It Depends: Lessons in Technology Leadership

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

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 the complexities of managing partially distributed engineering teams.

Kevin discusses the nuances of communication, collaboration, and culture in partially distributed teams, emphasizing the unique challenges that arise when some team members work remotely while others remain in the office. He highlights his experiences at companies like Adobe, Microsoft, and more, offering valuable lessons on effective management strategies and the importance of maintaining human connections in a digital work environment.

Whether you're a tech leader navigating the post-COVID landscape or simply interested in the future of work, this episode provides actionable insights and practical advice for fostering successful distributed teams

links:

• LeadDev New York
• Video and slides from Leading Distributed Teams
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• The newsletter

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 itself differs greatly from company to company. The episode includes chapter 10 from "It Depends: Writing on Technology Leadership 2012-2022," "Becoming a CTO." This chapter discusses the common skills needed for the CTO in almost any company and how the role differs between early-stage and mid-stage companies.

This is a repeat of an episode originally released on April 28, 2024.

• Seattle's Got Tech Event at Seattle Startup Week
• LeadDev New York
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith

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 bound to fail. We also explore how Spotify utilizes the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more.

This is a repeat of an episode originally released on January 20, 2024.

• Seattle's Got Tech Event at Seattle Startup Week
• LeadDev New York
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith

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 into the tension between competitive performance review systems and collaborative culture, drawing on his own experience at Microsoft to explain why some systems actively discourage the teamwork they claim to promote.

Next, Kevin explores how to balance innovation with product roadmap commitments, and whether guild structures can help break down team silos while fostering technical creativity. He shares practical strategies for channeling brilliant engineering ideas into strategic objectives without derailing quarterly deliverables.

Finally, he addresses a thoughtful question about advocating for accessibility and inclusive design in fast-paced startup environments. Kevin provides actionable advice on how individual contributors can influence technical strategy, make the business case for accessibility, and demonstrate measurable impact even when leadership views frontend work as "just making things pretty."

Throughout the episode, Kevin emphasizes that context matters in every decision, offering nuanced perspectives rather than one-size-fits-all solutions. Whether you're a staff engineer trying to drive collaboration, a technical leader scaling an AI platform, or an IC passionate about inclusive design, this episode delivers practical insights for navigating complex organizational challenges.

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

Host Kevin Goldsmith responds to six listener questions covering common leadership and career challenges in technology organizations.

Episode Content:

Learning and Development on Limited Resources - A team lead in Lagos asks about fostering continuous learning without access to expensive training programs. Kevin discusses free resources, including conference talks on YouTube, vendor training materials, online courseware, and strategies for organizing local meetups and knowledge-sharing sessions.

Personal Retrospective Systems - An SRE professional in Portland seeks structured approaches for personal leadership reflection. Kevin details his multi-layered system: weekly, monthly, quarterly, and bi-annual review processes, including his specific weekly questions and bullet journaling methodology.

Organizational Change Management - A manager struggles with department heads who verbally commit to transformation initiatives but show limited follow-through. Kevin addresses the brutal reality that sometimes personnel changes are necessary when key people resist required organizational shifts.

Technical Debt vs. Immediate Delivery - A healthcare technology professional faces pressure to implement quick patches while advocating for proper architectural redesign. Kevin emphasizes the importance of understanding business context and having frank discussions with leadership about trade-offs.

Early Career Overwhelm - A junior data engineer, hired as the first data person at a startup, feels overwhelmed balancing immediate requests with infrastructure foundations. Kevin provides perspective on realistic expectations for junior professionals and the importance of focusing on current competency over long-term planning.

Product-Engineering Team Dynamics - A product team leader experiences friction with engineering counterparts who prioritize their roadmap over product initiatives. Kevin identifies this as a fundamental structural issue, advocating for unified backlogs and shared accountability between product and engineering functions.

The episode offers direct, sometimes blunt advice about leadership realities, emphasizing practical frameworks over theoretical approaches. Kevin shares specific processes he uses personally and addresses the difficult decisions leaders must sometimes make.

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