Ep. 110 - Human by Design, AI by Default: Rewriting the Way We Work

Written By George Clode

Don’t fear losing your job to AI—fear losing it to someone who knows how to use AI better than you. It's time to stop treating AI as a tool and start treating it as your default way of working.

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Human by Design, AI by Default: Rewriting the Way We Work #110

What does it actually look like to rebuild a global, legacy brand with years of technical debt into a completely AI-native business from the ground up? As it turns out, it isn’t just a technological challenge—it is fundamentally an HR and communications mountain to climb.

This week, Gary and George are doubly thrilled to welcome back Groupon’s Chief People Officer, Nick Walker (marking his record third appearance on the show!), alongside Groupon's VP of Comms, Engagement, and Inclusion, Emma Coleman. Together, they take us behind the scenes of Groupon's massive cultural and structural transformation under their AI-savvy CEO, Dushan.

From reshaping employee mindsets and restructuring traditional departments into lean "speedboats" to managing the psychological fear of redundancy, Nick and Emma share the unfiltered reality of rewriting the way we work. They discuss why AI adoption is actually a massive transfer of power from legacy systems back to human beings, and how human judgment remains the ultimate corporate superpower.

Key takeaways from this episode:

  • Speeding Fines vs. Parking Tickets: To build an AI-native culture, leaders must encourage risk-taking. Groupon welcomes "speeding fines" (mistakes made while pushing boundaries and moving fast) but has zero tolerance for "parking tickets" (complacency or refusing to try).

  • Ditch the "Hand-Off Tax": Legacy organizations slow down because of continuous hand-offs between bloated, siloed teams. By structuring operations around "speedboats"—lean teams of 2 to 3 people running a complete workflow—you eliminate the friction and move exponentially faster.

  • Close the Execution Gap, Not the Judgment Gap: AI is incredibly efficient at closing the execution gap (handling processes and grunt work). However, humans still own the judgment gap. Your ability to understand context, see around corners, and apply emotional intelligence is irreplaceable.

  • Prompt Engineering is a Non-Negotiable Skill: Good inputs yield rich outputs. Investing time in mastering prompt engineering (sometimes spending up to an hour crafting a single prompt) is a major career differentiator that prevents "sloppy AI work."

Links & references:

Highlights:

  • “AI adoption will fail with people and HR functions before it fails in tech... because the tech is there, right?” - 06:22 - Nick Walker

  • “Awareness is: 'I heard about this.' Belief is: 'I’ve changed how I work.' And communications is kind of, you know, we light the fuse.” - 08:31 - Emma Coleman

  • “Don't fear losing your job to AI, fear losing your job to someone else who is using AI better than you.” - 13:59 - Nick Walker

  • “We’re closing the execution gap, not the judgment gap. And the judgment piece is where we talk to our teams and say, 'This is the value that you bring...'” - 16:56 - Emma Coleman

  • “While AI owns the process and the workflows, we own the judgment.” - 17:36 - Nick Walker

  • “Comms people are innately prompt engineers... That’s kind of what we’ve been doing in our jobs for years now.” - 27:55 - Emma Coleman

George Clode
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Ep. 109 - Managing Expectations Without Being a People Pleaser