The Youngest Bosses Are Hiring. What Do They See That We Don’t?

Two stories crossed my desk this week that I can’t stop putting side by side, and together they say a lot about hiring young workers right now. In one, the head of the International Monetary Fund stood up in Bangkok and said the people to worry about first, as AI spreads through the economy, are the young people just coming into the labor market. In the other, a new small business survey found that the owners most likely to be planning to hire this year are the youngest ones.

Here’s the thing. One story says the first rung of the ladder is getting harder to reach. The other says some leaders are still building rungs. That tells me the first job isn’t only something that happens to young people. It’s something leaders decide.

What happened this week

On October 13, Fortune’s Preston Fore reported on IMF chief Kristalina Georgieva’s warning that AI is a “slow-moving tsunami” for jobs. Speaking at an event tied to the IMF and World Bank annual meetings in Bangkok, Georgieva put it plainly:

The people to worry about first and foremost are young people that are coming into the labor market.

Kristalina Georgieva, IMF Managing Director, as reported by Fortune, October 13, 2026

The Associated Press coverage of the IMF’s new World Economic Outlook (Elaine Kurtenbach, October 13) adds the bigger frame. Georgieva estimated AI’s global job impact at about 40%, with jobs “augmented or downgraded or eliminated,” and said “we are already seeing some of this impact.” Fortune notes that workers with AI-related skills are earning more, but that hasn’t turned into broad job growth, while some lower-paying roles are growing.

Georgieva was also careful about something I want to be careful about too. She said AI is not shrinking demand for people right now; it is shifting it. In her words, “That may not be the case in the future.” Singapore’s President Tharman Shanmugaratnam, at the same event, named where that shift lands first: “The first rung in employment, your first job upon graduation, is now seeing less demand.”

And then he said the line that stuck with me all week:

You lose a whole set of intangible attributes, and you lose trust in the future.

Tharman Shanmugaratnam, President of Singapore, as reported by Fortune, October 13, 2026

Three days later, Fortune’s Muskaan Arshad reported on which business owners are still planning to hire. In the Q3 2026 Small Business Index from Justworks and the U.S. Chamber of Commerce, 46% of Gen Z and Millennial owners expect to add staff in the next year, compared with 19% of owners who are Baby Boomers or older. Younger owners are also more likely to plan to increase investment (50% vs. 18%) and to expect revenue growth (71% vs. 51%). Across all owners, only 36% expect to add staff, down from 44% a year earlier.

Justworks CEO Mike Seckler told Fortune, “Young entrepreneurs, like Gen Z and millennial entrepreneurs, are much more bullish about how their businesses look.” ZipRecruiter labor economist Nicole Bachaud described the other side of it, from the job seeker’s view: “The old model was: Graduate, find an entry-level job, climb from there.” Now, she said, “Grads are piecing together experience through internships, side work, stepping-stone roles.”

Here’s what the headline leaves out

The easy way to read the small business numbers is as a generational fight: young bosses hire, older bosses don’t. I don’t buy that, and I don’t think the data says it.

I’ll admit the gap is big. But the U.S. Chamber’s own executive summary of the index also notes that businesses that have been operating for less time hold more positive views of the future than older businesses. So how much of this is about the owner’s generation, and how much is about where a business is in its life? A newer business is often in growth mode. A business that’s been around for 30 years might be steady, or planning a succession, or just being careful in a cooling economy. Those are all reasonable places to be. The survey, as reported, doesn’t tell us which is driving the gap, and I’m not going to pretend it does.

What I will say is this: the gap is a signal worth paying attention to. Whoever is doing the hiring is deciding who gets the first rung. And right now, at least in this survey, the leaders most willing to make that bet on young people are, more often, people who were young workers themselves not that long ago.

Which leads to the question I think every leader should sit with. If AI is shifting demand away from the first job, who is going to decide to keep making first jobs anyway?

Hiring young workers is a decision about trust

Tharman’s line about trust is the part of this week’s news I don’t think we talk about enough. When we talk about AI and entry-level work, we talk about tasks. Which tasks can the machine do? What’s left for the junior employee? Anthropic CEO Dario Amodei, quoted in the same Fortune piece, put it this way: “If you automate 90% of the job, then everyone does the 10% of the job.”

