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So hey, we’re halfway through 2026, the backend of which could be awfully eventful.

Today, I’m breaking down five questions I have at the midpoint of 2026 about workforce, education, and whatever else is getting globbed into jobs policy these days. Not all will find answers in 2026, but some of these I haven’t seen or heard asked aloud, and I think it puts where we are and where we’re going in better context as we head into the last six months of the year.

Can the money match the rhetoric for Trump II’s workforce strategy?

Trump II is not without ambition on changing America’s workforce pipelines, you might have noticed, but the main way you tend to accomplish stuff in this space is by shaping public money.

The Administration’s ambition is a blended education and workforce system that leads more Americans to skilled jobs that don’t require college, particularly through things like apprenticeship. Even with pretty much that precise language living in executive summary sections of recent federal grant listings, the actual technical components of the grants have looked pretty similar to the federal workforce funding for much of the last couple decades. In my experience, that policy wiring tends to lead to the same types of grant projects we’ve seen for the last couple decades. And for an administration that’s talked up streamlining and freeing the money, the pathway to getting funded has been really complicated.

If you’re trying to change funding programs, I can’t overstate how in the weeds and how relentlessly focused you have to be to do it. The opinion among most of the people I talk to is that Trump II probably can’t do either, if only because it’s dealing with fewer staff and more unpredictability from its White House than a typical administration. It’s too early to say the Trump II approach definitively won’t work, but the odds are against its current trajectory, which seems likely to produce a lot of what’s come before.

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How quickly can Trump II get apprenticeship pay-to-train online, and will the incentives be easier to get than employers think?

There have been sky-high expectations within the Administration for the pay-to-train incentives meant to get employers to start apprenticeships or hire more apprentices. As of this writing, we know from funding records who will be handling the pay out of the incentives, but the Department of Labor still has not yet announced the awards. Apprenticeship for America, in a dispatch sent on July 1, said the organization had been told that “not all individual awards are currently reflected in publicly available federal spending records” and that an additional $17 million will go toward pay-to-train incentives. Well, that’s interesting.

All that in mind, the money won’t be immediately available, and it took Arkansas nearly seven months to be ready to pay out incentives. Will the Administration try to accelerate that timeline for these new projects? Can it? In light of everything it has to get lined up?

Bound up in getting the incentives online is making pay-to-train payouts relatively straightforward to get, something employers suspect will be quite hard based on the conditions the Administration has attached to the incentives. I don’t think the Administration will move off the many hooks it put into this money, but it can make satisfying those hooks less painful during implementation.

Who will get to an AI-and-jobs answer that’s worth replicating?

You might’ve read this week that AI leaders are walking back their claims that “Our Robots are the best Robots and therefore they will take all of the human jobs in the next two months forever and ever.” This makes sense given that AI is deeply unpopular, a development that, according to rather convincing research I’ve seen, seems rooted in people not wanting lose the jobs that they use to support themselves and their families.

Here’s where I think we are: AI CEOs have been selling their product in ways that appeal to investors and executives but are reasonably terrifying to the world at large, and all of the above have overestimated the ease in which companies can deploy the tech and underestimated the need for humans to do that deploying. I won’t say anyone will get it right anytime soon, but I do think we’re going to have a clearer idea in the next few months of what is a good AI-and-workforce project rooted in reality.

Who comes up with that answer will be very interesting. DOL’s apprenticeship-and-AI contract and Commerce’s AI implementation grant are the most promising federal efforts, but the Trump Administration largely continues to make big claims about job creation from AI—and overdefer to businesses figuring out their own AI answers—without a whole lot of specifics. It’s also perhaps a little too committed to DOL’s “AI literacy” framework, which, while certainly the best formulation of AI literacy I’ve seen, remains the best stab at a concept that seems stop well short of hirable AI skills (or be in the same solar system as them).

The more intriguing developments are outside of government, but we’re in the gap between concept and reality. Claude Corps remains the closest I’ve seen to a training model that teaches skills that could be useful to workers who need to regularly adapt to new tech. I’m excited by thinking I heard when I talked to the organizations implementing Claude Corps, but also curious to see how their model adapts to the unexpected.

The other big, recent development is the announcement of RAISE US, a bipartisan effort with a host of newsy backers and partners led by former Commerce Secretary Gina Raimondo. Given how overmatched the majorities on the Hill seem on building real AI-and-workforce policy, RAISE has wisely signaled that it plans to focus on states. That said, while I get the point of the bipartisan emphasis in the announcement, a lot of American workforce policies are firmly rooted in the political middle and frequently favored by establishment voices. And those bipartisan policies haven’t exactly moved in a direction that meets current workforce needs—or shown positive results for workers.

It’s so early, though. RAISE certainly looks like it will have the resources to do something big, and with what’s not happening federally, it’ll have the opportunity to do it. Let’s see what’s next.

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What lessons will the Workforce World take from this year’s midterms if they swing left?

After a spring of traveling the country, here’s something lost in anxiety and celebration about the leftward, anti-establishment outcomes in recent Democratic primaries: the candidates that are winning are talking about doing actual stuff—and different stuff—about problems that people see and feel with their normal human senses.

