It Depends: Lessons in Technology Leadership

Hosted by Kevin Goldsmith

Business Management Technology Education

Website RSS feed

Episodes

Latest episode

Aug 2026

Language

About the show

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

Listen to episodes

60 recent

August 16, 2026Episode 6932 min

Build vs Buy When Building Got Cheap

The 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 that comparison leaves out is that building has always had two costs, and AI only made one of them smaller. Kevin has spent most of his career firmly on the buy side, with a mantra he gave his teams for years: don't invent things that already exist. This episode is him revising that position rather than abandoning it, and being specific about how much smaller the revision is than the enthusiasm in the industry suggests. He walks through a four-question test to run before agreeing to build something that already exists, covering blast radius, ownership cost, differentiation, and whether there's an exit path. Along the way: where building genuinely does make sense now, where it still doesn't regardless of how cheap it has become, the license cost trap that catches CFOs, why supply chain risk has started cutting in both directions, and the version of this decision that shows up in headcount instead of software. Two stories anchor it: an auth decision that gave back every dollar it saved and came within about a month of being much worse, and a build made deliberately with an exit already planned. 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 )

August 2, 2026Episode 6827 min

ENCORE: Taking a thoughtful approach to the job search process

Chapter 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 in a role or company, and how I used the results to prepare for job interviews. I also discuss some of the mistakes people make when interviewing for roles during a downturn, particularly in how they present themselves. If you're currently looking for a job, or think you will in the future (we all will), this episode will be helpful. Some links: It Depends book information: https://itdependsbook.net Newsletter: https://kevingoldsmith.substack.com Questions/contact (I'll answer them in the podcast or newsletter): contact@itdependsbook.net Living in an Employer’s Market as a Developer article: https://blog.kevingoldsmith.com/2020/03/31/living-in-an-employers-market-as-a-developer/

July 19, 2026Episode 6725 min

ENCORE: Protecting Your Team From Layoffs

This 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 the individuals on the team. Managing performance. All of these things will help when someone is deciding whether anyone on your team should be laid off. This episode provides more information for individuals and explains that managers are judged more by their team's work and less by their own contributions. Links: The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith The newsletter My talk from Leading Eng 2024: The Director to CTO Path

July 5, 2026Episode 6621 min

ENCORE: Creating a Vernacular With Your Engineering Team

Teams 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 onboarding new members easier. Links: The newsletter with the text of the chapter: https://kevingoldsmith.substack.com/p/building-a-vernacular-with-your-engineering "It Depends: Writing on Technology Leadership 2012-2022" https://itdependsbook.net It Depends newsletter: https://kevingoldsmith.substack.com Questions/comments: contact@itdependsbook.net

June 21, 2026Episode 6539 min

Managing Sideways: Everyone Nodded, Then Nothing Happened.

A 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. Nobody had to change, so nobody did. That gap is the subject of this episode: driving change across teams you don't manage and can't order around. Kevin Goldsmith calls it managing sideways, and it runs on influence without authority, one of the most useful leadership skills and one of the hardest to build. He works through why the two obvious moves, forcing it yourself or getting an executive to force it for you, tend to produce shallow and short-lived compliance, and why being right turns out to be the cheap part of the problem. The center of the episode is a four-move approach Kevin calls Adoption Without a Mandate: start with the team that already wants the change, frame it as removing their work rather than adding to it, let the first team's results pull in the next one, and settle ownership before the thing scales. He grounds it in two of his own projects, a company-wide career framework he built at Spotify by assembling a coalition, and an early effort at Adobe, where he forced a team to comply and was still paying for it long after the project shipped. It's a practical episode for engineering leaders at any level who keep hitting the same wall, where everyone agrees on the right thing, and still no one does it. Kevin closes with a short exercise that listeners can run this week on whatever cross-team change they've been pushing. The P-Word (Politics at Work): https://itdependspod.com/episodes/the-p-word-politics-at-work/ Influence Without Authority Leading Change: An Action Plan from The World's Foremost Expert on Business Leadership 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 )

June 7, 2026Episode 6426 min

The Reliable Team Trap: Why Execution Excellence Doesn't Earn You Influence

Some 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 to be the same thing every time: more work, rarely more authority. Kevin Goldsmith calls this the reliable team trap, the point where being trusted to execute quietly stops translating into being trusted to decide. Kevin works through why it happens, drawing on seven years he once spent running a project that kept succeeding without ever advancing his own career, plus two leaders he currently mentors whose situations played out very differently. The throughline is uncomfortable: if you are not setting the direction for your part of the organization, someone above you is, which means leadership hears their framing of your work instead of yours. That, he argues, is the real difference between running an organization and leading one. From there, he lays out four moves to close the gap between being measured on output and being measured on judgment: show the thinking, build the bench, claim the contribution, and take a position. Three of them are about visibility, and one is about capacity, and he is direct about why you need both, and why working even harder is the one response that reliably makes the trap worse. It is aimed at engineering managers, directors, and senior leaders who deliver well and keep wondering why the direction-setting conversations seem to happen without them. Reliability is the floor. This episode is about making sure it does not become the ceiling. Own Your Calendar: 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 )

May 24, 2026Episode 6322 min

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 )

May 10, 2026Episode 6227 min

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 )

April 26, 2026Episode 6130 min

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 )

April 12, 2026Episode 6036 min

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)