The Four Questions That Define Your Career Stage

AI has not just sped up delivery; it has reshaped how careers progress.

Job titles and years of experience are noisy signals now. A “senior” title can mean execution in one company and strategic judgment in another. A clearer way to understand your actual career stage is to examine the question you are answering most frequently each week.

Are you focused on getting work shipped, choosing the right solution, challenging the problem itself, or setting the direction in uncertain times? Those four questions map to four levels of thinking. And because AI is absorbing a lot of task work, the old entry-level runway is disappearing. The new baseline is judgment, not output.

This week’s article breaks down the four questions, the traps at each level, and what “levelling up” looks like in the age of AI.

This Week’s Updates

Enabling the Team

AI Has Collapsed The Career Ladder. The Four Questions That Define Your Career Stage by Rory Madden
Your career stage isn't defined by what's printed on your business card. It's defined by the question you're primarily trying to answer in your work. There are four questions you should answer to know where you are, each representing a distinct level of thinking.

Stop Making Your Team Figure Out AI On Their Own by Laura Klein
Making everyone figure out AI alone creates chaos and risk. Ops teams must step up: analyze workflows, pilot tools, and support adoption systematically.

Product Direction