Welcome to today’s issue of HOW TO // AI. We’re glad you made it!

Simulate Objections and Stress-Test Your Strategy Before You Pitch It.

At this point, you’ve probably taken one (or several) brainstorming sessions to ChatGPT and said, “Give me 10 ideas for X.”

That’s fine for volume, but volume doesn’t equal insight. Without friction, ideas remain unexamined. That’s how you end up greenlighting the first thing that sounds good.

Instead of operating in an echo chamber, you can use an AI chatbot to act as an on-demand red team, helping you uncover weaknesses and prepare for objections before they ever get raised.

Here’s how to turn it into a creative sparring partner that makes your thinking stronger.

Before you ask AI to critique anything, you need something to push against. Summarize your idea clearly in just a paragraph or two. Then copy-paste that into ChatGPT, and prep the model for what’s coming:

This context matters. You're priming the model to simulate resistance, not provide support. You're creating useful tension.

Now give it your idea, and let it break it apart.

Here are 3 highly effective personas you can assign to ChatGPT to get different types of pushback:

🧢 The Skeptic:

The Skeptic helps identify where your reasoning may be built on sand. Use it to spot false confidence early.

👨 The Customer:

The Customer forces clarity. If your idea depends on someone adopting it, they need to understand it—and trust it.

🏁 The Competitor:

The Competitor flips the table. Now you're defending your idea from real-world pressure, not just theoretical failure.

The initial critique gives you a high-level view of your plan's vulnerabilities. The next step is to probe those weaknesses for more detail. Use follow-up prompts to understand the root of the objection and explore potential solutions.

For a specific weakness it raised, ask:

Or to force a trade-off:

These questions push the AI to give you actionable feedback you can use to strengthen your pitch.

There’s no substitute for real human thought. But with some clever prompting, you can use ChatGPT to pressure your thinking in ways you can’t always simulate alone.

This isn’t just useful for product ideas. You can use this method to:

It works because ChatGPT doesn’t have ego or status bias. You’re free to explore dead ends, bad takes, and worst-case scenarios without social cost.

📌 Key takeaway: Creative output without resistance is just a list. If you want stronger ideas, add friction on purpose. Use ChatGPT to push back, poke holes, and flip perspectives, then let your best ideas survive the fight.

For more info on this topic checkout - 6 Tips for Using ChatGPT to Brainstorm Better

The Rundown: OpenAI says its newest models are getting strong enough to help with real cyberattacks and cyber defense. They’re adding extra controls so security teams benefit while abuse is limited.

Details:

Takeaway: AI is becoming a real factor in hacking, not just a buzzword. OpenAI is trying to tilt that power toward defenders. Your move: test AI in your own security workflows and assume attackers are doing the same.

The Rundown: Switzerland launched Apertus, an open-source large language model trained exclusively on public, opt-in data. Available on HuggingFace, Apertus comes in 8 billion and 70 billion parameter versions and was trained on over 1,800 languages.

Details:

Takeaway: Apertus shows how Europe is pushing for transparent, legally compliant AI development. For your business, this signals a growing alternative to US proprietary models. If you operate in regulated industries, open models like Apertus may offer the auditability and legal clarity you need to deploy AI without compliance risk.

Snapchat released its “Imagine” Lens for premium users, letting them re-create photos with text prompts for custom looks and social content.

Roblox added AI tools that generate interactive items from prompts and launched real-time voice translation across English, Spanish, French, and German.

Amazon Music introduced “Weekly Vibe,” an AI feature that auto-curates new playlists every Monday based on each user’s recent listening habits.

Anthropic backed California’s AI transparency bill, requiring large companies to disclose safety testing protocols for their models.

Attorneys general from CA and DE warned OpenAI about chatbot safety after teen suicides were linked to prolonged interactions with ChatGPT.

Showrunner announced they will use AI and live-action footage to reconstruct 43 lost minutes of Orson Welles’ The Magnificent Ambersons.

Alibaba’s Qwen3-ASR-Flash model achieved under 4% error rates across multiple languages, outperforming Google and OpenAI in speech transcription.

Motion raised $38 million to expand its AI agent suite for small businesses, now serving over 10,000 companies with integrated assistant.

Stanford professor Jeremy Utley shares how to move beyond treating AI as just a tool. He explains why the most creative outcomes come from working with AI like a teammate. Creativity, he argues, is about pushing past “good enough” with AI as your partner.

Q: “I like the idea of using AI as a sparring partner, but I’m worried it’ll just tear my idea apart and leave me stuck. How do I balance keeping the project constructive, without either fluffing me up or tearing me down?”

A: Great question, because the point isn’t demolition, it’s durability. You want friction, not paralysis. Here’s how to keep the critique loop useful:

📌 Key takeaway: Critique without iteration is just criticism. When you design a custom feedback loop, you turn AI’s resistance into a training ground for stronger ideas.

Have a question you want answered? Email [email protected] and you just might be featured in an upcoming issue!

This newsletter is your starter kit for mastering AI with confidence. We keep things simple, show real examples, and focus on quick wins you can repeat.

Stay curious, stick with it, and watch your skills grow week by week!

Until next time :)