Karen A. Gilhooly on Leadership After AI Shifts Work

Karen A. Gilhooly on Leadership After AI Shifts Work

What remains when tasks change, and meaning needs to be rebuilt.

Work used to carry its own structure — tasks filled the day, progress was measurable, and people built a sense of value through repetition and output. That pattern is shifting as AI tools take on the work that once defined those routines. Karen A. Gilhooly, a leadership strategist with more than two decades of experience, focuses on what happens in that space. 

Her work centers on harder questions underneath that shift: whether people still feel necessary once the tasks that filled their time start to disappear. 

When Work Stops Proving Relevance

Completing tasks and staying busy have long been proof that someone is needed. Gilhooly frames the real challenge as the question of what replaces that proof once the structure starts to thin out.

Gilhooly explains, “AI doesn’t just automate the task. It answers the question people were afraid to ask. It says that the thing they did can be done without them.”

The Loss of Early Development Spaces

“Repetitive work once carried more value than it appeared on the surface. Entry-level tasks, manual reviews, and routine processes gave people a way to build instinct through exposure. Over time, patterns became familiar, and decision-making followed,” Gilhooly says.

When those experiences shrink, the pathway into judgment shifts with them. New employees may move into roles that expect more awareness without the same foundation underneath. 

Leaders feel that gap later, as fewer people feel ready to take ownership even as the demand for it stays steady. 

Where Judgment Actually Comes From

AI can generate output that looks complete. What it hasn’t experienced are consequences. 

“Judgment forms through situations where outcomes carry weight. It builds when decisions lead to mistakes, when someone has to repair what went wrong, and when responsibility stays with the person who made the call,” Gilhooly says. And that experience can cause what she describes as “scar tissue,” a form of judgment shaped by consequences rather than instruction.

Gilhooly’s perspective returns to that difference. Systems can assist with a decision. Only lived experience can carry it forward. 

Reading the Emotional State of a Team

Her framework divides employees into three states: “want-to,” people engaged and invested in their work; “autopilot,” people moving through the motions; and “have-to,” people operating from obligation, often carrying frustration that doesn’t surface immediately. Each state requires a different leadership response.

Each group responds differently to change. Motivated employees tend to stay engaged when they feel supported. Those on autopilot may need a shift in ownership or a challenge. The third group can be harder to reach, especially when disagreement has settled in over time.

Building Meaning With Intention

Ownership of a project, time set aside for reflection, or space to learn without immediate pressure all contribute to people’s understanding of their place in the system.

The structure shifts from task-based validation to something more deliberate. People begin to look for signals that their contribution still holds weight, even when the work itself changes. 

A Different Kind of Leadership Pressure

The pressure on leaders often changes direction. The focus moves toward sustaining the conditions where people can still develop, contribute, and stay connected to what they’re doing. 

Gilhooly’s work sits inside that transition. It looks at how leadership adapts when the familiar markers of progress start to fade. What remains is a question without an easy answer. If work no longer proves value on its own, leaders need to find other ways to make it visible.