It Depends: Lessons in Technology Leadership
by Kevin Goldsmith
Latest episode
The Role of QA When Agents Write the Tests: Why Quality Follows…
The Role of QA When Agents Write the Tests: Why Quality Follows…
About this podcast
Kevin Goldsmith serializes the audiobook for his new book, ”It Depends: Writing on Technology Leadership 2012-2022.” Sharing extra details about each chapter and answering listener questions along the way.
Episodes
The newest 20 of 75 episodes
- The Role of QA When Agents Write the Tests: Why Quality Follows Context · 23 min · Season 3 Episode 75When Kevin Goldsmith joined Microsoft, new graduates were often pushed into Software Development Engineer in Test, with the promise they could become “real” developers later…
- Leading Through a Crisis: What the Leader Does While Someone Else Fixes the Problem · 21 min · Episode 74Someone gets into a company’s systems, takes over its connection to an email vendor, and starts sending phishing emails. Everything else stops. The head of security runs the…
- Slight or Signal: Learning the Game at Work · 17 min · Season 3 Episode 73A leader is running an initiative, and at an executive meeting his boss gives three of his peers time to talk about it. He gets added at the end, almost as an afterthought. A few…
- The Outsider's Audit: Due Diligence on Your Own Org · 27 min · Season 3 Episode 72A CTO needs to hire more engineers, and the numbers are working against the argument. Engineering spend has fallen as a share of revenue because the company grew faster than the…
- Paying for Nothing to Happen: Budgeting for Security, Compliance, and Reliability · 36 min · Season 3 Episode 71A vendor the security team wanted, budgeted two years in a row, and never actually bought. When Kevin Goldsmith finally tried to spend the money, his CFO asked what the ROI was…
- The Agent Doesn't Know It's a Prototype: Team Autonomy in the Agentic Software Development Era · 32 min · Season 3 Episode 70A developer builds a working replacement for an internal platform over a weekend using AI tools, then asks leadership why they can't ship it on Tuesday. The code is clean, the…
- Build vs Buy When Building Got Cheap · 32 min · Episode 69The spreadsheet says building is cheaper now, and the spreadsheet isn't wrong. A vendor's annual license on one line, a couple of developers and some tokens on the other. What…
- ENCORE: Taking a thoughtful approach to the job search process · 27 min · Episode 68Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022 In this episode, we discuss my experience building an exercise to better understand what is important to me…
- ENCORE: Protecting Your Team From Layoffs · 25 min · Episode 67This chapter discusses what you can do as a manager to protect your team from layoffs: Ensure the team is aligned with company goals. Raising the visibility of the good work of…
- ENCORE: Creating a Vernacular With Your Engineering Team · 22 min · Episode 66Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team works together and make…
- Managing Sideways: Everyone Nodded, Then Nothing Happened. · 40 min · Episode 65A room full of managers agrees on a better way to do something. Everyone nods. Six months later, every team is still working exactly the way it did before. The idea was sound…
- The Reliable Team Trap: Why Execution Excellence Doesn't Earn You Influence · 26 min · Episode 64Some of the most valuable people in any company are those who consistently deliver. Their teams are healthy, the feedback is good, and the reward for all that reliability tends…
- The Conversation Before the Conversation · 22 min · Episode 63Most 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…
- The Interesting Changes Aren't Happening in the IDE · 28 min · Episode 62Have 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…
- Becoming a Business Leader · 30 min · Episode 61Most 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…
- Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest · 36 min · Episode 60The 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…
- Don't Let Your Boss Do Your Job · 27 min · Episode 59Your 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…
- Every Organization Is a System. Are You Designing It or Just Living in It? · 37 min · Episode 58Have 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…
- The Director to CTO Path: How to Follow It, or How to Mentor It · 41 min · Episode 57The 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…
- Talking to Executives: That's Not a Derailment, That's the Meeting · 33 min · Episode 56Have 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…
