Understanding AI Limitations

AI Over 40 Series – Week 4

When Your AI Therapist Outperforms Your AI Developer

When I asked Claude and ChatGPT to act as personal behavioral psychologists, I fed them a decade’s worth of personality assessments—DISC, Myers-Briggs, StrengthsFinder, and more—and challenged them to build a comprehensive psychometric profile. They synthesized fresh insights and tailored real-world career advice to my motivations and blind spots.

Buoyed by that success, I tasked them with something “simple”: build an AI agent to resolve my calendar-sharing fiasco across multiple domains. After hours of code scaffolding, API specs, and endless debugging, I had pages of half-baked scripts…and no working solution.

That’s when it struck me: AI’s limitations aren’t bugs—they’re signposts for how to deploy it wisely.

The Paradox of AI Capabilities

Through trial and error, I’ve learned that AI excels at:

• Complex synthesis: Drawing connections among disparate data.
• Pattern recognition: Spotting insights humans might miss.
• Multifaceted reasoning: Exploring problems from several angles.
• Role-playing: Adopting personas—whether consultant, competitor, or customer.
• Creative ideation: Generating novel scenarios and approaches.

Yet AI still stumbles when it comes to:

• End-to-end execution: Implementing production-ready, multi-step systems.
• Stateful orchestration: Persisting context across complex, interconnected workflows.
• Action over description: Doing the work rather than merely sketching it out.
• Nuanced judgment: Making subtle calls where human experience matters most.

By recognizing these patterns, you can leverage AI for what it’s best at—and avoid time-wasting dead ends.

The Calendar Agent’s Silver Lining

My calendar-agent experiment failed in execution but succeeded in insight. As the AI wrestled with authentication flows and scheduling APIs, its commentary uncovered a policy roadblock: a lack of free/busy sharing across domains. I didn’t need more code—I needed a policy exception. This pivot—prompted by AI’s analytical playbook—saved me hours of development and pointed me straight to a better solution. That’s the real power of understanding limitations: failure reveals new directions.

Why Knowing Limits Empowers You

When you accept that AI won’t build your entire infrastructure for you, you stop chasing unicorns and start maximizing ROI:

1. Use AI to explore problems. Frame challenges and let it map out possible avenues.
2. Iterate on ideas. Ask it to compare options, weigh pros and cons, or critique your thesis.
3. Synthesize diverse inputs. Feed it reports, meeting notes, and data—then mine it for hidden trends.
4. Personalize insights. Combine its reasoning with your domain expertise for tailored recommendations.

Think of your AI as an expert advisor, not a one-stop handyman. You still flip the switch—it just helps you decide which switch.

Cultivating an Experimentation Mindset

I no longer ask, “Can AI do this?” but rather, “What can I learn from AI’s attempt?” Each experiment—successful or not—informs my next move. Success becomes less about completion and more about discovery.

Your Week 4 Challenge: Push the Boundaries

Experiment 1: The Synthesis Test

• Gather a set of documents or data you know well.
• Ask your AI to uncover patterns or correlations you hadn’t noticed.
• Record surprises and assess whether these insights spark new ideas.

Experiment 2: The Failure Test

• Assign the AI a task you suspect is beyond its reach (e.g., deploy a microservice).
• Observe how it fails—what assumptions does it make?
• Ask, “What’s the real obstacle here?” Let its missteps guide you to a clearer strategy.

Document your process and reflections. Your goal isn’t flawless code—it’s a fresh perspective.

The bottom line

AI’s quirks aren’t shortcomings; they’re beacons. When you know where it shines and where it stumbles, you steer it toward maximum impact. My AI psychologist revealed hidden strengths; my AI developer steered me toward better questions. Both lessons sharpen my judgment and supercharge my outcomes.

Next Week: AI for Writing – AI-Enhanced Communications

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