It Depends: Lessons in Technology Leadership https://podcast.itdependsbook.net Kevin Goldsmith brings you lessons and advice from decades in the technology industry. Sun, 01 Mar 2026 00:04:00 -0800 https://podbean.com/?v=5.5 en Copyright 2024 All rights reserved. Business:Management 1440 episodic Kevin Goldsmith serializes the audiobook for his new book, ”It Depends: Writing on Technology Leadership 2012-2022.” Sharing extra details about each chapter and answering listener questions along the way. Kevin Goldsmith Kevin Goldsmith No false https://podcast.itdependsbook.net/feed.xml https://pbcdn1.podbean.com/imglogo/image-logo/17800819/Podcast_coverb350u.jpg It Depends: Lessons in Technology Leadership https://podcast.itdependsbook.net 144 144 The Director to CTO Path: How to Follow It, or How to Mentor It The Director to CTO Path: How to Follow It, or How to Mentor It https://podcast.itdependsbook.net/e/the-director-to-cto-path-how-to-follow-it-or-how-to-mentor-it/ https://podcast.itdependsbook.net/e/the-director-to-cto-path-how-to-follow-it-or-how-to-mentor-it/#comments Sun, 01 Mar 2026 00:04:00 -0800 itdepends.podbean.com/5415df4c-236f-315e-bc4c-884e26a66286 The path from Director to CTO isn't a single ladder. It's a gradual expansion across three dimensions: your focus widens from your team to the company to the industry, your orientation shifts from execution to operations to strategy, and your technical breadth grows from narrow specialist to broad generalist.

In this episode, Kevin maps out what that progression actually looks like at each level, drawing on his own career through Adobe, Spotify, and multiple startups. He shares practical ways to develop the skills you need before you need them, from taking finance people to lunch and shadowing unfamiliar teams, to aligning your team's work with company strategy, even when the company is moving in a direction you didn't expect.

Kevin also covers the mentoring side. If you're already a VP or CTO, how do you identify high-potential leaders and intentionally develop them? He talks about delegation, transparency, and giving feedback that's aimed at the next level, not just the current one.

Whether you're a director trying to figure out what VP-level thinking actually looks like, or a CTO thinking about how to grow the leaders behind you, this episode gives you a concrete framework for both.

]]> The path from Director to CTO isn't a single ladder. It's a gradual expansion across three dimensions: your focus widens from your team to the company to the industry, your orientation shifts from execution to operations to strategy, and your technical breadth grows from narrow specialist to broad generalist.

In this episode, Kevin maps out what that progression actually looks like at each level, drawing on his own career through Adobe, Spotify, and multiple startups. He shares practical ways to develop the skills you need before you need them, from taking finance people to lunch and shadowing unfamiliar teams, to aligning your team's work with company strategy, even when the company is moving in a direction you didn't expect.

Kevin also covers the mentoring side. If you're already a VP or CTO, how do you identify high-potential leaders and intentionally develop them? He talks about delegation, transparency, and giving feedback that's aimed at the next level, not just the current one.

Whether you're a director trying to figure out what VP-level thinking actually looks like, or a CTO thinking about how to grow the leaders behind you, this episode gives you a concrete framework for both.

]]> Kevin Goldsmith false No 2475 57 full Talking to Executives: That's Not a Derailment, That's the Meeting Talking to Executives: That's Not a Derailment, That's the Meeting https://podcast.itdependsbook.net/e/talking-to-executives-thats-not-a-derailment-thats-the-meeting/ https://podcast.itdependsbook.net/e/talking-to-executives-thats-not-a-derailment-thats-the-meeting/#comments Sun, 15 Feb 2026 00:20:00 -0800 itdepends.podbean.com/deffda62-ed6e-33a5-8251-1fbbb6a32469 Have you ever had an executive interrupt your presentation and completely take the conversation somewhere you weren't expecting? That's not a derailment. That's the meeting.

In this episode, Kevin talks about executive communication from both sides of the table. Early in his career, he learned the hard way that being right doesn't matter if you're not being understood (a Microsoft VP made sure he never forgot that lesson). Now, as a CTO, he watches people make the same mistakes he did.

Kevin shares a practical framework for communicating to executives: the Four C's of Clarity, Context, Consequence, and Control. He also talks about why executives interrupt, why they sometimes just get up and leave, and why protecting your credibility matters more than protecting your ego.

Whether you're presenting to senior leaders for the first time or trying to get better at it, this episode will help you walk in with more confidence and a better understanding of what's actually going on in the room.

]]> Have you ever had an executive interrupt your presentation and completely take the conversation somewhere you weren't expecting? That's not a derailment. That's the meeting.

In this episode, Kevin talks about executive communication from both sides of the table. Early in his career, he learned the hard way that being right doesn't matter if you're not being understood (a Microsoft VP made sure he never forgot that lesson). Now, as a CTO, he watches people make the same mistakes he did.

Kevin shares a practical framework for communicating to executives: the Four C's of Clarity, Context, Consequence, and Control. He also talks about why executives interrupt, why they sometimes just get up and leave, and why protecting your credibility matters more than protecting your ego.

Whether you're presenting to senior leaders for the first time or trying to get better at it, this episode will help you walk in with more confidence and a better understanding of what's actually going on in the room.

]]> Kevin Goldsmith false No 1999 56 full The Shift to Managing Managers The Shift to Managing Managers https://podcast.itdependsbook.net/e/the-shift-to-managing-managers/ https://podcast.itdependsbook.net/e/the-shift-to-managing-managers/#comments Sun, 01 Feb 2026 00:28:05 -0800 itdepends.podbean.com/bd922ad9-933c-3c7b-ac72-56c98f32f199 Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition, where staying too close to the work actually limited both his team's growth and his own.

The core challenge isn't autonomy versus control. It's leverage versus comfort. When you focus too far down into your organization, you become an information bottleneck, your managers lose ownership, and your own leadership growth stalls. The job fundamentally changes: your leverage no longer comes from making decisions, but from providing context.

Kevin covers the warning signs of overmanaging (managers escalating decisions that clearly belong to them, work slowing when you're unavailable), practical frameworks for delegating effectively, and why feeling indispensable is usually a red flag, not a success metric.

A key test: Could you step away for two weeks? Would your managers make good decisions without you? If not, you might be the problem.

]]> Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition, where staying too close to the work actually limited both his team's growth and his own.

The core challenge isn't autonomy versus control. It's leverage versus comfort. When you focus too far down into your organization, you become an information bottleneck, your managers lose ownership, and your own leadership growth stalls. The job fundamentally changes: your leverage no longer comes from making decisions, but from providing context.

Kevin covers the warning signs of overmanaging (managers escalating decisions that clearly belong to them, work slowing when you're unavailable), practical frameworks for delegating effectively, and why feeling indispensable is usually a red flag, not a success metric.

A key test: Could you step away for two weeks? Would your managers make good decisions without you? If not, you might be the problem.

]]> Kevin Goldsmith false No 2150 55 full Leading What You've Never Done Before Leading What You've Never Done Before https://podcast.itdependsbook.net/e/leading-what-youve-never-done-before/ https://podcast.itdependsbook.net/e/leading-what-youve-never-done-before/#comments Sun, 18 Jan 2026 00:21:00 -0800 itdepends.podbean.com/1e3b19d1-6a6e-335b-88b3-8f8d3afd749e Leading What You’ve Never Done Before is an episode about a leadership challenge almost everyone hits as they grow: your scope expands faster than your resume.

 

Most technology leaders start out managing what they already know, then suddenly find themselves responsible for domains they’ve never personally practiced. That can feel exposing, especially if you built your credibility as “the expert.” In this episode, Kevin breaks down why trying to become the expert in every new area is a trap, why ignoring unfamiliar teams is even worse, and what effective leadership looks like when you can’t rely on depth.

 

You’ll learn how to lead through intent, constraints, interfaces, and feedback loops, how to evaluate how decisions are made, not just what decisions were made, and how to stay accountable without becoming a bottleneck. Kevin also shares practical questions you can use in any domain, plus guidance on building trust with specialists, creating space for disagreement, and designing systems that consistently produce good outcomes.

 

If your responsibilities are growing into areas you’ve never owned before, this episode will help you lead them with confidence, and without pretending to be the smartest person in the room.

]]> Leading What You’ve Never Done Before is an episode about a leadership challenge almost everyone hits as they grow: your scope expands faster than your resume.

 

Most technology leaders start out managing what they already know, then suddenly find themselves responsible for domains they’ve never personally practiced. That can feel exposing, especially if you built your credibility as “the expert.” In this episode, Kevin breaks down why trying to become the expert in every new area is a trap, why ignoring unfamiliar teams is even worse, and what effective leadership looks like when you can’t rely on depth.

 

You’ll learn how to lead through intent, constraints, interfaces, and feedback loops, how to evaluate how decisions are made, not just what decisions were made, and how to stay accountable without becoming a bottleneck. Kevin also shares practical questions you can use in any domain, plus guidance on building trust with specialists, creating space for disagreement, and designing systems that consistently produce good outcomes.

 

If your responsibilities are growing into areas you’ve never owned before, this episode will help you lead them with confidence, and without pretending to be the smartest person in the room.

]]> Kevin Goldsmith false No 2127 54 full Success Makes You Dangerous: Why Comfortable Leaders Stop Growing Success Makes You Dangerous: Why Comfortable Leaders Stop Growing https://podcast.itdependsbook.net/e/success-makes-you-dangerous-why-comfortable-leaders-stop-growing/ https://podcast.itdependsbook.net/e/success-makes-you-dangerous-why-comfortable-leaders-stop-growing/#comments Sun, 04 Jan 2026 00:22:00 -0800 itdepends.podbean.com/735a5cf8-1475-3578-af10-acdd868d6da6 In this episode, Kevin tackles a paradox that most leaders don't see coming: the moment you get comfortable in your role is often the moment you stop improving. Drawing on his decade as a CTO, he explains why success and experience can become dangerous if you're not deliberately reflecting on how you work, why you make the choices you make, and where your blind spots might be hiding.

