Diagnose Your AI Gap: A Working Session for HR and Technical Leaders

When an AI initiative isn’t delivering the way you expected, it’s natural to check the model first: retrain it, swap tools, add more infrastructure. That’s a reasonable place to start, but it’s rarely where the real gap lives. More often, it’s the people between the technology and the outcome who are missing, such as the person who reviews an output and knows immediately whether it’s actually right for your business. That’s the layer we’ve spent the past year studying, and it’s exactly what this session is built to help you find in your own team. Join PowerToFly AI for an interactive session where we’ll walk you through what we found: a straightforward way to diagnose where your own AI initiative is falling short, and a strategy most organizations aren’t using yet, even as new regulations make getting this right less optional by the day. What you’ll leave with: A framework for diagnosing where your own AI initiative is stalling A clear look at the strategy most organizations are overlooking, and why the window to act is now A better sense of what closes the gap for good, for your team and the people on it

Mara Gates (She/Her)

Mara Gates is PowerToFly’s Director of Content Marketing. For the past 7 years, she’s focused on creating inclusive and impactful learning experiences in academic and corporate settings. Her mission is to empathetically educate and empower people to own their professional and leadership journeys.

AI is reshaping how organizations source, screen, and select talent — but speed and efficiency aren't the same as good judgment. In this fireside chat, AI strategist Lyndsay Sanborn joins PowertoFly for a candid conversation about what responsible AI adoption actually requires from talent leaders. Lyndsay brings something rare to this conversation: 25 years inside mission-driven organizations, combined with deep expertise in AI governance and human-centered strategy. She works with leaders who can't afford to get AI wrong — and she's built the frameworks to help them get it right. From bias embedded in screening tools to the governance gaps most hiring teams don't know they have, this conversation goes beyond the checklist. It's about building the leadership capacity to make values-driven decisions about AI — before a vendor, a deadline, or a headline makes them for you. You'll walk away with: A governance lens for evaluating AI tools in your hiring stack — not just features, but risk and accountability Lyndsay's AI Fit Test framework applied to common hiring use cases A model for keeping humans meaningfully in decision loops without slowing down your process The leadership questions you should be asking before your next AI procurement decision

Lyndsay Sanborn

Lyndsay Sanborn is an AI strategist and founder of Frame + Forge AI Strategy Studio, working at the intersection of AI and reproductive healthcare—one of the most ethically and legally complex spaces in tech. In a landscape where abortion is criminalized in much of the U.S., patient data can be subpoenaed, and historical harm has eroded trust, the stakes of AI are not theoretical—they are lived realities for the communities she serves.

Her work centers the core questions every technologist should confront: Who controls the data? How can it be used to harm? What does it mean to build for communities with justified distrust? Lyndsay has built her career addressing these challenges directly.

She created the Social Signal Pipeline, an AI system that detects reproductive health misinformation at scale across platforms like TikTok and YouTube, delivering clinician-ready insights to providers. She also developed an autonomous data verification agent to ensure Title X clinic data is accurate and accessible, and has designed AI governance frameworks within national reproductive health organizations.

Lyndsay holds Executive Certificates in AI Strategy, Leadership, and Product Innovation from MIT, training in Human-Centered Design from Stanford d.school, and a Master’s in Health Policy and Administration. She also publishes The Body Is the Interface, exploring AI, data governance, equity, and reproductive health.

By 2028, Gartner predicts that one in four job applicants could be fake. The future is already arriving: AI-powered tools enable both genuine and bot-driven candidates to submit thousands of applications in minutes. Meanwhile, some candidates are using AI to complete technical assessments—only to reveal gaps in qualifications once hired. Even more alarming, bad actors have exploited coding challenges to bypass firewalls and access sensitive company data. Is this the future of hiring—or a problem we can solve today?

Rob Ribar (He/Him)

Robert Ribar is a New York based professional with over fifteen years of experience in programming diverse content, community engagement, executing dynamic events and comprehensive marketing campaigns. He currently leads PowerToFly’s B2C and B2B events, including the Diversity Reboot virtual summit series, the biggest conference in DEIB. Rob also oversees the company’s dual marketplace marketing strategy as well as playing a key role in community growth and partnership programs. At PowerToFly, Rob has produced events for American Express, Meta, Morgan Stanley, Microsoft and Slack, just to name a few. Prior to joining PowerToFly, Rob served as Production Coordinator at DKC/Hangar4, working on events for Pixar, Jaguar LandRover, FanDuel, L’Oreal and producing the reopening of the Hudson Theatre on Broadway. He also worked as the Associate Producer for the Tony Award winning production company Triptyk Studios developing works for film, television and the stage with such artists as Stevie Wonder, Linda Perry and James Gandolfini. In his spare time, he co-hosts the Dear Watchers comic book podcast, writes scary stories and programs film screenings under the Sleepover Trading Company banner.

AI implementation is not failing because of technology. It is straining organizations because of acceleration. Across industries, leaders are introducing AI into already saturated systems — compressing timelines, redefining roles, and increasing velocity inside environments that were not designed for that speed. Most AI rollouts don’t collapse. They succeed — while quietly weakening trust, role clarity, and signal integrity underneath. This session with Kelly Blackmon, an organizational strategist and founder of B.E. Consulting, introduces an organizational stability lens for AI acceleration. Rather than focusing on tools, compliance, or change management tactics, we’ll examine the structural conditions that determine whether AI integration strengthens performance — or introduces destabilization risk that appears months later. Attendees will explore: Why AI resistance is often a systems signal, not a cultural flaw How acceleration outpacing absorption capacity creates silent drift The hidden lag between implementation success and workforce fracture The difference between pushing through friction and sequencing with stability guardrails This is not an AI strategy webinar. It is a leadership-level conversation about governance capacity, workforce interpretation, and the risk tolerance decisions most organizations are making without realizing it. Participants will leave with a clearer lens for assessing whether their current AI trajectory is structurally stable and what questions responsible leaders must ask before increasing velocity further.

Kelly Blackmon

Kelly Blackmon is an organizational strategist and founder of B.E. Consulting. His work focuses on culture architecture, AI integration, and leadership decision-making under acceleration. Through frameworks like AI-EQ and CultureEQ, he helps organizations assess stability, clarify risk exposure, and implement transformation without eroding trust or performance. Kelly has advised leaders across HR, talent, and executive functions on aligning innovation with workforce integrity.

AI adoption doesn't stall because the technology is too complicated. It stalls because leaders skip the harder work of trust, culture, and change management. In this fireside chat, John Adcock, co-founder of Kinsugi Labs and former Chief People Officer at Eventbrite, sits down to unpack what actually separates organizations where AI sticks from ones where it gets quietly abandoned. Drawing on two decades of executive HR leadership at Eventbrite and Expedia Group — and on Kinsugi Labs' current work guiding companies through live AI rollouts — John will share insights on what can sink AI adoption long before a single tool is rolled out, and how leaders can build AI directly into their broader business strategy from the start. Why more than 80% of AI failures come down to the human side of the equation, not technical limitations How psychological safety and frontline engagement shape whether AI training actually works How AI can sharpen — or quietly dull — your workforce's judgment, and how leaders design for the difference

John Adcock

John Adcock is a co-founder of Kinsugi Labs and a human-centered AI transformation strategist with over two decades of executive HR leadership, including roles as Chief People Officer at Eventbrite and Vice President of Human Resources at Expedia Group (HomeAway). He has led global workforce expansion, equity and compensation strategy, and large-scale organizational change for companies navigating growth, M&A, and technology adoption. At Kinsugi Labs, John applies that experience to help organizations build durable, people-first AI transformations.