It Depends: Lessons in Technology Leadership
Kevin Goldsmith
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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…
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.…
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,…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
Making Technology Choices That Last
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…
The Hidden Architecture of Engineering: Practical Lessons in Organizational Design
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.…
S2E46 Values → Culture → Everything: Why Company Culture Actually Matters
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…
How to Handle Career Gaps and What CTOs Actually Do All Day
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…
ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart
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.…
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It Depends: Lessons in Technology Leadership has published 63 episodes since January 2024, covering topics in Business, Education.
It Depends: Lessons in Technology Leadership is currently highly active with new episodes every 2 weeks. Average episode length is 36m.
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