Haley Glover: Building Employer Upskilling Strategies

Haley Glover, Senior Director of UpSkill America at the Aspen Institute, discusses how businesses can effectively upskill their workforce in an AI-driven economy. Drawing on her experience at Lumina Foundation, Amazon, and the Aspen Institute, Glover explains how upskilling has shifted from talent acquisition crisis management to strategic workforce planning focused on validated skills. She details findings from The Upskilling Playbook, emphasizing that successful AI adoption requires thoughtful, worker-focused training aligned with business strategy—not just technology purchases driven by peer pressure. The conversation also explores the All Learning Counts initiative, which advocates for recognizing skills regardless of where they were acquired, and new research on internship programs showing how companies find value through talent pipeline development, retention, and innovation from fresh thinking. Glover addresses distinct challenges facing small versus large employers and offers practical guidance for learners, educators, advocates, and employers to build resilient upskilling programs that withstand economic shocks.

Transcript

Julian Alssid: Welcome to the Work Forces podcast. I’m Julian Alssid.

Kaitlin LeMoine: And I’m Kaitlin LeMoine, and we speak with innovators who are shaping the future of work and learning.

Julian Alssid: Together, we unpack the complex elements of workforce and career preparation and offer practical solutions that can be scaled and sustained.

Kaitlin LeMoine: This podcast is an outgrowth of our workforce consulting practice. Through weekly discussions, we seek to share the trends and themes we see in our work and amplify impactful efforts happening in higher education, industry, and workforce development all across the country.

Julian Alssid: We are grateful to Lumina Foundation for its past support during the initial development and launch of this podcast, and invite future sponsors of this effort. Please check out our Work Forces podcast website to learn more. And so with that, let’s dive in.

Julian Alssid: Kaitlin, so much of the conversation around the future of work focuses on the what—what skills are needed, what jobs are disappearing. But the harder question, and the one that really determines success, is the how. How do businesses actually help their existing employees develop the skills they need to succeed in a changing economy?

Kaitlin LeMoine: Absolutely. While we know the need for and importance of upskilling initiatives, actually building an effective system that helps workers grow and advance is a really complex undertaking for employers.

Julian Alssid: Right. It's one thing to agree that upskilling is necessary; it's another to have a playbook that works for both the employee and the bottom line. To create that playbook, we need guidance from leaders who understand both the policy landscape and the operational reality of business.

Kaitlin LeMoine: Exactly. We need that along with insight into researched best practices across industries. And luckily, today we’re joined by someone who brings that multi-sector perspective to the table. Today we’re speaking with Haley Glover, Senior Director of UpSkill America, a national initiative of the Aspen Institute Economic Opportunities Program. UpSkill America drives research and efforts that promote employer-led education and training to help workers advance and help businesses compete.

Julian Alssid: Prior to this role, Haley was Senior Program Manager at Amazon, where she led college programming for the company’s Career Choice team. And before that, she served as a Strategy Director at Lumina Foundation—which is where we first met Haley—leading efforts to reduce racial disparities in credential attainment. Haley holds a bachelor's degree from Franklin College, a Master of Liberal Arts from St. John's College Graduate Institute, and an MPA from Syracuse University. Haley, welcome to Work Forces, we're thrilled to have you with us.

Haley Glover: Thanks, guys. Good morning.

Julian Alssid: Please tell us, in your own words, about your background and what led you to your role at Aspen Institute.

Haley Glover: In the spirit of time, I will give you the short journey instead of the meandering one. But fun story: you mentioned I was at Lumina Foundation, and I was there for a very long time—about 11 and a half, 12 years. I not only led the work in my last four years at Lumina focusing on eliminating racial disparities and that kind of thing, I also led portfolios focused on what we called "employer mobilization," which in my glib moments I described as getting employers to do stuff. But it was really focused on understanding and motivating how employers can take their considerable resources, influence, and that unique positioning in employees' lives to mobilize toward the credential attainment mission.

