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 your blind spots might be hiding.

Kevin breaks down why reflection isn't optional for senior leaders. At the C-level, you don't get much feedback or development; you're expected to figure it out yourself. Your peer group shrinks. The job gets easier because you've seen these problems before. And that comfort is exactly when autopilot kicks in, when you stop asking "why," and when you risk becoming less effective for the people who depend on you.

The episode covers Kevin's personal reflection system: a twice-yearly strategic offsite, quarterly goal-setting, monthly calendar reviews, and weekly time-tracking. But he emphasizes you don't need to copy his process; you need to find what works for you and evolve it over time. He shares practical advice on starting small, making time when you feel too busy, and why the practice matters more than perfection. Reflection isn't about having it all figured out; it's about staying deliberate, adaptive, and intentional as a leader.

Whether you're a new manager learning to step back from the work, a senior leader feeling too comfortable, or anywhere in between, this episode makes the case that you can't lead others to grow if you've stopped growing yourself.

• The Personal Strategy Offsite episode: https://itdependspod.com/episodes/the-personal-strategy-off-site/
• Own Your Calendar episode: 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)
• ConFoo 2026 (https://confoo.ca/en/2026)

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 solving.

Kevin introduces a practical framework for deciding when to add process and when you have too much. He explains how to identify the coordination problems you're actually trying to solve and find the lightest-weight solution, rather than copying what works at Google or Amazon. The episode covers the warning signs of too little process (chaos, rework, unclear accountability) versus too much (bottlenecks, loss of autonomy, slow decisions), and why the size and culture of your organization fundamentally changes what works.

Through real examples from his career, Kevin addresses common scenarios leaders face: the scrappy startup founder who resists process until the org becomes dysfunctional, the experienced big-company hire who imports heavy processes that crush a smaller team, and the risk-averse leader who adds gates after every incident. He explains the critical difference between enabling process (which helps teams move faster with confidence) and controlling process (which centralizes decisions and kills speed), and why involving your teams in process design dramatically increases adoption.

Whether you're an engineering leader wondering if you're choking your team, a founder trying to scale without losing your speed, or a manager navigating the tension between autonomy and coordination, this episode gives you a strategic lens for making better decisions about when and how to add process, and when to remove it.

• 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)
• ConFoo 2026 (https://confoo.ca/en/2026)

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.

Kevin introduces a practical four-part framework for understanding technical debt: pragmatic debt (taken on deliberately to validate ideas or meet constraints), required debt (that directly impacts reliability, security, or delivery capability), incidental debt (stable, low-risk code that's safe to ignore), and symptomatic debt (a signal of deeper organizational problems that code fixes won't solve). He explains how to identify each type and, more importantly, how to decide what deserves your team's attention and what doesn't.

The episode explores why teams often struggle to get product support for addressing technical debt, how to tie debt decisions to business outcomes, and why some debt is actually a symptom of broken systems rather than poor engineering choices. Kevin shares real examples from his own career, including inheriting a monolith that had outlived its usefulness and intentionally taking on debt at Spotify to learn faster.

Whether you're an engineering leader trying to prioritize what debt to fix, a product manager wondering why engineers keep talking about refactoring, or an executive trying to understand which debt threatens business outcomes, this episode provides a strategic lens for making better decisions about the inevitable trade-offs in software development.

• ConFoo 2026 (https://confoo.ca/en/2026)
• 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)

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 organization.

Kevin covers how boards think about risk, strategy, financial performance, and leadership effectiveness, and why these dynamics can shift depending on the company’s stage, the board's composition, and the CEO’s style. He also explains the CTO’s role at the table, how technical topics are translated into business terms, why preparation is critical, and what junior employees often misunderstand about how decisions actually get made.

If you’ve ever wondered what happens in those closed-door sessions—or you’re aiming for an executive role in the future—this episode gives you a clear and practical view of how board meetings work and why they matter.

• ConFoo 2026 (https://confoo.ca/en/2026)
• 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)

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 decisions.

Kevin outlines practical steps for building an effective strategy, including identifying business-aligned guiding principles, defining realistic technical bets, validating them with peers, and ensuring that every level of the organization maintains alignment. He also explores common pitfalls, including confusing strategy with a roadmap, making it too vague or too prescriptive, or failing to communicate it. He describes how a well-articulated strategy makes decisions easier, reduces friction, and gives teams greater autonomy and purpose.

It’s a clear, grounded guide for any engineering leader preparing for the new year, whether you’re a CTO shaping company direction or an EM ensuring your team’s work supports broader goals.

• ConFoo 2026 (https://confoo.ca/en/2026)
• 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)

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 decades of experience adopting everything from public cloud to AI tooling, he shares how to evaluate what’s worth your team’s attention and when to wait.

Kevin outlines a practical framework for making technology decisions that stick: discover → experiment → evaluate → adopt deliberately. He also explores how to guide both the eager early adopters and the skeptical veterans on your team, turning curiosity into a disciplined system for learning and innovation.

• ConFoo 2026 (https://confoo.ca/en/2026)
• 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)

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 organizations that actually work.

• Architecture and Organization talk (https://www.kevingoldsmith.com/talks/architecture-and-organization.html)
• Reinventing Organizations by Fredric Laloux (https://amzn.to/43fwrRk)
• Team Topologies by Skelton/Pais (https://amzn.to/4nPHVDA)
• 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)

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.

What you'll learn:

• The difference between stated company values and actual values (and a simple test to tell them apart)
• Why culture "eats strategy for breakfast" and how it can accelerate or sabotage company success
• How to build systems that reinforce positive culture through career ladders, hiring, and onboarding
• When and why firing for culture fit is necessary
• How to evaluate company culture during job interviews (especially what happens when companies face pressure)
• Why team culture vs. company culture tensions arise and how to navigate them
• What to do when company culture shifts rapidly due to acquisitions or leadership changes

Drawing from his experiences at Microsoft, Adobe, and Spotify, Kevin shares both successes and failures in culture building, including why he stayed at some companies for years and left others. He offers practical frameworks for managers building strong team cultures and individuals seeking workplaces aligned with their values.

Whether you're a team lead trying to strengthen your engineering culture, an individual contributor evaluating your current role, or someone interviewing for new positions, this episode provides actionable insights for understanding and navigating the often-invisible forces that shape our daily work experience.

• Taking a Thoughtful Approach to the Job Search Process (https://itdependspod.com/episodes/taking-a-thoughtful-approach-to-the-job-search-process/)
• Building a Strong Engineering Culture Keynote https://www.kevingoldsmith.com/talks/building-a-strong-engineering-culture.html
• LeadDev New York (Use code KEVIN25 for 25% off registration)
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith