It Depends: Lessons in Technology Leadership
Episodes
The Interesting Changes Aren't Happening in the IDE
10 May 2026
Contributed by Lukas
Have you noticed that every conversation in tech leadership now circles back to AI, and that none of those conversations actually feel resolved? That'...
Becoming a Business Leader
26 Apr 2026
Contributed by Lukas
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 tec...
Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest
12 Apr 2026
Contributed by Lukas
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 wro...
Don't Let Your Boss Do Your Job
29 Mar 2026
Contributed by Lukas
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 s...
Every Organization Is a System. Are You Designing It or Just Living in It?
15 Mar 2026
Contributed by Lukas
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,...
The Director to CTO Path: How to Follow It, or How to Mentor It
01 Mar 2026
Contributed by Lukas
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...
Talking to Executives: That's Not a Derailment, That's the Meeting
15 Feb 2026
Contributed by Lukas
Have you ever had an executive interrupt your presentation and completely take the conversation somewhere you weren't expecting? That's not a derailme...
The Shift to Managing Managers
01 Feb 2026
Contributed by Lukas
Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin...
Leading What You've Never Done Before
18 Jan 2026
Contributed by Lukas
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 y...
Success Makes You Dangerous: Why Comfortable Leaders Stop Growing
04 Jan 2026
Contributed by Lukas
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 ...
The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy
21 Dec 2025
Contributed by Lukas
In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith tackles one of the most contentious topics in growing companies: proc...
Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders
07 Dec 2025
Contributed by Lukas
In this episode, Kevin tackles one of the most misunderstood topics in software development: technical debt. Drawing on his experience at Microsoft, S...
Demystifying Board Meetings: A CTO's Perspective
23 Nov 2025
Contributed by Lukas
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...
Crafting a Technical Strategy
09 Nov 2025
Contributed by Lukas
In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith breaks down what it really means to craft a technical strategy that a...
Making Technology Choices That Last
26 Oct 2025
Contributed by Lukas
Avoiding shiny object syndrome, encouraging curiosity, and building a system for smart adoption Every few years, a new wave of technology arrives p...
The Hidden Architecture of Engineering: Practical Lessons in Organizational Design
12 Oct 2025
Contributed by Lukas
In this episode, Kevin digs into the often-ignored side of engineering leadership: organizational design. He explores how structure shapes communicati...
Values → Culture → Everything: Why Company Culture Actually Matters
28 Sep 2025
Contributed by Lukas
Kevin Goldsmith revisits his influential 2013 keynote on engineering culture, expanding the conversation beyond just engineering teams to address anyo...
How to Handle Career Gaps and What CTOs Actually Do All Day
14 Sep 2025
Contributed by Lukas
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...
ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart
31 Aug 2025
Contributed by Lukas
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. ...
ENCORE: Building a technical career path at Spotify
17 Aug 2025
Contributed by Lukas
This is a repeat of an episode originally released on March 2, 2025 In this episode of the "It Depends" podcast, host Kevin Goldsmith shares his un...
ENCORE: Addressing the challenges of partially distributed engineering teams
03 Aug 2025
Contributed by Lukas
This is a repeat of an episode originally released on August 4, 2024. In this episode of the It Depends podcast, host Kevin Goldsmith delves into th...
ENCORE: Becoming a CTO
20 Jul 2025
Contributed by Lukas
If you are on the technology management track, the final role is Chief Technology Officer. Still, the path to the role is not obvious because the role...
ENCORE: Fail Safe, Fail Smart... Succeed!
06 Jul 2025
Contributed by Lukas
We discuss how critical failure is to innovation and how to handle it effectively. We discuss how software used to be written, Clippy, and why it was ...
Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business
22 Jun 2025
Contributed by Lukas
In this season finale, Kevin pulls back the curtain on his entire book-writing and self-publishing journey. What started as a collection of blog pos...
Answers That Depend: Tech Leadership Q&A Part 3
08 Jun 2025
Contributed by Lukas
In this third and final Q&A episode of the season, Kevin addresses three challenging questions that many tech leaders face daily. First, he delves...
