It Depends

Lessons in Technology Leadership

Kevin Goldsmith brings you lessons and advice from decades in the technology industry.

Browse All Episodes

Listen on:

Spotify

Apple Podcasts

Pocket Casts

YouTube

Castbox

Recent Episodes

August 31, 2025

ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart

This is a repeat of an episode originally released on April 13, 2025In October 2025, I will once again be speaking at the Lead Dev New York event. Registration and information are available here. You...

cto engineering team

Read More Listen

August 17, 2025

ENCORE: Building a technical career path at Spotify

This is a repeat of an episode originally released on March 2, 2025 In this episode of the "It Depends" podcast, host Kevin Goldsmith shares his unique experience designing Spotify's engineering car...

leadership engineering team

Read More Listen

August 03, 2025

ENCORE: Addressing the challenges of partially distributed engineering teams

This is a repeat of an episode originally released on August 4, 2024. In this episode of the It Depends podcast, host Kevin Goldsmith delves into the complexities of managing partially distributed eng...

management engineering team

Read More Listen

July 20, 2025

ENCORE: Becoming a CTO

If you are on the technology management track, the final role is Chief Technology Officer. Still, the path to the role is not obvious because the role itself differs greatly from company to company. T...

leadership management cto

Read More Listen

July 06, 2025

ENCORE: Fail Safe, Fail Smart... Succeed!

We discuss how critical failure is to innovation and how to handle it effectively. We discuss how software used to be written, Clippy, and why it was bound to fail. We also explore how Spotify utilize...

technology startup

Read More Listen

June 22, 2025

Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business

In this season finale, Kevin pulls back the curtain on his entire book-writing and self-publishing journey. What started as a collection of blog posts became "It Depends: Writing on Technology Leaders...

leadership career technology

Read More Listen

View All Episodes

About the Podcast

"It Depends" explores the complex decisions and trade-offs that define technology leadership. Each episode dives deep into real-world scenarios, sharing practical insights from Kevin's extensive experience in the tech industry.

Learn More