It Depends: Lessons in Technology Leadership
Kevin Goldsmith brings you lessons and advice from decades in the technology industry.
Episodes
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.
...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.
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 w...
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 wron...
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.
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 shou...
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.
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 ...
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.
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 e...
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 y...
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 solvi...
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.
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 orga...
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 de...
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 d...
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...
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.
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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 ...
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 fla...
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