What 47 Leaders Told Us About Reinventing Work for the AI Era

Earlier this month, we ran our second Work Design Collaborative meetup, hosted at AWS in New York City, alongside The Learning Forum.

We gathered 47 senior leaders - heads of transformation, AI, human resources, and workforce strategy to work out how we are going to reinvent work for the AI era.

Here’s what I jotted down.. and what it says about where we’re heading.

“We don’t know what people actually do.”

Task-level visibility is still the exception. One leader said: “I don’t know what my team does. I know what they’re called.”

Without that level of clarity, we’re designing with a blindfold on.

“Our org charts don’t reflect reality.”

Several leaders admitted their structures haven’t been updated in years — or longer.

“We’re updating the plumbing while the building’s flooding.” That really stuck with me. Frameworks built for hierarchy aren’t built for responsiveness.

Some teams are 40% automated. Others are using intake forms.

Finance is moving. TA isn’t. This gap came up over and over. Leaders flagged it as a coordination failure — and a reputational risk.

“It looks like we have no plan.”

“We found the same task in five places.”

In a hands-on workshop, teams deconstructed real roles that live in their organizations. Red dots went on duplicate tasks. Many teams lit up immediately.

One exec said to me: “We’re duplicating effort and calling it collaboration.” 😮‍💨

“We’re not tracking what AI gives back.”

Everyone’s chasing time saved. No one’s measuring how it’s used.

Ben Schreiner, Head of AI and Modern Data Strategy Business Development at AWS, asked the room: “What are you tracking after automation?” 

Silence. 

This is a missed opportunity — and a strategic risk.

Teams are tired. And unclear.

This wasn’t just a systems conversation. People flagged burnout. Emotional drag. Confusion.

“We’re redesigning without recalibrating trust.” That’s why culture isn’t keeping up. Not because people won’t change — but because we haven’t told them what’s really changing.

Tech pressure is outpacing cultural readiness.

We heard it straight: “We’re building smart systems into brittle cultures.”

If you lead with tech, culture snaps. If you wait for culture, tech drags. There’s no playbook — just tradeoffs.

What’s Next

Job architecture is slow. It's rigid. It hides the real work.

You can’t build an AI-ready workforce on a broken system.

Start with what’s true:

• Break work into tasks. That’s where the signal is.
• Map what AI can do. Protect what humans should own.
• Use live data. Not frameworks frozen in time.
• Build a shared language of work. No silos. No guesswork.

The leaders in that room didn’t posture. They got clear. If you are reading this and you’re responsible for redesigning how your org runs, this is your sign to not wait. Build on real work. Test fast. Fix what’s slowing you down.

Siobhan 💜