Shaping tomorrow's talent strategy – Chicago

Oct 23, 2025   Updated Nov 11, 2025
By: Rick Rosario

Reflections from Chicago: Navigating the AI-powered talent landscape

Recently, I had the opportunity to join fellow talent leaders at Cielo’s Chicago roundtable, held in the historic Old Post Office and hosted by Walgreens. We spent time discussing how organizations are managing the intersection of AI, talent strategy, and workforce transformation, especially given today’s uncertain economic climate.

One thing that stood out was the mix of confidence and realism among talent leaders. Even with all the technological changes and economic challenges, there’s a sense of resilience, as many have already weathered a lot over the past five years.

As Robin Erickson from The Conference Board pointed out, 73% of leaders feel confident about handling the changes ahead. Still, this optimism is balanced by a practical approach. Leaders are working to blend new technology with a people-first mindset, while also adapting to shifting candidate behaviors and organizational needs.

Chicago: Innovation meets practicality

Chicago’s diverse industries — including healthcare, manufacturing and technology — made it a great place to explore how different sectors are approaching talent transformation. The city’s reputation for combining innovation with business sense reflects how many leaders are embracing new tech but staying focused on measurable results.

Our conversations in Chicago built on insights from previous roundtables in Singapore and London, adding a North American perspective to the global discussion about the future of talent strategy.

3 key insights shaping talent strategies

1. AI implementation: Bridging promise and practice

A recurring theme was the challenge of turning AI’s potential into real business value. Many organizations are quickly adopting AI tools, but connecting those investments to strategic outcomes isn’t always easy.

As one participant said, “It feels like we’re making the changes without the plan.” Technology is moving faster than strategy, which can work for some tech-driven teams but creates challenges for others.

North American leaders are taking a practical approach — starting with clear use cases that deliver measurable value. For example, one team saved an estimated 10,000 hours a year by automating interview scheduling and is now expanding into sourcing and screening. This step-by-step method helps organizations show value and build skills for more complex projects.

Still, getting people to adopt AI — especially hiring managers — remains a challenge, highlighting the need for good change management and user-friendly solutions. One talent leader emphasized, "Adoption of AI is really hard, especially for hiring managers."

2. The evolving labor market: Job security and candidate hesitancy

We also explored how candidate behavior is changing. Despite low unemployment, many professionals are hesitant to switch jobs.

One leader noted, “People aren’t looking for jobs … they’re afraid to move right now,” while another wondered if engagement strategies are finally working, which is contrary to the 10-year low in engagement scores reported by Gallup. This tension between risk avoidance and the need for improved retention strategies represents a fundamental shift in how organizations must approach talent acquisition.

Organizations need to rethink how they attract and retain talent. Many candidates prefer individual contributor roles over management positions, and economic uncertainty is leading companies to cut costs through hiring freezes, layoffs, and reduced benefits. Talent leaders are being asked to do more with less, all while responding to evolving candidate expectations.

3. Balancing technology and human connection in the candidate experience

The third major theme was finding the right balance between technological efficiency and human connection. It’s not just about using AI — it’s about using it in ways that enhance the candidate experience.

For example, a Stanford study found that while candidates appreciate the speed of algorithms, they generally prefer human involvement for empathy and authenticity. This means organizations need to design processes that use technology but keep the human touch where it matters.

Generational differences also play a role. Some younger candidates are comfortable interacting with AI, while others worry that technology can’t fully understand context or nuance. Leaders recognize the need for scalable solutions that don’t lose the personal element.

Building future-ready talent strategies

The Chicago roundtable showed that North American organizations are taking a pragmatic, results-oriented approach to talent transformation. Success will come to those who:

• Start AI projects with clear, valuable use cases that prove measurable business-related outcomes
• Adjust talent strategies to address job security and changing career goals
• Create candidate experiences that balance technology and human connection
• Develop new workforce planning approaches for uncertain times

This approach values innovation and efficiency, but not at the expense of people, and maintains confidence even in uncertain circumstances.

Connecting global talent conversations

Comparing Chicago’s insights to those from Singapore and London highlights interesting regional differences. Singapore focused on AI and the rise of talent advisors, London discussed changing timeframes and generational shifts, and Chicago emphasized practical AI implementation and adapting to candidate behavior.

These global conversations show that, while each region has its own perspective, talent leaders everywhere are facing similar challenges: using technology effectively, adapting to new workforce expectations, and building agile talent teams.

I’d love to hear how your organization is approaching these changes. How do you balance technology and human connection? What strategies are you using to respond to shifting candidate behavior?