It Depends: Lessons in Technology Leadership

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

  1. HACE 4 DÍAS

    How to Handle Career Gaps and What CTOs Actually Do All Day

    In this episode of It Depends: Lessons in Technology Leadership, Kevin returns from a summer break with a new podcast format and two big topics. First, he shares practical advice for navigating an unplanned career break—whether due to layoffs or a tough job market. From reframing “career break” on your résumé, to launching a consultancy, building a startup, or contributing to open source, Kevin outlines concrete ways to stay relevant, keep your skills sharp, and strengthen your positioning for the next opportunity. Then he pulls back the curtain on what a CTO really does all day. Drawing on his experience at mid-stage startups, Kevin explains the balance between executive responsibilities, one-on-ones, cross-functional collaboration, strategic thinking, and even the occasional coding. He highlights how priorities shift depending on company size, culture, and market, and why visibility, prioritization, and time management are crucial at the executive level.   This episode blends career survival strategies with an honest look at senior leadership—helpful both for those navigating career uncertainty and those aspiring to the CTO role. LeadDev New York (Use code KEVIN25 for 25% off registration) Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith

    47 min

  2. 31 AGO

    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, 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

    1 h y 7 min

  3. 17 AGO

    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 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

    46 min

  4. 3 AGO

    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 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

    34 min

  5. 20 JUL

    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," "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

    36 min

  6. 6 JUL

    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 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

    59 min

  7. 22 JUN

    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'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

    45 min

  8. 8 JUN

    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 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

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

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