Episode 8 | Assets UNSCRIPTED with Ashley Gross, The Alliance
The gap between what organisations say they want from AI and what they're actually ready for is rarely a technology problem. It's an operational one. Processes that don't work before AI don't start working after it. Departments that don't trust each other's data don't suddenly align because a new tool is in the room. Ashley Gross has spent the last several years helping organisations figure this out the hard way, so they don't have to.
In this episode of Assets UNSCRIPTED, Berend Booms sits down with Ashley Gross, founder and CEO of AI Workforce Alliance and author of The AI Workweek, published by Wiley. Ashley's entry into AI productivity came not from a technology background but from necessity: becoming a new mum in 2020 with no maternity leave and an 80-hour work week that had to change. She rebuilt it down to 15 hours before ChatGPT became a household name, and has since built a career helping Fortune 500 companies and mid-market leadership teams figure out what AI actually delivers in practice.
The conversation covers how AI readiness depends far more on communication and alignment than on tools, why AI is putting more pressure on senior leaders than on entry-level staff, and what Ashley does when a CEO walks in and asks for an AI win. It also touches on AI fatigue among frontline workers, the tension between boardroom mandates and shop-floor reality, and whether Dario Amodei's recent call to slow AI development is a genuine concern or well-timed positioning. Watch the full episode on YouTube, or listen on Spotify and Apple Podcasts.
From 80 Hours to 15: What Ashley Actually Did
Ashley's story starts in 2020, before the current wave of AI tools existed. Facing a new baby, no maternity leave, and an 80-hour work week, she started by doing something basic: timing her tasks. Every activity she logged, documented, and recorded herself talking through. That process surfaced what was actually eating her time, mostly administrative work she was doing for visibility and gratitude rather than real impact. The step after awareness was finding the right tools and testing them, one by one, with no playbook to follow. The discipline of that process, not the tools themselves, is what she's been teaching organization's since.
AI Is Coming for the Executives
One of the sharpest observations in the episode is Ashley's view on who AI is actually disrupting. Entry-level workers get the headlines. But Ashley's experience points somewhere else. It's coming for the executives, the senior managers, the C-suite. Not because AI is better than them at their jobs, but because the habits they built to get where they are no longer fit the pace of change. The leaders still running daily check-ins with every team member, still expecting two Slack updates a day, still operating the same way they did five years ago: those are the ones getting replaced. Not by AI, but by people who've adapted to it.
Why Does Your Win Need to Come from AI?
When a CEO walks into a meeting and says they need an AI win, Ashley's first question is the one that gives the episode its title: why does the win need to come from AI? It's a genuinely disorienting question to ask a CEO, which is exactly the point. AI is a vehicle that gets you from A to B faster. But you still need a driver who knows where they're going. Her case, made consistently throughout the conversation, is that organisations reach for AI before they've figured out what they're trying to do, and then blame the technology when the results don't materialise.
The Business Therapist
Ashley describes her role as sitting in rooms between IT and business teams doing what she calls business therapy. The problems she sees are rarely technical. They're communication failures dressed up as technology problems. Her example is sharp: a 500-person company where two analysts spend hours creating a report that Salesforce can generate automatically, because marketing doesn't trust a report pulled by sales and sales doesn't trust one pulled by marketing. The fix isn't a new tool. It's a 30-minute monthly check-in and a shared definition of what they're trying to measure.
AI Fatigue and the Frontline
Berend raises a tension that will resonate with anyone working in asset-intensive industries: frontline workers who couldn't care less about AI. Ashley's approach is to stop talking about the technology entirely. She asks people what their five-year goal looks like. Almost everyone says they want more time. Then she reverse architects from that number back to what AI could actually free up in their current week. It's a conversation about their goals, not about the technology. That reframe is usually what gets people to listen.
"AI is the vehicle that gets you from point A to point B faster, but you still have to have somebody driving that car who knows where point A and point B are."
- Ashley Gross, Founder and CEO, AI Workforce Alliance
Assets UNSCRIPTED is the Future of Assets podcast series hosted by Berend Booms. Each episode brings together leaders from across asset-intensive industries for authentic, unscripted conversations on the ideas, challenges, and innovations shaping the future of asset management. New episodes are published on YouTube, Spotify, and Apple Podcasts.