Kevin breaks down why reflection isn't optional for senior leaders. At the C-level, you don't get much feedback or development; you're expected to figure it out yourself. Your peer group shrinks. The job gets easier because you've seen these problems before. And that comfort is exactly when autopilot kicks in, when you stop asking "why," and when you risk becoming less effective for the people who depend on you.

The episode covers Kevin's personal reflection system: a twice-yearly strategic offsite, quarterly goal-setting, monthly calendar reviews, and weekly time-tracking. But he emphasizes you don't need to copy his process; you need to find what works for you and evolve it over time. He shares practical advice on starting small, making time when you feel too busy, and why the practice matters more than perfection. Reflection isn't about having it all figured out; it's about staying deliberate, adaptive, and intentional as a leader.

Whether you're a new manager learning to step back from the work, a senior leader feeling too comfortable, or anywhere in between, this episode makes the case that you can't lead others to grow if you've stopped growing yourself.

]]> In this episode, Kevin tackles a paradox that most leaders don't see coming: the moment you get comfortable in your role is often the moment you stop improving. Drawing on his decade as a CTO, he explains why success and experience can become dangerous if you're not deliberately reflecting on how you work, why you make the choices you make, and where your blind spots might be hiding.

Kevin breaks down why reflection isn't optional for senior leaders. At the C-level, you don't get much feedback or development; you're expected to figure it out yourself. Your peer group shrinks. The job gets easier because you've seen these problems before. And that comfort is exactly when autopilot kicks in, when you stop asking "why," and when you risk becoming less effective for the people who depend on you.

The episode covers Kevin's personal reflection system: a twice-yearly strategic offsite, quarterly goal-setting, monthly calendar reviews, and weekly time-tracking. But he emphasizes you don't need to copy his process; you need to find what works for you and evolve it over time. He shares practical advice on starting small, making time when you feel too busy, and why the practice matters more than perfection. Reflection isn't about having it all figured out; it's about staying deliberate, adaptive, and intentional as a leader.

Whether you're a new manager learning to step back from the work, a senior leader feeling too comfortable, or anywhere in between, this episode makes the case that you can't lead others to grow if you've stopped growing yourself.

]]> Kevin Goldsmith false No 1460 53 full The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy https://podcast.itdependsbook.net/e/the-right-amount-of-process-finding-the-balance-between-chaos-and-bureaucracy/ https://podcast.itdependsbook.net/e/the-right-amount-of-process-finding-the-balance-between-chaos-and-bureaucracy/#comments Sun, 21 Dec 2025 00:15:00 -0800 itdepends.podbean.com/400aff09-6130-3814-b020-b35baf1972d0 In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith tackles one of the most contentious topics in growing companies: process. Drawing on decades of leadership experience from IBM and Microsoft to Spotify and Adobe, he explores why process is neither inherently good nor bad; it's a tool that must fit the problem you're solving.

Kevin introduces a practical framework for deciding when to add process and when you have too much. He explains how to identify the coordination problems you're actually trying to solve and find the lightest-weight solution, rather than copying what works at Google or Amazon. The episode covers the warning signs of too little process (chaos, rework, unclear accountability) versus too much (bottlenecks, loss of autonomy, slow decisions), and why the size and culture of your organization fundamentally changes what works.

Through real examples from his career, Kevin addresses common scenarios leaders face: the scrappy startup founder who resists process until the org becomes dysfunctional, the experienced big-company hire who imports heavy processes that crush a smaller team, and the risk-averse leader who adds gates after every incident. He explains the critical difference between enabling process (which helps teams move faster with confidence) and controlling process (which centralizes decisions and kills speed), and why involving your teams in process design dramatically increases adoption.

Whether you're an engineering leader wondering if you're choking your team, a founder trying to scale without losing your speed, or a manager navigating the tension between autonomy and coordination, this episode gives you a strategic lens for making better decisions about when and how to add process, and when to remove it.

]]> In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith tackles one of the most contentious topics in growing companies: process. Drawing on decades of leadership experience from IBM and Microsoft to Spotify and Adobe, he explores why process is neither inherently good nor bad; it's a tool that must fit the problem you're solving.

Kevin introduces a practical framework for deciding when to add process and when you have too much. He explains how to identify the coordination problems you're actually trying to solve and find the lightest-weight solution, rather than copying what works at Google or Amazon. The episode covers the warning signs of too little process (chaos, rework, unclear accountability) versus too much (bottlenecks, loss of autonomy, slow decisions), and why the size and culture of your organization fundamentally changes what works.

Through real examples from his career, Kevin addresses common scenarios leaders face: the scrappy startup founder who resists process until the org becomes dysfunctional, the experienced big-company hire who imports heavy processes that crush a smaller team, and the risk-averse leader who adds gates after every incident. He explains the critical difference between enabling process (which helps teams move faster with confidence) and controlling process (which centralizes decisions and kills speed), and why involving your teams in process design dramatically increases adoption.

Whether you're an engineering leader wondering if you're choking your team, a founder trying to scale without losing your speed, or a manager navigating the tension between autonomy and coordination, this episode gives you a strategic lens for making better decisions about when and how to add process, and when to remove it.

]]> Kevin Goldsmith false No 2678 52 full Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders https://podcast.itdependsbook.net/e/technical-debt-isnt-the-enemy-a-strategic-framework-for-engineering-leaders/ https://podcast.itdependsbook.net/e/technical-debt-isnt-the-enemy-a-strategic-framework-for-engineering-leaders/#comments Sun, 07 Dec 2025 01:10:07 -0800 itdepends.podbean.com/50e52711-c45d-3ac7-a75f-c70e38909836 In this episode, Kevin tackles one of the most misunderstood topics in software development: technical debt. Drawing on his experience at Microsoft, Spotify, and early-stage startups, he challenges the common assumption that all technical debt is bad, explaining why healthy teams intentionally take on debt as part of shipping software effectively.

Kevin introduces a practical four-part framework for understanding technical debt: pragmatic debt (taken on deliberately to validate ideas or meet constraints), required debt (that directly impacts reliability, security, or delivery capability), incidental debt (stable, low-risk code that's safe to ignore), and symptomatic debt (a signal of deeper organizational problems that code fixes won't solve). He explains how to identify each type and, more importantly, how to decide what deserves your team's attention and what doesn't.

The episode explores why teams often struggle to get product support for addressing technical debt, how to tie debt decisions to business outcomes, and why some debt is actually a symptom of broken systems rather than poor engineering choices. Kevin shares real examples from his own career, including inheriting a monolith that had outlived its usefulness and intentionally taking on debt at Spotify to learn faster.

Whether you're an engineering leader trying to prioritize what debt to fix, a product manager wondering why engineers keep talking about refactoring, or an executive trying to understand which debt threatens business outcomes, this episode provides a strategic lens for making better decisions about the inevitable trade-offs in software development.

]]> In this episode, Kevin tackles one of the most misunderstood topics in software development: technical debt. Drawing on his experience at Microsoft, Spotify, and early-stage startups, he challenges the common assumption that all technical debt is bad, explaining why healthy teams intentionally take on debt as part of shipping software effectively.

Kevin introduces a practical four-part framework for understanding technical debt: pragmatic debt (taken on deliberately to validate ideas or meet constraints), required debt (that directly impacts reliability, security, or delivery capability), incidental debt (stable, low-risk code that's safe to ignore), and symptomatic debt (a signal of deeper organizational problems that code fixes won't solve). He explains how to identify each type and, more importantly, how to decide what deserves your team's attention and what doesn't.

The episode explores why teams often struggle to get product support for addressing technical debt, how to tie debt decisions to business outcomes, and why some debt is actually a symptom of broken systems rather than poor engineering choices. Kevin shares real examples from his own career, including inheriting a monolith that had outlived its usefulness and intentionally taking on debt at Spotify to learn faster.

Whether you're an engineering leader trying to prioritize what debt to fix, a product manager wondering why engineers keep talking about refactoring, or an executive trying to understand which debt threatens business outcomes, this episode provides a strategic lens for making better decisions about the inevitable trade-offs in software development.

]]> Kevin Goldsmith false No 2475 51 full Demystifying Board Meetings: A CTO's Perspective Demystifying Board Meetings: A CTO's Perspective https://podcast.itdependsbook.net/e/demystifying-board-meetings-a-ctos-perspective/ https://podcast.itdependsbook.net/e/demystifying-board-meetings-a-ctos-perspective/#comments Sun, 23 Nov 2025 03:37:44 -0800 itdepends.podbean.com/ea38eae1-e173-3219-ae80-b88806573288 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.

 

]]> 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.

 

]]> Kevin Goldsmith false No 3052 50 full Crafting a Technical Strategy Crafting a Technical Strategy https://podcast.itdependsbook.net/e/crafting-a-technical-strategy/ https://podcast.itdependsbook.net/e/crafting-a-technical-strategy/#comments Sun, 09 Nov 2025 01:15:39 -0800 itdepends.podbean.com/1b867d98-3a16-37c7-b3e8-cefb199f82e4 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.

 

]]> 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.

 

]]> Kevin Goldsmith false No 1779 49 full Making Technology Choices That Last Making Technology Choices That Last https://podcast.itdependsbook.net/e/making-technology-choices-that-last/ https://podcast.itdependsbook.net/e/making-technology-choices-that-last/#comments Sun, 26 Oct 2025 00:39:39 -0700 itdepends.podbean.com/6cace5d5-fca8-3422-a839-6e7470b1455a 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.

]]> 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.

]]> Kevin Goldsmith false No 2539 48 full The Hidden Architecture of Engineering: Practical Lessons in Organizational Design The Hidden Architecture of Engineering: Practical Lessons in Organizational Design https://podcast.itdependsbook.net/e/the-hidden-architecture-of-engineering-practical-lessons-in-organizational-design/ https://podcast.itdependsbook.net/e/the-hidden-architecture-of-engineering-practical-lessons-in-organizational-design/#comments Sun, 12 Oct 2025 02:17:15 -0700 itdepends.podbean.com/1d40b09a-b4c2-304a-a4e0-d82e542536d1 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.

]]> 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.

]]> Kevin Goldsmith false No 2821 47 full Values → Culture → Everything: Why Company Culture Actually Matters Values → Culture → Everything: Why Company Culture Actually Matters https://podcast.itdependsbook.net/e/values-%e2%86%92-culture-%e2%86%92-everything-why-company-culture-actually-matters/ https://podcast.itdependsbook.net/e/values-%e2%86%92-culture-%e2%86%92-everything-why-company-culture-actually-matters/#comments Sun, 28 Sep 2025 03:30:31 -0700 itdepends.podbean.com/b5280840-f7b0-3188-82ea-ede247a458dc 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.

]]> 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.

]]> Kevin Goldsmith false No 3864 2 46 full How to Handle Career Gaps and What CTOs Actually Do All Day How to Handle Career Gaps and What CTOs Actually Do All Day https://podcast.itdependsbook.net/e/how-to-handle-career-gaps-and-what-ctos-actually-do-all-day/ https://podcast.itdependsbook.net/e/how-to-handle-career-gaps-and-what-ctos-actually-do-all-day/#comments Sun, 14 Sep 2025 01:30:26 -0700 itdepends.podbean.com/cadd6dd2-492e-36d3-9465-01d3781ec3e8 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.

]]> 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.

]]> Kevin returns with practical ways to turn an unplanned career break into momentum, then demystifies what a startup CTO actually does all day. Kevin Goldsmith false No 2816 45 full ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart https://podcast.itdependsbook.net/e/encore-the-myth-of-the-startup-in-a-large-company-with-kevin-stewart/ https://podcast.itdependsbook.net/e/encore-the-myth-of-the-startup-in-a-large-company-with-kevin-stewart/#comments Sun, 31 Aug 2025 00:06:00 -0700 itdepends.podbean.com/724ebf79-8609-3177-b005-49120b559504 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.

 

]]> 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.

 

]]> Kevin Goldsmith false No 4015 44 full ENCORE: Building a technical career path at Spotify ENCORE: Building a technical career path at Spotify https://podcast.itdependsbook.net/e/encore-building-a-technical-career-path-at-spotify/ https://podcast.itdependsbook.net/e/encore-building-a-technical-career-path-at-spotify/#comments Sun, 17 Aug 2025 00:10:26 -0700 itdepends.podbean.com/3c61eaa9-acf2-3ea3-8c4c-27a00100423c 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.

]]> 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.

]]> Kevin Goldsmith false No 2738 43 full ENCORE: Addressing the challenges of partially distributed engineering teams ENCORE: Addressing the challenges of partially distributed engineering teams https://podcast.itdependsbook.net/e/encore-addressing-the-challenges-of-partially-distributed-engineering-teams/ https://podcast.itdependsbook.net/e/encore-addressing-the-challenges-of-partially-distributed-engineering-teams/#comments Sun, 03 Aug 2025 00:39:00 -0700 itdepends.podbean.com/36661bed-e27a-31e2-baa8-9f69c39ee1e7 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:

]]> 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:

]]> Kevin Goldsmith false No 2055 42 full ENCORE: Becoming a CTO ENCORE: Becoming a CTO https://podcast.itdependsbook.net/e/encore-becoming-a-cto/ https://podcast.itdependsbook.net/e/encore-becoming-a-cto/#comments Sun, 20 Jul 2025 00:34:00 -0700 itdepends.podbean.com/fb9ab1c8-9c55-341f-8aa2-82c5cdaa333e 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.

]]> 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.

]]> Kevin Goldsmith false No 2161 41 full ENCORE: Fail Safe, Fail Smart... Succeed! ENCORE: Fail Safe, Fail Smart... Succeed! https://podcast.itdependsbook.net/e/encore-fail-safe-fail-smart-succeed/ https://podcast.itdependsbook.net/e/encore-fail-safe-fail-smart-succeed/#comments Sun, 06 Jul 2025 00:01:59 -0700 itdepends.podbean.com/595e1c17-cd9c-3b8d-ab46-eebd87116470 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.

]]> 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.

]]> Kevin Goldsmith false No 3531 40 full Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business https://podcast.itdependsbook.net/e/why-i-wrote-a-book-a-meta-episode-on-self-publishing-and-diy-business/ https://podcast.itdependsbook.net/e/why-i-wrote-a-book-a-meta-episode-on-self-publishing-and-diy-business/#comments Sun, 22 Jun 2025 04:05:14 -0700 itdepends.podbean.com/8d713dec-c08e-3a6e-b55a-0e7dc53dd4d4 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.

]]> 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.

]]> Kevin Goldsmith false No 2712 39 full Answers That Depend: Tech Leadership Q&A Part 3 Answers That Depend: Tech Leadership Q&A Part 3 https://podcast.itdependsbook.net/e/answers-that-depend-tech-leadership-qa-part-3/ https://podcast.itdependsbook.net/e/answers-that-depend-tech-leadership-qa-part-3/#comments Sun, 08 Jun 2025 02:21:10 -0700 itdepends.podbean.com/6c7b2d99-092b-3b43-9597-9c04120cbaf7 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.

]]> 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.

]]> Kevin Goldsmith false No 2522 38 full Answers that Depend: Tech Leadership Q & A pt 2 Answers that Depend: Tech Leadership Q & A pt 2 https://podcast.itdependsbook.net/e/answers-that-depend-q-a-pt-2/ https://podcast.itdependsbook.net/e/answers-that-depend-q-a-pt-2/#comments Sun, 25 May 2025 02:04:29 -0700 itdepends.podbean.com/f8cb9d4e-0b7e-3fb5-a4e6-925fbfbe9a65 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.

]]> 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.

]]> Kevin Goldsmith false No 2568 37 full Answers That Depend: Tech Leadership Q&A Part 1 Answers That Depend: Tech Leadership Q&A Part 1 https://podcast.itdependsbook.net/e/answers-that-depend-tech-leadership-qa-part-1/ https://podcast.itdependsbook.net/e/answers-that-depend-tech-leadership-qa-part-1/#comments Sun, 11 May 2025 02:48:39 -0700 itdepends.podbean.com/d203abc8-0b4e-380b-a0a2-38546729217b 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.

]]> 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.

]]> Kevin Goldsmith false No 2266 36 full Succession for Scale Succession for Scale https://podcast.itdependsbook.net/e/succession-for-scale/ https://podcast.itdependsbook.net/e/succession-for-scale/#comments Sun, 27 Apr 2025 01:38:21 -0700 itdepends.podbean.com/21c181be-2301-3e90-bcce-f8da764ad15b 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.

 

]]> 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.

 

]]> Kevin Goldsmith false No 1548 35 full The Myth of the Startup in a Large Company with Kevin Stewart The Myth of the Startup in a Large Company with Kevin Stewart https://podcast.itdependsbook.net/e/the-myth-of-the-startup-in-a-large-company-with-kevin-stewart/ https://podcast.itdependsbook.net/e/the-myth-of-the-startup-in-a-large-company-with-kevin-stewart/#comments Sun, 13 Apr 2025 00:26:00 -0700 itdepends.podbean.com/d1bbcb70-8e66-35c4-add9-b20ea5a692c4 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.

]]> 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.

]]> Kevin Goldsmith false No 3945 34 full Lessons From Creating The Spotify Technology Career Steps Lessons From Creating The Spotify Technology Career Steps https://podcast.itdependsbook.net/e/lessons-from-creating-the-spotify-technology-career-steps/ https://podcast.itdependsbook.net/e/lessons-from-creating-the-spotify-technology-career-steps/#comments Sun, 30 Mar 2025 00:51:48 -0700 itdepends.podbean.com/b50b37a5-1513-31c4-86ee-ecbe052fed7f 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.

]]> 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.

]]> Kevin Goldsmith false No 2682 33 full Spotify Technology Career Steps Spotify Technology Career Steps https://podcast.itdependsbook.net/e/spotify-technology-career-steps/ https://podcast.itdependsbook.net/e/spotify-technology-career-steps/#comments Sun, 16 Mar 2025 00:43:22 -0700 itdepends.podbean.com/c6b12ec8-aa67-34a8-b821-c8b69bb23cc2 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.

]]> 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.

]]> Kevin Goldsmith false No 3040 32 full Building a technical career path at Spotify Building a technical career path at Spotify https://podcast.itdependsbook.net/e/building-a-technical-career-path-at-spotify/ https://podcast.itdependsbook.net/e/building-a-technical-career-path-at-spotify/#comments Sun, 02 Mar 2025 02:07:28 -0800 itdepends.podbean.com/2879aa79-80cf-3376-b6d4-20bc8311fff8 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.

]]> 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.

]]> Kevin Goldsmith false No 2669 31 full Changing Hiring Practices to Build a More Diverse Technology Organization Changing Hiring Practices to Build a More Diverse Technology Organization https://podcast.itdependsbook.net/e/changing-hiring-practices-to-build-a-more-diverse-technology-organization/ https://podcast.itdependsbook.net/e/changing-hiring-practices-to-build-a-more-diverse-technology-organization/#comments Sun, 16 Feb 2025 02:42:39 -0800 itdepends.podbean.com/1c9230fc-b1ff-3b56-aaaf-52ae8c12b776 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.

]]> 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.

