It Depends: Lessons in Technology Leadership

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

  1. 3D AGO

    Talking to Executives: That's Not a Derailment, That's the Meeting

    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. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com)

    33 min

  2. FEB 1

    The Shift to Managing Managers

    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. Using Agile Techniques to Build a More Inclusive Team: https://www.youtube.com/watch?v=Atfxtk2Q90k Every Decision Creates a Policy: https://itdependspod.com/episodes/every-decision-creates-a-policy/ "Turn the Ship Around!: A True Story of Building Leaders by Breaking the Rules" by L. David Marquet: https://amzn.to/49XH2Ty Delegation Poker from Jurgen Appelo: https://medium.com/@jurgenappelo/unclear-team-responsibilities-use-delegation-levels-985537dbea38 Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) ConFoo 2026 (https://confoo.ca/en/2026)

    36 min

  3. JAN 18

    Leading What You've Never Done Before

    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. When, why, and how to stop coding as your day job talk: https://www.kevingoldsmith.com/talks/when-why-and-how-to-stop-coding-as-your-day-job.html Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) ConFoo 2026 (https://confoo.ca/en/2026)

    35 min

  4. JAN 4

    Success Makes You Dangerous: Why Comfortable Leaders Stop Growing

    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. The Personal Strategy Offsite episode: https://itdependspod.com/episodes/the-personal-strategy-off-site/ Own Your Calendar episode: https://itdependspod.com/episodes/own-your-calendar-work-deliberately/ Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) ConFoo 2026 (https://confoo.ca/en/2026)

    24 min

  5. 12/21/2025

    The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy

    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. Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com) ConFoo 2026 (https://confoo.ca/en/2026)

    45 min

  6. 12/07/2025

    Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders

    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. ConFoo 2026 (https://confoo.ca/en/2026) Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com)

    41 min

  7. 11/23/2025

    Demystifying Board Meetings: A CTO's Perspective

    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. ConFoo 2026 (https://confoo.ca/en/2026) Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com)

    51 min

  8. 11/09/2025

    Crafting a Technical Strategy

    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. ConFoo 2026 (https://confoo.ca/en/2026) Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net) Your host: Kevin Goldsmith (https://kevingoldsmith.com)

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

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