Explore every episode of the podcast It Depends: Lessons in Technology Leadership
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Slight or Signal: Learning the Game at Work | 11 Oct 2026 | 00:16:44 | |
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. Both of them were reacting to the small part of the situation they could see. The obvious question is whether the boss meant it. The more useful one is how to read someone whose context you mostly can’t see. That starts with understanding the game, which Kevin defines as a company’s real system and culture: what actually gets rewarded, and how decisions really get made. Kevin draws on eight years at Microsoft that trained him to read every interaction as political, and a moment at Adobe when that wiring led him to badly misread his own boss. He lays out a five-step framework for telling a slight from a signal. It starts with separating what you saw from the story you told yourself, and ends with deciding whether the game is one you want to play. Along the way, he brings in logical empathy and David Foster Wallace’s idea of default settings. The episode also turns the question around. Managers create these moments for their own teams, usually through omission, and Kevin shares a time he got it wrong, and what he does now to close the loops his reports can’t see. It’s for engineering leaders who answer to a boss and have people answering to them.
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| The Outsider's Audit: Due Diligence on Your Own Org | 27 Sep 2026 | 00:26:58 | |
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 Goldsmith's advice was to stop arguing from within and examine the organization as an acquirer would. Kevin has led due diligence as an acquirer at large companies and startups, and he's been examined as a target through acquisitions and investor rounds. From both seats, the same pattern keeps showing up: the organizations that come through well are the ones whose leaders already know where the problems are and have a plan for them. The catch is that the longer a leader has been in an organization, the less its workarounds look like problems. The framework here is the Outsider's Audit, four questions anyone doing diligence will ask, turned on your own team: Worth, Dependencies, Flow, and Risk. Kevin walks through each one practically, including building spare capacity at the org level so a resignation doesn't cancel a quarter of work, tracing a single ticket to find where work actually stalls, trading audits with a peer, and handling the people side, right up to the moment the team starts wondering if the company is being sold. The episode is aimed at CTOs and VPs who may face funding or acquisition diligence someday, but the approach works just as well for a director or engineering manager who needs to make the case for their team with evidence rather than instinct.
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| Paying for Nothing to Happen: Budgeting for Security, Compliance, and Reliability | 13 Sep 2026 | 00:36:08 | |
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 him he was underinvesting in cybersecurity. Same company, same customers, same risk, completely different verdict. Every technology leader owns budgets where the best possible outcome is that nothing happens. Security, compliance, reliability, backups, disaster recovery. They're the easiest money in the company to cut and the hardest to defend, because success looks identical to having never spent the money at all. This episode is about how to decide how much to spend, and how to defend the number when finance asks. Kevin lays out four price tags that other people are already attaching to your risk: the deal price your customers set, the insurance price your insurer sets, the compliance price regulators set, and the survival price you have to estimate yourself. He compares three companies where the right answer ranged from a large security team to a fraction of one person, revisits COVID as the disaster recovery test nobody scheduled, and covers the failure modes that show up again and again, including the raided line item and the backup nobody has ever restored from. Useful for CTOs, VPs of engineering, and directors heading into a budgeting cycle who need a defensible number rather than a benchmark, and for anyone who has been told in the same year that they're spending too much and not enough.
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| The Agent Doesn't Know It's a Prototype: Team Autonomy in the Agentic Software Development Era | 30 Aug 2026 | 00:32:25 | |
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-powered development speed outpaces the organizational guardrails that once kept teams aligned. This episode explores the tension between team autonomy and organizational coherence in an era when building software has become dramatically faster, but deciding what to build has not. Kevin draws on Spotify's aligned autonomy model, his own experience watching founder-speed culture collide with a growing engineering team, and a practical framework he calls the Blast Radius Test: three questions that help teams determine whether a decision is theirs to make or requires a wider conversation. The episode also tackles the blurring line between prototypes and MVPs. When an AI agent produces a prototype with clean architecture, test coverage, and error handling, the output can look identical to a first production implementation. Kevin makes the case that the distinction now has to come from intent and organizational readiness rather than code quality, and shares a story about handing a team his own prototype only to watch them spend weeks trying to ship his throwaway code. This is for engineering leaders trying to figure out how to give teams room to move fast without losing organizational coherence.
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| Build vs Buy When Building Got Cheap | 16 Aug 2026 | 00:32:24 | |
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. Kevin has spent most of his career firmly on the buy side, with a mantra he gave his teams for years: don't invent things that already exist. This episode is him revising that position rather than abandoning it, and being specific about how much smaller the revision is than the enthusiasm in the industry suggests. He walks through a four-question test to run before agreeing to build something that already exists, covering blast radius, ownership cost, differentiation, and whether there's an exit path. Along the way: where building genuinely does make sense now, where it still doesn't regardless of how cheap it has become, the license cost trap that catches CFOs, why supply chain risk has started cutting in both directions, and the version of this decision that shows up in headcount instead of software. Two stories anchor it: an auth decision that gave back every dollar it saved and came within about a month of being much worse, and a build made deliberately with an exit already planned.
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| ENCORE: Taking a thoughtful approach to the job search process | 02 Aug 2026 | 00:27:12 | |
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 mistakes people make when interviewing for roles during a downturn, particularly in how they present themselves. If you're currently looking for a job, or think you will in the future (we all will), this episode will be helpful. Some links:
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| ENCORE: Protecting Your Team From Layoffs | 19 Jul 2026 | 00:25:24 | |
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 on your team should be laid off. This episode provides more information for individuals and explains that managers are judged more by their team's work and less by their own contributions. Links:
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| ENCORE: Creating a Vernacular With Your Engineering Team | 05 Jul 2026 | 00:21:39 | |
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:
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| Managing Sideways: Everyone Nodded, Then Nothing Happened. | 21 Jun 2026 | 00:39:41 | |
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't manage and can't order around. Kevin Goldsmith calls it managing sideways, and it runs on influence without authority, one of the most useful leadership skills and one of the hardest to build. He works through why the two obvious moves, forcing it yourself or getting an executive to force it for you, tend to produce shallow and short-lived compliance, and why being right turns out to be the cheap part of the problem. The center of the episode is a four-move approach Kevin calls Adoption Without a Mandate: start with the team that already wants the change, frame it as removing their work rather than adding to it, let the first team's results pull in the next one, and settle ownership before the thing scales. He grounds it in two of his own projects, a company-wide career framework he built at Spotify by assembling a coalition, and an early effort at Adobe, where he forced a team to comply and was still paying for it long after the project shipped. It's a practical episode for engineering leaders at any level who keep hitting the same wall, where everyone agrees on the right thing, and still no one does it. Kevin closes with a short exercise that listeners can run this week on whatever cross-team change they've been pushing.
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| The Reliable Team Trap: Why Execution Excellence Doesn't Earn You Influence | 07 Jun 2026 | 00:26:00 | |
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, the point where being trusted to execute quietly stops translating into being trusted to decide. Kevin works through why it happens, drawing on seven years he once spent running a project that kept succeeding without ever advancing his own career, plus two leaders he currently mentors whose situations played out very differently. The throughline is uncomfortable: if you are not setting the direction for your part of the organization, someone above you is, which means leadership hears their framing of your work instead of yours. That, he argues, is the real difference between running an organization and leading one. From there, he lays out four moves to close the gap between being measured on output and being measured on judgment: show the thinking, build the bench, claim the contribution, and take a position. Three of them are about visibility, and one is about capacity, and he is direct about why you need both, and why working even harder is the one response that reliably makes the trap worse. It is aimed at engineering managers, directors, and senior leaders who deliver well and keep wondering why the direction-setting conversations seem to happen without them. Reliability is the floor. This episode is about making sure it does not become the ceiling.
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| The Conversation Before the Conversation | 24 May 2026 | 00:22:18 | |
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 that they kept postponing until they weren't easy anymore. This episode makes the case for the earlier, smaller, cheaper version of every difficult conversation, the one most leaders talk themselves out of by insisting they don't have enough information yet. Kevin draws on two of his own misses, including a senior engineer at Adobe, whom he lost because he avoided a confrontation with other developers on the team, and a prioritization conflict at his first CTO job, which he let run until the CEO noticed and got involved. At the center is a practical test: five signals that tell you a conversation is already overdue. Pattern, distance, workarounds, cognitive load, and inflation. If two or more are present, the decision to speak up has already been made, and the only thing left to negotiate is how expensive the wait becomes. It's a short episode with a single, useful idea for anyone who manages people and has caught themselves waiting for the right moment that never quite arrives.
