This article is republished with permission from Wonder Tools, a newsletter that helps you discover the most useful sites and apps.
My brain’s nearly melting in this ongoing heat wave. To avoid the temptation to outsource my thinking to AI, I’m pushing in the opposite direction.
How can I use AI to challenge me to think more, not less? Read on for five tactics I’m leaning on to avoid cognitive surrender when my brain’s overheating.
1. Challenge Me, Don’t Praise Me
- The Tactic: Use AI as an intellectual sparring partner.
- Explore alternative perspectives. Ask an AI assistant: How might someone from X or Y professional background think about this? What tough questions would they ask?
- The Benefit: Identify potential blind spots and weak assumptions before finalizing a presentation or making an important decision.
- Try This: Present a plan, idea, draft, or decision to an AI assistant with instructions to challenge your thinking in multiple ways. Identify risks you haven’t considered and add nuance to your analysis.
Prompt Template
I’m planning to [decision/plan] because [reasoning] and with a goal of [objective]. Play devil’s advocate. Give me multiple perspectives on this. Be bold and surprising in your reply, and address these questions:
- What are the strongest arguments against this approach?
- What alternatives should I consider?
- What risks might I be overlooking?
- What questions should I be asking myself?
- What challenges should I expect to face?
- What could I do to learn more before I move forward?
- Who else could I talk to about this?
- What could I do to increase the chances of success?
Pro Tip: Ask your AI assistant to role-play. It can respond as a coach, a teacher, a family member, a competitor, or an audience member. Varied viewpoints can be useful. Or ask it to act like a person you admire, living or dead, real or fictional. You can even ask it to simulate a council of advisors, each with a distinct perspective. Ethan Mollick has written about using that tactic for feedback on material in his book.
Microsoft’s Copilot AI now has a new free “Team of Advisors” experimental feature to give you multiple perspectives from an animated expert panel. Here’s an example of what a panel suggested in reply to my open-ended query (though you won’t hear the animated voices). And here’s the transcript.
- Limitation: Unless you provide detailed context, you may get bland responses.
- To Keep it Private: Use a free offline AI tool like Jan, which I wrote about recently.
- Example: During a dialogue with ChatGPT about a new morning routine I was adopting, I realized I had left several things out of my planning. In addition to posing questions that helped me think more carefully about my goals and my timing, it produced a PDF plan with tables.
2. Think Out Loud
- The Tactic: I like talking out loud to clarify my ideas. It’s my way of free writing. I use voice AI tools to turn my stream of consciousness into organized text. I call it bionic dictation. The AI assistant records and transcribes what I say. It then goes a step beyond dictation by transforming my words into an outline or summary. That helps me add structure to my meandering thoughts.
Step 1: Pick an AI dictation app.
Apple Notes and Google Keep work well for free mobile dictation. They won’t summarize your text or transform your words into an outline, as Letterly can.
- Letterly is the reliable mobile app I prefer. It’s a standalone app, or you can use it within your iPhone keyboard to dictate texts, email, or notes. I make lots of typos when thumb typing, so I often use my voice instead in any app. It’s more accurate than the iPhone’s built-in dictation. It now also works on my laptop.
- Wispr Flow is what I often use on my computer. It lets me hold a function key to dictate into any app. It’s several times faster than typing and works in 100+ languages. It’s free for 2,000 weekly words, or $12/month for unlimited use.
- Lispr is a good new free alternative to Wispr. It can instantly translate your spoken words into any of 99 languages. I tested it by dictating various messages and translating an email reply into Portuguese, which worked well.
- MacWhisper is another excellent free option. It can record your system audio for online meetings, or even transcribe uploaded audio files. I paid $73 for a one-time upgrade to use the best AI models, but the free version has almost all of the same features.
Step 2. Create a new note.
Hit record. Talk. The app won’t judge you or care whether you speak quickly or slowly. It doesn’t care whether you’re saying something brilliant or sputtering nonsense. When you finish it will summarize your rambling. It doesn’t care how long you pause, or whether you contradict yourself or digress. It just patiently transcribes and then sums up your words.
- Pro Tip: Record with AirPods while walking, screen off. The lack of a visual editing screen frees me up to just talk. The editing part of my brain interferes less when I’m talking than when I’m typing.
- Limitation: Voice AI won’t sharpen weak thinking. Read and edit your own words and refine them before sending anything important.
- Example: I sometimes start my day at work by talking through my priorities for a few minutes with a voice AI tool.
3. Do Deep Research Before a Big Decision
- The Tactic: Before making an important decision or beginning a new phase of a project, I run multiple deep research queries. Within 5 to 25 minutes I have a citation-rich report that would in the past have taken days to prepare. After reading I can follow-up on the most promising citations and links.
- The Tools: ChatGPT, Gemini, Perplexity, Copilot, and Claude all have similar deep research modes.
