“Steve Jobs is notorious for being [into] all the details; you could say he was a micromanager,” Chesky explained to CNBC. But after speaking to Jony Ive, who used to be Apple’s chief design officer, Chesky says that the negative label misses what was really happening. 

“I said, ‘Do you ever feel like Steve Jobs micromanaged you? Because he was in every detail.’ And he said, ‘No. He didn’t micromanage me. He partnered with me. We were working on problems together, and I felt like him being [into] the details made me better.’”

Jobs’ “obsession with detail” didn’t diminish Ive’s autonomy, or make him feel like his boss was hovering over or undermining him.

Instead, it made him feel his manager was invested, raised the bar, and pushed him toward a more expansive version of his own talent—one that would go on to shape some of the most iconic products of the modern era, from the Apple Watch to the iPad. Today, he remains one of the most influential creative leaders in tech.

That’s why, as Chesky points out, the issue isn’t actually whether a leader is deeply involved. It’s whether their involvement expands their workers’ thinking and therefore propels their career forward—or quietly boxes it in.

“So here’s the question: If I’m in the details with somebody, am I making them better or am I disempowering them? And I hope that when people feel like I’m involved in projects, they feel like I’m helping them push to think bigger.”

How Chesky micromanages his 7,300 Airbnb employees

With 4,500,000 listings in over 65,000 cities in 191 countries, and over 7,300 employees at Airbnb, Chesky also argues that getting into the weeds is a necessity in getting things done swiftly.

“There’s a paradox where being in the details sounds like micromanagement; it sounds like it’s slowing teams down,” the 44-year-old entrepreneur said. “But when you’re in the details, you can actually help make decisions faster.”

Essentially, layers of approval, endless meetings, and hours wasted in workers’ time can be saved, when someone with actual sign-off power is in the room.

“The number of people in organizations that [have] to get through managers and managers and managers to approve something, but then all these leaders have to agree to something, there’s a bunch of meetings—peers can’t make fast decisions,” Chesky added. “Only a leader can make a quick decision in a room. I bring everyone in the room, everyone makes a recommendation, and we can make a really, really fast decision.

“I think that’s the key of a leader, to make decisions,” he said.

But that’s having a double whammy impact on Gen Z’s careers

Although being deeply invested in the work of star talent can make them feel mentored and accelerate their careers, it’s having a double whammy effect on the careers of young people: If you zoom out, Gen Zers are watching leaders’ increased involvement essentially wipe out what used to be the job of middle managers—and it’s making them not even want to climb the greasy pole.   

In fact, 72% of the youngest generation of workers say they’d rather progress in an individual contributor role than become middle managers, according to recruitment firm Robert Walters.

Over half of Gen Zers specifically expressed that they don’t want to be middle managers—and sadly, over a third of the young respondents who said they do anticipate stepping into a managerial position at some point in their careers, admitted they don’t actually want to. 

It’s hardly surprising. As Chesky pointed out, middle managers today have little autonomy. They’re not reimbursed as well as leaders, yet they aren’t regarded as “one of the team” by those below. They’re statistically the most stressed out, overwhelmed, and burned out cohort of the workforce. And to top that off, they’re increasingly being told that they’re the most disposable.

Many tech companies have spent recent years flattening their structure by cutting middle management at a record rate. 

It’s giving leaders that closer access to individual contributors—letting them micromanage and make decisions faster, as Chesky describes—but the message to young workers is clear: Climbing the corporate ladder comes with more risk than reward.