Back in 2015, when UpSkill started, I actually was one of the first funders of UpSkill at Aspen and helped try to kick that off back in the day. So my time with UpSkill started right at the beginning. Obviously, the initiative changed a lot over a decade, along with the economy, the workforce, and all of the things. But that is how I found myself here about three and a half years ago. This idea, this question about how employers can not only benefit from investment in skill development but create benefits for individuals, their companies, society, and our country—that has been a throughline of work that I’ve been doing for quite a long time. Between my past life as an educator, working in economic development, working in nonprofits, government, and philanthropy, as well as the private sector, that's been the river running through my work: trying to blend the streams and get more people to think very critically about how we leverage all of the power we need to get people the skills they need to thrive.

Kaitlin LeMoine: Thank you for that overview and that story of how you got to where you are. I’m curious to know: how has the focus of your work through UpSkill America evolved over the last few years? You mentioned all the changes that are occurring—what do you see as the primary focus, and how do you see that shifting?

Haley Glover: That is a fantastic question. I think there's a very simple answer, which is that the economy we're in in January 2026 is not the economy we were in when I came to UpSkill back in the summer of 2022. Three and a half years ago, employers were absolutely just falling over themselves to acquire and retain talent. The question of the time was: how do I find people with the right skills? How do I keep people with the right skills? How do I get the mass that I need in order to proceed?

That is not the question now. Now, I think employers are really leaning into: what skills and competencies do I actually need to not only fill tasks and roles that I have right now, but to take me into the future? How do I not just retain talent, but retain the right talent in particular roles that are going to have strategic value for me going forward? How do I create robust pipelines that guarantee that I, as an employer, am not going to be wasting time, energy, and effort on the upfront acquisition? How do I build my workforce strategy muscles in order to understand with much more nuance and robustness this idea of what I'm going to need in the future?

So, it's pivoted from a "fire on my front line right now" focus three or four years ago to a need to think much more critically about what's down the road and into the future. That’s been huge.

From the work that UpSkill is doing, we’ve leaned more heavily into this idea of getting much more specific and intentional. With the addition of AI—which is both a positive in that it can help people do things with less time, energy, and effort, but also a complicator—you've got this skills validation issue. I just read a piece the other day about a $600 billion resume fraud issue, which is really asking the question about skills validation. We are trying to make sure that (1) we get people to understand and be recognized for the things that they know and are able to do, regardless of where they acquired them.

We've been calling this movement "All Learning Counts" for a very long time. It is this idea that it shouldn't matter whether you attended the most prestigious elite institution or you gained your skills through work. If you've got the same skills, you should be competing in the same way. What we do right now is we conflate a lot of different things with being "better" at something instead of really understanding what people can really bring to the table. So this idea of skills validation has become a much more important part of our work because it addresses both sides of the coin: employers need validated skills, and people need to understand their own skill set.

A lot of people will go through education programs, training programs, and work experiences and not develop what we call this metacognition of what they know. Knowing what you know and knowing what you're able to do can be a very powerful, empowering scenario for an individual. It can also be the thing that sets you apart in an interview or a process because you can say, "I know what I know, and here's how I know it, and here's what I did to show it." We’re also trying to really help the employer get specific about what skills they need and how to find them through this validated skills movement. So, we're much deeper into technology than I think we ever thought we would be, or that I ever wanted to be, frankly, because it is not my primary language. But it is the method that I think will ultimately produce the right kind of results for both people and the employers they work for.

Julian Alssid: So Haley, I mentioned earlier in your intro that we need that playbook—how do you do it? You have produced a playbook: The Upskilling Playbook: AI Skill Development in the Workforce. Tell us about it. What are your findings? What have you learned, and what’s in that playbook?

Haley Glover: Yeah. Well, so the playbook is not just that AI chapter, which was our latest addition, but essentially pulling together all of the things we've been learning, doing, hearing, and writing about for many years now. The idea is that companies are not necessarily encouraged or inclined to share the things that they're doing. In fact, a lot of companies will fight against that sharing because it's "secret sauce"—the thing that we do that creates our own special business value. So when we have the opportunity to share broadly—like "here's what's worked at one company," or "here are results from another company," or "here's a process that appears to work across multiple companies"—that's our bread-and-butter activity. We can shine lights on things and make these secretive or specialized processes much more visible for other people.

