Two-Part Definition of Strategic

What people really mean when they say “I want someone who's strategic.” A two-part test: you must both (1) articulate a compelling, simple “why” and (2) champion hard changes for the long-term. Having one without the other means people won't see you as strategic.

Where it comes from

Anneka Gupta, CPO at Rubrik, developed this definition after receiving feedback — twice — that she wasn't strategic enough. Once in a performance review, and again years later while interviewing for head of product roles. She reflected and realized both cases pointed to the same gap. From the conversation with Lenny: > When people say I want someone that's strategic, what they're really saying is I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product. [...] And the second piece is I want someone that's going to champion and be a change agent to do things that may be hard but actually best for the long-term interest of the product or company.

The insight

Strategy isn't just thinking big thoughts — it's the combination of clear articulation and courageous action. The formula is both/and, not either/or.

Where it is argued

1 note

01Systems Thinkers Over SpecialistsElizabeth Stone, CPTO of Netflix, argues that the AI era demands systems thinkers who abstract across domains over narrow specialists — while insisting that craft excellence remains scarce and essential. She explores how AI blurs functional roles without making them obsolete, why Netflix's “excellence as an operating system” (high talent density, autonomy, comfort with discomfort) maps directly onto how top AI labs operate, and how AI is reshaping entertainment from production through personalization.