Explore every episode of the podcast It Depends: Lessons in Technology Leadership
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Writing Useful Performance Reviews: Assembling the data | 01 Sep 2024 | 00:26:22 | |
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 development. Tune in to transform how you approach performance reviews, making them a powerful tool for leadership and growth. Whether you're a seasoned manager or a new leader, this podcast promises valuable lessons in nurturing talent effectively. Links to things mentioned in the podcast:
| |||
| Twenty Questions For Your One-on-Ones | 18 Aug 2024 | 00:23:24 | |
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 conversation. He emphasizes the need for consistency in holding one-on-ones, particularly in remote work settings, and discusses how these meetings are crucial for building trust and ensuring that employees feel valued. This episode is a must-listen for managers looking to enhance their leadership skills and foster better communication with their teams. Links to things mentioned in the podcast:
| |||
| How I Get My Focused Work Done / The Known Unknowns | 14 Apr 2024 | 00:23:36 | |
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://itdependsbook.net/ Questions/Comments/Suggestions contact@itdependsbook.net
| |||
| Own Your Calendar / Work Deliberately | 31 Mar 2024 | 00:27:12 | |
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 book: https://itdependsbook.net/ Ask a question or request a signed copy: contact@itdependsbook.net The newsletter: https://kevingoldsmith.substack.com/ | |||
| The Personal Strategy Off-site | 17 Mar 2024 | 00:22:31 | |
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: Writing on Technology Leadership 2012-2022" by Kevin Goldsmith. It Depends Book website: https://itdependsbook.net/ CTO Podcast link: https://pod.link/1356275803/episode/7a88eac00279eb4bd3172b9a59d21ab7 Jason Cavness Experience Podcast Link: https://www.youtube.com/watch?v=aoUR0bj9BGQ&list=PLh4aquRHsHCZfVVGNO7IY9-5Z0IF8XgwZ Have a question you'd like me to answer? Send it to: contact@itdependsbook.net Buy the book on Amazon or bookshop.org | |||
| When, why, and how to stop coding as your day job | 03 Mar 2024 | 00:26:48 | |
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 is all about that. I include Chapter 4 of the audiobook for It Depends: Writing on Technology Leadership 2012-2022, which is all about this step in your development as a more senior engineering leader. Links:
| |||
| Taking a thoughtful approach to the job search process | 18 Feb 2024 | 00:26:52 | |
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 the mistakes people make when interviewing for roles in a downturn with how they present themselves in job interviews. If you're currently looking for a job, or thing you will in the future (we all will), this episode will be helpful. Some links:
| |||
| The challenge of top-down change and the Microsoft layoffs | 04 Feb 2024 | 00:20:58 | |
How can top-down culture change be effective? Looking at Microsoft and Yahoo as examples.
Links: It Depends book: https://itdependsbook.net Questions/comments: contact@itdependsbook.net | |||
| Fail Safe, Fail Smart... Succeed! | 21 Jan 2024 | 00:57:10 | |
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... links:
| |||
| Introduction | 08 Jan 2024 | 00:08:18 | |
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/
| |||
| Addressing the challenges of partially distributed engineering teams | 04 Aug 2024 | 00:33:05 | |
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:
| |||
| A Resignation Can Be an Opportunity | 21 Jul 2024 | 00:30:39 | |
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," Kevin delves into how a resignation can actually present a unique opportunity for growth and improvement within a team.
Kevin discusses the emotional and professional impacts of resignations, the pitfalls of unhealthy retention, and the importance of fostering a dynamic team environment. He shares anecdotes from his career, including experiences at Adobe and Spotify, highlighting how to handle resignations constructively and turn them into opportunities for positive change.
Listen in to learn how to transform the challenge of losing a team member into a strategic advantage, improve your management skills, and create a more resilient and innovative team. | |||
| What do I look for when hiring an engineer? | 07 Jul 2024 | 00:33:53 | |
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 more context and behind-the-scenes stories.
