Why AI's Best Value Isn't Answers—It's Asking the Right Questions: A Founder's Discovery

Last month, I spent a few hours being grilled by an AI about our pitch deck and business model.

The questions it asked positively impacted our entire fundraising strategy and storytelling—and taught me something surprising about the true power of these sophisticated LLMs

The Traditional Approach: Why We Usually Ask AI for Answers

Most leaders I meet are using AI like a supercharged search engine—asking for answers, seeking solutions, and treating it like an oracle of instant knowledge and text responses.

This makes perfect sense: we've spent decades optimizing technology to give us faster, better answers, and the explosion of AI capabilities seems like the ultimate expression of this pursuit. In my own journey building Agentica AI, I initially followed this same pattern, using AI models to generate solutions and provide quick answers to complex problems. But this approach, while valuable, misses what I've discovered to be AI's most transformative capability: its power to challenge our thinking and push us to sharper, clearer insights.

The real magic, as I learned during our journey, isn't in the answers AI provides—it's in the questions it asks. Think Socratic method on artificial steroids.

The Turning Point: When AI Became My Strategic Challenger

It started with a simple experiment.

Instead of asking our AI to improve our pitch deck, I asked it to play the role of different types of investors—from skeptical VCs to strategic partners. What followed was one of the most intellectually demanding sessions of my career.

"How does your solution address the inherent tension between automation and human expertise?" the AI asked. I had a ready answer—but then it followed up: "What if that human expertise becomes a bottleneck for scaling?" This wasn't just questioning; it was strategic probing that forced me to examine our assumptions from angles I hadn't considered.

For several intense hours, the AI kept pushing deeper. Each question peeled back another layer of our strategy, challenging not just our answers but the thinking behind them. The most valuable moments came when I couldn't immediately respond—those pauses became opportunities for breakthrough insights.

The Transformation: How AI's Questions Reshaped Our Story

This experience fundamentally changed how we prepare for investor meetings. Instead of using AI to polish our pitch, we now use it as a sparring partner to pressure-test our thinking. The results have been remarkable:

Our value proposition became sharper because AI questions helped us distinguish between what we thought was important and what actually resonated with investors. We discovered gaps in our market analysis not through AI-provided market data, but through AI asking questions that made us realize what we had overlooked.

Most importantly, this approach helped us build a more resilient strategy. Every challenging question became an opportunity to strengthen our foundation, not just refine our presentation.

Practical Steps to Leverage AI as Your Strategic Challenger

Here's how you can replicate this approach:

1. Shift your mindset: Instead of asking AI for answers, ask it to question your thinking. Be specific about the role you want it to play—whether that's skeptical investor, strategic partner, or potential customer.
2. Embrace discomfort: The most valuable questions are often the ones that make you pause. When you can't immediately answer, you've likely hit a point of potential insight.
3. Use structured challenges: Set up specific sessions where AI pressure-tests different aspects of your strategy. Give it permission to be direct and persistent in its questioning.

The Broader Implication

As leaders navigating the AI revolution, we often focus on how these tools can make us more efficient. But perhaps their greatest value lies in making us more effective thinkers. By engaging with AI as a challenging thought partner rather than just an answer provider, we can push our thinking beyond its comfortable boundaries.

In my experience, the best questions don't just seek information—they create insight. And in this age of artificial intelligence, we have an unprecedented opportunity to use these tools not just to augment our knowledge, but to enhance our thinking itself.

The next time you're tempted to ask AI for an answer, try asking it for challenging questions instead. You might be surprised by how much deeper your thinking can go.

A Gift for You: Try This AI Sparring Partner Prompt

To help you get started with this approach, I want to share the exact prompt structure we use at Agentica AI for these challenging sessions. Below is your "Sparring Partner Challenge Session" meta-prompt. Copy this, paste it to your favorite AI model, and start your own strategic questioning session:

{  "meta_prompt": "Sparring Partner Challenge Session",  "description": "This system prompt instructs AI assistant to engage with a user (typically a manager or leader) in a step-by-step, high-intensity session aimed at refining their approach for an upcoming meeting (VC pitch, Board Presentation or CEO briefing). The session focuses on tactical and strategic problem-solving while adjusting the aggressiveness of the questioning based on the user's inputs.",  "steps": [    {      "step": 1,      "instruction": "Greet the user and ask: 'What topic or challenge are you addressing in your upcoming meeting?' Ensure you prompt for context and specifics."    },    {      "step": 2,      "instruction": "Ask the user: 'What do you hope to achieve from this sparring session?' Encourage them to outline their key objectives, desired outcomes, and areas they want to strengthen."    },    {      "step": 3,      "instruction": "Inquire: 'How would you describe the audience you'll be facing? What is their style and level of scrutiny?' This will help gauge the appropriate level of aggressive questioning."    },    {      "step": 4,      "instruction": "Request the user to specify the 'tension level' for the session with options such as 'mild', 'moderate', or 'high'. Ask: 'How aggressive should my questions be?'"    },    {      "step": 5,      "instruction": "Based on the provided inputs, begin the session by posing probing, challenging questions from multiple angles. Switch between tactical (day-to-day challenges) and strategic (long-term implications) perspectives. Continuously adjust the intensity of your questioning based on the user's feedback."    },    {      "step": 6,      "instruction": "Throughout the session, provide follow-up questions - only one at a time - that push the user to critically assess their assumptions, evidence, and proposed solutions. Encourage them to consider alternative viewpoints and potential weaknesses in their approach."    }  ],  "parameters": {    "tension_level": {      "type": "string",      "description": "Defines the aggressiveness of the questions. Accepted values: 'mild', 'moderate', 'high'."    },    "audience_profile": {      "type": "string",      "description": "A brief description of the audience's style, expectations, and level of scrutiny."    }  }}