It Depends: Lessons in Technology Leadership

This is a repeat of an episode originally released on April 13, 2025 In 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, Kevin Goldsmith is joined by longtime friend and peer Kevin Stewart, SVP of Engineering at Splice, to challenge the familiar yet flawed narrative: that a team within a large 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 real startup environments fundamentally different. This wide-ranging conversation explores culture, risk, incentives, and why resource contention, rather than imagination, hinders corporate innovation. Whether you lead a startup or a legacy company trying to move faster, this episode offers a valuable perspective. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith The Guest: Kevin Stewart  

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 Spotify's distinct career pathing system was developed, a system that reinforced its unique engineering culture rather than undermining it. Kevin explains the delicate balance of timing when implementing a career framework. Waiting too long (as Spotify did) can cause problems, but implementing too early can stifle a growing organization. He emphasizes how career pathing must align with company values, as it directly influences what behaviors get rewarded and ultimately shapes your culture. The episode covers Spotify's collaborative approach to creating its "Career Steps" framework, involving representatives from across the organization rather than simply adopting another company's model. Kevin shares their guiding principles, including the crucial shift from focusing on achievements to behaviors, supporting specialists and generalists, and defining career growth by expanding spheres of influence. Whether you're a tech leader contemplating how to structure growth paths for your team or an individual contributor wondering how career frameworks influence company culture, this episode is a must-listen. It offers valuable insights into one of the most foundational aspects of engineering leadership, insights that are relevant and beneficial for both roles. LeadDev New York (Use the discount code “KEVIN15” for 15% off on your registration) Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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 distributed teams, emphasizing the unique challenges that arise when some team members work remotely while others remain in the office. He highlights his experiences at companies like Adobe, Microsoft, and more, offering valuable lessons on effective management strategies and the importance of maintaining human connections in a digital work environment. Whether you're a tech leader navigating the post-COVID landscape or simply interested in the future of work, this episode provides actionable insights and practical advice for fostering successful distributed teams links: LeadDev New York Video and slides from Leading Distributed Teams The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith The newsletter

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 how the role differs between early-stage and mid-stage companies. This is a repeat of an episode originally released on April 28, 2024. Seattle's Got Tech Event at Seattle Startup Week LeadDev New York Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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 Startup Week LeadDev New York Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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-publishing vs. traditional publishing Specific tools and workflows: from WordPress to Word, ChatGPT for indexing, and recording audiobooks at home The business side: Amazon KDP vs. Ingram Spark, profit margins, and what actually sells Costly mistakes to avoid (spoiler: don't waste time on fancy tooling) How to promote without feeling like a sleazy self-promoter Perfect for: Anyone considering writing a book or starting a content business Tech leaders thinking about building their personal brand Entrepreneurs curious about the nuts and bolts of launching a creative venture Even if you never plan to write a book, Kevin's approach to learning a new business from scratch offers valuable lessons for any side project or career pivot. Plus, you'll get the honest truth about royalties, sales numbers, and whether it's actually worth the effort. This episode doubles as both a practical how-to guide and a case study in DIY entrepreneurship. Kevin's Gen X, do-it-yourself approach (honed from years running a record label) provides a refreshing alternative to the usual "scale fast or die" startup mentality. Seattle's Got Tech Event at Seattle Startup Week LeadDev New York Will Larson's Blog Post on self-publishing vs traditional publishing Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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 balance innovation with product roadmap commitments, and whether guild structures can help break down team silos while fostering technical creativity. He shares practical strategies for channeling brilliant engineering ideas into strategic objectives without derailing quarterly deliverables. Finally, he addresses a thoughtful question about advocating for accessibility and inclusive design in fast-paced startup environments. Kevin provides actionable advice on how individual contributors can influence technical strategy, make the business case for accessibility, and demonstrate measurable impact even when leadership views frontend work as "just making things pretty." Throughout the episode, Kevin emphasizes that context matters in every decision, offering nuanced perspectives rather than one-size-fits-all solutions. Whether you're a staff engineer trying to drive collaboration, a technical leader scaling an AI platform, or an IC passionate about inclusive design, this episode delivers practical insights for navigating complex organizational challenges. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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 materials, online courseware, and strategies for organizing local meetups and knowledge-sharing sessions. Personal Retrospective Systems - An SRE professional in Portland seeks structured approaches for personal leadership reflection. Kevin details his multi-layered system: weekly, monthly, quarterly, and bi-annual review processes, including his specific weekly questions and bullet journaling methodology. Organizational Change Management - A manager struggles with department heads who verbally commit to transformation initiatives but show limited follow-through. Kevin addresses the brutal reality that sometimes personnel changes are necessary when key people resist required organizational shifts. Technical Debt vs. Immediate Delivery - A healthcare technology professional faces pressure to implement quick patches while advocating for proper architectural redesign. Kevin emphasizes the importance of understanding business context and having frank discussions with leadership about trade-offs. Early Career Overwhelm - A junior data engineer, hired as the first data person at a startup, feels overwhelmed balancing immediate requests with infrastructure foundations. Kevin provides perspective on realistic expectations for junior professionals and the importance of focusing on current competency over long-term planning. Product-Engineering Team Dynamics - A product team leader experiences friction with engineering counterparts who prioritize their roadmap over product initiatives. Kevin identifies this as a fundamental structural issue, advocating for unified backlogs and shared accountability between product and engineering functions. The episode offers direct, sometimes blunt advice about leadership realities, emphasizing practical frameworks over theoretical approaches. Kevin shares specific processes he uses personally and addresses the difficult decisions leaders must sometimes make. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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 balancing engineering ownership with product and design partnerships, revealing how to avoid the common pitfalls of siloed thinking without sacrificing sprint commitments. Tatiana, a data science leader from Estonia, presents two thought-provoking questions. First, how can technically-oriented leaders effectively evaluate the "soft contributions" that don't show up in quantitative metrics? Kevin shares his battle-tested 360-review approach that helps quantify the unquantifiable. Then, Tatiana asks about transitioning from data science leadership to a CTO role. Kevin maps out multiple potential career paths, with specific guidance on which skills to develop and strategic moves to consider. Finally, Priya, a newly promoted team lead from Bangalore, seeks advice on protecting her team amid industry-wide layoffs. Kevin delivers straight talk on becoming "the franchise" – positioning your team on the company's critical path and ensuring your contributions remain visible and directly tied to revenue. Whether you're battling matrix confusion, struggling with performance reviews that capture true value, plotting your next career move, or navigating uncertain economic waters, this episode delivers actionable insights from someone who's been in the trenches. Download now to arm yourself with practical leadership strategies you can implement immediately. Because in tech leadership, the right answer almost always "depends" on your unique situation. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

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/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith  

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 real startup environments fundamentally different. This wide-ranging conversation touches on culture, risk, incentives, and why resource contention, not imagination, derails corporate innovation. Whether you lead a startup or a legacy company trying to move faster, this episode offers valuable perspective. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith The Guest: Kevin Stewart This chapter in the newsletter: https://kevingoldsmith.substack.com/p/the-myth-of-the-startup-in-a-large-5c7

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 achievements in career growth, the importance of aligning career pathing systems with company culture, and the complexities of integrating the framework with compensation. Kevin also reflects on how Spotify's technology-driven culture influenced the approach and how the company's evolution affected the longevity of the framework. Tune in to hear Kevin's thoughts on what he would do differently today and how his experiences continue to shape his approach to career pathing in leadership roles. Plus, Kevin offers advice for technology leaders who are looking to develop similar frameworks within their own organizations. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/things-we-learned-creating-technology

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 performance management. Kevin explains how the Spotify framework was carefully designed to: Emphasize team over individual contribution (reflecting Swedish vs. American cultural differences) Focus on behaviors and professional maturity rather than achievements Define spheres of impact that expand with seniority Align individual success with company success Provide flexibility in career choices He describes the careful considerations that went into creating the framework, including being conservative with the number of levels and keeping step designations private to avoid embarrassing employees. Kevin also shares personal experiences from Microsoft that influenced his approach. This episode is part of a trio on career pathing, with the next episode covering lessons learned from implementing the framework. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/spotify-technology-career-steps

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 balance of timing when implementing a career framework. Waiting too long (as Spotify did) can cause problems, but implementing too early can stifle a growing organization. He emphasizes how career pathing must align with company values, as it directly influences what behaviors get rewarded and ultimately shapes your culture. The episode covers Spotify's collaborative approach to creating its "Career Steps" framework, involving representatives from across the organization rather than simply adopting another company's model. Kevin shares their guiding principles, including the crucial shift from focusing on achievements to behaviors, supporting specialists and generalists, and defining career growth by expanding spheres of influence. Whether you're a tech leader contemplating how to structure growth paths for your team or an individual contributor wondering how career frameworks influence company culture, this episode is a must-listen. It offers valuable insights into one of the most foundational aspects of engineering leadership, insights that are relevant and beneficial for both roles. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/building-a-technical-career-path ELC Seattle meetup: https://elc.community/home/clubs/seattle-kcr/events/elc-x-airbnb-seattle-meetup-7oxyok5u0d

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 excessive pre-interview work—and offers actionable steps to reduce bias in the hiring process. If you're a tech leader, hiring manager, or aspiring executive, this episode is packed with insights on creating a fairer, more equitable hiring pipeline—without lowering the bar. Tune in to learn how intentional changes can lead to stronger, more diverse teams, benefiting your company and the industry. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/changing-hiring-practices-to-build

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 meaningful impact, and explains why prioritizing diversity isn't just the right thing to do—it’s also smart business. Tune in to hear why building an inclusive team can be a competitive advantage and get a preview of the next episode’s discussion on practical strategies for hiring a diverse tech team. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/a-diversity-challenge-tech-start

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, including collaborative exercises to identify training priorities and designing tailored development programs to support technology leaders. Discover actionable insights on fostering a strong management culture, balancing technical and managerial responsibilities, and creating effective learning experiences for teams. Whether you're an aspiring manager, an experienced leader, or part of a team looking to improve, this episode offers practical guidance and inspiration. Tune in to learn how to build a management training framework that elevates your organization! Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/building-a-management-training-curriculum

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 challenges of managing small teams, the necessity of fostering team autonomy while maintaining accountability, and the crucial role of leadership in balancing top-down constraints with bottom-up ownership. Kevin dives into the process of moving from a traditional hierarchy to a matrix organization and ultimately to journey teams. He explains how self-selection played a key role in empowering teams, fostering engagement, and driving sustainable growth in a fast-scaling company. Listeners will gain practical insights into building adaptable organizational structures tailored to company culture, evolving leadership styles, and scaling strategies for tech teams. If you’re a technology leader navigating team scaling, culture transformation, or thinking of adopting self-selection and journey teams in your organization, this episode is packed with actionable takeaways. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith This chapter in the newsletter: https://kevingoldsmith.substack.com/p/using-self-selection-to-create-journey    

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 the cultural nuances that influence its effectiveness. Kevin recounts how the model's flexibility and autonomy transformed team dynamics and how its structure has been adapted (or misapplied) by other companies. He also discusses how the U.S. workplace culture, rooted in individualism, impacted the adoption of Spotify’s collaborative team-oriented practices. The episode is filled with insights on organizational scaling, the benefits of full-stack teams, and the pivotal role of company-specific cultural alignment in applying the model. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith Interviews with Kevin (about the Spotify model and other things): https://www.kevingoldsmith.com/resume.html#interviews For your start of year planning: The Personal Strategy Off-site, Own your Calendar The newsletter issue with the text of this chapter: https://kevingoldsmith.substack.com/p/thoughts-on-emulating-spotifys-matrix The Spotify Model Whitepaper: https://blog.crisp.se/wp-content/uploads/2012/11/SpotifyScaling.pdf

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 form, dissolve, and remix based on company needs. He also addresses some common misconceptions about its application and reflects on lessons learned from the Spotify model and how to adapt its principles to other organizations. Don’t forget to subscribe to the accompanying newsletter and share your thoughts via the linked listener survey to help shape the future of the podcast! Links to things mentioned in the podcast: Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith The newsletter issue with the text of this chapter: https://kevingoldsmith.substack.com/p/the-spotify-model The Spotify Model Whitepaper: https://blog.crisp.se/wp-content/uploads/2012/11/SpotifyScaling.pdf The Spotify Model videos: https://blog.crisp.se/2014/03/27/henrikkniberg/spotify-engineering-culture-part-1 Spotify Q3 2024 Numbers (640 MAU): https://variety.com/2024/digital/news/spotify-q3-2024-earnings-premium-subscribers-1236207771/