This week, Kevin revisits a chapter from 2013: What Do I Look for When Hiring an Engineer? Tune in as he discusses the evolution of hiring practices in the tech industry, shares personal anecdotes from his days at Microsoft, and provides valuable advice on navigating the ever-changing landscape of job interviews. Links:
| |||
| Every Decision Creates a Policy | 23 Jun 2024 | 00:30:44 | |
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 and their long-term effects on company culture and consistency. Kevin shares his extensive experience to illustrate how seemingly simple approvals can set precedents, inadvertently shaping future policies. He explains scenarios where inconsistent decisions led to perceived favoritism and ultimately necessitated the imposition of strict, rigid policies that curtailed previously enjoyed freedoms. The episode emphasizes the importance of consistency and transparency in managerial decisions to maintain trust and morale within the team. Listeners will gain insights into the nuanced impact of their decisions and learn practical strategies for aligning individual managerial actions with broader organizational values. This episode is crucial for managers, leaders, and anyone interested in understanding the ripple effects of their choices in a corporate environment.
Links:
| |||
| Protecting Your Team From Layoffs | 09 Jun 2024 | 00:29:05 | |
This chapter discusses what you can do as a manager to protect your team from layoffs: Ensure the team is aligned with company goals. Raising the visibility of the good work of the individuals on the team. Managing performance. All of these things will help when someone is trying to decide if anyone from your team should be laid off. This episode adds more information for individuals and talks about how managers are judged more by the work of their team and less by their own individual contributions. Links:
| |||
| The P Word (Politics at work) | 26 May 2024 | 00:29:20 | |
Politics! The word has such a negative connotation when discussing work and corporate culture. Political tactics or maneuvers aren't inherently bad. It is the intent behind them that makes them so. You can leverage those same tactics for good instead of evil. 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.
Links:
| |||
| Creating a Vernacular With Your Engineering Team | 12 May 2024 | 00:21:20 | |
Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team works together and to make it easier when onboarding new members.
Links:
| |||
| Becoming a CTO | 28 Apr 2024 | 00:34:22 | |
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. More information about the book is at itdependsbook.net Questions/comments? contact@itdependsbook.net The newsletter: kevingoldsmith.substack.com Your Host: Kevin Goldsmith | |||
| Building a Management Training Curriculum at Avvo | 19 Jan 2025 | 00:29:58 | |
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!
| |||
| Using Self-Selection to Create Journey Teams at Avvo | 05 Jan 2025 | 00:47:43 | |
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.
| |||
| Thoughts on emulating Spotify’s matrix organization in other companies | 22 Dec 2024 | 00:44:06 | |
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.
| |||
| The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative | 08 Dec 2024 | 00:30:22 | |
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:
| |||
| Transcript of my speech from OPEX Week Summer 2018 | 24 Nov 2024 | 00:24:23 | |
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 speaking at OpEx conferences and collaborating with leaders in industries where quality is critical, such as manufacturing and hardware. He highlights the contrasts between OpEx's failure-averse approach and Agile's embrace of learning through small, manageable failures. Through engaging anecdotes and lessons learned, Kevin emphasizes stepping outside your comfort zone to engage with professionals in different fields. This episode offers valuable insights for leaders in technology and beyond. It explores how diverse perspectives can challenge assumptions and foster growth. Tune in to learn how principles of operational excellence can complement tech leadership while avoiding the pitfalls of over-applying rigid frameworks. 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:
| |||
| Hiring Agile Coaches | 10 Nov 2024 | 00:35:14 | |
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 boost productivity and collaboration, although sometimes misunderstood. He also explores the current state of Agile and muses on what might come next for the industry. Tune in to learn about the nuances of agile coaching, the evolution of Agile, and strategies for demonstrating the value of agile practices beyond the engineering team. Links to things mentioned in the podcast:
| |||
| Management and Systems Thinking | 27 Oct 2024 | 00:30:50 | |
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 challenges of fostering alignment across teams with different goals. Whether you're a seasoned leader or just stepping into management, this episode is packed with actionable advice to help you cultivate high-performing teams. 🌱
Links to things mentioned in the podcast:
| |||
| Writing Useful Performance Reviews: Delivering the Review | 13 Oct 2024 | 00:37:21 | |
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-evaluation and growth, including the importance of building a personal advisory board and seeking feedback from direct reports. Tune in to gain valuable insights into navigating performance reviews at all levels of leadership. Links to things mentioned in the podcast: | |||
| Writing Useful Performance Reviews: Making a Raise Recommendation | 29 Sep 2024 | 00:38:41 | |
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 processes behind salary budgeting and recommendations. He shares insights on how companies allocate salary budgets, manage compensation, and the importance of understanding cross-functional dynamics for CTOs and tech leaders. This episode is part three of a four-part series on writing performance reviews. It is essential listening for managers, leaders, and anyone navigating the complexities of pay raises and team performance in a corporate setting. Listeners will also gain valuable advice on preparing for job interviews, understanding the broader aspects of company leadership, and Kevin's reflections on alternative compensation systems like those used by GitLab and Buffer. Whether you're an aspiring leader or a seasoned CTO, this episode offers a unique perspective on a crucial aspect of leadership that is often left unexplored. Tune in for actionable insights, real-world examples, and practical advice for anyone involved in making raise recommendations or leading a technology organization. Links to things mentioned in the podcast: | |||
| Writing Useful Performance Reviews: Evaluating the data and writing the review | 15 Sep 2024 | 00:34:34 | |
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 series on performance reviews, focuses on how to take the data you've gathered and craft meaningful, actionable feedback for your team. Kevin also reflects on his personal experiences with both successful and flawed review systems, offering advice on how to navigate various company processes. Whether you're a new manager or a seasoned executive, this episode is packed with practical advice and cautionary tales to help you master the review process. Links to things mentioned in the podcast:
| |||
| A diversity challenge: tech start-ups have a great opportunity | 02 Feb 2025 | 00:21:17 | |
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.
