Context is King—Your Smartest Hire Needs It
June 22nd, 2025
Happy Sunday Friends!
Here’s one quote I’m musing on this week, two core ideas, three favorite things, and one question to carry with you into the week ahead.
One Quote I’m Musing
“Don’t ask the mirror to smile—smile first.”
| Zen Proverb
We’ve spent recent weeks exploring the personal, the philosophical, and the quietly powerful edges of leadership.
This week, let’s bring that lens back to the tech we know and love (or love-hate):
Artificial Intelligence.
Specifically, the Large Language Models (LLMs) that have become our most unpredictable coworkers—ChatGPT, Claude, Llama, Grok, and their ever-growing cohort.
I’ve fielded a mountain of questions about prompt engineering lately.
How do you get ChatGPT to do what you want?
What’s the best structure for a prompt?
Why does Claude nail it one day and miss the mark the next?
Well, Context is King.
We’re zooming out to explore how these models have evolved over the last five years: from rigid pattern-matching systems to dynamic conversational partners, from tools you use… to teammates you collaborate with.
This isn’t just about writing better prompts—it's about rethinking the relationship.
And if you’ve been treating AI like a machine that needs wrangling, it’s time to treat it like your newest—and smartest—hire or risk falling behind.
🚀 From Tool to Teammate: A 5-Year Evolution
AI used to be autocomplete on steroids—responding based on patterns, limited nuance, and minimal creativity.
Then came fine-tuning and supervised learning, training AI to perform tasks more naturally.
Now, we’re in the RLHF era—Reinforcement Learning with Human Feedback—where models are shaped by human preferences and context.
They reason, plan, and even anticipate your needs.
But here’s the catch: they still don’t know what you want unless you clearly tell them.
The capability is there.
The clarity? That’s on us.
🎯 Prompt Engineering Isn’t the Game Anymore—Clarity Is
Last week, my friend, we’ll call him Steve, came to me with a problem. He was struggling to get Claude 3.5 to respond effectively. Steve crafted a beautifully elaborate prompt—complex, layered, impressive—but not getting him what he needed.
I asked him plainly, “Forget the prompt—what do you actually want?”
Steve explained clearly, like talking to a person (I’ve been known to be one from time to time).
I typed his explanation nearly verbatim, only framed as a question.
Claude responded perfectly.
It wasn’t magic—it was clarity.
🧠 Framing Over Roleplay: A Secret Insight
Many still try to outsmart AI:
“You are a world-class expert with 20 years of experience and have read 12 billion books…”
Impressive, but unnecessary.
Today’s models are intelligent. They don’t need elaborate roleplay—they need clear context.
📋 Mini How-To: Ask the Model How to Be Asked
I like the way Ali Abdaal slides in fun and useful how-to’s, so here’s my version.
Here's a simple, underrated prompt:
“I want to ask you a question about [insert topic].
What’s the best way to ask this so I get the most useful answer?”
Let the model teach you how it wants to interact. It’s onboarding your AI through the AI itself.
Here’s how it works:
Start with the topic: “I’m deciding between Claude or GPT for a planning session.”
Frame your meta-question: “Before asking, what information do you need to offer the best advice?”
Let the model guide you: Clarifying tone, audience, or purpose.
Build the conversation: You’re not prompting—you’re partnering.
Found this useful? Forward this simple trick to someone who’s stuck in prompt purgatory.
🧠 BJ Fogg’s Behavior Model in Action
Behavior = Motivation × Ability × Prompt
For better outputs:
Motivation: Clarify why it matters.
Ability: Provide usable context.
Prompt: Spark clear, simple actions.
Prompting is about clarity, not control.
🔮 Where This Is Going: The Future of Working with AI
We’re still early.
Most see AI as smarter assistants. But what's next is deeper.
We’re entering the era of agentic models—AI that plans, acts, and adapts across tasks and systems.
My prediction?
The future of work won’t be about writing better prompts—it’ll be leading smarter systems.
The skill won’t be knowing what to type—it’ll be:
Sharing intent
Clarifying context
Co-architecting outcomes
Leaders who master clarity with AI gain an exponential edge.
Socrates didn’t lecture—he asked clear, powerful questions of people. Your AI relationship thrives the same way.
💡 Two Core Insights
1. The clearer you are, the more capable it becomes.
2. The best prompt is a clear conversation.
✨ Three Favorite Things (This Week)
1. 🛠️ Tool: Claude 3.5—treat it as a collaborator, not code.
2. 📚 Idea: “Ask the model how to be asked.” Simple, elegant, powerful.
3. 💡 Quote: “The future of work won’t be about writing better prompts. It’ll be about managing smarter systems.”
❓One Question to Reflect On
What’s stopping you from having a clearer conversation—with your AI, your team, or yourself?
Have you tried asking?
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Until Sunday My Friends.
Stay adaptable. Stay present.
Think Dangerously.
–e
