All Episodes

44 episodes of lessons and advice from decades in the technology industry.

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 can use the discount code “KEVIN15” to receive 15% off your registration. In this special episode, K...
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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 career framework. As the leader of this initiative, Kevin provides a behind-the-scenes look at how Spot...
leadership engineering team culture career technology growth
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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 engineering teams.Kevin discusses the nuances of communication, collaboration, and culture in partially...
management engineering team culture technology
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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. The episode includes chapter 10 from "It Depends: Writing on Technology Leadership 2012-2022," "Becom...
leadership management cto technology startup
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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 utilizes the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more.This is a r...
technology startup
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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 Leadership, 2012 to 2022" – but why go the DIY route instead of working with a traditional publisher? You'l...
leadership career technology startup
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Answers That Depend: Tech Leadership Q&A Part 3

In this third and final Q&A episode of the season, Kevin addresses three challenging questions that many tech leaders face daily. First, he delves into the tension between competitive performance review systems and collaborative culture, drawing on his own experience at Microsoft to explain why...
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Answers that Depend: Tech Leadership Q & A pt 2

Host Kevin Goldsmith responds to six listener questions covering common leadership and career challenges in technology organizations. Episode Content: Learning and Development on Limited Resources - A team lead in Lagos asks about fostering continuous learning without access to expensive training pr...
leadership management engineering team career technology startup
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Answers That Depend: Tech Leadership Q&A Part 1

In this first post-book Q&A episode, host Kevin Goldsmith dives into the real challenges tech leaders face daily, answering questions from listeners around the globe. The episode unpacks several critical leadership dilemmas: Luca from Milan asks how to maintain clear accountability while fosteri...
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Succession for Scale

In this episode, Kevin shares the final chapter of It Depends: Writing on Technology Leadership, focusing on what it takes to grow with a scaling company, or recognize when it’s time for new leadership. Drawing on his real-world experience, he discusses succession planning, self-awareness, and culti...
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The Myth of the Startup in a Large Company with Kevin Stewart

In this special episode, Kevin Goldsmith is joined by longtime friend and peer Kevin Stewart, SVP of Engineering at Splice, to challenge the familiar but flawed narrative: that a team inside a big company can "operate like a startup." Drawing on their shared experiences at Adobe and divergent paths...
engineering team culture technology startup
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Lessons From Creating The Spotify Technology Career Steps

In this episode of the "It Depends" podcast, host Kevin Goldsmith discusses the lessons learned from creating Spotify's Technology Career Steps framework. Kevin shares insights from his experience leading the effort to build a structured career path for Spotify's technology team, discussing the proc...
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Spotify Technology Career Steps

In this episode of "It Depends: Lessons in Technology Leadership," host Kevin Goldsmith discusses Chapter 33 of his book, which details the career framework he helped develop at Spotify. Kevin emphasizes that a career pathing framework is the most critical document for engineering leaders. It serves...
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Building a technical career path at Spotify

In this episode of the "It Depends" podcast, host Kevin Goldsmith shares his unique experience designing Spotify's engineering career framework. As the leader of this initiative, Kevin provides a behind-the-scenes look at how Spotify's distinct career pathing system was developed, a system that rein...
leadership engineering team culture career technology growth
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Changing Hiring Practices to Build a More Diverse Technology Organization

Are your hiring practices unintentionally limiting diversity in your organization? In this episode of It Depends host Kevin Goldsmith explores the critical changes that can help technology companies build more inclusive and high-performing teams. Drawing on his experience scaling engineering teams,...
engineering scaling team hiring technology
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A diversity challenge: tech start-ups have a great opportunity

As major tech companies retreat from their commitments to diversity, equity, and inclusion, startups can lead the way. In this episode, Kevin Goldsmith explores why diverse teams consistently build better products and create stronger, more effective workplaces. He reflects on personal experiences in...
leadership team hiring technology startup
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Building a Management Training Curriculum at Avvo

In Episode 27 of It Depends: Lessons in Technology Leadership, Kevin Goldsmith explores the process of creating a management training curriculum at Avvo. Reflecting on his journey as a manager and lessons learned from his early days at Microsoft and Adobe, Kevin highlights the importance of intentio...
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Using Self-Selection to Create Journey Teams at Avvo

In this insightful episode of The It Depends Podcast, host Kevin Goldsmith, seasoned CTO and author, takes listeners behind the scenes of his first CTO role at Avvo, a legal tech company. Kevin shares his real-world experience in transforming the organizational structure by introducing journey teams...
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The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative

In this episode of It Depends, host Kevin Goldsmith dives into Chapter 26 of his book It Depends: Writing on Technology Leadership 2012–2022. Kevin shares his firsthand experiences with the Spotify model—a revolutionary approach to team organization designed to foster agility, innovation, and collab...
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Transcript of my speech from OPEX Week Summer 2018

Kevin Goldsmith, Chief Technology Officer and author of It Depends: Writing on Technology Leadership (2012–2022), shares a unique chapter from his audiobook in this episode of It Depends. Recorded on the road in Chicago, Kevin reflects on his unexpected journey into the Operational Excellence (OpEx)...
leadership technology growth
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Hiring Agile Coaches

