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AI-Forward Insights for the Modern Chief of Staff
THIS WEEK’S BRIEF
The pressure in this role is almost always to move faster. Clear the backlog. Turn around the brief. Get the decision in front of the right person before the window closes. AI is very good at helping with all of that.
But the skill that actually determines whether you are effective is not speed. It is judgment. Whether the recommendation holds up. Whether you saw the objection before someone else raised it. Whether you were right when it mattered. This week is about the habit that has moved my track record on that more than anything else I have built into my workflow.
THE USE CASE
Before I bring a major recommendation to an executive, a college, or one of my clients, I run it through a pre-decision brief. I give AI the full context: what I am recommending, why, what the stakes are, and who is in the room. Then I ask it to argue against me. Hard.
What comes back is uncomfortable. It surfaces the objections I half-knew were there but hoped no one would raise. It catches assumptions I had not named out loud. It has changed how I framed a recommendation more than once, and it has sent me back to gather information I thought I already had enough of.
The output takes longer to produce. Every call I use it for lands with more precision.
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