]]> Kevin Goldsmith false No 2177 1 30 full A diversity challenge: tech start-ups have a great opportunity A diversity challenge: tech start-ups have a great opportunity https://podcast.itdependsbook.net/e/a-diversity-challenge-tech-start-ups-have-a-great-opportunity/ https://podcast.itdependsbook.net/e/a-diversity-challenge-tech-start-ups-have-a-great-opportunity/#comments Sun, 02 Feb 2025 01:50:07 -0800 itdepends.podbean.com/4eb636a7-02ad-3328-9b3f-71e3f2a1679c 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.

]]> 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.

]]> Kevin Goldsmith false No 1277 29 full Building a Management Training Curriculum at Avvo Building a Management Training Curriculum at Avvo https://podcast.itdependsbook.net/e/building-a-management-training-curriculum-at-avvo/ https://podcast.itdependsbook.net/e/building-a-management-training-curriculum-at-avvo/#comments Sun, 19 Jan 2025 00:35:00 -0800 itdepends.podbean.com/52c3dc9d-4702-325b-a1be-42e52442d950 In Episode 27 of It Depends: Lessons in Technology Leadership, Kevin Goldsmith explores the process of creating a management training curriculum at Avvo. Reflecting on his journey as a manager and lessons learned from his early days at Microsoft and Adobe, Kevin highlights the importance of intentional training for engineering managers. This episode delves into the innovative approach used at Avvo, including collaborative exercises to identify training priorities and designing tailored development programs to support technology leaders.

Discover actionable insights on fostering a strong management culture, balancing technical and managerial responsibilities, and creating effective learning experiences for teams. Whether you're an aspiring manager, an experienced leader, or part of a team looking to improve, this episode offers practical guidance and inspiration. Tune in to learn how to build a management training framework that elevates your organization!

]]> In Episode 27 of It Depends: Lessons in Technology Leadership, Kevin Goldsmith explores the process of creating a management training curriculum at Avvo. Reflecting on his journey as a manager and lessons learned from his early days at Microsoft and Adobe, Kevin highlights the importance of intentional training for engineering managers. This episode delves into the innovative approach used at Avvo, including collaborative exercises to identify training priorities and designing tailored development programs to support technology leaders.

Discover actionable insights on fostering a strong management culture, balancing technical and managerial responsibilities, and creating effective learning experiences for teams. Whether you're an aspiring manager, an experienced leader, or part of a team looking to improve, this episode offers practical guidance and inspiration. Tune in to learn how to build a management training framework that elevates your organization!

]]> Kevin Goldsmith false No 1798 1 28 full Using Self-Selection to Create Journey Teams at Avvo Using Self-Selection to Create Journey Teams at Avvo https://podcast.itdependsbook.net/e/using-self-selection-to-create-journey-teams-at-avvo/ https://podcast.itdependsbook.net/e/using-self-selection-to-create-journey-teams-at-avvo/#comments Sun, 05 Jan 2025 00:13:31 -0800 itdepends.podbean.com/918de49e-52f3-3dfb-a04f-e689db7591d9 In this insightful episode of The It Depends Podcast, host Kevin Goldsmith, seasoned CTO and author, takes listeners behind the scenes of his first CTO role at Avvo, a legal tech company. Kevin shares his real-world experience in transforming the organizational structure by introducing journey teams—an innovative approach influenced by, but distinct from, Spotify’s model. He discusses the challenges of managing small teams, the necessity of fostering team autonomy while maintaining accountability, and the crucial role of leadership in balancing top-down constraints with bottom-up ownership.

Kevin dives into the process of moving from a traditional hierarchy to a matrix organization and ultimately to journey teams. He explains how self-selection played a key role in empowering teams, fostering engagement, and driving sustainable growth in a fast-scaling company. Listeners will gain practical insights into building adaptable organizational structures tailored to company culture, evolving leadership styles, and scaling strategies for tech teams.

If you’re a technology leader navigating team scaling, culture transformation, or thinking of adopting self-selection and journey teams in your organization, this episode is packed with actionable takeaways.

 

 

]]> In this insightful episode of The It Depends Podcast, host Kevin Goldsmith, seasoned CTO and author, takes listeners behind the scenes of his first CTO role at Avvo, a legal tech company. Kevin shares his real-world experience in transforming the organizational structure by introducing journey teams—an innovative approach influenced by, but distinct from, Spotify’s model. He discusses the challenges of managing small teams, the necessity of fostering team autonomy while maintaining accountability, and the crucial role of leadership in balancing top-down constraints with bottom-up ownership.

Kevin dives into the process of moving from a traditional hierarchy to a matrix organization and ultimately to journey teams. He explains how self-selection played a key role in empowering teams, fostering engagement, and driving sustainable growth in a fast-scaling company. Listeners will gain practical insights into building adaptable organizational structures tailored to company culture, evolving leadership styles, and scaling strategies for tech teams.

If you’re a technology leader navigating team scaling, culture transformation, or thinking of adopting self-selection and journey teams in your organization, this episode is packed with actionable takeaways.