In this episode of The It Depends Podcast, host Kevin Goldsmith dives into the intricacies of hiring agile coaches—a role he discovered while working at Spotify and which has been transformative in his approach to building high-performing teams. Kevin shares personal stories of successes and challen...
engineering team hiring technology
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Management and Systems Thinking

In this episode of It Depends host Kevin Goldsmith dives into the art of management through the lens of systems thinking. Using the metaphor of gardening, Kevin explores how leaders can “plant the seeds” for success by setting up the right environment, empowering teams, and stepping back to let grow...
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Writing Useful Performance Reviews: Delivering the Review

In this episode of It Depends, Kevin Goldsmith wraps up his insightful series on crafting and delivering effective performance reviews. Drawing from his extensive experience as a CTO and tech leader, Kevin discusses the challenges and nuances of giving feedback, especially for senior leaders who mig...
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Writing Useful Performance Reviews: Making a Raise Recommendation

In this episode of the It Depends podcast, host Kevin Goldsmith, an experienced CTO and technology leader with over 30 years in the industry, dives into the intricacies of making raise recommendations as part of performance reviews. Drawing from his book "It Depends: Writings on Technology Leadershi...
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Writing Useful Performance Reviews: Assembling the data

Join Kevin Goldsmith on the "It Depends" podcast as he explores the nuanced world of performance reviews in technology leadership. Drawing from his extensive experience and his book, Kevin offers actionable insights on making performance reviews more effective and less burdensome. This episode guide...
leadership technology growth
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Twenty Questions For Your One-on-Ones

In this episode of the "It Depends" podcast, Kevin Goldsmith, a seasoned Chief Technology Officer, explores the importance of effective one-on-one meetings between managers and their direct reports. Drawing from his extensive experience, Kevin offers practical tips for making these meetings more pro...
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Addressing the challenges of partially distributed engineering teams

In this episode of the It Depends podcast, host Kevin Goldsmith delves into the complexities of managing partially distributed engineering teams.Kevin discusses the nuances of communication, collaboration, and culture in partially distributed teams, emphasizing the unique challenges that arise when...
management engineering team culture technology
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A Resignation Can Be an Opportunity

In this episode of the "It Depends" podcast, host Kevin Goldsmith, a seasoned CTO and tech executive, explores the valuable lessons that can be gleaned from employee resignations. Drawing from his extensive experience and insights from his book "It Depends: Writing on Technology Leadership 2012-2022...
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What do I look for when hiring an engineer?

Welcome to the It Depends podcast with your host, Kevin Goldsmith! Kevin is a seasoned Chief Technology Officer with over 30 years of experience in software development, having worked in both colossal companies and budding startups. In each episode, Kevin delves deeper into the chapters, offering mo...
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Every Decision Creates a Policy

In this episode of the "It Depends" podcast, host Kevin Goldsmith delves into the complexities of decision-making in management and its implications on organizational policy. Titled "Every Decision Creates a Policy," this chapter is particularly significant, highlighting common managerial pitfalls a...
management team culture technology
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Protecting Your Team From Layoffs

While nothing can guarantee you will never have to lay off someone from your team, ensuring the team is aligned with company goals and that the team’s good work is visible will help protect them. This episode includes specific tips to help.
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The P Word (Politics at work)

In this episode, Kevin delves into ’The P Word’ and discusses the good and bad sides of politics in the workplace based on his own experiences. Whether you’re navigating corporate hallways or startup pathways, this one’s packed with insights you don’t want to miss.
startup
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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. The episode includes chapter 10 from ”It Depends: Writing on Technology Leadership 2012-2022,” ”Becom...
leadership management cto technology
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How I Get My Focused Work Done / The Known Unknowns

Once again, two shorter chapters in this podcast from the book. How I get my focused work done:When you are a manager, constantly interrupted, how can you get focus time to devote to your projects? The Known Unknowns:Understanding the mastery curve. Links:Book/Podcast/Newsletter website: https://itd...
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Own Your Calendar / Work Deliberately

Two chapters from the book this week! Discussing a deliberate approach to managing your calendar and tracking how you actually are using your time, and then how to approach your work with thoughtfulness and decisiveness instead of just making decisions based on instinct.More information about the bo...
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The Personal Strategy Off-site

Taking a day, once, twice, or even four times a year to reflect on how things are going and think about where you want to go next is a valuable practice. This episode includes how to approach this practice and get value from it. This episode also includes Chapter 5 of the audiobook "It Depends: Writ...
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When, why, and how to stop coding as your day job

One of the questions I most frequently get from engineering leaders or aspiring leads is "how much coding do you do?" or "How do you handle coding and managing?" One of the hardest things for me in my development journey was letting go of developing features on the products I worked on. This episode...
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Taking a thoughtful approach to the job search process

Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022 In this episode, we discuss my experience building an exercise to help me better understand what is important to me in a role or company and then how I used the results to help prepare for job interviews. I also discuss some of th...
leadership technology
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Fail Safe, Fail Smart... Succeed!

We discuss how critical failure is to innovation and how to handle failure well. We talk about how software used to be written, Clippy and why it was bound to fail, how Spotify uses the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more...
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Introduction

Welcome to the podcast! This episode introduces the podcast and includes the introduction to the book ”It Depends: Writing on Technology Leadership 2012-2022” by Kevin Goldsmith. Links: Book info https://itdependsbook.net/ Blog https://blog.kevingoldsmith.com/
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