By assigning roles like a contrarian, an expansionist, and a first-principles thinker to a single LLM, founders can get multi-faceted feedback on critical questions. The model debates itself and provides a synthesized recommendation, revealing blind spots that a single-prompt approach would miss.

Use Claude Cowork to spin up multiple "sub-agents" with distinct personas (e.g., your boss, customer, skeptic). These agents review your work from different perspectives, providing objective, multi-faceted feedback before you present it to real stakeholders.

Create distinct AI agents representing key executives (e.g., CEO, CMO, CSO). By posing strategic questions to each, you can simulate how different departments might react, identify potential misalignments in priorities, and refine proposals before presenting them to real stakeholders.

Instead of relying on a single AI, use different models (e.g., ChatGPT for internal context, Claude for an objective view) for the same problem. This multi-model approach generates diverse perspectives and higher-quality strategic outputs.

Instead of accepting a single answer, prompt the AI to generate multiple options and then argue the pros and cons of each. This "debating partner" technique forces the model to stress-test its own logic, leading to more robust and nuanced outputs for strategic decision-making.

Move beyond simple prompts by designing detailed interactions with specific AI personas, like a "critic" or a "big thinker." This allows teams to debate concepts back and forth, transforming AI from a task automator into a true thought partner that amplifies rigor.

Instead of just using one AI, create a "team" of specialized assistants. Use one AI as your chief architect for trade-offs, another for coding, and a third for product strategy and planning. This approach accelerates both learning and project execution.

Markup AI's CEO built AI profiles for figures like Steve Jobs. Before board meetings, he runs his deck by this "fantasy board" to get instant, diverse feedback, effectively bringing expertise into the room that isn't physically there.

Leverage AI to gain external perspectives without meetings. Prompt it to act as a specific persona—like a skeptical CEO, an enthusiastic user, or a New York Times reviewer—to critique your work. This reveals blind spots and strengthens your idea before sharing it.