What a Year of Working With ChatGPT Taught Me About Strategy
This year, ChatGPT shifted from an answer engine to a thinking partner. By asking better questions and iterating faster, I strengthened my judgment and learned that AI works best when it sharpens rather than replaces human thinking.
This was the year that I finally embraced AI. I was previously hesitant to use it for fear of what it would do to me as a writer, thinker, and doer. However, what I’ve realized is that it makes me stronger in those places. At first, I admit I was using Chatty McChatsBot more like a faster search engine or, occasionally, a sentence-polishing tool.
But over the past several months, that relationship changed.
What I learned wasn’t just how to write faster or generate ideas more quickly. I learned how an AI tool could support strategic thinking. In order to get the good stuff out of AI, you have to put good stuff in. You have to ask it specific questions, give it details, and follow up in the same fashion I did when I was a working journalist. The first answer rarely is the one that makes it on the air or in a presentation.
From only answers to thinking partner
Early on, my prompts were transactional: “Can you rephrase this?”, “Can you summarize that?”, “Can you define this term?”
Over time, I started using ChatGPT less as an answer machine and more as a thinking partner. I brought half-formed ideas, competing constraints, and messy drafts into the conversation. Instead of asking for “the right answer,” I asked for alternatives, implications, and framing.
The biggest shift was realizing that the quality of the output mirrored the clarity of the input. Better questions led to better thinking. This was true of Chatty and of me.
Strategy benefits from externalized thinking
Most strategic work happens invisibly. It’s in your head, between meetings, or in the margins of documents. ChatGPT gave me a place to externalize that thinking quickly.
I used it to:
- Pressure-test assumptions before sharing them
- Explore how a decision might land with different stakeholders
- Translate complex ideas into clearer language
- Sanity-check scope, tradeoffs, and tone
This didn’t replace judgment. It sharpened it. Seeing my own reasoning reflected back—sometimes challenged, sometimes clarified—made gaps more obvious and decisions more intentional.
Confidence came from iteration, not automation
One unexpected outcome this year was increased confidence. This wasn’t because ChatGPT told me what to do, but because it helped me iterate faster.
I could try multiple phrasings, explore different levels of directness, and sense-check decisions before putting them in front of clients or colleagues. That repetition made patterns visible: what I consistently believed, where I tended to hedge, and when I already knew the answer but needed to hear it reflected back.
Over time, I relied less on the tool for validation and more for refinement.
The human work stayed human
Despite the efficiency gains, the most important parts of my role didn’t change. Relationship-building, judgment calls, empathy, and accountability all remained firmly human responsibilities.
ChatGPT helped me prepare better, think more clearly, and communicate more effectively—but it didn’t make decisions for me. It didn’t replace experience. It didn’t remove responsibility.
If anything, it raised the bar for how intentional I needed to be.
My focus for 2026
Looking ahead to next year, I’ll spend less time asking for polish and more time inviting friction. This year, the moments where ChatGPT pushed back, reframed a question, or exposed a blind spot were far more valuable than the moments where it simply made something sound better.
The tool was most useful when I treated it like a collaborator who could challenge me, not a service that existed to agree.
But most of all
Using ChatGPT helped me learn more about myself – how I think, how I decide, and it helped to validate my knowledge.
The biggest lesson this year wasn’t that AI can do my job faster. It’s that, when used thoughtfully, it can make my thinking better.
And that’s a shift that deserves attention.