That’s a useful way to think about the work. But a first job was never only about tasks. It’s where you learn how a workplace runs, how to take feedback, how to recover from a mistake in front of people. Those are the “intangible attributes” Tharman was talking about. You don’t get them from a course. You get them from someone deciding to give you a shot.

In The Next Turn, I write about the value exchange between young employees and the organizations they work for, and how quickly young workers re-evaluate when that exchange stops making sense. One line from the book keeps coming back to me this week: “Organizations do not get loyalty upfront. They get scrutiny upfront.” Here’s the part I think leaders miss. That scrutiny doesn’t start on day one. It starts with whether you’re hiring at all. A generation that watches the first rung disappear, while hearing that AI is the reason, is forming its view of employers right now. Before they ever fill out an application.

So when an organization pauses all entry-level hiring because “AI can handle it for now,” it’s not just making a staffing decision. It’s making a trust decision. And trust is a lot harder to rebuild than a job posting.

I wrote back in 2013, in Millennials and the Job Market, about how young people needed to be able to show their work, not just list it on a paper resume. I still believe that. But this week reminded me there’s another half to that sentence. Young people can show up with a portfolio full of real work, and it doesn’t matter if nobody on the other side is willing to look at it.

We say we’re about preparing students for their future, not our past. The leaders hiring them are part of that future too.

What leaders can do this week

You don’t need a new program to start. Here are five moves any manager or executive can make before Friday:

1. Look at your last 12 months of hires by career stage. How many were someone’s first or second job? If the answer is zero, was that a decision someone made, or something that just happened?
2. Name the 10%. Pick one entry-level role. If AI took the routine tasks, what judgment, relationship or customer work would be left? Rewrite the role around that, and keep the role.
3. Protect one first rung. Commit to at least one paid internship, apprenticeship or entry-level role this year, even in a slow market. Put a name next to it as the person responsible for that new hire’s learning.
4. Ask your youngest managers what they see. If the survey is right that younger owners are more bullish, the people closest to that view may already work for you. Ask them where they’d hire and why.
5. Make your hiring visible. Young job seekers are watching who’s still hiring. Tell schools, colleges and your community what entry-level paths you offer, and what you look for.

Frequently asked questions

Is AI really taking entry-level jobs?

It’s mixed. The IMF estimates about 40% of jobs worldwide will be affected by AI, but that means augmented, downgraded or eliminated, not all lost. Georgieva said AI is shifting demand for people right now rather than shrinking it, and Singapore’s president said first jobs after graduation are seeing less demand. The honest answer is that the first rung is changing, and how much is AI versus a cooling economy is still being studied.

Why should my company keep hiring young workers if AI can do junior tasks?

Because a first job builds more than task skills. It’s where people learn judgment, workplace norms and how to handle feedback, which is the pipeline for your future mid-level and senior staff. Skipping it saves money now and can cost you trust and talent later.

Are younger business owners really more likely to hire?

In the Justworks and U.S. Chamber of Commerce Q3 2026 Small Business Index, as reported by Fortune, 46% of Gen Z and Millennial owners expected to add staff in the next year, compared with 19% of Baby Boomer or older owners. The Chamber also notes newer businesses are more optimistic than older ones, so business age may be part of the gap, not just the owner’s generation.

The question for leaders

I keep thinking about Tharman’s word: trust. Young people aren’t asking for a guarantee. They’re asking whether anyone is still willing to bet on them while they learn. Some leaders clearly are. The rest of us get to decide.

If your organization is trying to figure out what entry-level work looks like now that AI is part of the job, this is exactly the work I do with leaders. You can find me at JeffUtecht.com.

So here’s my question for you: when was the last time your organization hired someone into their very first job, and what did you learn from it?

Sources

• IMF chief warns AI’s ‘slow-moving tsunami’ is coming—and it could leave Gen Z graduates stuck making lattes at Starbucks — Fortune, Preston Fore, October 13, 2026
• IMF says AI boom driving world growth, but warns it’s a ‘slow-moving tsunami’ for jobs — The Associated Press (via NBC New York), Elaine Kurtenbach, October 13, 2026
• Gen Z founders are hiring as boomers’ corporate America freezes them out — Fortune, Muskaan Arshad, October 16, 2026