That's a really positive thing. That's what the playbook is about. The AI Skill Development in the Workforce chapter was a call that we decided to put out within the last couple of months here. It was less about "here's how companies should approach AI." I don't know how companies should approach AI. That is very much a "them" decision—what vendors they use, how they embed it, all of those things. That is a them decision.

What we've been observing, though—and you can see this if you read stuff and pay attention—is that a lot of companies are doing a sort of "silver bullet" kind of approach to their AI work. They’re saying, "Oh, if I just give this self-directed module and training on AI to all my people, it'll solve my problems." That’s, of course, not true. "If I just buy a tool, it'll all work." Also not true. "If I feel like I must invest as an employer in this thing..." Peer pressure never solved really anything.

So, what we are calling for and what we really are observing in this moment is that AI—when it is accompanied by thoughtful, humane, and worker-focused training and opportunities—that works. Product acquisition, when it is solving a business problem and serving a discrete business purpose, that works. Don't just hop on board. And leadership and workforce planning that is really thinking about AI in service of future goals, in service of those broader strategies, that works too.

None of the findings surprised me because we are always going to take a sort of human-first lens on all of our work. But what I hope we are starting to contribute is this idea that any product, technology, or process absent workforce strategy and workforce planning won't work as well as it could. You have to do the work of understanding what your workforce needs, who your workforce is, and how to best support them to be able to do the things that you want and need. And then to know with great precision, as much as possible—two years out, four years out, whatever—what they're going to need to do and how they're going to be doing it. It's when those things interconnect, powered by AI, that something magical can happen.

Kaitlin LeMoine: Haley, it strikes me that I think one of the complicated things about this moment is that AI tools are emerging constantly, right? And there's this historic concept that strategy can take a while, and yet we're moving at this very fast pace. In your research and the conversations you’ve been having, how are people balancing that reality? When do you say, "You know what, we're going to commit to these tools for a little while because we feel they meet these business goals and this broader strategy," and when do you say, "You know what, let's try this instead"? It seems like a very tricky balancing act right now.

Haley Glover: I think that's going to be a different question for every company and every industry, because it's a question of tolerance. What is your tolerance for risk, for experimentation, for all of those "what-ifs"? And then, what is your strategy for evaluation? What do you care about?

It does sort of speak to some of the things that we wrote about in the piece where, you know, if your evaluation strategy is, "Well, I had X number of sign-ons," or "X modules completed," or "this many instances purchased," what does that tell you? And if that is the only thing you're really looking at, you're probably not going to be in a position to really effectively understand if it worked or if it changed anything. What you might see are downstream effects like morale is bad, or managers are getting way overloaded with things that are coming from both sides, or you don't have enough information to really effectively evaluate your contract renewal. There's a thousand things that can happen on the other side of "piloting" if you don't really understand why you're doing it.

So, I'm not suggesting that companies are just willy-nilly running in and just buying stuff. And yet, I think what we do observe is that workforce strategy is the muscle that companies need to exercise that can make these things work better. Because like I said, if you do know why you're doing it, what you want out of it, and how you're going to measure the outcome you really want to see within your workforce and within your organization, then you can really understand how it's all coming together. So, that might be a bit of a lame answer, but I think it is the truth. We see a lot of experimentation with technology without necessarily complementary thought around the other side of it.

Julian Alssid: To complicate it further, Haley, you look at companies large and small in your work, don’t you? So, can you speak a little bit—because that too brings a whole other world of issues—to how we compare Fortune 500s to more typically sized medium and smaller businesses? Can you speak to tech as it relates to the smaller ones?

Haley Glover: The tech question is really very similar to other questions about evaluation and implementation of new processes and tools by industry size. Everything that we've found suggests that the things that we say "work" for large companies are sort of not relevant in many ways to small organizations for a lot of reasons. These will be obvious to you: if you've got an HR team that is HR and compliance and workforce and technology and also operating, that's too many hats for one human to wear and an environment in which decisions are made differently than when you've got a team working on each of those things.

There's a capacity question, which is the biggest "duh" of them all: when somebody's wearing five hats, how in the world do they do another thing that can require a huge amount of compliance? This comes up a lot in apprenticeship: "Well, why if apprenticeship is such a great model, why doesn't it work for some people?" And that's because it requires a lot of work to really get the benefits of those programs.