| |||
| Changing Hiring Practices to Build a More Diverse Technology Organization | 16 Feb 2025 | 00:36:17 | |
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.
| |||
| The Shift to Managing Managers | 01 Feb 2026 | 00:35:50 | |
Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition, where staying too close to the work actually limited both his team's growth and his own. The core challenge isn't autonomy versus control. It's leverage versus comfort. When you focus too far down into your organization, you become an information bottleneck, your managers lose ownership, and your own leadership growth stalls. The job fundamentally changes: your leverage no longer comes from making decisions, but from providing context. Kevin covers the warning signs of overmanaging (managers escalating decisions that clearly belong to them, work slowing when you're unavailable), practical frameworks for delegating effectively, and why feeling indispensable is usually a red flag, not a success metric. A key test: Could you step away for two weeks? Would your managers make good decisions without you? If not, you might be the problem.
| |||
| Leading What You've Never Done Before | 18 Jan 2026 | 00:35:27 | |
Leading What You’ve Never Done Before is an episode about a leadership challenge almost everyone hits as they grow: your scope expands faster than your resume.
Most technology leaders start out managing what they already know, then suddenly find themselves responsible for domains they’ve never personally practiced. That can feel exposing, especially if you built your credibility as “the expert.” In this episode, Kevin breaks down why trying to become the expert in every new area is a trap, why ignoring unfamiliar teams is even worse, and what effective leadership looks like when you can’t rely on depth.
You’ll learn how to lead through intent, constraints, interfaces, and feedback loops, how to evaluate how decisions are made, not just what decisions were made, and how to stay accountable without becoming a bottleneck. Kevin also shares practical questions you can use in any domain, plus guidance on building trust with specialists, creating space for disagreement, and designing systems that consistently produce good outcomes.
If your responsibilities are growing into areas you’ve never owned before, this episode will help you lead them with confidence, and without pretending to be the smartest person in the room.
| |||
| How to Handle Career Gaps and What CTOs Actually Do All Day | 14 Sep 2025 | 00:46:56 | |
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.
| |||
| ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart | 31 Aug 2025 | 01:06:55 | |
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.
| |||
| ENCORE: Building a technical career path at Spotify | 17 Aug 2025 | 00:45:38 | |
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.
| |||
| ENCORE: Addressing the challenges of partially distributed engineering teams | 03 Aug 2025 | 00:34:15 | |
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:
| |||
| ENCORE: Becoming a CTO | 20 Jul 2025 | 00:36:01 | |
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.
| |||
| ENCORE: Fail Safe, Fail Smart... Succeed! | 06 Jul 2025 | 00:58:51 | |
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.
| |||
| Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business | 22 Jun 2025 | 00:45:12 | |
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:
Perfect for:
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. | |||
| Answers That Depend: Tech Leadership Q&A Part 3 | 08 Jun 2025 | 00:42:02 | |
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.
| |||
| Answers that Depend: Tech Leadership Q & A pt 2 | 25 May 2025 | 00:42:48 | |
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.
| |||
| Answers That Depend: Tech Leadership Q&A Part 1 | 11 May 2025 | 00:37:46 | |
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.
