It Depends: Lessons in Technology Leadership

Answers That Depend: Tech Leadership Q&A Part 1

In this first post-book Q&A episode, host Kevin Goldsmith dives into the real challenges tech leaders face daily, answering questions from listeners around the globe.

The episode unpacks several critical leadership dilemmas:

Luca from Milan asks how to maintain clear accountability while fostering cross-functional collaboration in a matrix organization. Kevin provides practical advice on balancing engineering ownership with product and design partnerships, revealing how to avoid the common pitfalls of siloed thinking without sacrificing sprint commitments.

Tatiana, a data science leader from Estonia, presents two thought-provoking questions. First, how can technically-oriented leaders effectively evaluate the "soft contributions" that don't show up in quantitative metrics? Kevin shares his battle-tested 360-review approach that helps quantify the unquantifiable. Then, Tatiana asks about transitioning from data science leadership to a CTO role. Kevin maps out multiple potential career paths, with specific guidance on which skills to develop and strategic moves to consider.

Finally, Priya, a newly promoted team lead from Bangalore, seeks advice on protecting her team amid industry-wide layoffs. Kevin delivers straight talk on becoming "the franchise" – positioning your team on the company's critical path and ensuring your contributions remain visible and directly tied to revenue.

Whether you're battling matrix confusion, struggling with performance reviews that capture true value, plotting your next career move, or navigating uncertain economic waters, this episode delivers actionable insights from someone who's been in the trenches.

Download now to arm yourself with practical leadership strategies you can implement immediately. Because in tech leadership, the right answer almost always "depends" on your unique situation.

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

Succession for Scale

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 company, or recognize when it’s time for new leadership. Drawing on his real-world experience, he discusses succession planning, self-awareness, and cultivating a culture that fosters growth at every stage.

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

 

The Myth of the Startup in a Large Company with Kevin Stewart

In this special episode, Kevin Goldsmith is joined by longtime friend and peer Kevin Stewart, SVP of Engineering at Splice, to challenge the familiar but flawed narrative: that a team inside a big 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 touches on culture, risk, incentives, and why resource contention, not imagination, derails corporate innovation. Whether you lead a startup or a legacy company trying to move faster, this episode offers 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 chapter in the newsletter: https://kevingoldsmith.substack.com/p/the-myth-of-the-startup-in-a-large-5c7

Lessons From Creating The Spotify Technology Career Steps

In this episode of the "It Depends" podcast, host Kevin Goldsmith discusses the lessons learned from creating Spotify's Technology Career Steps framework. Kevin shares insights from his experience leading the effort to build a structured career path for Spotify's technology team, discussing the process's challenges and successes.

The episode covers key topics such as balancing behaviors versus achievements in career growth, the importance of aligning career pathing systems with company culture, and the complexities of integrating the framework with compensation. Kevin also reflects on how Spotify's technology-driven culture influenced the approach and how the company's evolution affected the longevity of the framework.

Tune in to hear Kevin's thoughts on what he would do differently today and how his experiences continue to shape his approach to career pathing in leadership roles. Plus, Kevin offers advice for technology leaders who are looking to develop similar frameworks within their own organizations.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• This chapter in the newsletter: https://kevingoldsmith.substack.com/p/things-we-learned-creating-technology

Spotify Technology Career Steps

In this episode of "It Depends: Lessons in Technology Leadership," host Kevin Goldsmith discusses Chapter 33 of his book, which details the career framework he helped develop at Spotify. Kevin emphasizes that a career pathing framework is the most critical document for engineering leaders. It serves as the backbone of organizational culture by reinforcing desired behaviors through promotion and performance management.

Kevin explains how the Spotify framework was carefully designed to:

• Emphasize team over individual contribution (reflecting Swedish vs. American cultural differences)
• Focus on behaviors and professional maturity rather than achievements
• Define spheres of impact that expand with seniority
• Align individual success with company success
• Provide flexibility in career choices

He describes the careful considerations that went into creating the framework, including being conservative with the number of levels and keeping step designations private to avoid embarrassing employees. Kevin also shares personal experiences from Microsoft that influenced his approach.

This episode is part of a trio on career pathing, with the next episode covering lessons learned from implementing the framework.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• This chapter in the newsletter: https://kevingoldsmith.substack.com/p/spotify-technology-career-steps

Building a technical career path at Spotify

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.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• This chapter in the newsletter: https://kevingoldsmith.substack.com/p/building-a-technical-career-path
• ELC Seattle meetup: https://elc.community/home/clubs/seattle-kcr/events/elc-x-airbnb-seattle-meetup-7oxyok5u0d

Changing Hiring Practices to Build a More Diverse Technology Organization

Are your hiring practices unintentionally limiting diversity in your organization? In this episode of It Depends host Kevin Goldsmith explores the critical changes that can help technology companies build more inclusive and high-performing teams. Drawing on his experience scaling engineering teams, Kevin challenges conventional hiring biases—such as prioritizing certain universities or requiring excessive pre-interview work—and offers actionable steps to reduce bias in the hiring process.

If you're a tech leader, hiring manager, or aspiring executive, this episode is packed with insights on creating a fairer, more equitable hiring pipeline—without lowering the bar. Tune in to learn how intentional changes can lead to stronger, more diverse teams, benefiting your company and the industry.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• This chapter in the newsletter: https://kevingoldsmith.substack.com/p/changing-hiring-practices-to-build

A diversity challenge: tech start-ups have a great opportunity

As major tech companies retreat from their commitments to diversity, equity, and inclusion, startups can lead the way. In this episode, Kevin Goldsmith explores why diverse teams consistently build better products and create stronger, more effective workplaces. He reflects on personal experiences in leadership, shares insights on how startups can leverage the "law of small numbers" to make a meaningful impact, and explains why prioritizing diversity isn't just the right thing to do—it’s also smart business.

Tune in to hear why building an inclusive team can be a competitive advantage and get a preview of the next episode’s discussion on practical strategies for hiring a diverse tech team.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022
• Your host: Kevin Goldsmith
• This chapter in the newsletter: https://kevingoldsmith.substack.com/p/a-diversity-challenge-tech-start