Stop Me From Being Stupid—AI as a Creative and Strategic Partner
Part 6 of our 20 part series
Welcome to AI as a Creative and Strategic Partner—Funmentum™ Style!🎉🎉🎉
Our new series on harnessing Generative AI like Chat GPT, Copilot, Gemini, etc. for both fun and breakthrough results. Many people use GenAI for low level tasks like summarizing meeting notes, writing simple emails, researching industry trends, etc.
This series is focused on the opposite—Gen AI is strongest as a high level thought partner. Not replacing you or doing your work in an average/generic way, rather pushing your thinking as a strategic challenger, creative muse, and feedback focuser. All to create higher quality work, which is approved faster, with less and time/effort. And it’s a lot of fun!
Make sure to subscribe and follow along—new posts every Friday at 5am PT/8am ET for the next 14 weeks!
Chapter 2 of 4: Strategic Challenger
For the next 5 posts, we'll explore how AI can help you get to “right” faster on your most important projects. I’ve run high cost strategy engagements that take months—consider this a mini-version you can do yourself in 15 minutes.
#6: Stop Me From Being Stupid
Charlie Munger said it best:
"All I want to know is where I'm going to die so I'll never go there."
We’re often better served by trying to avoid making mistakes, than hitting home runs of brilliance.
⚠️ Blind spots are dangerous because by definition we don’t know we have them. With the right prompting, AI can open up your aperture—helping you identify assumptions and spot potential failures before they happen.
🔍 The Blind Spot Detector Prompt
Take on the role of a seasoned strategic consultant at a global firm. You've facilitated hundreds of pre-mortem sessions for Fortune 500 companies, startups, and non-profits. You're known for your uncanny ability to spot potential disasters that teams miss because they're too close to their own work. Your clients often say, "That single workshop saved us from a million-dollar mistake." You combine ruthless analytical thinking with a supportive approach that helps people hear hard truths without becoming defensive.
Here's everything I know about my project: [VOICE RECORD: talk about your project, the audience, your goals, key constraints, current ideas, concerns, etc.]
Here's all documents related to my project: [UPLOAD DOCUMENT or PASTE notes, drafts, outlines, whatever you have]
Before you provide any analysis, please interview me with 3 questions, one at a time, to challenge my thinking based on what I provided.
For each question, go through these 2 steps:
- Step 1: Ask me a question that challenges my thinking about a specific aspect of my project, and provide 2-3 thought starters or examples to assist me with my thinking.
- Step 2: After I respond, synthesize your insights and my response before moving to the next question.IMPORTANT: Please complete the entire 3 question interview process before providing your final analysis.
After our interview, create a pre-mortem analysis that imagines my project has failed completely one year from now.
Detail:
- The 3 most likely reasons for failure
- Hidden assumptions I might be making
- Stakeholders or perspectives I may have overlooked
- A recommended revision approach that addresses these blind spotsBe brutally honest — I need to hear what could go wrong now, not learn it the hard way later. Make sure that you ask me these 3 questions first, one at a time, before delivering your pre-mortem analysis.
A Mini-Workshop in Your Head
When you run this prompt, the AI transforms into a strategy consultant that challenges your thinking with targeted questions.
Here are examples of questions your AI might ask you:
Where in your timeline is most likely to be delays? Another team you’re dependent on, or an area you’re not as familiar with?
Who internally might feel threatened by this project's success? An expert in the old way of doing things, or a leader who might lose headcount?
What company priorities could shift to derail this initiative? Competing projects or org changes?
How might your users react differently than you expect? Maybe they won’t change their workflow or your solution is too complex?
The AI is forcing you to think through these questions, but also giving you fodder to consider as a thought partner. These are just examples - the genius is that the AI will find the 3 most relevant questions to ask you, based on everything that you gave it up top. So give it as much as possible!
I find this process to be really fun, especially when I lower the pressure to have a “perfect” answer and I just turn on voice record and talk to it.
Real-World Value
Here’s some examples of how different roles could benefit from this mini-workshop:
Product Manager: realize their rollout plan overlooked training needs for the support team, potentially creating a customer service nightmare at launch.
Non-profit Director: realize that their fundraising campaign messaging would alienate their strongest long-term donors while attracting only one-time contributors.
Marketing Team Lead: realize that their campaign timeline overlapped with a competitor's annual product launch, which would significantly reduce media attention.
HR Executive: realize that their process change would create unintended bottlenecks in adjacent teams, potentially causing organizational friction.
It’s not that everything in the AI’s final analysis will be right. But if you gain one new insight that stops a big mistake, that will be 15 minutes well spent. Also remember, don’t just think about it as a single prompt, it’s about the iteration and pushing that comes afterwards (see: be fickle and hard to please).
When I allow myself to be loose and improvise, these mini strategy workshops can be both enjoyable and transformative. What is the most important project on your work plate right now? Try this today.
Remember—stop yourself from being stupid before reality does it for you!
💡That’s your one thing for this week!
Make sure to subscribe to get the next 14 posts, every Friday morning at 5am PT/8am ET! Let’s make Friday our day to grow our AI skills experimenting on high level work challenges.
I count on word-of-mouth to grow this series, please consider sharing it with a friend.
👋Thanks,
Devin McNulty
Co-Founder Funmentum™ Labs
👀👀👀
P.S. I can get your team acting like this—book 15 minutes to pick my brain.
P.P.S. Try Funware Ideator for free, the world’s first ever automatic brainstorm, powered by AI (of course)!
🦾AI as a Creative and Strategic Partner
As we progress, each post will be linked below for reference.
Chapter 1: Mindset is the Magic
Chapter 2: Strategic Challenger
Post #6: Stop Me From Being Stupid (this post!)