There's a cost thing: if your margins are low, you do not have extra resources to spend on doing the experimental and piloting work. You need ready-made solutions that are affordable or no-cost, and often you need support from organizations that are going to be wrapping around you and working with you—workforce boards, intermediaries, others. So there's multiple layers of why strategies and things that would work for very large companies just don't apply.

And I do think, too, the risks for smaller organizations are higher because of margins, capacities, and otherwise. If you invest in a program or a technology and you're a small organization, that may be somebody you can't hire next year. That may be a contract you can't bid for. That may be something you can't purchase that you need. It's those kinds of really real challenges and real barriers that prevent us from saying unilaterally "employers should do this." It's always about context, about industry size, geography, and every other factor—which makes this work very challenging but, you know, we try to be attentive to it as much as we can.

Kaitlin LeMoine: So Haley, you mentioned apprenticeships. I know you’ve been exploring work-based learning, internship programs, and the value of those in the workplace for employers and employees. Can you tell us some of what you've been learning as it pertains to that initiative?

Haley Glover: Yeah, absolutely. And this is really exciting. We've got a piece coming out quite soon which I'm happy to share with you when it is released, but I'll give you a little sneak peek right now. Over the summer, we sort of were grappling with this issue of "business case," "value case." This is a truth, I think, for every question we have to ask of employers: we have to couch it in what value it provides to your organization. Altruism is not the motivating factor for the private sector. I think we all know that, but it can be harder, particularly for advocates, when you're thinking about why an employer might do something.

So where we were taking a look is—we have a really great understanding. We did some ROI studies on tuition benefits back when I was at Lumina, and those are—I still use those all the time and they are used broadly in the field. We've got some interesting ROI information out of apprenticeship programs, though colleagues over at the Brookings Institution just released findings yesterday really showing that it's very, very hard to use ROI insights generally because the applications are, like I was talking about, context matters so much. So you have to really be careful about understanding those.

And then we were looking around for—we have a general understanding of why employers do internships. And we really understand that the demand for internships, based on work by NACE and others, is huge. Eight-some million students seeking internships; about half got them. And as we think about the situation we're in with impacts on entry-level talent from AI and automation and all of those other things, people have to get work experience in order to get jobs. That's at least how we work now. And internships are a great way to do that.

But how in the world do we think about growing the number of employers offering internships or growing the number of internships? So we sort of tackled this question of: where do employers find value? Why do they offer internships? What is driving them to keep these things on, especially as we enter sort of tumultuous economic times?

We interviewed about 40 employers to sort of get under the hood of their internship programs to understand why they did them, what business objective they were trying to seek. And those findings, I think, were actually quite standard. We’re not surprised really by anything that we found because employers are doing internships for the reasons that we would understand: their talent pipeline is not sufficient; they’re not getting what they need from typical sources. They’re trying to remediate against sort of a poorly prepared workforce; they’re trying to say, "You need exposure in my industry. I’ll take a chance on you, but if you don't have production experience, you don't have insight into where I am, we're really going to try to focus on that with internships." Things like low retention—creating a level of "stickiness" within new hires—is a really big priority. And then creating new opportunities for people who are managers or who are emerging managers to lead.

Those are four big problems that they're looking to solve through internships. And we also looked at: what are the conditions within companies that make internships sustainable and successful? Those come down to conditions that can often be sort of hard to replicate, but you know that they're there when they are or aren't. Those are things like executive sponsorship: having an executive leader who is bought in and really on board with the program can be the difference between it thriving and being a part of the actual talent pipeline, and just dying on the vine when things get rough. Integrating across an organization: when the internship program is just this little pocket and they get dropped in, interns get dropped into departments and people are like, "What do I do with these people?", that can be a problem. So this cross-functional integration helps leaders see. Leveraging external partnerships: states are investing a lot in work-based learning and those, particularly for smaller businesses, can be ways of maximizing resources.

And really thinking then primarily about effective programming: having actual learning outcomes, actual work that interns can do, actual supervision and mentorship, actual accountability. Those are all things that, from an organization perspective, can be really powerful.

