How AI Is Transforming Work and What It Really Takes to Stay Ahead

Terry Gerton: Mika, I’d like to begin with you. We both previously worked at the Labor Department, which has been championing AI fluency as an essential workforce skill. This suggests a widespread lack of AI familiarity. How is the department working to close this gap?

Mika Cross: It’s great to be here as a proud former DOL leader. It’s heartening to see this framework establish a national baseline—for K-12 education, workforce development, employers, and skills trainers. The goal is to equip the workforce at every level with the competencies needed to navigate the future of work successfully. This includes foundational knowledge of AI, learning to use tools effectively, comparing outputs, applying AI ethically and responsibly, and blending in vital human skills like critical judgment and decision-making. For groups that have often faced employment barriers, this approach aims to create a solid starting point, preparing organizations to get their future workforce ready for today’s and tomorrow’s job market complexities. This encompasses individuals in rural communities, those with disabilities or medical conditions, transitioning military, veterans, caregivers, parents, and naturally, the next generation of talent.

Terry Gerton: Ted, you’re focused on applying this AI framework to support veterans. Describe the first group in your Mission Ready AI Readiness cohort.

Ted Adair: We gathered 13 veterans representing all eras from Vietnam to today, including the Army, Navy, Air Force, Marine Corps, and Coast Guard, with both men and women participating. The aim is to address a gap we identified: veterans seeking various career paths—whether as entrepreneurs or to upskill in AI. This cohort, designed by veterans for veterans, builds not only an understanding of AI tools but also hands-on skills. By the final day, participants had created and presented live demonstrations of AI agents they developed.

Terry Gerton: Did participants begin the cohort with substantial AI experience, or were they starting from scratch?

Ted Adair: Initial surveys showed many had experimented with AI but lacked confidence in using the tools. By the program’s end, post-exit surveys revealed veterans felt highly confident in what they had built and delivered.

Terry Gerton: What does the curriculum look like? How do you move people from basic familiarity to practical skill?

Ted Adair: The program includes three weeks of daily 30-minute online modules, created with our partner Lead with AI. We also offered faculty-led office hours, multiple “ask me anything” sessions, and ongoing mentorship. This structure—30 minutes a day plus weekly sessions—is designed for people with busy lives. Then, in the final two weeks, participants developed several solutions, culminating in a demonstration on the last day where they showcased creative ways to apply AI and streamline daily tasks.

Terry Gerton: Could you share an example?

Ted Adair: One participant had difficulty managing multiple calendars. He successfully integrated his sports, family, and work calendars into a single-view dashboard, allowing him to see all commitments in one place and resolve scheduling conflicts instantly from his phone.

Terry Gerton: Useful for just about anyone.

Ted Adair: Absolutely.

Terry Gerton: I’m speaking with Mika Cross, founder of Strategy@Work, and Ted Adair, founder and president of Oath and Oak. Mika, circling back—we’ve discussed digital skills, but AI feels different: faster-moving, more disruptive. How does AI fluency actually affect someone’s employability?

Mika Cross: The first step is building basic comfort with the skills. One key element emphasized in the Mission Ready cohort is being tool-agnostic. The curriculum encourages comparing outputs across different platforms—whether using Microsoft Copilot, Claude, or another tool—to check for accuracy and conduct deeper research. It’s equally important to meet people where they are. Leading AI training organizations recognize that most participants aren’t technical experts. The goal is to put AI into the hands of everyday users for their specific needs. For Mission Ready, we offered three pathways: career transitions and job searching, business growth and entrepreneurship, or general skills development. Combining the on-demand curriculum Ted mentioned with volunteer AI coaches from the military-connected community provided practical, relevant expertise. You didn’t need to be a technical expert—just curious, adaptable, and willing to learn the right skills for your goals.

Terry Gerton: Ted, could you elaborate on how this worked for veterans in the career transition track?

Ted Adair: For those focused on career transitions, we addressed questions about roles like forward-deployed engineers—defining these positions and the required skills. We broke down the practical consulting abilities they would need.

…and then place the right tools directly into their hands. But what truly sets this apart is the coaching and, more importantly, the peer-driven element. For most military veterans, the very first obstacle or confidence course was never tackled alone—it was a team effort. As you climbed that wall, you were either pulling someone up behind you or reaching for a hand from the other side. That’s exactly what our peer-based model captures. So as veterans navigate their military transition and ask, “How do I prepare myself to use AI as a practical toolkit?” they’re doing it alongside fellow veterans—in a shared, supportive environment. I believe there’s no substitute for that. And doing it in person made all the difference. Early on, we intentionally brought people into the same room—especially in a time when AI and social media often remove that human connection. We made it a priority to get everyone together face to face.

Terry Gerton: Mika, this pilot sounds incredibly promising—but it’s still just a pilot. Based on your knowledge of the workforce system, how do you see scaling this cohort model? Where do you envision it fitting into existing military transition programs or workforce training centers?

Mika Cross: It’s an exciting window for growth and scaling to see what’s possible. In fact, a new national initiative called AI Ready was just launched—by the National Science Foundation, USDA, Department of Labor, and Department of Commerce—right as we were wrapping up our cohort. We’d already been brainstorming how to link up with workforce systems, nonprofits, academia, veteran-serving organizations, and employers. But here’s what we’ve learned, Terry: the employment landscape doesn’t work in isolation. There’s no one-size-fits-all solution. So we’re actively seeking the right partners—communities and organizations—who see this cohort as a differentiator aligned with the Department of Labor’s AI framework. And part of that is community building. How do you bring people together? How do you foster psychological safety? You give them the basics, build their AI literacy and fluency—but crucially, ensure they’re not going it alone. Most training is designed for individual learners. Ours was blended—a community of people with shared lived experiences. It was built by and for veterans and military-connected individuals. And we know it will keep evolving. Our volunteer faculty included AI experts like U.S. Army Colonel Kris Saling (who’s transitioning herself), former OPM AI officer Taka Ariga, human-centered design specialists from government and the military, and military spouse entrepreneurs who volunteered as AI coaches and career mentors. There’s also a strong link to the Patriot Boot Camp program—one I personally benefited from as a veteran business owner. One of our first faculty members was a Patriot Boot Camp alum who built an AI agent during the program, showcased it for the entire Mission Ready cohort, and now has a working assistant app to grow her own business.

Terry Gerton: I love hearing about all those connections. Ted, let’s turn back to you. You’ve completed one cohort—what’s next? Are you planning more, larger groups? And what policy or legislative support would help you scale this?

Ted Adair: We absolutely plan multiple cohorts. Many of our graduates have already asked to return as mentors—and in true military fashion, we want to build a “train the trainer” pipeline as the program grows. On the policy front, educational benefits for this kind of training will be key. Yes, there’s top-tier free online content out there—but it’s self-paced and solitary. What we’ve created is peer-driven, veteran-led. Think back to PT days: you could do solo runs, but the real growth happened in group sessions—especially for veterans who were initially hesitant about new tech tools. We saw remarkable progress over just three weeks, culminating in a powerful demo day.