Leading Through the AI Era: Takeaways from Config's Leadership Collective

Sightlines is a newsletter for design, product, and engineering leaders, and the inaugural issue focuses on the leadership discussions from Config. The central theme from the Leadership Collective talks is that there is no playbook yet for this moment. Leaders are learning how to fold AI into their products and processes while preserving the fundamentals of good leadership.

The questions on everyone's mind are practical: How do you lead a transformation you're still navigating yourself? Which pre-AI working habits are worth keeping? And how should teams be restructured for this era? The consensus is that everyone is still figuring it out, but several themes emerged.

  • Pre-AI leadership fundamentals still apply. Building teams of curious, critical thinkers and maintaining a high bar for craft remain essential.
  • Leaders are adopting a beginner's mindset. They are pushing teams to experiment from first principles while prototyping alongside them.
  • Collaboration is more important, not less. With AI tools enabling solo workflows, leaders are emphasizing group crits, open feedback, and collective debate.
  • Taste is the real differentiator. As more production becomes automated, human judgment becomes the most valuable asset.

The Questions Leaders Brought to Config

These insights came from a session where participants gathered to discuss guiding teams through change, the evolving definition of expertise, and how to maintain quality at a faster pace. A related post expands on those conversations, and another offers advice from design leader Jen Dunnam on keeping teams steady through constant change, drawing on her experience at Patreon and Shopify.

Quotes Worth Repeating

Several lines from the leaders at Config stood out for their clarity on the current moment.

"We'll go through a period where there's some bad work, some bad design—we'll be swimming in slop for a while. But the great work will always rise above it. The judgment, the great editing, and the ability to dream as creators will always matter." — Teo Connor, VP of Design, Airbnb
"I show up to my team as a designer and human first. There’s a high risk of chasing the tool, but fundamentally we’re designing for humans, and that's not changing." — Jen Dunnam, former VP of Design, Patreon
"As a leader, you need to learn how to let go—you can’t possibly keep track of every single thing going on. Hiring people you trust goes a long way." — Ian Silber, Head of Product Design, OpenAI
"Design is the ultimate way to show a customer that you care, because you sweat the details. If they feel you've taken meticulous care building something for them, you get an emotional reaction, not just a logical one." — Jeetu Patel, President and Chief Product Officer, Cisco