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

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