Judgment, task maturity, and iteration

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used.

In today's episode, we discuss:

• Why design leaders who stop designing stop leading
• The four pillars every design manager must master
• How to delegate when you're a perfectionist
• Why leaders need strong opinions
• How to scale good judgment
• What Rippling's operating system teaches about speed and commitments

References:

• Airbnb: https://www.airbnb.com/
• Amazon: https://www.amazon.com/
• Apple: https://www.apple.com/
• Asana: https://www.asana.com/
• Brian Chesky: https://www.linkedin.com/in/brianchesky/
• CrossFit: https://www.crossfit.com/
• Figma: https://www.figma.com/
• Honeywell: https://www.honeywell.com/
• Liz Sanders: https://www.linkedin.com/in/sandersliz/
• Nest: https://store.google.com/category/google_nest
• Notion: https://www.notion.so/
• Parker Conrad: https://www.linkedin.com/in/parkerconrad/
• Patrick Collison: https://www.linkedin.com/in/patrickcollison/
• Retool: https://retool.com/
• Rippling: https://www.rippling.com/
• Stripe: https://www.stripe.com/

Where to find Ryan:

• LinkedIn: https://www.linkedin.com/in/ryanwlucas/

Where to find Brett:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter/X: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

Timestamps:

00:00 Intro

00:08 What design actually does at a software company

01:40 The roots of design: from industrial design to software

03:29 Useful, usable, desirable — and used

04:49 How design relates to engineering, product, and marketing

08:15 Measuring success as a design leader

12:40 The gap between director and VP-level design leadership

14:23 Why great design leaders jump up and down in altitude

19:26 The four pillars every design manager must master

21:34 Over-indexing on quality and the perfectionist trap

25:11 When lowering the quality bar actually cost the business

27:53 How to build judgment through pattern matching

31:25 How Ryan's design team differs from the rest

34:31 Why Figma is not the source of truth

36:32 How Ryan spends his week: recruiting, crits, and staff meetings

38:39 The "Do/Try/Consider" framework

42:12 The most important decisions of the past year

44:05 Should one-on-ones exist?

46:45 How to scale judgment

50:49 What to look for when hiring your first design leader

54:54 Advice for young designers who want to lead

58:24 Demanding yet supportive: A balanced management style

01:02:43 What Rippling's operating system teaches about execution