Last month, I was struggling with a product roadmap decision. I thought I had considered all angles, but through this dialogue, I discovered I was unconsciously prioritizing technical elegance over customer adoption speed. This wasn't a deliberate choice -- it was an unexamined assumption the conversation helped surface.
This works because explaining my reasoning forces precision. I spot gaps in my logic. I catch leaps based on unstated assumptions. I notice when I'm dodging hard questions.
I've found this particularly valuable when working on problems where I have deep domain expertise. The more you know about a subject, the harder it is to question your fundamental assumptions about it. The AI has no such constraints -- it asks basic questions I might skip over.
A Real Example: Support Pricing Strategy
We needed to reconsider support pricing. Basic support was free, which worked for getting customers started but created problems with larger customers who used support like a professional services team.
Through the dialogue, I realized I was conflating several problems: defining the boundary between standard and premium support, creating pricing tiers, maintaining good customer experience, and preventing support from becoming backdoor consulting.
Separating these let me address each with focused strategy. The AI didn't solve it. The conversation organized my thinking.
When Wrong Suggestions Help
Sometimes the AI suggests something wrong that sparks new thinking. In one session on go-to-market strategy, it suggested a partnership approach we couldn't resource. But that wrong suggestion highlighted a gap in our channel strategy, which led to a stronger approach for mid-market customers.
Why This Works Better Than Traditional Methods
I've tried many approaches to strategic thinking -- solo contemplation to whiteboarding with the executive team. Each has its place, but this dialogue approach offers unique advantages:
Getting Started
If you want to try this approach:
AI won't replace your judgment. But it will expose the assumptions you're making without realizing it. That alone makes it worth the conversation.