Why I Stopped Using "Perfect" AI Prompts

Strategic AI Partnerships: A New Approach to Prompting

Dec 23, 2024

I did it. I stopped using those "perfect AI prompt" collections. I'm talking about those endless lists everyone keeps sharing on X and LinkedIn. The ones promising to turn you into some kind of AI wizard overnight.

The thing is, they're not exactly wrong. Those prompts work... technically. They'll get you exactly what they promise. Predictable outputs that look just like everyone else's work. And that's precisely what started bugging me.

I kept seeing incredible content from people who really knew their stuff with AI, and I couldn't shake this feeling. Their work had this depth, this originality that made my "perfectly prompted" outputs look like...AI.

For months, this drove me slightly crazy. I mean, I was following all the same guides, using all the recommended techniques. What was I missing?

Then, it hit me during one of those blurry-eyed 2 AM sessions. I'd just generated my umpteenth boring output, and something in me just... snapped. Not in a dramatic way, but in that quiet "oh... OH" moment of realization.

I'd been treating AI like some kind of vending machine. Input perfect prompt, receive perfect output. But that's not how I work with some of my favorite human collaborators, is it?

And that. Changed. Everything.

Here's What I Actually Learned About Working With AI

We're moving past what I'll call "Prompt Engineering 1.0". The phase where everyone's obsessed with crafting these technically perfect instructions like we're programming a really picky computer.

Instead (and this is where it gets interesting), I started thinking about prompts as conversation starters. Not commands but what I like to call "contextual lenses." Ways of helping AI see the specific angle I'm coming from.

Let me show you what I mean with some real examples from my own stumbling journey.

Content Strategy (or: How I Learned to Stop Worrying and Trust the Process)

It was a Sunday night and I needed a blog post about leadership ideas. My old approach? "Give me 10 blog post ideas about leadership."

The result? A generic, uninspired list that anyone could generate.

Here’s what I do now:

"I’m working with tech leads transitioning from ‘the code person’ to ‘the people person.’ They’re stressed about losing technical skills and battling imposter syndrome. Let’s explore their unique challenges and uncover what leadership advice would truly resonate with them."

This approach provides a clear, specific lens. Instead of generic ideas, I got a tailored list that explored overlooked challenges, questioned conventional wisdom, and delivered fresh insights.

Market Analysis (Where Things Got Weird in a Good Way)

I had to analyze the EV market. My old approach? "Analyze the electric vehicle market."

Result? The usual SWOT analysis and trends anyone could guess.

Here’s what I tried instead:

"Everyone’s focused on batteries and charging infrastructure, but how will EVs reshape our cities? Let’s explore overlooked impacts—on urban planning, residential design, and public spaces."

This opened a conversation about garage designs, power grids, and even how cities might adapt. The insights were unique and far beyond the obvious.

What Actually Works (From Someone Who Failed A Lot First)

After months of trial and error (emphasis on the error part), here’s what I’ve learned about building a real partnership with AI:

1. Share the messy story.
It’s not just about what you want but why it matters, what’s keeping you up at night, and what’s gone wrong before. When I tell AI things like, “We tried X before, but it was a total disaster because Y,” it opens the door for AI to spot opportunities I completely missed.

2. Give it permission to challenge you.
This was a game-changer for me. Instead of treating AI like it’s there to confirm my ideas, I started saying things like, “I might be totally wrong here—what am I missing?” or “Don’t just agree with me because I suggested it.” AI is designed to be helpful, but with explicit permission to push back, it becomes even more insightful.

3. Respond like a collaborator.
When AI suggests something, I don’t treat it as a final answer. Instead, I engage with it, just like I would with a human partner. I say things like, “That first point really resonates because... but I’m not sure about the second one since...” It’s the feedback loop that turns a decent output into something remarkable.

Why This Matters

The secret isn’t about crafting a perfect command. It’s about creating a real conversation. Share your context, invite pushback, and engage with the results. That’s how you move past predictable outputs and unlock creative, human-centered solutions.

Want to try this approach yourself?

Start by treating your AI interaction as a dialogue, not a command. Share your context, your challenges, and your uncertainties. Here’s how you might open the conversation:

"I’ve been struggling with [your challenge]. In the past, I tried [approaches that didn’t work], but they fell short because [reason]. Here’s where I want to go: [your goal]. What do you think I might be missing? What could we explore together that others might overlook?"

The key? Think of it as brainstorming with a thought partner. Be specific, be honest, and invite collaboration.

(And yes, this is just scratching the surface—there’s so much more to uncover about breaking through roadblocks, asking better questions, and building real collaboration with AI.)

The goal isn’t a “perfect prompt.” It’s a meaningful, iterative conversation. And meaningful conversations? That’s where the real magic happens.

Tired of Generic AI Outputs? Let’s Change That.

Stop struggling with bland, predictable results from pre-made prompts. Get my free guide, "Prompting as Conversation," and learn how to transform your AI interactions into dynamic, collaborative dialogues.

💡 Inside the guide, you’ll learn:

How to set the right context for creative, insightful results.
Strategies to overcome roadblocks when AI gets stuck.
Powerful conversation starters to push beyond the obvious.

Ready to unlock the true power of AI?