It Depends: Lessons in Technology Leadership

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

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 unplanned career break—whether due to layoffs or a tough job market. From reframing “career break” on your résumé, to launching a consultancy, building a startup, or contributing to open source, Kevin outlines concrete ways to stay relevant, keep your skills sharp, and strengthen your positioning for the next opportunity.

Then he pulls back the curtain on what a CTO really does all day. Drawing on his experience at mid-stage startups, Kevin explains the balance between executive responsibilities, one-on-ones, cross-functional collaboration, strategic thinking, and even the occasional coding. He highlights how priorities shift depending on company size, culture, and market, and why visibility, prioritization, and time management are crucial at the executive level.

This episode blends career survival strategies with an honest look at senior leadership—helpful both for those navigating career uncertainty and those aspiring to the CTO role.

• 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

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. You can use the discount code “KEVIN15” to receive 15% off your registration.

In this special episode, Kevin Goldsmith is joined by longtime friend and peer Kevin Stewart, SVP of Engineering at Splice, to challenge the familiar yet flawed narrative: that a team within a large company can "operate like a startup." Drawing on their shared experiences at Adobe and divergent paths through startups, they explore why innovation often stalls inside large organizations and what makes real startup environments fundamentally different.

This wide-ranging conversation explores culture, risk, incentives, and why resource contention, rather than imagination, hinders corporate innovation. Whether you lead a startup or a legacy company trying to move faster, this episode offers a valuable perspective.

• • Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
  • The book: It Depends: Writing on Technology 2012-2022
  • Your host: Kevin Goldsmith
  • The Guest: Kevin Stewart

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 unique experience designing Spotify's engineering career framework. As the leader of this initiative, Kevin provides a behind-the-scenes look at how Spotify's distinct career pathing system was developed, a system that reinforced its unique engineering culture rather than undermining it.

Kevin explains the delicate balance of timing when implementing a career framework. Waiting too long (as Spotify did) can cause problems, but implementing too early can stifle a growing organization. He emphasizes how career pathing must align with company values, as it directly influences what behaviors get rewarded and ultimately shapes your culture.

The episode covers Spotify's collaborative approach to creating its "Career Steps" framework, involving representatives from across the organization rather than simply adopting another company's model. Kevin shares their guiding principles, including the crucial shift from focusing on achievements to behaviors, supporting specialists and generalists, and defining career growth by expanding spheres of influence.

Whether you're a tech leader contemplating how to structure growth paths for your team or an individual contributor wondering how career frameworks influence company culture, this episode is a must-listen. It offers valuable insights into one of the most foundational aspects of engineering leadership, insights that are relevant and beneficial for both roles.

• LeadDev New York (Use the discount code “KEVIN15” for 15% off on your registration)
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith