It Depends: Lessons in Technology Leadership

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," "Becoming a CTO." This chapter discusses the common skills needed for the CTO in almost any company and ho...

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 repeat of an episode originally released on January 20, 2024. Seattle's Got Tech Event at Seattle St...

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'll learn: The real reasons tech leaders should (or shouldn't) write books Detailed breakdown of self-...

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 some systems actively discourage the teamwork they claim to promote. Next, Kevin explores how to bal...

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 programs. Kevin discusses free resources, including conference talks on YouTube, vendor training mater...

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 fostering cross-functional collaboration in a matrix organization. Kevin provides practical advice on balan...

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 cultivating a culture that fosters growth at every stage. Listener Survey: https://forms.gle/JVeKHsHJKhEM...

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 through startups, they explore why innovation often stalls inside large organizations and what makes...

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 process's challenges and successes. The episode covers key topics such as balancing behaviors versus ach...

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 as the backbone of organizational culture by reinforcing desired behaviors through promotion and pe...

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 reinforced its unique engineering culture rather than undermining it. Kevin explains the delicate balanc...

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, Kevin challenges conventional hiring biases—such as prioritizing certain universities or requiring e...

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, shares insights on how startups can leverage the "law of small numbers" to make a meani...

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 intentional training for engineering managers. This episode delves into the innovative approach used 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—an innovative approach influenced by, but distinct from, Spotify’s model. He discusses the challeng...

In this episode of It Depends, host Kevin Goldsmith, a seasoned technology leader and CTO, explores the intricacies of Spotify's famed matrix organization model and its applicability to other companies. Drawing from his firsthand experiences at Spotify during its formative years, Kevin delves into the successes and challenges of implementing the Spotify model, addressing common misconceptions and...

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 collaboration. Drawing on his years at Spotify, Kevin explains how the model allows teams to dynamically f...

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) community, a world rooted in Six Sigma and Lean methodologies. Kevin recounts his experiences speak...

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 challenges with agile coaches across different companies, reflecting on how this role can dramatically boos...

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 growth happen organically. He shares practical insights on Kanban boards, the power of autonomy, and the...

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 might not receive regular performance reviews themselves. He shares practical strategies for self-evalu...

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 Leadership" and a talk he delivered at Lead Dev Berlin in 2019, Kevin unpacks the often misunderstood process...

In this insightful episode of The It Depends Podcast, host Kevin Goldsmith delves into a critical aspect of leadership: writing effective and fair performance reviews. Kevin, an experienced CTO and author of It Depends: Writing on Technology Leadership, shares lessons from his own career spanning over 30 years, including his time at Adobe, Spotify, and Microsoft. This episode, part of a four-part...

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 guides listeners through assembling relevant data and providing feedback that genuinely aids employee dev...

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 productive and engaging, such as taking walks during the meetings or using tactile objects to encourage...