Answers that Depend: Tech Leadership Q & A pt 2
25 May 2025
Contributed by Lukas
Host Kevin Goldsmith responds to six listener questions covering common leadership and career challenges in technology organizations. Episode Content:...
Answers That Depend: Tech Leadership Q&A Part 1
11 May 2025
Contributed by Lukas
In this first post-book Q&A episode, host Kevin Goldsmith dives into the real challenges tech leaders face daily, answering questions from listene...
Succession for Scale
27 Apr 2025
Contributed by Lukas
In this episode, Kevin shares the final chapter of It Depends: Writing on Technology Leadership, focusing on what it takes to grow with a scaling comp...
The Myth of the Startup in a Large Company with Kevin Stewart
13 Apr 2025
Contributed by Lukas
In this special episode, Kevin Goldsmith is joined by longtime friend and peer Kevin Stewart, SVP of Engineering at Splice, to challenge the familiar ...
Lessons From Creating The Spotify Technology Career Steps
30 Mar 2025
Contributed by Lukas
In this episode of the "It Depends" podcast, host Kevin Goldsmith discusses the lessons learned from creating Spotify's Technology Career Steps framew...
Spotify Technology Career Steps
16 Mar 2025
Contributed by Lukas
In this episode of "It Depends: Lessons in Technology Leadership," host Kevin Goldsmith discusses Chapter 33 of his book, which details the career ...
Building a technical career path at Spotify
02 Mar 2025
Contributed by Lukas
In this episode of the "It Depends" podcast, host Kevin Goldsmith shares his unique experience designing Spotify's engineering career framework. As th...
Changing Hiring Practices to Build a More Diverse Technology Organization
16 Feb 2025
Contributed by Lukas
Are your hiring practices unintentionally limiting diversity in your organization? In this episode of It Depends host Kevin Goldsmith explores the c...
A diversity challenge: tech start-ups have a great opportunity
02 Feb 2025
Contributed by Lukas
As major tech companies retreat from their commitments to diversity, equity, and inclusion, startups can lead the way. In this episode, Kevin Goldsmit...
Building a Management Training Curriculum at Avvo
19 Jan 2025
Contributed by Lukas
In Episode 27 of It Depends: Lessons in Technology Leadership, Kevin Goldsmith explores the process of creating a management training curriculum at Av...
Using Self-Selection to Create Journey Teams at Avvo
05 Jan 2025
Contributed by Lukas
In this insightful episode of The It Depends Podcast, host Kevin Goldsmith, seasoned CTO and author, takes listeners behind the scenes of his first CT...
Thoughts on emulating Spotify’s matrix organization in other companies
22 Dec 2024
Contributed by Lukas
In this episode of It Depends, host Kevin Goldsmith, a seasoned technology leader and CTO, explores the intricacies of Spotify's famed matrix organiza...
The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative
08 Dec 2024
Contributed by Lukas
In this episode of It Depends, host Kevin Goldsmith dives into Chapter 26 of his book It Depends: Writing on Technology Leadership 2012–2022. Kevin ...
Transcript of my speech from OPEX Week Summer 2018
24 Nov 2024
Contributed by Lukas
Kevin Goldsmith, Chief Technology Officer and author of It Depends: Writing on Technology Leadership (2012–2022), shares a unique chapter from his ...
Hiring Agile Coaches
10 Nov 2024
Contributed by Lukas
In this episode of The It Depends Podcast, host Kevin Goldsmith dives into the intricacies of hiring agile coaches—a role he discovered while workin...
Management and Systems Thinking
27 Oct 2024
Contributed by Lukas
In this episode of It Depends host Kevin Goldsmith dives into the art of management through the lens of systems thinking. Using the metaphor of garde...
Writing Useful Performance Reviews: Delivering the Review
13 Oct 2024
Contributed by Lukas
In this episode of It Depends, Kevin Goldsmith wraps up his insightful series on crafting and delivering effective performance reviews. Drawing from h...
