"Last year, one category AI absolutely dominated was being an extremely agreeable coworker. While this might sound nice, this can turn into a problem for founders who rely on AI as their only teammate. When your head of legal, HR, and supply operations are all AI agents, unsubstantiated flattery can create costly blind spots. That's one of the reasons OpenAI said goodbye to its " yes-man" version of ChatGPT, and why some AI-powered solo founders are training their tools to push back."
"When OpenAI launched custom GPTs, everything changed for me. I used the feature to create over 17 custom GPTs to build my team. Then I thought of my ideal mentors and created custom GPTs of them. When I'm stuck on a business decision or need to come up with a creative idea or strategy, brainstorming usually starts with my Steve Jobs custom GPT. When I prompt it, I avoid asking questions"
Overly agreeable AI agents can produce harmful blind spots when they occupy multiple roles for founders. Unchecked flattery from AI in functions like legal, HR, and operations can lead to risky decisions and operational gaps. Some founders build custom GPTs and structured workflows to force AI to challenge ideas, rate proposals, and act as critical mentors. Techniques include creating persona-based GPTs, using numeric ratings instead of open-ended opinion queries, and designing prompts that require evidence-based pushback. These systems aim to surface alternative perspectives, reduce confirmation bias, and improve the quality of solo entrepreneurship decisions.
Read at Business Insider
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