How I built My AI Chief of Staff

Groupon CEO Dušan Šenkypl shares how he built an AI Chief of Staff using Claude Code - and why agentic AI is changing the way leaders plan, research, review, and execute.

One reassuring thing about teaching leaders to work with AI: They've been building AI skills their whole careers... without realizing it. The trick is unlocking what they already know so they can level up with AI.

Judgment, context, and institutional memory don’t disappear just because the tools change. They become more valuable.

More insight, less noise → decision.substack.com

#Leadership #DecisionQuality #ExecutiveAI

One thing AI failures expose quickly: implicit assumptions.

With people, shared context fills the gaps.
With machines, silence gets interpreted as permission.

That difference explains a lot of “AI went wrong” stories.

#StrategicThinking #ExecutiveAI #Leadership