In the first episode of Winslow’s new video series, where we have conversations with HR and AI leaders about the future of work, CEO Niel Robertson sits down with Steve Thomas, a longtime HR executive and digital transformation leader. Together, they explore why AI councils are becoming a critical part of how modern organizations navigate change.
Watch the video below or continue reading.
Making the Case for AI Councils
“AI requires an enterprise-wide strategy,” Steve explained. “It needs a stake in the ground from your CEO. This isn’t something IT can experiment with in isolation.”
Here are the key responsibilities an effective AI council should own, according to Steve:
- Cross-functional guidance: Include leaders from HR, IT, legal, finance, operations, and customer-facing teams.
- Training and fluency: Implement a company-wide learning program, even a brief one, to ensure employees understand the basics, such as LLMs and data policies.
- Guardrails, not gatekeeping: Councils should enable responsible experimentation. “The only thing stopping people from experimenting should be the budget,” Steve said.
- Shared vendor standards: Develop a clear checklist for evaluating AI tools to avoid delays and duplication.
A Strategic Mandate for HR
For HR leaders, the opportunity is clear: AI councils offer a structure to ensure tools like Winslow are deployed thoughtfully and securely, while also accelerating transformation. Steve emphasized that HR can’t afford to wait on the sidelines:
“This isn’t just about productivity. It’s about freeing up HR’s time to focus on strategic work, culture, development, and retention.”
With AI now part of the tech stack, HR needs to guide:
- AI policy creation that reflects privacy and ethical labor practices
- Training programs that address skills gaps across the workforce
- Risk assessments for people-facing AI implementations
- Evaluation of tools that touch sensitive data (e.g. employee records, payroll, performance management)
AI councils provide a platform for doing that work cross-functionally.
Balancing Speed and Governance
Niel raised a concern that many vendors share: enterprise AI governance risks becoming a bottleneck, like IT did in the early SaaS days. Steve agreed. “It sounds like bureaucracy,” he admitted, but emphasized that councils exist to accelerate, not stall:
“This is why the CEO has to lead. The message has to be: we’re innovating. The council makes sure we’re doing it properly.”
He recommends that AI councils push for:
- Clear upskilling paths
- Rapid pilot approval workflows
- Regular vendor re-evaluations as the tech evolves (“two LLMs ago” is already a problem)
Why It Matters Now
Steve warned against the “wait and see” approach. As generative AI changes the pace and shape of work, organizations that don’t invest risk being leapfrogged by adjacent competitors. The CEO’s job is no longer just optimization, it’s expansion:
“You’re not just cutting cost. You’re freeing up capacity to reinvest in growth.”
And for HR?
“HR leaders need to help their companies experiment in a smart, responsible way. That’s what this is all about.”
What This Means for Winslow
We’re building Winslow to be the secure, context-aware AI assistant for HR teams. With tools that automate common employee questions, support manager enablement, and integrate into existing HRIS systems, Winslow is designed to make HR more agile and strategic.
If you’re standing up an AI council or navigating HR AI adoption, this episode is a must-watch. And we’re just getting started.
Welcome, Steve
We’re excited to share that Steve Thomas has joined Winslow as an advisor.
Steve brings decades of HR leadership experience across life sciences, technology, and services industries. He has served as CHRO, led global Workday deployments, supported major M&A integrations, and most recently built out a digital HR strategy in a Fortune 500 company. His weekly newsletter Future Tense is a thoughtful read on the future of people, power, and performance in an AI-driven world.
His insights are helping shape Winslow into the kind of AI partner HR teams not only trust, but champion.
Watch the full conversation and learn more about Steve’s role at Winslow.
