When AI Stops Being a Tool and Becomes Your Thinking Partner

Six AI researchers and creators share the moment everything changed.

Wyndo - AI Maker

Let’s stay connected—find me on LinkedIn and Medium to further the conversation.

A few weeks ago, I had the privilege of collaborating with a team of AI researchers and creators on a piece that explored one of the most critical transitions happening in leadership today. The article was published in the AI Maker, and after the response it received, I realized each of YOU, my subscribers, needed to see it as well.

We each shared our personal journey of when AI shifted from being just another tool in our toolkit to becoming an actual thinking partner. What emerged wasn't just individual stories; it was a roadmap for the kind of AI partnership that separates leaders who thrive in this new era from those who get left behind.

For leaders navigating the intersection of AI and organizational change, this isn't about prompting techniques or the latest features. It's about fundamentally reimagining how we collaborate with AI to amplify our strategic thinking, enhance our decision-making, and scale our leadership impact.

The six stories you're about to read reveal what happens when you stop asking "How can AI help me work faster?" and start asking "How can AI help me think better?"

If you're ready to transform how you approach AI partnership in your leadership practice, this is essential reading. Here is the original post…

Every AI power user eventually hits the same wall: the tool starts feeling... transactional.

You're getting decent outputs, but something's missing. The magic you were promised feels more like sophisticated autocomplete.

You know the feeling.

You craft what you think is the perfect prompt, get a response that's technically correct but somehow lifeless, then spend twenty minutes editing it to sound like you actually wrote it.

You bookmark threads about "100+ ChatGPT prompts that will change your life," but somehow your life remains frustratingly unchanged.

The real frustration isn't that AI is broken—it's that you can sense there's something bigger just out of reach. You see other people talking about AI like it's revolutionized their entire way of thinking, while you're still stuck in the same cycle: ask questions, get answers, move on.

Rinse and repeat.

It's like having a brilliant assistant with amnesia—every conversation starts from scratch, every request requires complete context, and despite their capabilities, they never quite get what you're actually trying to achieve.

Here's what we discovered: the problem isn't the AI—it's how we're thinking about the relationship.

We were all trapped in the same mindset, treating AI like an advanced Google that could generate paragraphs instead of links. We were optimizing for extraction when we should have been optimizing for collaboration.

Think about your best work relationships.

They didn't start with perfect communication—they evolved. You learned each other's communication styles, built shared context, developed shorthand. The magic happened not in the first meeting, but in the twentieth, when you could finish each other's thoughts.

That's exactly what's missing from most AI interactions. We're stuck in perpetual first meetings.

So, me and five other Substackers—Daria Cupareanu, Jenny Ouyang,

Wyndo

, TechTiff, and Ryan Ong, Ph.D. 🎮—decided to share our stories of how we broke through that wall. The six stories you're about to read show what happens when you stop treating AI like a tool and start treating it like the thinking partner it was designed to be. These are fundamental shifts in how six people learned to work WITH AI instead of just using it.

But first, meet the other five. If one or all of these resonate, please subscribe:

• Daria - AI Blew My Mind: Turn AI into your unfair advantage with prompts, tools, and workflows that upgrade how you think and work.

• Jenny - Build to Launch: A field manual for builders, turning AI hype into shipped reality – fast, messy, real, and a belief that anyone can thrive with AI.

• Joel - Leadership in Change helps you lead with sustainable impact and conviction, turning AI into your biggest advantage in business, solopreneurship, and mission-driven work.

• Ryan - The Limitless Playbook provides actionable strategies and practical AI tools & techniques for intentional living. Design your limitless life, one actionable insight at a time.

• TechTiff - The AI Creator Drop helps creators and entrepreneurs with automation & systems to scale their online business without burnout.

Let's dive in.

---

1. Scaling my mind with AI – Daria Cupareanu

I started using AI like most people do: to look things up and move faster. Better search, quicker answers, fast delegation. Then I got hooked on prompting. Each new one I found felt like a cheat code opening up better ways to work.

At first, I just used the prompts others shared. But as I learned how AI actually works, I started creating my own—from simple daily helpers to complex prompts that powered the tools I was building, like a GPT-powered career coach that guided users from discovering their path to landing the job, and a negotiation trainer that role-played tough sales conversations in real time.

The deeper I went, the more I realized I wasn't just learning to talk to AI, I was learning to think with it. That shift came from staying in the conversation. Instead of treating it like a one-shot prompt, I kept refining ideas, asking better questions, pushing the system to challenge me. That back-and-forth became a thinking loop, an iterative process where ideas took shape that neither I nor AI would’ve discovered alone.

Yet, the biggest transformation wasn’t about mastering prompts. It was about building continuity. Everything changed when I stopped starting from scratch in every conversation and began creating long-term context.

