Our First Real Un-Robocall: When AI Asks the Right Questions
Published on: June 16, 2024
What happens when AI asks you questions using your own interests and background? We filmed our first "Un-Robocall" session with Dr. Benito R. Fernández, PhD—a tech founder who loves soccer, dominoes, and sailing. Instead of selling him something, we used our AI to ask five personalized coaching questions. Here's what we learned.
The AI knew to use soccer metaphors because Benito coached for 12 years. It referenced dominoes because that's in his LinkedIn profile. When he scored himself a "3" on mission alignment? That's the honest moment that makes coaching useful instead of feel-good fluff.
How Our Recipe System Works
0:17 - The Foundation - We're not building another chatbot. Our system combines 75+ "recipe" prompts with someone's social media profile to create personalized coaching questions. The goal isn't answers—it's helping you think about things you might not otherwise consider.
The Five Questions (With Scores)
1. The Soccer Question: Mission Alignment (Score: 3/9)
1:23 - Mission Focus - "Are you working on the right stuff today?"
We asked Benito to imagine being a soccer striker choosing the perfect moment to shoot instead of chasing every pass. His honest answer? A 3 out of 9 for mission alignment because he was "preoccupied with other things."
Theta Insight: The soccer metaphor worked because Benito coached for 12 years. It made an abstract business concept concrete and personal. This is how AI moves beyond generic advice to actual insight.
2. The Dominoes Question: Team Leadership (Score: 7/9)
2:50 - Leadership Scale - "Can your team win without you?"
Using dominoes table strategy—where each player knows the game so well they can win without guidance. Benito scored his leadership scalability a 7, pretty strong for a CTO managing multiple companies.
Theta Insight: This targets "founder bottleneck syndrome." The dominoes metaphor resonates with his Venezuelan heritage, making business assessment feel natural instead of clinical.
3. The Sailboat Question: Process Efficiency (Score: 9/9)
3:37 - Workflow Optimization - "Do your workflows help or hurt you?"
We used a sailboat metaphor—perfectly tuned to harness wind. Benito gave this a 9, his highest score, showing The Whisper Company has genuinely streamlined processes.
Theta Insight: A 9 from a technical founder suggests real operational excellence, not just good intentions. The sailing metaphor connected personal passion to critical business assessment.
4. The Lighthouse Question: Ethical Alignment
4:18 - Values Check - "Would you be proud if everyone knew how you make decisions?"
Using lighthouse imagery tied to Venezuelan coastal waters, asking about alignment with his privacy and security tech work.
Learning Moment: Benito needed clarification here, showing even well-crafted prompts can miss. This is why we're building a learning system—real feedback beats theoretical perfection.
5. The Time Design Question: Strategic Balance (Score: 6-7/9)
5:08 - Day Design - "Are you designing your days or just reacting?"
Another dominoes metaphor—each move deliberately setting up the next. Benito scored this 6-7, acknowledging the challenge of balancing multiple ventures.
6:18 - The Real Issue: He mentioned "too many balls in the air," perfectly illustrating why time design (not time management) matters for high-impact leaders.
What We Discovered
Metaphors Make Abstract Concepts Stick
10:12 - The Method - People think in stories, not spreadsheets. We combined Benito's social media with our recipe library to create questions that felt personal, not generic.
Theta Insight: This represents context-aware AI versus rule-based systems. By encoding personal interests into business metaphors, we create "analogical transfer"—using familiar concepts to understand complex ones.
Scoring Creates Actionable Awareness
Numbers make feelings concrete. Benito's scores (3, 7, 9, 6-7) instantly revealed strengths (processes) and challenges (mission alignment, time design).
Theta Insight: The 0-9 scale serves as an "externalization tool"—helping people assess objectively rather than emotionally. When Benito scored mission alignment a 3, he identified a specific improvement area, not just a bad day.
Organic Expansion Reveals Hidden Value
7:40 - Venezuelan Community - The best insights came off-script. Benito shared his Austin Venezuelan Association work.
12:54 - Quimby Discovery - He recommended Quimby, a mental health startup using similar prompting approaches.
Theta Insight: This "associative emergence" happens when structured prompts create space for unexpected connections. The Quimby recommendation revealed a potential partnership—showing how the Un-Robocall helps you discover questions you didn't know you had.
The Quimby Connection: A Patterns Recognition
Benito introduced us to Quimby, a mental health company using prompting questions for emotional well-being rather than strategic alignment.
Theta Insight: This reveals the "Prompting Economy"—AI systems that enhance thinking through better questions, not better answers. Both companies recognize the most valuable AI doesn't know the most—it helps you think best.
What's Next: Scaling Personal Coaching
10:46 - The Vision - Make this automatic and available to everyone. An AI that proactively reaches out with the right questions at the right time, based on your goals, patterns, and context.
The Challenge: Solving the "Contextual Timing Problem"—not just what to ask, but when. Our thinking map technology creates dynamic models of priorities, energy patterns, and decision context.
Theta Insight: This session shows AI can enhance strategic thinking through personalized, contextual prompting. As we refine this approach, we're building toward AI that genuinely improves human judgment.
Key Takeaways for Leaders
Personal metaphors drive engagement - Questions tied to your background break through resistance and create genuine reflection.
Scoring makes concepts actionable - The 0-9 scale transforms vague feelings into specific improvement areas.
Process becomes competitive advantage - Benito's 9 for workflow efficiency shows how streamlined processes become strategic weapons.
Time design beats time management - Moving from reactive to proactive daily design is crucial for high-impact leaders.
Structured prompts unlock serendipity - The organic Quimby mention shows how good questions lead to unexpected opportunities.
Experience It Yourself
Ready for personalized AI coaching? Sign up for early access and see how our Un-Robocall system can help align your daily work with your bigger mission—just like it did for Benito.
What resonated with you from this session? Would the soccer striker metaphor work for your situation, or would you need different analogies? Share your thoughts and let us know what metaphors would resonate with your background.
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