WeWork CEO John Santora's warning to senior leaders on Gen Z: 'AI is not going to provide empathy, leadership, and mentoring.'

WeWork CEO John Santora's warning to senior leaders on Gen Z: “AI is not going to provide empathy and leadership and mentoring and all those skills that you need to lead a company for a company to be successful.”

If you graduated two or three years ago, the job market is probably nothing like you were told it would be. Landing an entry-level job in areas such as marketing, finance, and media is harder than ever. Large-scale layoffs, hiring freezes, and the creeping spread of AI tools have left a lot of young professionals asking themselves whether there’s even a seat at the table for them anymore.

There is genuine anxiety, but some people who run big companies say the doom-and-gloom may be getting ahead of the facts.


The entry-level crunch is real, but familiar
“There's no question that the entry-level hire is under pressure,” WeWork CEO John Santora said plainly at Fortune's recent Workplace Innovation Summit. Santora, who rose from building engineer to COO at Cushman & Wakefield in 47 years before taking the helm at WeWork in 2024, knows something about long careers shaped by disruption. His opinion? History repeats itself.

“We go through these cycles and have,” he said, “and every time there's a new technology change or an industry change.” His pitch is that AI, like every other technological change before it, will eventually force companies to grow, and grow means hiring.

That view isn’t going to soothe every nervous 25-year-old, but it’s worth sitting with.

Companies may be using AI as cover
Upwork President and CEO Hayden Brown summed it up more harshly: a lot of what’s being called “AI-driven job cuts” is actually something else. Companies, she said, are “AI-washing” their decisions to cut headcount in a difficult economy, using AI as the excuse for cuts that aren’t really about automation but about volatility.

The data support her. In a landmark study published by the National Bureau of Economic Research, over 90 percent of executives reported that AI has not affected their firm’s employment levels in the last three years, and 89 percent reported that it has not affected labor productivity. The research surveyed nearly 6,000 CEOs, CFOs, and senior finance managers from the US, UK, Germany, and Australia, and found that while two-thirds of executives said they personally used AI during a typical week, their use averaged just 1.5 hours per week.

In other words, the technology is everywhere, but its real impact on employment has been far less dramatic than the headlines have implied so far.

The freelance revolution is taking hold
While the traditional job market catches up to reality, something else is already happening. More and more young workers, especially Gen Z and millennials, are building careers outside the nine-to-five. Brown, who runs one of the world’s biggest freelance platforms, sees a clear generational shift towards independent work. The freedom, flexibility, and control it provides are becoming non-negotiable for many people entering the workforce.

A survey of 3,000 recent college graduates found that about 38% are considering starting their own business, 32.5% are considering gig work, and 28% are considering freelance work as their primary career path. These are not backup plans. They are becoming the first choice.

This is where it gets interesting from the AI angle. Brown says freelancers are actually better equipped to adjust to AI than traditional employees. They are self-motivated to always upskill, as their next contract depends on it. That’s why businesses are increasingly looking for them. They don’t need to be trained on tools they know how to use.

But it’s not all smooth sailing for independent workers. A study published in Organization Science found that Upwork freelancers in jobs more exposed to generative AI experienced a 2% reduction in contracts and a 5% reduction in earnings since the advent of new AI software to the market in 2022. Adaptation is important, and not everybody is adapting at the same speed.

What young workers can really do
Santora’s advice is sharp but sincere, “I would look at it with bright eyes if I was 25.” Boomers are retiring. Gaps are forming. AI is not going to mimic empathy, mentorship, or leadership, the skills that actually keep organizations together.

The workers who will thrive are those who see AI as a tool to improve their jobs, not as one to threaten their existence. That means learning the tools, yes, but it means doubling down on the human skills no software can replace.

Things are changing. The playing field is shifting. But it's been shifting for every generation that came before. What’s different is that now you can see it happening in real time, which, if you use it right, is actually an advantage.