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Steve Jobs taught Gap’s former CEO that micromanaging can be a good thing

November 28, 2025
in Business
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Steve Jobs taught Gap’s former CEO that micromanaging can be a good thing

One of the great debates in leadership is how much managing is too much. Psychologists argue micromanagement is harmful, saying it stifles creativity, dampens motivation, and reduces productivity. 

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But some of the greats in business have shown micromanaging can lead to great success. Take Steve Jobs, for example. The former CEO of Apple, who died in 2011 from pancreatic cancer, continues to be revered as one of the greatest leaders in business history, but he’s also among some of the most famous micromanagers. 

“He’s a corporate dictator who makes every critical decision—and oodles of seemingly noncritical calls too, from the design of the shuttle buses that ferry employees to and from San Francisco to what food will be served in the cafeteria,” Adam Lashinsky wrote in a Fortune article about Jobs published just about a month before his death.

But Jobs and other business leaders have shown micromanaging works and that it gets a bad rap. In an episode of the Opening Bid podcast with Yahoo Finance executive editor Brian Sozzi, former Gap CEO Mickey Drexler made the case for this management practice, saying it was one of his major leadership takeaways from working with Jobs on the board of Apple.

Jobs was “unique, once-in-a-lifetime, and [his death] a loss to America,” Drexler said. “He was a difficult person, mercurial, incredibly creative, and made sure the screws on all the products were horizontal.” Jobs also backed a “no-bozos policy,” or hiring people who actually knew how to manage others and get results. 

“Micromanaging is what it is. If you’re managing as a leader, set the tone. I’m proud to be a micromanager for what a customer sees, feels, and hears,” said Drexler, who also previously served as the CEO of J. Crew and currently serves as the chairman of Alex Mill. “So yes, I do micromanage, but [also] provide leadership. People know what is important.” 

Merchandising mastermind Drexler also previously worked at Ann Taylor, Bloomingdale’s, and Macy’s, and served on Apple’s board from 1999 to 2015.

When Drexler first started serving on the board at Apple, Gap was worth $15 billion, which was bigger than Apple at the time. 

Apple is now a behemoth worth $4 trillion, with Jobs’ fingerprints still seen on its devices. Much of Jobs’ success had to do with bringing products to the market customers didn’t even know they wanted. 

“Some people say, ‘Give the customers what they want.’ But that’s not my approach,” Jobs once said. “Our job is to figure out what they’re going to want before they do.”

By a slightly different token, Drexler is more focused on responding to customer concerns while also planning expectations for the future.

“I think the world’s become kind of average in its standards,” Drexler said. “But average is not good enough to me. It’s [about] managing a customer’s expectations and what they should get: best-of-class. Don’t give a customer a reason not to buy something.”

And while Drexler said he learned from Jobs, he’s stayed true to his own leadership style.

“I didn’t learn to be extremely demanding [from Jobs],” Drexler said. “That’s what I’ve always been: a tough boss.” 

A version of this story appeared on Fortune.com on December 9, 2024.

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