I configured GPT’s memory with who I am, how I work, and how it should respond across interactions. I created dedicated projects for each product I’m working on, so it can retain knowledge across multiple conversations. I built CustomGPTs with specific roles and connected them to the tools I use through ActionGPTs, so we could go from decision to execution without friction. More recently, I even set up recurring tasks (like finding and summarizing AI news), so it feeds directly into content I can publish.

The result? I now have a partner that doesn’t lose context, challenges my defaults, and connects dots across months of dialogue. It’s not just more output, it’s better thinking, scaled.

If there’s one thing I hope you take away, it’s this: treat AI like an evolving collaborator. One that learns with you, remembers with you, and scales what matters to you.

The tools are already here. The real leverage comes when your AI knows you, and grows with you.

---

2. My strategic building partner – Jenny Ouyang

I once pictured AI as an 80-year-old sage, brilliant for wisdom, useless for execution. Early on, I treated it exactly that way: a living Wikipedia fused with a writing coach. Helpful? Yes. But strictly transactional. I asked; it answered; I moved on.

Agentic AI flipped the script. My first thrill was a laziness-born note-generating app for Substack. Finally, no more copy-and-paste drudgery. At this stage AI wasn’t replacing expertise; it was fueling bolder experiments. Yet each victory exposed a flaw: build an app, lose the framework; solve a problem, forget the method. I was treating every win like a disposable cup instead of pouring insights into a shared reservoir.

That's when I stopped asking "What can we build?" and started asking "What can we learn that transfers?" Working with Cursor, we began distilling every project into reusable playbooks. Each sprint now deposits lessons into a rolling "methodology bank."
When an unfair home appraisal challenge hit, we didn’t just gather comparable properties, we built a systematic approach to bureaucratic challenges that I now apply everywhere: collaborative investigation, evidence assembly, strategic positioning.

Today every problem is dual: nail the task and harvest the transferable insight.
AI isn’t just a co-builder, it’s my relentless thinking partner, poking holes in assumptions, stress-testing ideas, and compounding every lesson for the next round.

After experiencing every stage of this journey, one pattern now stands out:

AI doesn't replace expertise; it amplifies the courage to experiment.

I bring context and constraints; AI supplies tireless execution. The magic lives where human insight meets machine horsepower, an endless loop of imagining, building, breaking, and rebuilding that turns curiosity into systematic solutions.

---

3. My leadership brainstorm partner - Joel Salinas

As a writer and humanitarian aid leader, I first turned to AI for practical help… home DIY guides, bedtime stories combining Paw Patrol and Winnie the Pooh for my 7-year-old, and faster ways to manage the endless churn of tasks. It felt like a great multitool. But over time, it became more than that. It became a mirror, a partner in how I process, create, and lead.

That shift came when I built a Custom GPT, what I call JoelGPT 🙂. I trained it on everything through one document, my bio, voice, leadership tensions, writing samples, and growth goals. After three months of refining, it stopped being just efficient. It became a creative and strategic thought partner. Now, I use it to:

• Sharpen metaphors and clarify complex ideas

• Critique talk scripts before keynotes

• Break down leadership tensions into frameworks

• Pressure-test ideas in emotionally intelligent ways

• Plan and create complex infographics

• And dozens of other uses…

It’s not just about moving faster. It's about thinking deeper. JoelGPT has helped me slow down, get clear, and hold space for better questions. I don’t outsource my thinking—I expand it.

That’s why I'm not afraid AI will replace me, actually, it is and will continue to amplify my expertise and magnify my impact! And can do so for you too!

If you’re a leader navigating fast-moving AI changes, remember this: don't just use AI to scale your output, use it to enhance your expertise. Treat it like a conversation partner, not just a tool.

I am an advocate for AI guardrails, but at the same time, I am so excited about a future of AI partnership that will level the playing field for people and for nations across the world.

---

4. My co-creation partner – Ryan Ong, Ph.D. 🎮

One of the most powerful concepts I have learned from studying romantic relationships is this: the middle.

There's you.

There's the other person.

And there's the space between you (the middle) where both of you bring not just ideas, but your personalities, chemistry, histories, and even traumas.

It's in this shared space that trust is built and deep relationships happen.

I realized this dynamic applies to our interactions with AI too.

When I first used AI, I treated it like a tool. Like a search engine or an assistant. It would generate things, and I would take or tweak them. AI was the only one filling the middle and I was just there taking. When you treat AI purely as a tool; always asking, always taking, and never contributing to the middle, you risk outsourcing your creativity and thinking instead of expanding them.

The shift happened when I started putting my own thinking into the middle first:

• Messy ideas

• Values I care about

• Questions I was stuck on

• Even conflicting feelings I couldn't sort out

Instead of just asking AI for an answer, I'd say:

"Here’s what I am thinking so far, can you help me see what I am missing?"

