I see the same trend of 2-3 new AI reports every week.
They never say anything that new. People are mostly using AI to create more content but at speed.
We’re expecting people to just figure out how to do better with tools.
My experience has taught me that it rarely succeeds. You need to show people the enormity of the possible. There’s a controversial Steve Jobs quote I reflect on when new tech lands:
“Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!'” People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.”
Steve Jobs
Our industry (and many others) has fallen into the trap of a faster horse!
We acquire a powerful tool only to use it to 10x the very things that cripple us. Certainly not working smarter. The thing is it’s not your fault.
Too many people keep writing reports when we need to show the way. I’m bringing my own contribution to this with my weekly LinkedIn videos and YouTube tutorials.
This leads me to today’s big thought to explore together → examples of unexpected ways AI can increase your critical thinking skills.

AI is not killing your critical thinking
AI has been getting a bad reputation with critical thinking skills of late.
Here’s the thing: AI is not killing your critical thinking – You Are!
While click-baity headlines try to shock you, digging a little deeper gets to the truth of the matter. Those who see a regression in critical thinking skills have a high over-reliance and trust in AI.
Typically they fall into 3 columns:
- Don’t have the necessary level of competency with critical skills without AI
- Are lazy and can’t be bothered to analyse AI’s work
- Seek instant gratification, and blame ‘lack of time’ for the inability to think critically
AI is only as good as the human using it.
In this case, don’t blame the tool when you’re in control. The choice to forgo critical thinking is a human one.
AI can both amplify and destroy many skills, the choice to do that is yours.
As an example of amplifying critical thinking skills with AI, here’s a little story…
I hate writers block
I can only describe it as staring at a wall with no door.
You’re constantly wondering “How do I get through this thing”. It’s a mixed bag of emotions.
Confusion leads to frustration, which leads to disenchantment.
One day, for no apparent reason, I flipped open my browser to find myself on ChatGPT. The loveable, divisive and often misunderstood digital conversationalist of our time.
I love AI, but I’m not in love with it.
Writing is so personal to me that I let nothing touch the edges of my words and thus the thoughts captured within them. Yet, I found an unexpected value in our little AI friend.
Our conversations, despite how dumb they were from time to time, were firing my neurons so much that the annoying wall was crumbling quickly.
In some way, my conversations with AI were making me think deeply, critically and more meaningfully.
I had to consider:
- How could I translate what I was trying to overcome to this digital being?
- What were the right words?
- Which examples would illustrate the mythical wall to a non-alive creation?
It turns out there’s a lot more thinking involved when working with AI than you would first assume.
I believe that’s a good thing.
Unbundling yourself from the framework of search engines is vital if you want to make valuable use of your local AI friend.
The first conversation was simple, but it sparked curiosity
ChatGPT has no idea what writers block is.
Not in the way I experience it as a human. This is actually an advantage. It’s not overcome with the emotions of frustration and the want to bang your head off a table.
It’s far more stoic in its assessment, which is what you need.
This became an asset when I was ideating around the first live event I planned to host in my city. I was brainstorming how I want to position the event and what I want it to achieve.
Two problems hit me:
- I couldn’t make sense of the endless streams in my head
- I was doing an awful job at trying to explain that to ChatGPT
I decided to flip the script.
Since I’d shared a bunch of context (more like ramblings) with ChatGPT already. I thought it would be better if it could ask me questions to clarify my thinking instead.
So that’s what I did.
I asked my little digital companion ”Ok, let’s try a different tactic. Ask me key questions to help create a compelling offer.”
Then came this gem ↓

