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04Precedent · how it went for them

The situation“I need to work out what's actually wrong before I can fix it.”

Leaders who made the same call — what each did, and how it went.

WorkedShouldn’t have been tried

Worked · Rachel Tipograph, Gap, 2012 onwards

When Rachel Tipograph joined Gap in 2012 as the retailer's youngest director of global digital and social media, she was 27, and the problem she was handed at the top level was legible but diffuse: Gap's relevance to its historical core customer — the 18-to-34-year-old urban woman — was declining in ways the company's own metrics did not cleanly explain.

Worked · Stewart Butterfield, Slack, 2012–2014

Butterfield had founded a multiplayer gaming company called Tiny Speck that was building a game called Glitch.

Shouldn’t have been tried · Elizabeth Holmes, Theranos, 2003–2018

Theranos promised a single finger-prick of blood could produce hundreds of diagnostic results.