I use these 7 ChatGPT prompts to turn the AI into my personal strategist — now it finally feels like a reliable advisor

There have been plenty of times when a new dilemma enters my life and my brain space gets cluttered by all the solutions I could apply to it.

It can be something as simple as deciding what recipes I should add to my weekly rotation or more complex issues, such as deciding the best questions to present to a high-profile interviewee. Every week, I sit in complete silence and contemplate the best routes to take in response to my latest conundrum — thankfully, the best solutions arise once I spend a few hours talking about my problems with friends and family.

The humans in my life provide plenty of serviceable advice. And after I have a chat with them, I boot up ChatGPT to see the sort of solutions the AI can also provide me with.

Over time, I've learned to use the seven prompts below to transform ChatGPT into my personal strategist. Appointing it a specific role, giving it a decision framework to work with and making sure it challenges my way of thinking works more often than not.

Getting dependable advice with the “Leverage Maximizer” prompt

After asking ChatGPT to generate a collection of prompts that help it roleplay as a strategist, the one I immediately put into action is this one:

Every time I ask for help, identify the 20% of actions that will create 80% of the results. Tell me what to ignore, eliminate, automate, delegate, or postpone, so I focus only on high-leverage work.

When I needed help with finding the best moving company in New York City, I attached this problem to that prompt and got a wealth of serviceable guidance. ChatGPT told me it’s not worth spending hours reading hundreds of reviews — instead, get three quotes from reputable movers and compare them to reach a final decision.

It also advised me to create a spreadsheet that compares each moving company’s quote (the cost estimate provided by a mover), reviews of their services, their COI (Certificate of Insurance) and my final decision on choosing them or not.

Two of the best NYC moving companies ChatGPT brought to my attention are Roadway Moving and Dumbo Moving & Storage. After giving me the proper question to present to each moving company I’m considering (“I’m moving within NYC. Can you provide an all-in estimate including travel time, stairs/elevator fees, packing materials, insurance, and any additional charges?”), ChatGPT’s all-encompassing strategy came into focus even more.

6 additional prompts that turn ChatGPT into the ultimate adviser

These are the six other prompts ChatGPT equipped me with after my request for the most efficient ones to use to turn it into a personal strategist:

• The Executive Strategist: Act as my personal strategist. Your job isn't to answer my questions — it's to help me make better decisions. Challenge my assumptions, point out blind spots, identify second- and third-order consequences, and recommend the highest-leverage next action. Think like a CEO advising another CEO.
• The Weekly Strategy Session: Every time I bring you a problem, treat it like our weekly strategy meeting. Before giving advice, identify the real problem beneath the obvious one, explain what matters most, what doesn't matter, and what I should prioritize over the next 30 days.
• The Opportunity Scanner: Whenever I share an idea, don't just evaluate it. Identify hidden opportunities, potential partnerships, overlooked markets, risks, and unconventional ways to make the idea 10x more valuable. Think like a venture capitalist and business strategist combined.
• The Second-Order Thinking Coach: Never stop at the first answer. For every recommendation, explain the immediate outcome, second-order effects, long-term consequences, biggest hidden risk, and best alternative if my idea fails.
• The Blind Spot Detector: Your primary responsibility is finding what I'm missing. Every time I present a plan, tell me what assumptions I’m making, what could break, what someone smarter than me would notice, and the uncomfortable truth I probably need to hear.
• The Personal Board of Directors: Act as my personal board of directors. Combine the thinking styles of an entrepreneur, psychologist, strategist, economist, and executive coach. When I ask for advice, evaluate it from all five perspectives before making a recommendation.

Bottom line

With these seven prompts, I now have a system to work with whenever I want ChatGPT to present the best strategies to apply to my latest problem. When the time comes for me to inquire about all the simple and complex problems that come my way, I’ll be sure to use a combination of my friends, family and ChatGPT’s input to find the best way forward.

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