To be frank, that’s different than what you get from the moderate wings of both parties, neither of which has a great recent track record of actually producing clear and clearly good results. The middle also tends to be more aligned with big business, and in the past few years, a vast majority of Americans have diminishing confidence in big business (something likely not helped by the “Let’s fire all the expensive humans!” excitement of investors about AI).

Workforce tends to live in the political middle (which is certainly safe a thing to do if you’re an organization reliant on federal funding), but as I’ve written quite a bit about in recent months, it also tends to react very strongly to the politics of the moment. So what happens if Democrats win back one (or less likely, both) chambers of Congress despite aggressive gerrymandering and do it using explicitly progressive candidates?

The thinking among establishment Democrats coming out of 2024—and fueled by things that haven’t really caught on with voters like Abundance—was to move toward the center or generally as less-liberal as possible. It would be a hell of a swing for workforce orgs that moved with those winds and the Trump Administration’s workforce efforts if the winds were to swing back farther leftward.

It’s not always been clear what direction to tilt workforce policy toward for Democratic Socialists. The critique I heard frequently last year about New York City Mayor (and fellow Knicks fan) Zohran Mamdani was that he was mostly a blank slate on workforce issues. Some of this year’s insurgent New York congressional nominees have called for a federal guarantee of a job—and a good one—which is interesting and different, but definitely far from the establishment of either party’s comfort zone on these issues. Good jobs, though, is definitely a concept that a lot of workforce organizations have plenty of paper on.

That said, some of these candidates aren’t exactly breaking new ground on workforce. There’s pretty standard “Apprenticeship and vocational training is good!” language in the platform of Dr. Abdul Al-Sayed, the liberal candidate who polling shows is leading a closely watched Democratic primary for the open Senate seat here in Michigan. (He’s also narrowly leading Republican Mike Rogers in recent polling on a head-to-head matchup). Intriguingly, though, Al-Sayed’s platform labels workforce as an education issue—arguably a step further than Trump II has gone in this space while talking up its efforts to merge the two fields (often by bashing education).

I wouldn’t expect much out of the next Congress in terms of new workforce policy absent an amount of turnover in the President’s policy staff I think is unlikely at this point. But workforce is an area that needs fresh answers. I’m curious to see if candidates who have done a good job offering answers to things voters see with their eyes can come up with clear workforce development strategies that are different.

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If employers don’t want the Trump II approach ‘employer-led’ workforce programs, what do they want, and can we get there?

Upon occasion, I’ve heard complaints from business and employer interests that they struggle with getting the realities of running a business through to Republican political staff who have a very entrenched political idea of what business does. As someone who spent several years covering Republican politics who now runs a business, I definitely can relate.

Now, to be clear, I don’t think the business world is about to run to Democrats with open arms, and my impression is there are business leaders who just assume no one anywhere near a government office understands business. That said, I’ve thought more about those conversations since we’ve had hints that employers and business aren’t thrilled with the Trump II approach to workforce meant to appeal to employers and business.

But what policy approach does thrill employers enough to do something on workforce that gets people hired and fills their needs? Hiring is broken, we need more pathways to a good jobs, but employers don’t have a whole lot of incentive to change. And is what could get them to change a policy approach a thing that politics and government can actually deliver?

I don’t think we’ll have a good answer to this question by the end of this administration, but beyond the need for more public money—where Republican lawmakers most certainly aren’t listening to big business—the answer probably lies in thinking about how much employers are willing to invest, even if that’s just thought. We definitely need strong employer input in the direction of workforce training to avoid training for jobs that don’t exist. But that doesn’t mean endless deference for the sake of deference, or expecting that businesses will build programs for the government—something the Trump Administration has seems like it’s floating at times. If only because they have other things to do—like running a business.

The folks that build good programs for employers and workers do a lot of research to make sure they’re working with the right employers, meaning employers willing to invest resources and thought into training and an open-mindedness about what it takes to attract and retain talent. That approach involves focus and recruitment and not trying to serve 475 unrelated industries at once, which a lot of workforce programs and projects try to do.

That’s hard work, and it’s not very safe in the current funding environment. It doesn’t fit with what political leaders seem to mean when they talk about “scale” in this space, which can produce less distinct and less effective programs in the hopes they might produce a Big Honkin’ Number of hires.

But if actual people aren’t happy with the current policy approaches—including the people who this Administration has signaled it is building policy to make very happy—we might want to try something else.

Card subject to change.

First, I hope your Independence Day Weekend was spent as well as mine, which involved eating an assortment of Michigan’s fine tubed meats by a lake, playing mini golf with my kids, and watching a Fourth of July parade that included the truck for a spray-foam insulation company—complete with a guy in full spray-foam insulation protective equipment. Talk about taking opportunities to model career pathways! (Also he looked very, very hot in Saturday’s weather.)

Second, next week is Jobs for the Future’s Horizons conference (a.k.a. Workforce Comic-Con), and I’ll be breaking out my stackable and portable shirt to catch up with the Workforce World for a few days. Last year, I had a blast doing an open call for meeting with anybody who wanted to meet. I still have some space in my calendar, so shoot me a message if you want to grab some time.

Third, I’ll be back on Thursday with THE MONEY, by which the Trump Administration might have announced its big workforce awards that are quite well out in the open by now. I suspect I’ll also have some thoughts on the regulatory front, plus I’ll break down a big-money federal workforce funding opportunity that’s a little different than the usual.

See you then.


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