So why this idea of why do employers invest? Really articulated key business values: attraction. Employers, to almost a person, talked about how their internship programs are creating buzz on college campuses if they’re recruiting; how interns from one summer go back to their campuses and say, "I had a great experience, you should apply." They love that because it is really creating a level of advertising and acquisition and outreach that they could never do on their own. They’re really looking for readiness when it comes to having students or having interns start as full-time hires without the need for expanded onboarding, without a ton of time like "where is the break room?" They know already; they're ready to go. That can be a big cost saver as well.

As I said, engagement and retention—keeping people longer—is always going to be a primary mission. They also benefit from increased workload capacity because if interns are doing real work, that can really benefit the bottom line. And there's also other effects that they want to have within their communities and their industries and their regions that should not be understated.

So long story short, this piece will come out in the next several weeks and we're excited about it. But it puts a fine point on this idea that employers invest in talent in a lot of different ways, and building the business case—really understanding from all sides why, how the value gets created in the organization, how to maximize the impact of these investments—that is the thing that we’re chasing. Because it's a positive thing we know for students; we want to make it just as positive for the employers that they're working with.

Julian Alssid: Haley, did this research look at companies across multiple industries and, again, size of businesses and geographies? I know that this isn't publicly released yet, but are there any nuggets you can share of insight about where you're really seeing traction or where some of the challenges are?

Haley Glover: Yeah. Well, so we did 40 employers—it is not representative, but we did seek for representation of all different sizes. So we talked to 20-to-50-people companies and 50,000-people companies. We talked to manufacturing, finance, insurance, services, tech—all of the industries. And then we tried to get a very solid geographic distribution. We had a little bit more representation from Midwestern companies because, as you know, getting in the door often requires a relationship, and that’s where I’m based and where many of our partners are based.

So yeah, I mean, a couple of findings: Small businesses, as I’ve sort of said before, they obviously can benefit I think a little bit more from the publicly resourced models that you have out there that are either reimbursing or replacing wages. They kind of look at it as: "This is a way we're meeting our talent goals and risk is defrayed by public investment." And so they, I think, are very pro those public programs, which is great because they’re actually serving a public service; students are getting work experience and they are acquiring skills as a part of their programs of study and it is really working on both sides of the equation.

Small businesses also struggle a little bit more with the administration and the overhead and the mentoring required. As a result, they often do smaller cohorts. We do understand from larger companies that cohort models can often be really successful because you’re creating shared experiences, networks, groups to rely on and learn from and work together with. So there's a tradeoff there.

And I think coming back to the workforce strategy question, it’s always going to be: what kind of work do you have your interns do? What I think was really cool to hear from employers across the board—large, small, every state we talked to, every industry—is they are, to a person, I think really excited about the innovation and fresh thinking that interns bring. Whether it's something like what would have taken our staff member hours to do because they don't really know the tools, it took our intern 45 minutes to do because they’d been exposed to AI or whatever tool—they did it easily. Or they saw things in a different way than our team did and really helped us get over a hurdle that it would have taken us time to do. It’s those kinds of things that I think are harder to understand the business value—like yes, of course, saving time equals saving money. But it is a really important factor in a lot of our value that employers get: this innovation and fresh thinking that comes from introducing a new generation of students with different experiences and not people who are entrenched.

And positively, on the incumbent workforce side, a lot of employers talked about the "breath of fresh air" that this gives to their workers. Mentoring a new generation, sharing what you know, telling people how you do things and teaching them can sort of reinvigorate folks and get them re-engaged with their role.

Kaitlin LeMoine: So you have offered many tips, strategies, potential practices. However, I would love to give you the space—we ask this question of all of our guests—what are, if you have any other practical steps you’d like to share around how our listeners can work with employers to become forces in this complex place that is work and learning, or help learners themselves? Take the question in whatever direction you’d like.

Haley Glover: I really love the question because you said that word "complex." It’s complex and it's complicated. And I don't think it's going to get less complex or complicated as we go forward. In this moment, leaning into learning as much as we can, into supporting each other, and being mindful that the decisions we make now, we are going to see the downstream effects of them in 20 years, is really, really important.

