The TL;DR, With The One AI Prompt That's Better Than Your Board Of Advisors


A bi-weekly roundup of opinions from your secret cabal of AI advisors
July 12 - July 25

Advice, But 5x Better

Last week I was grappling with a range of tough decisions and because I'm a total nerd for AI, I was talking it out with Gemini. I journaled out the context, jotted down my personal thoughts, and uploaded a few files into that chatbox.

After the AI went brr, it basically told me what I wanted to hear.

This is a common AI problem: they're designed to be syncophants. However, with this in mind, I experimented and told it to NOT be a syncophant and to explicitly tell me what I didn't want to hear.

Here's the exact wording I used:

I appreciate this insight, but I'd like your responses to be more unflattering and un-sycophantic. I need a harder thought partner. I need a dose of reality.

Massive improvement in the response! It called me out in a way that cut deep, but since I asked it to be no-nonsense, I was prepared to hear something uncomfortable. When the AI explicitly named a fear that I hadn't verbalized but absolutely agreed with, I said OUT LOUD, "Damn, son."

This got me thinking: what if I told it to look at the scenario from another perspective? And then another perspective? And then one like Steve Jobs?

After five perspectives, I felt supremely confident with my next steps. It took weeks of dithering (and probably a couple bottles of wine) and turned it into a super-productive nuanced experience that catalyzed me into action.

I shared this experience at last week's "Show Me Something Cool With AI" monthly meetup (write back if you'd like to be invited!) and the response from attendees encouraged me to share it with all of you.

I've improved the prompt so it's easy for anyone to one-click copy-paste the prompt into your AI tool of choice. All you have to do is paste the text it into your AI tool and it'll ask you what it needs in order to give you advice.

Not only that, I but I also created five "scenarios" so you can try it out and see how the prompt behaves.

I think this is a very low-stakes way to help you make more intentional thoughtful decisions. Whether you're trying to figure out whether to keep dating that person, or working that job, or wearing that shirt, having five different robot opinions weigh in will give you a wealth of perspective on what you ultimately choose to do.

TL;DR: I created a one-click prompt to help you reason through that next tough choice.


A TL;DR from the CRO

If you've got a tough question to answer, my hourly rate is "walk."

-Roman Noodles, Chief Ruff Officer


Other Learning Nerds That We Like


The Summer of Strengths Continues!

If you're putting on your AI-augmented thinking cap, you're probably also leaning into your Strategic Thinking strengths. Your Strategic Thinking strengths are your unique lens for making sense of the world, enabling you to anticipate the future and navigate complexity like CRO Roman Noodles.

The Strategic Thinking domain is one of four clusters of strengths. Here are the eight strengths in this theme:

  • Analytical: You seek data and logic to find the objective truth.
  • Context: You look to the past to understand the present.
  • Futuristic: You are inspired by the future and what could be.
  • Ideation: You are fascinated by ideas and can find connections between seemingly disparate concepts.
  • Input: You have a craving to know more and love to collect information.
  • Intellection: You enjoy deep, introspective thought and reflection.
  • Learner: You have a great desire to learn and want to continuously improve.
  • Strategic: You can quickly spot the relevant patterns and issues to chart the best way forward.

Explore the Strategic Thinking domain of CliftonStrengths with our deep dive and see through the chaos, devise plans, and navigate complexities with ease.

PS. Discover the strategic side of yourself and your team with the Team Strengths Accelerator, $500 off until September 1st as part of our Summer of Strengths promo.


I'm relaxing on a beach when this newsletter is due to go out. It's summer vacation, baby.

When you think hard about it, if you enjoy the beach then you enjoy hanging out with teeny-tiny rocks that have been tumbling for thousands of years.

Rather than shiny rocks, I could be making beach sand in my basement.

Yeah, vacation brain is definitely already on.

Roasting on itty-bitty-tumbled rocks,

Dan from Learn to Scale


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PS. There's not much better than an ice cream sandwich on the beach...except watching machines make ice cream sandwiches.

Dan Newman

Entrepreneur, Professional Learner, & Proud Failure. Writes about sales, marketing, and entrepreneurship from the eyes of a learning and development nerd. Lead teams, manage people, scale a business, and learn better through the biweekly irreverent newsletter, the TL;DR.

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