AI and Staying Current

The reader of this newsletter has already used ChatGPT and Claude. The question is no longer whether to engage with these tools. The question is whether four decades of pattern recognition still has a market when a 28 year old with a good prompt can produce a passable strategy memo in nine seconds.

The honest answer is that judgment is more valuable now, not less, but only for operators who do two specific things. The first is acquiring enough fluency that a CTO does not clock you as a tourist within ninety seconds of conversation. That bar is lower than most people think and higher than most senior operators have cleared. The second is learning to use these tools as a research analyst who works for you at three in the morning, rather than as an oracle. The operators who treat the model as a peer get flattened. The ones who treat it as a brilliant junior who needs supervision get leverage.

A working starting point: pick one decision you are making this quarter and run it through Claude or ChatGPT three different ways before you talk to anyone human about it. Not to get the answer. To stress test your own framing and discover where your assumptions fall apart on contact with a model that has read more than you have. Most senior operators skip this step because it feels like cheating. It is not cheating. It is the new version of the analyst memo you used to commission.

In the briefs, we will cover the AI advisory pitch that is quietly embarrassing senior operators in 2026, what credible technical fluency actually looks like at the VP and SVP level, where these tools are confidently wrong about your industry, and how to position your judgment in a market that is briefly confused about what it is willing to pay for.