It Depends: Lessons in Technology Leadership

A leader is running an initiative, and at an executive meeting his boss gives three of his peers time to talk about it. He gets added at the end, almost as an afterthought. A few days later, Kevin Goldsmith had his own version: a meeting he’d contributed slides to went ahead without him. Both of them were reacting to the small part of the situation they could see.

The obvious question is whether the boss meant it. The more useful one is how to read someone whose context you mostly can’t see. That starts with understanding the game, which Kevin defines as a company’s real system and culture: what actually gets rewarded, and how decisions really get made.

Kevin draws on eight years at Microsoft that trained him to read every interaction as political, and a moment at Adobe when that wiring led him to badly misread his own boss. He lays out a five-step framework for telling a slight from a signal. It starts with separating what you saw from the story you told yourself, and ends with deciding whether the game is one you want to play. Along the way, he brings in logical empathy and David Foster Wallace’s idea of default settings.

The episode also turns the question around. Managers create these moments for their own teams, usually through omission, and Kevin shares a time he got it wrong, and what he does now to close the loops his reports can’t see. It’s for engineering leaders who answer to a boss and have people answering to them.

• John Godfrey Saxe, “The Blind Men and the Elephant” (1872)
• Episode: “Every Organization Is a System. Are You Designing It or Just Living in It?” (Mar 2026)
• Episode: “Values → Culture → Everything: Why Company Culture Actually Matters” (Sept 2025)
• Chris Argyris’s Ladder of Inference
• Episode: “Logical Empathy”
• David Foster Wallace, “This Is Water,” Kenyon College commencement (2005)
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)
• The theme song artist: Answers to April