ChatGPT Operator vs. Remote Executive Assistant

OpenAI’s newest $200/mo upgrade is called ChatGPT Operator. It is self-described as, “an AI agent that can perform tasks on the web for users.” It’s pretty amazing and can do some really great stuff.

I recently prompted ChatGPT with this exact prompt: “I want a real comparison of what OpenAI’s Operator upgrade can do vs what an EA can do. Are you able to speak specifically to that?”

Here’s what it said:

Where AI Excels and Where Humans Still Win

1️⃣ Task Execution vs. Task Ownership

Operator: AI can process information, generate content, book appointments, send reminders, and even integrate with apps like Slack, Notion, and Gmail.
EA: Can not only execute tasks but also own projects, ensuring they move forward, following up on key deliverables, and adjusting plans when things go sideways.

👑 Winner: EA. AI can check the box, but an EA ensures completion, accountability, and impact.

2️⃣ Communication & Tone

Operator: AI can draft emails, summarize conversations, and even send responses on your behalf—but it lacks true relationship management and may struggle with nuance.
EA: Knows how to read the subtext of an email, navigate office politics, and manage sensitive communications with care.

👑 Winner: EA. While AI can generate text, context matters—and only a human truly understands when and how to say something.

3️⃣ Decision-Making & Prioritization

Operator: AI can suggest priorities based on data, but it can’t weigh business implications, emotional intelligence, or strategic goals.
EA: Knows which fires to put out first, anticipates what needs to happen next, and strategically adjusts based on real-time business needs.

👑 Winner: EA. AI suggests—a great EA decides and acts.

4️⃣ Handling the Unexpected

Operator: AI follows pre-programmed rules and workflows but struggles with adaptability in chaotic, real-world scenarios.
EA: Can pivot instantly, handle last-minute schedule changes, and smooth over interpersonal or client issues with tact and intelligence.

👑 Winner: EA. Business is unpredictable—and humans excel in real-time problem-solving.

5️⃣ Personalization & Emotional Intelligence

Operator: AI can remember past conversations and suggest responses, but it doesn’t genuinely care or build relationships.
EA: Forms real connections, learns personal and business preferences over time, and proactively adjusts support accordingly.

👑 Winner: EA. Trust and relationships can’t be automated.

6️⃣ Complex Project Management

Operator: AI can generate checklists and assist with planning, but it doesn’t lead teams, ensure accountability, or drive projects across the finish line.
EA: Can coordinate multiple stakeholders, track progress, and proactively remove bottlenecks to keep things moving.

👑 Winner: EA. AI can help organize, but an EA is the driving force behind execution.

7️⃣ Business Strategy & Leadership Support

Operator: AI can analyze data and provide insights, but it doesn’t think strategically or align with long-term business goals.
EA: Understands your vision, your priorities, and your leadership style, making them a trusted thought partner.

👑 Winner: EA. AI can crunch numbers, but humans make the calls that matter.

Final Verdict: EA + AI = The Power Duo

AI is an incredible tool, but it works best as an enhancement, not a replacement for human intelligence, decision-making, and relationship management.

💡 The real magic happens when an EA integrates AI into their workflow—using it to speed up administrative work while maintaining the human touch that makes businesses thrive.

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That’s what ChatGPT said and here’s what I say.

👉 If you think ChatGPT will handle all your executive support needs, you might be saving a few bucks while losing time, strategy, and human connection.

The best setup? An EA who embraces AI.Need a real-life, proactive EA on your team? Let’s talk about finding your perfect-fit EA.

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