface
Here’s what makes a great EA irreplaceable:
- Human Interface - Nuanced judgment, anticipation, multi-domain skills
- Trust & Rapport - They care about getting it right, not just executing a script
- Living Context - Over time, they absorb your goals, schedule, preferences, relationships - across work and life
Could AI do email triage? Sure.
Could it draft reports? Absolutely.
But can it understand you across every domain of your life and make judgment calls on your behalf? Not yet.
And here’s the key insight: The solution isn’t to replace the EA with AI.
It’s to train the EA to use AI as their operating system.
The New Job Description: AI-Powered EA
Instead of asking founders to become AI workflow engineers (you don’t have time), we flip it:
Make the EA the interface. Equip them with AI as their second brain.
Here’s what that looks like in practice:
1. Context Layer: Super RAG
Instead of the EA manually reading every email, attending every meeting, and taking notes - we ingest everything into a unified context engine:
- Every Fireflies transcript
- Every email sent/received
- Every Notion task and project
- Calendar history and patterns
Now the EA has an all-knowing assistant they can query: “What did Aaron say about pricing in Q4?” or “What are his top 3 priorities this month?”
The EA still makes the decisions. But they have instant access to perfect recall.
2. Execution Layer: Custom AI Agents
Some tasks are better done by AI:
- Meeting reminders with agenda prep
- Email categorization and flagging
- Report generation from data
- Follow-up tracking
Instead of the founder building these workflows (and getting stuck in Zapier/Claude hell), the EA builds and manages them.
The EA becomes a workflow architect - configuring agents, monitoring outputs, gathering feedback, and refining SOPs.
3. Feedback Loop: Continuous Improvement
This is where most AI tools fail. They’re static. But an EA + AI system is alive:
- Founder gives feedback on an email draft → EA updates the prompt
- Meeting prep format changes → EA adjusts the agent
- New priority emerges → EA rebuilds the workflow
The system gets smarter because the EA is in the loop.
What We’re Building at FreedUp
There’s no exact timeline for this yet, but I see us over the next year, we’re developing:
1. AI Bootcamp for EAs
In my past life, I build four different software engineering bootcamps. I think we can build an intensive training program teaching our EAs to:
- Use tools like Claude, cursor, and custom APIs
- Build client-specific AI workflows
- Configure and manage autonomous agents
- Continuously improve systems with founder feedback
2. Command Center (our AI toolkit)
Lately we’ve been prototyping a tool called “Command Center”. It’s a unified platform that gives EAs:
- Cross-domain context (Super RAG architecture)
- Agent configuration studio (no-code workflow builder)
- Feedback orchestration (learning from every interaction)
- Performance monitoring (what’s working, what’s not)
The goal? Make every EA feel like a Chief of Staff - even if they’re just 3 months in.
The Bottom Line
The future of founder productivity isn’t:
- ❌ Founders learning to prompt engineer
- ❌ Replacing EAs with ChatGPT
- ❌ Duct-taping 10 different AI tools together
It’s:
- ✅ Keeping the EA as your interface
- ✅ Equipping them with AI superpowers
- ✅ Building systems that learn and improve over time
Because business problems haven’t changed. CEOs still need to focus on high-leverage decisions, relationships, and growth.
What has changed is that the right-hand person supporting you can now move 10x faster, with better consistency, and zero fatigue.
That’s the future. And it’s not about choosing between human or machine.
It’s about giving your EA a second brain - so you can finally buy back your time.
What’s one task you wish your EA could do faster or better? Hit reply - I read every response.
Happy Friday,
Aaron