It Depends: Lessons In Technology Leadership podcast

#Tech #MBA #Business #Podcasting Education #Self-Improvement #Kevin Goldsmith

44:49

Digital intelligence is reshaping how organizations work, and success depends on integrating multiple domains, using real-time analytics, and ensuring strong cyber protections as data grows and risks increase This week, Dave, Esmee, and Rob talk with Chris Carter, Director - Key Accounts and Australia at BAE Systems Digital Intelligence, to explore the fast-moving world of digital intelligence, data, and analytics and dive into the complexities of the work, how rapidly the landscape is evolving, and the major challenges organizations face today. TLDR : 00:41 Introduction of Chris Carter 03:00 Rob is confused by the idea of renting out brain capacity for compute power 07:13 Chris discusses the fusion of data, AI, and human judgment in complex environments 34:30 Are we giving enough attention to human cognitive capacity? 42:34 Rugby tickets with the family Guest Chris Carter: https://www.linkedin.com/in/chriscarter3/ Hosts Dave Chapman: https://www.linkedin.com/in/chapmandr/ Rob Kernahan: https://www.linkedin.com/in/rob-kernahan/ Esmee van de Giessen: https://www.linkedin.com/in/esmeevandegiessen/ Production Marcel van der Burg: https://www.linkedin.com/in/marcel-vd-burg/ Dave Chapman: https://www.linkedin.com/in/chapmandr/ Sound Ben Corbett: https://www.linkedin.com/in/ben-corbett-3b6a11135/ Louis Corbett: https://www.linkedin.com/in/louis-corbett-087250264/ ' Cloud Realities' is an original podcast from Capgemini…

It Depends: Lessons in Technology Leadership

साझा करें

शृंखला होम•Feed

Kevin Goldsmith brings you lessons and advice from decades in the technology industry.

50 एपिसोडस

It Depends: Lessons in Technology Leadership

updated 5 days ago

साझा करें

शृंखला होम•Feed

Kevin Goldsmith brings you lessons and advice from decades in the technology industry.

50 एपिसोडस

#Tech #MBA #Business #Podcasting Education #Self-Improvement #Kevin Goldsmith

सभी एपिसोड

1
Demystifying Board Meetings: A CTO's Perspective 50:52

5 days ago50:52

50:52

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 )…

1
Crafting a Technical Strategy 29:39

19 days ago29:39

29:39

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 )…

1
Making Technology Choices That Last 42:19

5 weeks ago42:19

42:19

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 )…

1
The Hidden Architecture of Engineering: Practical Lessons in Organizational Design 47:01

7 weeks ago47:01

47:01

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 )…

1
Values → Culture → Everything: Why Company Culture Actually Matters 1:04:24

9 weeks ago1:04:24

1:04:24

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…

1
How to Handle Career Gaps and What CTOs Actually Do All Day 46:56

11 weeks ago46:56

46:56

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…

1
ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart 1:06:55

13 weeks ago1:06:55

1:06:55

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…

1
ENCORE: Building a technical career path at Spotify 45:38

15 weeks ago45:38

45:38

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…

1
ENCORE: Addressing the challenges of partially distributed engineering teams 34:15

17 weeks ago34:15

34:15

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…

1
ENCORE: Becoming a CTO 36:01

19 weeks ago36:01

36:01

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…

1
ENCORE: Fail Safe, Fail Smart... Succeed! 58:51

21 weeks ago58:51

58:51

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…

1
Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business 45:12

23 weeks ago45:12

45:12

In this season finale, Kevin pulls back the curtain on his entire book-writing and self-publishing journey. What started as a collection of blog posts became "It Depends: Writing on Technology Leadership, 2012 to 2022" – but why go the DIY route instead of working with a traditional publisher? You'll learn: The real reasons tech leaders should (or shouldn't) write books Detailed breakdown of self-publishing vs. traditional publishing Specific tools and workflows: from WordPress to Word, ChatGPT for indexing, and recording audiobooks at home The business side: Amazon KDP vs. Ingram Spark, profit margins, and what actually sells Costly mistakes to avoid (spoiler: don't waste time on fancy tooling) How to promote without feeling like a sleazy self-promoter Perfect for: Anyone considering writing a book or starting a content business Tech leaders thinking about building their personal brand Entrepreneurs curious about the nuts and bolts of launching a creative venture Even if you never plan to write a book, Kevin's approach to learning a new business from scratch offers valuable lessons for any side project or career pivot. Plus, you'll get the honest truth about royalties, sales numbers, and whether it's actually worth the effort. This episode doubles as both a practical how-to guide and a case study in DIY entrepreneurship. Kevin's Gen X, do-it-yourself approach (honed from years running a record label) provides a refreshing alternative to the usual "scale fast or die" startup mentality. Seattle's Got Tech Event at Seattle Startup Week LeadDev New York Will Larson's Blog Post on self-publishing vs traditional publishing Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6 The book: It Depends: Writing on Technology 2012-2022 Your host: Kevin Goldsmith…

1
Answers That Depend: Tech Leadership Q&A Part 3 42:02

25 weeks ago42:02

42:02

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…

1
Answers that Depend: Tech Leadership Q & A pt 2 42:48

27 weeks ago42:48

42:48

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…

1
Answers That Depend: Tech Leadership Q&A Part 1 37:46

29 weeks ago37:46