It Depends: Lessons in Technology Leadership

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

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

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

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

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

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