75 episodes of lessons and advice from decades in the technology industry.
When Kevin Goldsmith joined Microsoft, new graduates were often pushed into Software Development Engineer in Test, with the promise they could become “real” developers later. Decades later, a startup leader he mentors is asking a version of the same question about a senior manual tester...
Someone gets into a company’s systems, takes over its connection to an email vendor, and starts sending phishing emails. Everything else stops. The head of security runs the response, which is exactly right. The CTO’s job turns out to be something different, and Kevin Goldsmith argues i...
A leader is running an initiative, and at an executive meeting his boss gives three of his peers time to talk about it. He gets added at the end, almost as an afterthought. A few days later, Kevin Goldsmith had his own version: a meeting he’d contributed slides to went ahead without him...
A CTO needs to hire more engineers, and the numbers are working against the argument. Engineering spend has fallen as a share of revenue because the company grew faster than the team, so on paper it looks like efficiency. In practice, one resignation could sink the roadmap. Kevin Goldsm...
A vendor the security team wanted, budgeted two years in a row, and never actually bought. When Kevin Goldsmith finally tried to spend the money, his CFO asked what the ROI was, and he didn't have an answer good enough to win the argument. Not long after, a new board arrived and told hi...
A developer builds a working replacement for an internal platform over a weekend using AI tools, then asks leadership why they can't ship it on Tuesday. The code is clean, the architecture is real, and the team is confused about the holdup. Kevin Goldsmith explores what happens when AI-...
The spreadsheet says building is cheaper now, and the spreadsheet isn't wrong. A vendor's annual license on one line, a couple of developers and some tokens on the other. What that comparison leaves out is that building has always had two costs, and AI only made one of them smaller.
...Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022
In this episode, we discuss my experience building an exercise to better understand what is important to me in a role or company, and how I used the results to prepare for job interviews. I also discuss some of the mista...
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 deciding whether anyone...
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 make onboarding new members easier.
Links:
A room full of managers agrees on a better way to do something. Everyone nods. Six months later, every team is still working exactly the way it did before. The idea was sound. Nobody had to change, so nobody did.
That gap is the subject of this episode: driving change across teams you don'...
Some of the most valuable people in any company are those who consistently deliver. Their teams are healthy, the feedback is good, and the reward for all that reliability tends to be the same thing every time: more work, rarely more authority. Kevin Goldsmith calls this the reliable team trap, th...
Most leadership advice is about how to have a hard conversation. Far less of it is about when. In this episode, Kevin Goldsmith argues that the when is usually where things break, and that the conversations leaders end up regretting are rarely the difficult ones they had. They're the easy ones th...
Have you noticed that every conversation in tech leadership now circles back to AI, and that none of those conversations actually feel resolved? That's because AI adoption is not a tooling problem. It is an organizational redesign happening in real time, whether you lead it or not.
In this...
Most technical leaders assume the path to executive is paved with more technical excellence. It isn't. At a certain level, the ceiling stops being technical and starts being about business fluency, and that ceiling is invisible until you've hit it.
In this episode, Kevin walks through the...
The CTO-to-CEO relationship is the highest leverage relationship in your career as a technology leader, and it's the one where getting the balance wrong has the biggest blast radius. You need to be close enough to influence, independent enough to be honest, and aligned enough to execute even when...
Your boss doesn't step into your area because they want to micromanage. They step in because nobody said "I got it," and silence looks the same as not paying attention. This episode is about the ownership behavior that separates leaders who are trusted to run their area from leaders whose bosses...
Have you ever felt like you're solving the same problems over and over, just in different forms? That's usually a sign you're working transactionally, fixing what surfaces instead of addressing the structures underneath.
In this episode, Kevin tries to do something he should have done a lo...
The path from Director to CTO isn't a single ladder. It's a gradual expansion across three dimensions: your focus widens from your team to the company to the industry, your orientation shifts from execution to operations to strategy, and your technical breadth grows from narrow specialist to broa...
Have you ever had an executive interrupt your presentation and completely take the conversation somewhere you weren't expecting? That's not a derailment. That's the meeting.
In this episode, Kevin talks about executive communication from both sides of the table. Early in his career, he lea...
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.
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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.
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Most technology leaders start out managing what they already know, then suddenly find themselves responsible for domains...
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...
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 inherentl...
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 ta...
In this episode, Kevin breaks down what really happens inside a company board meeting: why they exist, what gets discussed, and why they carry so much weight for an executive team. Drawing from a decade of attending and presenting in boardrooms across startups and later-stage companies, he explai...
In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith breaks down what it really means to craft a technical strategy that aligns your engineering organization with business goals. Drawing on decades of experience as a technology leader and CTO, he explains why...
Avoiding shiny object syndrome, encouraging curiosity, and building a system for smart adoption
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Every few years, a new wave of technology arrives promising to change everything. Right now, it’s generative AI, but it wasn’t long ago that we were saying the same thing about...
In this episode, Kevin digs into the often-ignored side of engineering leadership: organizational design. He explores how structure shapes communication, culture, and even software architecture. Conway’s Law still applies. Kevin shares practical ways to diagnose bottlenecks, refactor teams, and e...
Kevin Goldsmith revisits his influential 2013 keynote on engineering culture, expanding the conversation beyond just engineering teams to address anyone navigating workplace dynamics. This episode breaks down the real mechanics of how organizational values create culture, and how culture shapes e...
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...
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 “KEVI...
This is a repeat of an episode originally released on March 2, 2025
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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...
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 communi...
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," "Be...
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.
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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?
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 w...
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 t...
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 accountabil...
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-awarenes...
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 pat...
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 p...
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 ser...
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 r...
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 enginee...
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 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...
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 j...
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 d...
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, i...
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 Excel...
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...
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...
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 lea...
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 Leader...
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 o...
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 gu...
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...
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 c...
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 2012-2...
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,...
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 pitfall...
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 any...
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...
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.
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Links:
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," "Be...
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:
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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 informa...
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: W...
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 epis...
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...
How can top-down culture change be effective? Looking at Microsoft and Yahoo as examples.
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Links:
It Depends book: https://itdependsbook.net
Questions/comments: contact@itdependsbook.ne...
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:
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.
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Links:
Book info https://itdependsbook.net/
Blo...