Writing Useful Performance Reviews: Making a Raise Recommendation
29 Sep 2024
Contributed by Lukas
In this episode of the It Depends podcast, host Kevin Goldsmith, an experienced CTO and technology leader with over 30 years in the industry, dives i...
Writing Useful Performance Reviews: Evaluating the data and writing the review
15 Sep 2024
Contributed by Lukas
In this insightful episode of The It Depends Podcast, host Kevin Goldsmith delves into a critical aspect of leadership: writing effective and fair per...
Writing Useful Performance Reviews: Assembling the data
01 Sep 2024
Contributed by Lukas
Join Kevin Goldsmith on the "It Depends" podcast as he explores the nuanced world of performance reviews in technology leadership. Drawing from his ex...
Twenty Questions For Your One-on-Ones
18 Aug 2024
Contributed by Lukas
In this episode of the "It Depends" podcast, Kevin Goldsmith, a seasoned Chief Technology Officer, explores the importance of effective one-on-one mee...
Addressing the challenges of partially distributed engineering teams
04 Aug 2024
Contributed by Lukas
In this episode of the It Depends podcast, host Kevin Goldsmith delves into the complexities of managing partially distributed engineering teams. Kev...
A Resignation Can Be an Opportunity
21 Jul 2024
Contributed by Lukas
In this episode of the "It Depends" podcast, host Kevin Goldsmith, a seasoned CTO and tech executive, explores the valuable lessons that can be gleane...
What do I look for when hiring an engineer?
07 Jul 2024
Contributed by Lukas
Welcome to the It Depends podcast with your host, Kevin Goldsmith! Kevin is a seasoned Chief Technology Officer with over 30 years of experience in so...
Every Decision Creates a Policy
23 Jun 2024
Contributed by Lukas
In this episode of the "It Depends" podcast, host Kevin Goldsmith delves into the complexities of decision-making in management and its implications o...
Protecting Your Team From Layoffs
09 Jun 2024
Contributed by Lukas
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 visi...
The P Word (Politics at work)
26 May 2024
Contributed by Lukas
Politics! The word has such a negative connotation when discussing work and corporate culture. Political tactics or maneuvers aren't inherently bad. I...
Creating a Vernacular With Your Engineering Team
12 May 2024
Contributed by Lukas
Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team wo...
Becoming a CTO
28 Apr 2024
Contributed by Lukas
If you are on the technology management track, the final role is Chief Technology Officer. Still, the path to the role is not obvious because the role...
How I Get My Focused Work Done / The Known Unknowns
14 Apr 2024
Contributed by Lukas
Once again, two shorter chapters in this podcast from the book. How I get my focused work done: When you are a manager, constantly interrupted, how ca...
Own Your Calendar / Work Deliberately
31 Mar 2024
Contributed by Lukas
Two chapters from the book this week! Discussing a deliberate approach to managing your calendar and tracking how you actually are using your time, an...
The Personal Strategy Off-site
17 Mar 2024
Contributed by Lukas
Taking a day, once, twice, or even four times a year to reflect on how things are going and think about where you want to go next is a valuable practi...
When, why, and how to stop coding as your day job
03 Mar 2024
Contributed by Lukas
One of the questions I most frequently get from engineering leaders or aspiring leads is "how much coding do you do?" or "How do you handle coding and...
Taking a thoughtful approach to the job search process
18 Feb 2024
Contributed by Lukas
Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022 In this episode, we discuss my experience building an exercise to help me better...
The challenge of top-down change and the Microsoft layoffs
04 Feb 2024
Contributed by Lukas
How can top-down culture change be effective? Looking at Microsoft and Yahoo as examples. Links: It Depends book: https://itdependsbook.net Questio...
Fail Safe, Fail Smart... Succeed!
21 Jan 2024
Contributed by Lukas
We discuss how critical failure is to innovation and how to handle failure well. We talk about how software used to be written, Clippy and why it was ...
Introduction
08 Jan 2024
Contributed by Lukas
Welcome to the podcast! This episode introduces the podcast and includes the introduction to the book "It Depends: Writing on Technology Leadership 20...