How I Used ChatGPT to Discover My Founder Identity
Most founders spend years refining their leadership style, often through trial and error. But what if you could get an instant, data-driven reflection of your founder identity? That’s exactly what I did—using ChatGPT.
In a recent episode of the Operations podcast recorded live at Startup Boston Week, I interviewed Dr. Shari Worthington, an expert in entrepreneurship who has researched the different identities founders embody. Her findings intrigued me, so I decided to take it a step further to see what I could learn about my own strengths and weaknesses. I uploaded her research into ChatGPT and asked it to analyze my founder identity.
What ChatGPT Told Me About My Founder Identity
ChatGPT’s response was surprisingly insightful. Based on my background, approach to leadership, and decision-making style, it categorized me as:
60% Execution-Driven
✅ I optimize, get things done, and avoid reckless pivots.
❌ But I might resist pivoting until there's clear evidence it's necessary.
30% Community-Driven
✅ I deeply value my network and audience, letting them guide my strategy.
❌ I might struggle with balancing business decisions that could alienate part of my audience.
10% Visionary
✅ I have a clear lighthouse vision but balance it with pragmatism.
❌ I might hold onto certain ideas longer than necessary if they align with my long-term vision.
Not only did ChatGPT break down my identity, but it also highlighted the weaknesses associated with each type—insights directly pulled from Shari’s research. This level of reflection was makes a compelling case for how founders can use AI for self-assessment.
Why This Matters for Founders
Understanding your founder identity isn’t just an intellectual exercise—it has real implications for how you make decisions, build teams, and grow your company. For me, If I’m too execution-driven, I might overlook long-term vision. If I lean too much on community, I may struggle with independent decision-making.
For me, the exercise was validating. It put into words the instincts and tendencies I’ve had for years but never formally defined. More importantly, it made me aware of potential blind spots I need to address.
How You Can Use AI for Self-Reflection
If you’re a founder (or even an operator) looking to gain a better understanding of your leadership style, here’s a simple framework to follow:
Find a Model or Framework – Whether it’s Shari Worthington’s research on founder identities or another well-established framework, start with a reliable source.
Feed It Into ChatGPT – Upload the research and provide context about your background, experiences, and leadership style.
Ask for an Analysis – Have ChatGPT categorize your identity and highlight potential strengths and weaknesses.
Validate with Real-World Examples – Compare ChatGPT’s insights with past experiences and get feedback from peers.
Act on the Findings – Use the insights to refine your approach, balance your strengths, and work on your blind spots.
The Future of AI-Powered Self-Awareness
ChatGPT didn’t define my founder identity—it simply articulated what was already there. But the fact that it could take complex academic research and turn it into a personalized reflection in minutes is powerful. As AI tools become more advanced, I see huge potential for founders to use them not just for content generation, but for leadership development and self-awareness.
If you’re curious about what kind of founder you are, try this experiment for yourself. You might be surprised at what you learn.
