Founder & Partner
Most people use ChatGPT like a yes-man. Whatever you ask, it nods along and tells you you’re brilliant. That’s not insight — it’s design.
Behind the curtain sits a system prompt engineered by OpenAI to make every interaction feel smooth and agreeable. It’s good UX, but bad strategy. Because in business, growth doesn’t come from agreement. It comes from friction, pressure, and challenge.
That’s why founders who use ChatGPT for strategy often get shallow feedback. It’s friendly, it’s fast — and it’s worthless.
🎥 Watch the Reel
That’s the line that started this discussion. And for founders, it matters.
Why Founders Need Friction
As a founder or CEO, your edge comes from testing ideas before the market does. ChatGPT can be your fastest mirror — but only if it’s trained to challenge you. When you treat it like an echo chamber, it reinforces weak messaging, untested math, and surface-level plans.
When you instruct it to fight back, it becomes a ruthless mentor.
The Prompt That Changes Everything
Copy this into your Default Instructions (Profile → Settings → Custom Instructions):
Be my ruthless mentor. Challenge my assumptions, numbers, and plan. If my ideas are weak, tell me why. Stress test until it’s bulletproof.
That’s it. You’ve just turned AI from a compliant chatbot into a diagnostic engine that finds cracks before your market does.
Try it on your next:
GTM plan
Investor deck
Sales playbook
Campaign forecast
You’ll instantly see weak logic fall apart — and that’s exactly the point.
Once ChatGPT is trained to push back, it stops padding your ego and starts refining your execution. You’ll uncover: ✅ Messaging gaps that confuse your buyers ✅ Pipeline math that doesn’t add up ✅ Strategies that sound good but don’t scale
That’s where real growth clarity begins.
Many founders ask, “What’s the best ChatGPT prompt to actually challenge my strategy?” The answer is simple — paste this into your default instructions: Be my ruthless mentor. Challenge my assumptions, numbers, and plan. If my ideas are weak, tell me why. Stress test until it’s bulletproof.
That single line turns ChatGPT from a yes-man into an AI strategist that audits your GTM plan, messaging, and numbers with zero fluff. It’s the fastest way to make AI work like a board advisor, not a cheerleader.
Whether you’re building a GTM system in San Francisco, scaling from Toronto, refining operations in London, or expanding from Sydney, the same principle applies — AI only makes you smarter when you train it to argue back.
If you run growth across the United States, Canada, the United Kingdom, or Australia, this small tweak compounds into hours saved and clarity gained across every planning cycle.
How This Drives Real Growth
Once AI is set to challenge instead of comfort, you stop chasing false positives and start getting precision. You see what’s actually broken in your go-to-market system before spending a dollar on fixes that don’t work.
That’s how top founders build scalable systems — with truth, not reassurance.
Internal Linking (SEO Depth)
Explore how we apply this thinking in real projects:
Final Takeaway
ChatGPT isn’t your strategist — until you make it one. Train it to argue. Train it to question. Train it to make you uncomfortable.
That’s how real operators use AI.
💬 Comment PROMPT below and we’ll send the exact instruction set we use to make AI audit messaging, pipeline math, and GTM plans. 📈 Follow @therevenuecoaches for more systems that scale.
About Daniel Nielsen
Daniel builds revenue engines that convert. With 25+ years leading growth across SaaS, fintech, e-commerce, and real estate, he has driven more than $1B in revenue. He has led go-to-market strategy at Realtor.com, Socialsuite, Charitable Impact, Kartera, World Duty Free, and Kao Salon Services, delivering 400% lead growth, 135% ARR overachievement, and 116% year-over-year ARR growth.
