By default, AI models are designed to be agreeable. To get true value, explicitly instruct the AI to act as a critic or 'devil's advocate.' Ask it to challenge your assumptions and list potential risks. This exposes blind spots and leads to stronger, more resilient strategies than you would develop with a simple 'yes-man' assistant.

To preempt investor objections, founders should use AI to generate a critical investment memo on their own company. Prompting the AI to identify potential reasons for failure reveals weaknesses in the business plan and pitch, allowing founders to address them proactively before the meeting.

Move beyond using AI for data consolidation and generation by treating it as a tough critic. Prompt it with questions like, "What have I missed?" or "If you were a top consultant, what would you have spotted?" This reframes the AI as a thought partner, forcing it to challenge your assumptions and uncover strategic blind spots.

To expose vulnerabilities, run a "murder board" offsite. Task your team with a simple goal: if you were a new, well-funded competitor, how would you kill our company? This exercise forces brutal honesty, counters a culture of overly positive "optics," and reveals weaknesses before the market does.

Rather than waiting for a competitor to replicate your product with AI, proactively use AI tools to see how easily your own features can be commoditized. This internal "red team" exercise helps identify true moats versus superficial ones, forcing a focus on defensibility from day one.

Move beyond using AI as an assistant and program it to be a critical sparring partner. Pendo's Field CPO had his AI analyze his codebase and brutally call him out for building a system for himself, not for others, forcing a strategic realignment.

After an AI agent synthesizes competitor websites, messaging, or market data, don't stop at the summary. Use the power prompt: "Based on everything you found, what's the gap I can attack, and how can I exploit it?" This transforms data analysis directly into strategic action.

Instead of using AI as a compliant assistant, program it to be a challenging 'sparring partner.' Ask it to find holes in your logic or anticipate all the critical questions your CEO might ask. This transforms it from a content generator into a powerful strategic tool for preparation.

Advanced AI tools can model an organization's internal investment beliefs and processes. This allows investment committees to use the AI to "red team" proposals by prompting it to generate a memo with a negative stance or to re-evaluate a deal based on a new assumption, like a net-zero mandate.