Reflections on Engineering Leadership and Changing Perspectives

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership.

—

In today’s episode, we discuss:

• Lopp’s “utopia” — where engineers have time to create and invent
• What makes an excellent engineering leader
• The flexibility required for managerial roles in different contexts
• Navigating internal dynamics between design, engineering, and product
• How to build and grow effective engineering orgs
• The importance of understanding individual motivations
• Key lessons from over 30 years in the industry

—

Referenced:

• AOL: https://aol.com
• Apple: https://www.apple.com
• Borland: https://en.wikipedia.org/wiki/Borland
• Netscape: https://en.wikipedia.org/wiki/Netscape
• Palantir: https://www.palantir.com/
• Phillipe Kahn: https://www.linkedin.com/in/philippekahn/
• Pinterest: https://www.pinterest.com/
• Slack: https://slack.com
• Stewart Butterfield: https://www.linkedin.com/in/butterfield/
• Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/

—

Where to find Michael Lopp:

• Blog: https://randsinrepose.com/
• LinkedIn: https://www.linkedin.com/in/michaellopp/
• Twitter/X: https://twitter.com/rands

—

Where to find Brett Berson:

• 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: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

—

Timestamps:

(00:00) Introduction

(02:20) Beginning career at Borland

(05:41) The difficulty with shipping software at scale

(07:52) Why it’s harder to ship today than ever before

(09:42) What makes a startup operationally sound

(11:23) Why engineers should have concrete time to invent

(19:42) How PMs can improve engineering culture

(21:35) An engineer’s perspective on good product management

(23:36) The role of product compared to design and engineering

(26:38) How micromanagement kills creativity

(29:35) Fostering a debate culture in an org

(31:26) Declarative versus prescriptive leadership

(36:09) 3 ideas on leadership from Lopp’s upcoming book

(38:29) Understanding employee motivation

(42:28) Advice on discovering what motivates people

(46:06) Why teams should reorg every 6 months

(48:32) One thing all successful leaders do

(52:22) Why sound judgment is crucial for decision-making

(53:45) Crystallized lessons from working at software giants

(56:19) Why Lopp is afraid of becoming irrelevant

(57:58) The number one leadership lesson from Lopp’s career

(59:32) What Lopp has changed his mind on over time

(61:12) People who had an outsized impact on Lopp