| |||
| Success Makes You Dangerous: Why Comfortable Leaders Stop Growing | 04 Jan 2026 | 00:24:20 | |
In this episode, Kevin tackles a paradox that most leaders don't see coming: the moment you get comfortable in your role is often the moment you stop improving. Drawing on his decade as a CTO, he explains why success and experience can become dangerous if you're not deliberately reflecting on how you work, why you make the choices you make, and where your blind spots might be hiding. Kevin breaks down why reflection isn't optional for senior leaders. At the C-level, you don't get much feedback or development; you're expected to figure it out yourself. Your peer group shrinks. The job gets easier because you've seen these problems before. And that comfort is exactly when autopilot kicks in, when you stop asking "why," and when you risk becoming less effective for the people who depend on you. The episode covers Kevin's personal reflection system: a twice-yearly strategic offsite, quarterly goal-setting, monthly calendar reviews, and weekly time-tracking. But he emphasizes you don't need to copy his process; you need to find what works for you and evolve it over time. He shares practical advice on starting small, making time when you feel too busy, and why the practice matters more than perfection. Reflection isn't about having it all figured out; it's about staying deliberate, adaptive, and intentional as a leader. Whether you're a new manager learning to step back from the work, a senior leader feeling too comfortable, or anywhere in between, this episode makes the case that you can't lead others to grow if you've stopped growing yourself.
| |||
| Succession for Scale | 27 Apr 2025 | 00:25:48 | |
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.
| |||
| The Myth of the Startup in a Large Company with Kevin Stewart | 13 Apr 2025 | 01:05:45 | |
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.
| |||
| Lessons From Creating The Spotify Technology Career Steps | 30 Mar 2025 | 00:44:42 | |
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.
| |||
| Spotify Technology Career Steps | 16 Mar 2025 | 00:50:40 | |
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:
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.
| |||
| Building a technical career path at Spotify | 02 Mar 2025 | 00:44:29 | |
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.
| |||
| The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy | 21 Dec 2025 | 00:44:38 | |
In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith tackles one of the most contentious topics in growing companies: process. Drawing on decades of leadership experience from IBM and Microsoft to Spotify and Adobe, he explores why process is neither inherently good nor bad; it's a tool that must fit the problem you're solving. Kevin introduces a practical framework for deciding when to add process and when you have too much. He explains how to identify the coordination problems you're actually trying to solve and find the lightest-weight solution, rather than copying what works at Google or Amazon. The episode covers the warning signs of too little process (chaos, rework, unclear accountability) versus too much (bottlenecks, loss of autonomy, slow decisions), and why the size and culture of your organization fundamentally changes what works. Through real examples from his career, Kevin addresses common scenarios leaders face: the scrappy startup founder who resists process until the org becomes dysfunctional, the experienced big-company hire who imports heavy processes that crush a smaller team, and the risk-averse leader who adds gates after every incident. He explains the critical difference between enabling process (which helps teams move faster with confidence) and controlling process (which centralizes decisions and kills speed), and why involving your teams in process design dramatically increases adoption. Whether you're an engineering leader wondering if you're choking your team, a founder trying to scale without losing your speed, or a manager navigating the tension between autonomy and coordination, this episode gives you a strategic lens for making better decisions about when and how to add process, and when to remove it.
| |||
| Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders | 07 Dec 2025 | 00:41:15 | |
In this episode, Kevin tackles one of the most misunderstood topics in software development: technical debt. Drawing on his experience at Microsoft, Spotify, and early-stage startups, he challenges the common assumption that all technical debt is bad, explaining why healthy teams intentionally take on debt as part of shipping software effectively. Kevin introduces a practical four-part framework for understanding technical debt: pragmatic debt (taken on deliberately to validate ideas or meet constraints), required debt (that directly impacts reliability, security, or delivery capability), incidental debt (stable, low-risk code that's safe to ignore), and symptomatic debt (a signal of deeper organizational problems that code fixes won't solve). He explains how to identify each type and, more importantly, how to decide what deserves your team's attention and what doesn't. The episode explores why teams often struggle to get product support for addressing technical debt, how to tie debt decisions to business outcomes, and why some debt is actually a symptom of broken systems rather than poor engineering choices. Kevin shares real examples from his own career, including inheriting a monolith that had outlived its usefulness and intentionally taking on debt at Spotify to learn faster. Whether you're an engineering leader trying to prioritize what debt to fix, a product manager wondering why engineers keep talking about refactoring, or an executive trying to understand which debt threatens business outcomes, this episode provides a strategic lens for making better decisions about the inevitable trade-offs in software development.
| |||