Introduction

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.

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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

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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/

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Where to find Michael Lopp:

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

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Where to find Brett Berson:

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

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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

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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