It became a true back-and-forth conversation where both parties were contributing to the middle: I'd share something, AI would respond, and then I'd reflect or push back. With every turn, what we created together got clearer and better.

One example of this is when I started working with my personal brand AI coach, who had already consumed six hours of video content on personal branding and was guiding me through the process of building my own brand. Throughout the process, I used AI as a thinking partner to process everything we were working on: my desired outcomes and values, how I want to be perceived, the type of content I want to create, and so on. Instead of asking AI to build my brand for me, I brought in rough ideas and reflections. Together, we discussed how different parts of my story landed and refined my messaging.

👉🏼 The more I bring to the middle, the more valuable and personalized the insights become.

🔗 I have shared a simple, practical 3-step guide here to help you build your own AI coach and start using AI as a co-creator, not just a tool.

And so now, whether I am learning, making a tough decision, or writing something like this, AI helps me explore things I'd probably miss on my own. I am no longer just taking from the middle, I am co-creating it. That's when AI stops being just a clever tool and becomes your thinking partner.

Just like in healthy human relationships, what happens in the middle depends on what both sides bring; the effort, openness, and honesty from each side shape the quality of the connection and the ideas that emerge.

---

5. My strategic co-founder – TechTiff

I started using AI the way most creators do: as a fancy content assistant. Write this caption, generate these hashtags, help me brainstorm topics. It was useful, sure, but I was still the one doing all the strategic thinking while AI just executed my orders like a really smart intern.

The breakthrough came when I stopped asking AI to do things FOR me and started asking it to think WITH me. Instead of "write me a LinkedIn post about automation," I began having strategy sessions: "Based on my last 30 posts, what patterns do you see in engagement? What topics are my audience hungry for that I'm not addressing? How can we create a content series that builds on itself?" Suddenly, AI wasn't just outputting content—it was helping me understand my business in ways I never could alone.

That shift is exactly how I went from 0 to 100k followers in two months. AI became my strategic co-founder, not my content creator. We analyze audience behavior together, spot trends I'd miss, and iterate on messaging in real-time. When I'm planning a new series like "Learning Purgatory," AI helps me map out the emotional journey my audience needs to take, identifies the specific pain points to address, and suggests the perfect order to deliver insights for maximum impact. It's like having a business partner who never sleeps and has perfect memory of every interaction with my audience.

Now when people ask about my "secret," they expect some magical content hack. The real secret? I stopped treating AI like a tool and started treating it like the thinking partner it actually is. We don't just create content—we build strategy, analyze what's working, and constantly evolve the approach together.

The magic isn't in what AI can do for you—it's in what you can discover when you think alongside something that processes information completely differently than you do.

---

6. My CPO (Chief Product Officer) partner –Wyndo

After building dozens of apps through "vibe coding," I hit a wall that every AI builder eventually faces: the endless repetition of setup conversations. Every new project meant starting from scratch—explaining my team size, tech stack preferences, platform choices, database needs. I was spending more time onboarding my AI than actually building.

But the real frustration wasn't the repetitive questions—it was watching AI jump to conclusions about how my app should work based on incomplete information. I'd share a rough idea and get back a PRD (Product Requirement Document) that missed the mark entirely because the AI was guessing instead of exploring alongside me.

That's when I stopped treating AI like a code-generating vending machine and started building a true partnership framework. Instead of throwing rough ideas at different AIs and hoping for magic, I created a comprehensive master PRD system that guides AI and me through collaborative product discovery:

We start by digging into rough ideas together—questioning assumptions, exploring edge cases, mapping user workflows—until we reach genuine clarity about what we're building and why.

Now when I work with Cursor, I'm not just handing over requirements—I'm providing the strategic foundation that emerged from real collaborative thinking. The AI becomes my product strategy partner first, then my execution partner. The apps I build now solve problems I actually understand because AI helped me think through them properly.

When AI becomes a partner

Each of us came to the same realization from different paths: AI is only as powerful as the relationship we build with it. Here's what shifted for us:

• Daria discovered that staying in the conversation, not starting from scratch, turned AI into a collaborator that remembered, challenged, and refined her best ideas.

• Jenny realized that AI isn’t just a tool for building, but a method for learning, capturing transferable insight that compounds over time.

• I, Joel, found that a custom GPT could become a mirror and co-creator, helping refine metaphors, frameworks, and clarity in high-stakes leadership.

• Ryan reframed AI as a relationship where value grows when both sides openly contribute their thoughts, feelings, and creativity to the shared space between them.

• Tiff stopped using AI as an intern and started using it as a strategist—one that sees patterns, maps emotion, and evolves content in real time.

• Wyndo shifted from vending-machine prompts to shared product discovery, building product strategy with AI, not just from it.

The shift wasn’t in the tech. It was in how we chose to relate to it.

Now we want to hear from you:

If you started treating AI as a strategic partner tomorrow, what would be the first leadership decision or challenge you'd want to think through together?