At a recent Chicago-area summit hosted by Ian Ziskin and Cheryl Perkins, a mix of CHROs, CEOs, academics, coaches and workforce strategists gathered to take an unvarnished look at what’s not working at work and to test ideas for what comes next.
“Organizations are navigating unprecedented levels of complexity,” said Perkins. “Leaders are balancing workforce shifts, AI acceleration, evolving expectations and constant change while still trying to build healthy, high-performing organizations.”
She added that this summit, which was attended by HR Executive, was designed to foster the kind of candid dialogue that helps leaders move from frustration to possibility. “When people come together across organizations and disciplines to challenge assumptions, new pathways emerge for making work more human, effective and sustainable.”
The experts said that many organizations are convinced they are dealing with a tech transformation when they really have a human transformation on their hands. The symptoms of this mismatch are widely reported: Change fatigue, workforce disengagement, leadership overload and fragmented tech adoption seem to lead back to the same root cause.
“I think we’re approaching this concept of AI transformation incorrectly,” said Josh Greenwald, chief people officer at Sword Health. “This is more about human transformation. We spend too much emphasis on technology. Technology is just the medium to actually make us smarter.”
Two panels focused on what leaders are facing and what organizations need to rethink. Jamie Jacobs, CEO of Gig Talent, framed up the “low tide” problem: When times are good, organizations rarely dig into what’s really wrong. Now that conditions have tightened in many workplaces, everything that was once submerged is visible. “We’re seeing the things on the beach,” Jacobs said. “Legacy organizational systems, leadership models designed for a different time; these are the root things.”
Founder of Reframe.Work Inc. and faculty at NYU, Stela Lupushor, said the intersection of human-centered design and technology investment is finally maturing, but most organizations are still treating adoption as the goal rather than digging into more material organizational gains.
Meanwhile, organizations are deploying AI across siloed systems, generating modest efficiencies and then concluding that the investment didn’t work. “No systems are talking amongst themselves,” said Srikant Chellappa, CEO of Engagedly. “Deploying AI with the right use cases, in the right context…nobody knows what that is.”
Shifting patterns in traditional employment, the rise of gig and fractional work arrangements, and the move toward skills‑based organizations are all responses to growing pressure, said Anthony Nyberg, director of the Center for Executive Succession at the University of South Carolina’s Darla Moore School of Business. He noted that this evolving environment redistributes burdens in ways existing policies and support systems were not designed to handle. “The risks are no longer bundled by organizations,” Nyberg said. “They’ve transferred onto the workers.”
Leaders in a silo
Execs are being asked to lead through this period while they are struggling themselves, and most organizations aren’t supporting them enough. Harriet Harty, founder and CEO of Harriet Harty Executive Solutions and former chief human resources officer at Allstate Insurance, believes that leaders are increasingly isolated. “I think leaders are in a silo right now,” she said. “They know what needs to happen, but don’t have the clarity around where they need to go. The how has never been given to them.”
That isolation is connected to talent strategy, according to Liz Huldin, CHRO at Great Day Improvements. Misalignment at the exec level leads to dissatisfaction, even among the strongest performers who have invested heavily in their careers but are unable to move at the speed being required of them.
Another key analogy surfaced, illustrating that organizations approach problems like machines to be fixed, rather than gardens to be tended, said Gabriel Machado, director of contract manufacturing services at Rockline Industries. “It’s more about creating the conditions so that things can move in the right direction,” he said. “The human element is a big component.”
One audience member argued that a deeper trust problem lies beneath the change‑management challenges, technology adoption gaps and questions about workforce readiness. Organizations are moving quickly, communicating inconsistently and asking employees to absorb constant uncertainty without giving them the support or resources to make sense of it. “Where is the conversation in all of this?” she asked. “Leaders talk about what we’re going to say to them, but we’re not necessarily talking with them.”
‘Don’t overcomplicate it’
Major employers, including Microsoft and Amazon, have pulled back on hiring new graduates because entry-level work is increasingly being handled by AI agents, said Shannon Wallis, founder of Cascade Leadership. This means that managers being asked to step up responsibility have never had the chance to build their leadership muscle. “You don’t go from 0 to 10 masterfully,” she said.
Jill Wrobel, executive vice president and CHRO at Brunswick Corporation, which hosted the summit, said her firm has implemented productivity tools that are appreciate by many employees. But moving from incremental productivity gains requires workflow redesign and business model choices. “In order to get the tech investment to pay off, we actually have to change how this works,” she said.
“If we just focus on those four things and don’t try to overcomplicate it, you create a whole new generation of the workforce,” said Greenwald. He proposed that companies need to build these capabilities in their workforces:
- AI fluency, or understanding what AI can actually do
- Value literacy, meaning how value is created at the company, team and role level
- Critical thinking and problem-solving
- And what he called adaptive execution, the capacity to operationalize change quickly and continuously
‘Change-ready and resilient’
These observations come at a time when, as Nyberg put it, disruption lands differently than in the past. Earlier waves of automation mainly affected frontline and operational roles, but the AI era is reshaping knowledge work and management. He noted that those with the most power at work are now being disrupted most directly and they are also the ones with the greatest ability to slow change if they feel threatened. “This is the first time in the history of our industrial society that the change is happening from supervisor up,” he said.
Ziskin, the Summit co-founder, summarized the event as follows: “Fear, uncertainty and a constant sense of feeling overwhelmed are currently paralyzing leaders and the workforce. We must rethink our approach to defining and building leadership capabilities and help all people feel more change-ready and resilient. AI is a powerful tool to help, but it is not a substitute for common sense and human touch.”
The What’s Not Working @ Work? Summit was presented by Ian Ziskin, president of EXec EXcel Group, and Cheryl Perkins, CEO of Innovationedge LLC. Sponsors included the Center for Executive Succession at the University of South Carolina, Engagedly, Gig Talent, the Innovation Resource Center for HR, Talent Connections, Cyberhill Partners and Brunswick Corporation.
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