Episode #16
Work Forces Rewind: 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: As we continue our summer break before returning with a new season later in August, we're revisiting our conversation with Haley Glover of UpSkill America. With AI reshaping jobs faster than most organizations can respond, and so much in flux around how we fund and support workforce development, this conversation feels more relevant than ever. Haley discusses how businesses can effectively upskill their workforce in an ever-changing, AI-driven economy, while recognizing this is an ongoing and unfolding conversation. We hope you enjoy it. Here's our episode with Haley Glover. 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 yo