- How it Works: Dictate or type in an extensive research query. The AI assistant will then analyze your query and search through dozens of sites, or sometimes hundreds. It will synthesize its findings in a report with citations, so you can go to the original sources. I usually export the analysis into a Google Doc for easier reading or printing.
Try This: Toggle on the deep research setting in your AI of choice. Then write a query that includes:
- What you’re researching and why you care.
- Any relevant supplemental documents. You can attach relevant PDFs or other materials you’ve already gathered.
- What format you want. Maybe you’d like tables, or a timeline, or a beginner’s step-by-step guide, adapted for your specific context.
- What level of understanding you’re aiming for, or what you already know. Are you a scientist looking for updates on a field related to yours, or a novice trying to make sense of something brand new?
- Which sources to prioritize, if you have preferences or favorites. Maybe you want only peer-reviewed research, or info from particular publications or specific countries or government agencies.
- What questions the report needs to address, and what it should avoid. If you’re not interested in historical background or scientific explanations, say so. If you don’t want it to assume prior knowledge, say that.
Vague queries produce generic reports. Detailed direction is what makes deep research worth the wait.
- Pro Tip: Tell the AI assistant to ask you questions to clarify your objectives before it begins the research. That gives you an extra chance to refine your query.
- Edit the Research Plan: ChatGPT, Gemini, and Copilot let you review and edit their research plans before beginning. When editing, narrow or broaden the scope based on what you care about most.
- Limitation: A report is only as good as its sources. For sparse topics, AI may lean on publishers with flimsy fact-checking. Specifying preferred sources can help. Afterwards, check the source list. Spot-check the citations, which don’t guarantee accuracy.
- Each Model’s Strengths: Perplexity races to return results in three minutes. It’s concise and clear. Gemini is also fast, and exports neatly into a Google Doc. ChatGPT produces exhaustive reports and helpful tables. It can sometimes take 20 to 30 minutes. Claude is similarly thorough. It researched 574 sites in 17 minutes for one report.
- Examples: Copilot took 10 minutes to prepare this brief summary report about why some nations excel at the World Cup. Gemini’s analysis on the same query was much more detailed.
4. Learn Something New
Design Your Own Curriculum: Ask your AI assistant to guide you through whatever you’re curious about. Unlike textbooks or generic explanatory sites (e.g. Wikipedia) designed for anyone and everyone, an AI assistant can tutor you in ways you prefer. ChatGPT has Study and Learn mode. Gemini has Guided Learning. These prioritize helping you learn, not giving you answers.
- Ask for diagrams, analogies, examples, or case studies that relate to topics or places or people that interest you. Get a detailed overview of key concepts in archeology, or a beginner’s guide to soccer’s offside rule. Specify your prior understanding. Ask follow-up questions.
- Space your learning over days or weeks. AI assistants excel at creating structured learning plans tailored to your schedule and interests. And they’re better now than they used to be at keeping track of what you’ve already learned.
Summarize Your Learning Preferences
- Include context about what you want to learn, why, and how. Specify sources you prefer. Explain what you already know.
- Note whether you learn best by reading, listening, watching, or trying something yourself.
- Mention if you like quizzes, drills, or exercises you can do while commuting or during breaks at work. Ask for learning games.
- Ask for specific book or article recommendations using web search or deep research. Hallucinations are less common now, but ask for verification links and check them yourself.
- If you need a human learning partner, ask for guidance on finding one. Or ask for sample language you can adapt when reaching out to someone.
- Connect your calendar to ChatGPT or Claude to have the AI schedule learning time for you. Making the plan concrete increases the likelihood you’ll follow through.
Pro Tip: Request a learning plan you can print out. Get suggestions for useful experts to follow and strategies for avoiding learning pitfalls. Ask for help setting learning targets, measuring progress, choosing resources, and motivating yourself.
Short Prompt Template: Make a [timeframe] learning plan for me so I can learn more about [skill/topic] because [reasons for learning]. I’d like to spend [hours/week]. As a [beginner/professional/other skill level], I prefer to learn in [learning style]. I have the following [learning goals]. Include milestones, resources, and practice ideas.
5. Make a Learning Dashboard
You can ask an AI assistant to help you make an app to track reading or eating goals, fitness metrics, your Wordle streaks, or your book writing progress.
- Try This: Describe an idea you have for a learning tracker. Experiment with Claude Artifacts or Gemini’s Canvas. Or try Lovable or Bolt, specialized AI tools that make it easy for anyone to create a site or app. Glaze is another option for making a mini app that lives on your computer.
- Bonus: I like these examples of how journalist David Bauer uses AI.
- Resources: Here’s my Glaze guide, and tips on making artifacts.
This article is republished with permission from Wonder Tools, a newsletter that helps you discover the most useful sites and apps.