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| The Interesting Changes Aren't Happening in the IDE | 10 May 2026 | 00:27:48 | |
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 episode, Kevin gets off the fence about a topic he has been deliberately avoiding. He walks through how his thinking about AI in engineering organizations has evolved over the last two years, and introduces a four-layer model for understanding where AI adoption actually breaks down: tooling, process, structure, and judgment. Most companies are working at layer one and quietly ignoring the rest. Kevin also breaks down the four types of people you will encounter on your team during this transition (eager adopters, skeptics, the quietly worried, and the early adopters who fell behind), the new and growing problem of CEOs handing engineering teams "finished" AI prototypes and expecting them to ship, and why the leadership skill we need most right now is judgment about output quality, which nobody is hiring for yet. If you are an engineering leader trying to figure out where to put your energy, this episode will help you stop solving tooling problems with more tools and start identifying the layer where your real work actually lives.
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| Becoming a Business Leader | 26 Apr 2026 | 00:30:22 | |
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 shift that CTOs, VPs, and directors need to make to actually lead at the executive level, and why the skills that got them there are the ones they have to partially unlearn. He shares a framework he calls the four moves of business fluency (translate, trade off, commit, compound) and the four contexts where technical leaders either build this skill or fail to: P&L, sales and customer work, fundraising and investor relations, and strategy. This one is for senior engineering leaders eyeing an executive seat, current CTOs who want to stop being read as specialists at their own exec table, and anyone whose career has started to feel capped despite shipping well.
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| Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest | 12 Apr 2026 | 00:36:06 | |
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 you disagree. Most people get at least one of those wrong. This episode lays out a framework for building CEO trust around four foundations: competence, candor, commitment, and context. It also gets into the different types of CEOs you'll encounter, from founder-developers who still have strong technical opinions to operators who are completely hands-off on tech, and why your approach has to change depending on which one you're working with. There's also an honest look at what happens when the relationship starts to erode, how to spot the warning signs on both sides, and when repairing it is worth the effort versus when it's time to go.
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| Don't Let Your Boss Do Your Job | 29 Mar 2026 | 00:26:32 | |
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 keep checking in. Kevin introduces the Ownership Triangle (Signal, Route, Verify), a simple loop that works at every level from engineering manager to CTO. He talks about the lesson his CEO taught him at his first CTO job about catching problems before they escalate, the difference between ownership and accountability, and why "I was planning to handle it" doesn't count if you never said so out loud. He also gets honest about a trap he still falls into: being too busy to delegate the things he's too busy to do himself.
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| Every Organization Is a System. Are You Designing It or Just Living in It? | 15 Mar 2026 | 00:37:08 | |
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 long time ago: actually teach how to develop systems thinking. He's talked about its importance plenty of times on the show, but he realized he'd never given people a practical path to build the skill. So he lays out a four-stage progression, from learning to see the system around you, to mapping it, to understanding how it constrains and enables your teams, to intervening with awareness of cascading effects. Kevin shares a story about a time he built the right system but failed to communicate it to his peers, and what that cost him. He also talks about how AI is making systems thinking more urgent, because speeding up one part of your process without understanding the whole system just creates new bottlenecks. Whether you're a new manager trying to think more strategically or a senior leader who wants to get better at teaching this skill to others, this episode gives you concrete exercises you can try this week.
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| The Director to CTO Path: How to Follow It, or How to Mentor It | 01 Mar 2026 | 00:41:15 | |
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 broad generalist. In this episode, Kevin maps out what that progression actually looks like at each level, drawing on his own career through Adobe, Spotify, and multiple startups. He shares practical ways to develop the skills you need before you need them, from taking finance people to lunch and shadowing unfamiliar teams, to aligning your team's work with company strategy, even when the company is moving in a direction you didn't expect. Kevin also covers the mentoring side. If you're already a VP or CTO, how do you identify high-potential leaders and intentionally develop them? He talks about delegation, transparency, and giving feedback that's aimed at the next level, not just the current one. Whether you're a director trying to figure out what VP-level thinking actually looks like, or a CTO thinking about how to grow the leaders behind you, this episode gives you a concrete framework for both.
