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What’s Your AI Working Style: Skeptic, Settler, Trailblazer

Liza Adams · June 11, 2025 ·

Many teams think they’re good at AI. They’re actually stuck in patterns they don’t realize.

In my work with GTM teams on AI adoption, I see the same cycles everywhere. Teams hit walls they can’t see that limit what’s possible.

► AI Skeptic

Tries AI for strategic work but gets disappointing results. “We tested it for competitive analysis and market research. The outputs were generic. AI just isn’t ready for complex thinking.” They’ve given up on AI for anything beyond basic tasks.

► AI Settler

Gets solid value from AI and considers it part of their workflow. “We use it for email drafts, call summaries, and content outlines. Saves us 5 hours a week. We’ve got this figured out.” They’re satisfied with current results and stopped looking for more.

► AI Trailblazer

Understands that AI’s real power comes from rethinking problems, not just solving them. They use AI to challenge assumptions, try new approaches, and get better insights by asking better questions.

The difference between these three isn’t skill level or prompting technique. It’s how they think about problems before they ever talk to AI.

Most teams plateau because they optimize what they’re already doing. Big results come from doing things completely differently.

Take this 60-second assessment to discover your AI working style and get personalized strategies to uplevel how you guide AI.

Let me know what you got. Did anything surprise you?

Tomorrow’s (June 12) newsletter shows the 7 thinking moves that turn AI from a tool into a strategic partner. Subscribe so you don’t miss it.

AI Working Style Assessment

AI Working Style Assessment

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