So for learners: I was on a panel here in Indy before the holidays and they were asking, "How as a student should I best position myself?" It was a technology conference. And I said, "I can’t tell you anything other than work." Obviously, try to find a job that is field-aligned, that will give you the sort of exposure to the industry and role that you want to have. Absent that opportunity: work. Because there is learning and knowledge and insight to be gained in any role. Our society doesn't, I think, give adequate credit to learning gained in some roles, and I think that’s a tragedy. But employers are looking for experience and work ethic and the capacity to do the job, and the best way to understand what those things look like is to do them. So, work if you can.

And for advocates and institutions, it is about supporting learners to know what they know. I think that’s a big, big problem and a big solution too. We should not, in 2026, have somebody graduate with a credential and say, "Okay, now what?" or "How do I reframe these experiences that I've had in terms of skills that employers can recognize and appreciate?" Like, that stops. We’ve got to get past that problem of making sure that everything is as transparent as possible and that learners have evidence of the things that they know how to do and things that they know. So that's the higher education call: shift toward competency-based education as much as you can and be very, very articulate about helping students understand their own skill sets.

And the advocates: know your business case. In trying to bring employers over to our side, to doing the programming, to expanding what they’re doing, you have to couch it—especially now—in ways that the employer will benefit from. And if you can’t share, if you can’t tell employers what you know and how they can understand how this will impact them, you’re going to have a much, much harder time because the economics are just different now. So learn that.

And for employers: chances are, every single employer who would ultimately listen to this podcast is doing something. I’ve not encountered an employer who doesn't care deeply about the skills of their workforce. Now, some employers program more, some less, depending on all kinds of different things. But the point is: keep doing it. Make what you’re doing more visible to employees and to others. Share your stories and think about how what you’re doing is creating value for your organization. The thing that frightens me—back in 2020, when the pandemic hit, we’d been doing so much work to focus on the employer business case and really understanding how employers were advancing education for their incumbent workforce. And when the pandemic hit, I was like, "I think this is all going to go away." I was so worried that in the shock of that economic shock, we were going to lose programs that were investing in students and their education and pipeline and all of that. And what we saw, I think due to unique circumstances that the pandemic produced, was actually a doubling down and huge expansion of supported education.

I’m not positive that the next economic shock won’t be different, but I keep thinking that if we really understand how this is contributing to the bottom line, we really understand how this is benefiting employees, employers, our communities, our nation, we create just that bulkhead against the shock. So those are I think the four levels of how I would think about what to do next: make this work bulletproof, and then we can really keep it going.

Julian Alssid: Yeah, and it’s, you know, I feel like you’re singing our tune and I couldn't agree more. Such words of wisdom, Haley. So, how can our listeners continue to learn more and follow your work?

Haley Glover: Sure. So, we're upskillamerica.org if you're interested in doing old-school website spelunking. We’re pretty prolific when it comes to papers, so there is that. And then follow us on LinkedIn—both for UpSkill, but also I'm always happy to engage on LinkedIn with people individually, I do a lot of that too. And then, you know, don't be afraid to drop us a line. I'm always interested in learning more about what’s working and our model is to partner and elevate as much as we can. And so, please don't hesitate to get in touch.

Julian Alssid: Great. Well, thank you so, so much for taking the time.

Haley Glover: Awesome. It was fun, and I'm really glad, Julian, we’re still friends after all of these years. It's been a while fast, yeah.

Julian Alssid: There you go.

Kaitlin LeMoine: It was great to see you today, Haley. Thank you.

Kaitlin LeMoine: We hope you enjoyed today’s conversation and appreciate you tuning in to Work Forces. Thank you to our listeners and guests for their ongoing support, and a special thanks to our producer, Dustin Ramsdell. If you’re interested in sponsoring the podcast or want to check out more episodes, please visit workforces.info/podcast. You can also find Work Forces wherever you regularly listen to your favorite podcasts. If you enjoyed this episode, please subscribe, like, and share it with your colleagues and friends. And if you’re interested in learning more about Workforce Consulting, please visit workforces.info/consulting for more details about our multi-service practice.