I was impressed, that’s for sure.
Challenging AI’s perspectives widened my own
I tend to do these kind of exercises a lot.
Often, I’ll feed a conversational AI tool a piece of my work or an idea I’m working on.
I’ll ask it to:
- Poke holes in my thesis
- Highlight anything I could have missed
- Opportunities to view the topic from a different cultural viewpoint
These are some of my favourite ways to enhance my human skills.
I can see issues from angles I might not have considered before. That is a useful tool, imo.
Try it yourself with these ideas:
📊 Data analysis
Scenario: Working with AI to analyse your data or reports.
Ask:
- Challenge my assumptions about ‘x’
- What’s another way to look at this insight?
- Here’s my thoughts, am I missing anything here?
🤔 Product Review
Scenario: Reviewing a potential new feature for your Product with AI
Ask:
- What am I being overly optimistic about?
- What is a macro or micro event that can change the outcomes of this feature?
- Tell me 5 reasons this feature won’t work as intended
- Tell me 5 unintended consequences of this feature
More unexpected benefits
Now, what I didn’t expect in these interactions with AI was a spillover into human conversations.
Spending so much time thinking about how can I explain ‘x’ to AI improved both my thought process and the structure of conversations with humans. In short, my ability to convey ideas and assess the level of detail needed improved.
It was odd to notice, but very much welcomed.
Interestingly, Google has discovered the same in experiments that showed how AI is reshaping how we learn through metacognition. I wrote about this experiment when we explored the real impact of AI on our skills.
One of the standout quotes from the research perfectly aligns with today’s exploration:
“In a world where AI can generate content at the push of a button, the real value lies in understanding how to direct that process, how to critically evaluate the output, and how to refine one’s own thinking based on those interactions.”
Ben Kornell, managing partner of the Common Sense Growth Fund
AI doesn’t like one-liners
Spending the last 25 years using one way to surface content online has built a strong auto-pilot in us all.
Working with generative AI is the total opposite of searching for content on Google.
One sentence questions stuffed with keywords don’t work here. You need to give conversational AI tools like ChatGPT lots of context and clear instruction. A prompt is just a instruction to a database after all.
It takes a lot more work to get a decent response from these tools than social media portrays.
Here’s an example of that in action with a report I was distilling ↓
Notice how I don’t just say: “Review this report”.

Prep the mind, perfect the prompt
Full disclosure: There’s no such thing as a perfect prompt.
They’re often messy, don’t always work every time in the same pattern and need continuous iteration.
Saying that, you can do a lot (and I mean a lot!) to set yourself up for success. Here’s a (sorta framework) I use to help think critically before, during and after working with AI.

How to think critically with AI
Step 1: Assess
Can AI even help with your task? (It’s not magic, so yes, you need to ask that)
Step 2: Before the prompt
- What does the LLM need to know to successfully support you?
- What does ‘good look like’?
- Do you have examples?
And, most importantly, don’t prompt and ghost.
Step 3: Analyse the output
- Does this sound correct?
- Is it factual?
- What’s missing?
Step 4: Challenge & question
I’m not talking about a police investigation here.
Just ask:
- Based on my desired outcome, have we missed anything?
- From what you know about me, is there anything else I should know about ‘x’? (works best with ChatGPT custom instructions and memory)
- What could be a contrarian take on this?
Step 5: Flip the script
Now we turn the tables by asking ChatGPT to ask you questions:
Using the data/provided context or content (delete as needed), you will ask me clarifying questions to help shape my understanding of the material.
They should be critical and encourage me to think deeply about the topics and outcomes we've covered so far. Let's start with one question at a time, and build on this
This is a powerful way to develop your critical skills and how you collaborate with AI.

🧪 Experiment to try
Feed your AI tool of choice with an example of your work.
This could be a workshop, email or a proposal. Whatever you’re working on right now. Make sure it’s not something sensitive if you’re not using enterprise AI tools.
Then ask the LLM to:
- Review your work and provide an abstract on what it thinks the topic is.
- Suggest points that could be improved and how.
- What could be missing?
Feel free to add your own too.
👩💻 Prompt playground
A prompt for the above could look a little like this:
# Context
I'm a [insert role] creating a [thing you're building].
I've attached a document which is an outline of my work so far. I want to improve this, specifically looking at:
- [suggestion 1]
- [suggestion 2]
- [suggestion 3]
# Task
Your task is to review my work and provide the following:
- A maximum 100 word abstract on what the document is about
- Points that could be improved
- Anything I'm missing about the topic
- Analysis of the tone, style and structure
Be direct in your feedback. Challenge me when needed. Your goal is to help me uncover blindspots to improve my work.
If you're unsure of any of the above points, ask me questions to clarify your outputs.
Present these bullet points back to me with:
- a header
- Bullet point summary
- numbered suggestions (if applicable)
- examples for the suggestions you recommended. Ensure to include links to these materials
Confine your review to my [topic].
Let's begin with our first task.
Write a 100 word abstract about the topic of this document as you understand it.
[Example] Unearth better insights from data

Final Thoughts
The key to preserving and enhancing skills is you.
You’re the main character of your choices. If AI even has a chance of killing your critical thinking skills, you need to have a good level in the first place.
→ If you’ve found this helpful, please consider sharing it wherever you hang out online, tag me in and share your thoughts.
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