It Depends: Lessons in Technology Leadership

Kevin Goldsmith
  • 5.0 (4)
  • Management
  • Updated Semimonthly

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

  1. May 24

    The Conversation Before the Conversation

    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. Nonviolent Communication - the book I mentioned: https://amzn.to/4tOK8kZ 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)

    22 min

  2. May 10

    The Interesting Changes Aren't Happening in the IDE

    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. 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)

    28 min

  3. Apr 26

    Becoming a Business Leader

    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. 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

  4. Apr 12

    Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest

    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. 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) "The Five Dysfunctions of a Team: A Leadership Fable" by Patrick M. Lencioni (Amazon Link)

    36 min

  5. Mar 29

    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

  6. 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

  7. 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

  8. 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
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Kevin Goldsmith brings you lessons and advice from decades in the technology industry.

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