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

    Don't Let Your Boss Do Your Job

    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. 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) Team of Teams: New Rules of Engagement for a Complex World, General Stanley McChrystal (Amazon Link)

    27 min

  2. MAR 15

    Every Organization Is a System. Are You Designing It or Just Living in It?

    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. 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) Thinking in Systems: A Primer, Donella H. Meadows (Amazon Link) Management 3.0: Leading Agile Developers, Developing Agile Leaders, Jurgen Appelo (Amazon Link)

    37 min

  3. MAR 1

    The Director to CTO Path: How to Follow It, or How to Mentor It

    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. 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

  4. FEB 15

    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

  5. 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

  6. 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

  7. 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

  8. 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
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4 Ratings

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

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