Sightlines issue no.1: Insights from Config

Sightlines is our newsletter for design, product, and engineering leaders. In each issue, we'll bring you the sharpest insights from senior leaders at companies like Cisco, OpenAI, Airbnb, and more on how they're navigating product development and design in the age of AI.

First up: everything we took away from leadership talks at Config.

What industry leaders are wrestling with right now

We went into Leadership Collective with questions we were hoping our peers could answer. Questions like: How do you lead a change you're still figuring out for yourself? Which parts of how we worked before AI are worth keeping? And how should we be structuring our teams for the AI era?

The TL;DR: Most of us are still figuring it out. Everyone's working out how to fold AI into their products, teams, and systems, and how to harness its speed without sacrificing quality. But a few things are clear.

• The pre-AI fundamentals still hold: What makes a good leader hasn’t changed. That means building curious teams full of critical thinkers and keeping a high bar for craft.
• Everyone's adopting a beginner's mindset: Leaders are pushing their teams to start from first principles and experiment. And they’re doing the same themselves, prototyping right alongside their teams.
• Collaboration matters more, not less: As so many AI tools pull people toward solo workflows, leaders are doubling down on working together—crits, feedback in the open, showing their work, and debating the best outcome as a group.
• Taste is still the real differentiator: As more gets built automatically, human judgment becomes the thing that matters most.

Go deeper on the insights from Leadership Collective at Config:

→ 7 questions we brought to Leadership Collective, and what leaders had to say

→ How to lead design teams through the AI era

How to keep design teams steady through constant change

Drawing on her time at Patreon and Shopify, design leader Jen Dunnam offers her advice for this new age of AI—from building a strong team to how to think about speed.

Worth repeating

A few lines that stuck with us:

“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