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| Talking to Executives: That's Not a Derailment, That's the Meeting | 15 Feb 2026 | 00:33:19 | |
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 learned the hard way that being right doesn't matter if you're not being understood (a Microsoft VP made sure he never forgot that lesson). Now, as a CTO, he watches people make the same mistakes he did. Kevin shares a practical framework for communicating to executives: the Four C's of Clarity, Context, Consequence, and Control. He also talks about why executives interrupt, why they sometimes just get up and leave, and why protecting your credibility matters more than protecting your ego. Whether you're presenting to senior leaders for the first time or trying to get better at it, this episode will help you walk in with more confidence and a better understanding of what's actually going on in the room.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| Demystifying Board Meetings: A CTO's Perspective | 23 Nov 2025 | 00:50:52 | |
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 explains the board’s role as the company’s oversight body and why each quarterly meeting functions like a performance review for the entire organization. Kevin covers how boards think about risk, strategy, financial performance, and leadership effectiveness, and why these dynamics can shift depending on the company’s stage, the board's composition, and the CEO’s style. He also explains the CTO’s role at the table, how technical topics are translated into business terms, why preparation is critical, and what junior employees often misunderstand about how decisions actually get made. If you’ve ever wondered what happens in those closed-door sessions—or you’re aiming for an executive role in the future—this episode gives you a clear and practical view of how board meetings work and why they matter.
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| Crafting a Technical Strategy | 09 Nov 2025 | 00:29:39 | |
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 simply having a plan in your head isn’t enough: a strategy must be documented, shared, and revisited regularly if it’s going to guide meaningful decisions. Kevin outlines practical steps for building an effective strategy, including identifying business-aligned guiding principles, defining realistic technical bets, validating them with peers, and ensuring that every level of the organization maintains alignment. He also explores common pitfalls, including confusing strategy with a roadmap, making it too vague or too prescriptive, or failing to communicate it. He describes how a well-articulated strategy makes decisions easier, reduces friction, and gives teams greater autonomy and purpose. It’s a clear, grounded guide for any engineering leader preparing for the new year, whether you’re a CTO shaping company direction or an EM ensuring your team’s work supports broader goals.
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| Making Technology Choices That Last | 26 Oct 2025 | 00:42:19 | |
Avoiding shiny object syndrome, encouraging curiosity, and building a system for smart adoption
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 mobile, cloud, or Web3. In this episode, Kevin Goldsmith reflects on how leaders can navigate emerging technologies without falling for the hype. Drawing from decades of experience adopting everything from public cloud to AI tooling, he shares how to evaluate what’s worth your team’s attention and when to wait. Kevin outlines a practical framework for making technology decisions that stick: discover → experiment → evaluate → adopt deliberately. He also explores how to guide both the eager early adopters and the skeptical veterans on your team, turning curiosity into a disciplined system for learning and innovation.
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| The Hidden Architecture of Engineering: Practical Lessons in Organizational Design | 12 Oct 2025 | 00:47:01 | |
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 evolve your organization with intent. From mapping the flow of work to understanding team topologies, this is a grounded guide to designing organizations that actually work.
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| Values → Culture → Everything: Why Company Culture Actually Matters | 28 Sep 2025 | 01:04:24 | |
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 everything from hiring decisions to performance reviews. What you'll learn:
Drawing from his experiences at Microsoft, Adobe, and Spotify, Kevin shares both successes and failures in culture building, including why he stayed at some companies for years and left others. He offers practical frameworks for managers building strong team cultures and individuals seeking workplaces aligned with their values. Whether you're a team lead trying to strengthen your engineering culture, an individual contributor evaluating your current role, or someone interviewing for new positions, this episode provides actionable insights for understanding and navigating the often-invisible forces that shape our daily work experience.
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| 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.
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| 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.
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| 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.
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| 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:
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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.
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| 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!
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| 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.
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| 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.
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| 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:
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| 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:
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