 

 

]]> Kevin Goldsmith false No 2863 27 full Thoughts on emulating Spotify’s matrix organization in other companies Thoughts on emulating Spotify’s matrix organization in other companies https://podcast.itdependsbook.net/e/thoughts-on-emulating-spotify-s-matrix-organization-in-other-companies/ https://podcast.itdependsbook.net/e/thoughts-on-emulating-spotify-s-matrix-organization-in-other-companies/#comments Sun, 22 Dec 2024 00:32:52 -0800 itdepends.podbean.com/6f05e194-a53f-3d50-a6a8-fee0532ba9ef In this episode of It Depends, host Kevin Goldsmith, a seasoned technology leader and CTO, explores the intricacies of Spotify's famed matrix organization model and its applicability to other companies. Drawing from his firsthand experiences at Spotify during its formative years, Kevin delves into the successes and challenges of implementing the Spotify model, addressing common misconceptions and the cultural nuances that influence its effectiveness.

Kevin recounts how the model's flexibility and autonomy transformed team dynamics and how its structure has been adapted (or misapplied) by other companies. He also discusses how the U.S. workplace culture, rooted in individualism, impacted the adoption of Spotify’s collaborative team-oriented practices. The episode is filled with insights on organizational scaling, the benefits of full-stack teams, and the pivotal role of company-specific cultural alignment in applying the model.

]]> In this episode of It Depends, host Kevin Goldsmith, a seasoned technology leader and CTO, explores the intricacies of Spotify's famed matrix organization model and its applicability to other companies. Drawing from his firsthand experiences at Spotify during its formative years, Kevin delves into the successes and challenges of implementing the Spotify model, addressing common misconceptions and the cultural nuances that influence its effectiveness.

Kevin recounts how the model's flexibility and autonomy transformed team dynamics and how its structure has been adapted (or misapplied) by other companies. He also discusses how the U.S. workplace culture, rooted in individualism, impacted the adoption of Spotify’s collaborative team-oriented practices. The episode is filled with insights on organizational scaling, the benefits of full-stack teams, and the pivotal role of company-specific cultural alignment in applying the model.

]]> Kevin Goldsmith false No 2646 26 full The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative https://podcast.itdependsbook.net/e/the-spotify-model-how-to-create-dissolve-and-remix-teams-to-be-more-dynamic-and-more-innovative/ https://podcast.itdependsbook.net/e/the-spotify-model-how-to-create-dissolve-and-remix-teams-to-be-more-dynamic-and-more-innovative/#comments Sun, 08 Dec 2024 01:24:35 -0800 itdepends.podbean.com/e49062ee-1ed7-35c9-881f-e5cd878c38ad In this episode of It Depends, host Kevin Goldsmith dives into Chapter 26 of his book It Depends: Writing on Technology Leadership 2012–2022. Kevin shares his firsthand experiences with the Spotify model—a revolutionary approach to team organization designed to foster agility, innovation, and collaboration.

Drawing on his years at Spotify, Kevin explains how the model allows teams to dynamically form, dissolve, and remix based on company needs. He also addresses some common misconceptions about its application and reflects on lessons learned from the Spotify model and how to adapt its principles to other organizations.

Don’t forget to subscribe to the accompanying newsletter and share your thoughts via the linked listener survey to help shape the future of the podcast!

Links to things mentioned in the podcast:

]]> In this episode of It Depends, host Kevin Goldsmith dives into Chapter 26 of his book It Depends: Writing on Technology Leadership 2012–2022. Kevin shares his firsthand experiences with the Spotify model—a revolutionary approach to team organization designed to foster agility, innovation, and collaboration.

Drawing on his years at Spotify, Kevin explains how the model allows teams to dynamically form, dissolve, and remix based on company needs. He also addresses some common misconceptions about its application and reflects on lessons learned from the Spotify model and how to adapt its principles to other organizations.

Don’t forget to subscribe to the accompanying newsletter and share your thoughts via the linked listener survey to help shape the future of the podcast!

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 1822 25 full Transcript of my speech from OPEX Week Summer 2018 Transcript of my speech from OPEX Week Summer 2018 https://podcast.itdependsbook.net/e/transcript-of-my-speech-from-opex-week-summer-2018/ https://podcast.itdependsbook.net/e/transcript-of-my-speech-from-opex-week-summer-2018/#comments Sun, 24 Nov 2024 00:15:00 -0800 itdepends.podbean.com/dfcc384c-c4ca-376e-8545-df2a94289962 Kevin Goldsmith, Chief Technology Officer and author of It Depends: Writing on Technology Leadership (2012–2022), shares a unique chapter from his audiobook in this episode of It Depends. Recorded on the road in Chicago, Kevin reflects on his unexpected journey into the Operational Excellence (OpEx) community, a world rooted in Six Sigma and Lean methodologies.

Kevin recounts his experiences speaking at OpEx conferences and collaborating with leaders in industries where quality is critical, such as manufacturing and hardware. He highlights the contrasts between OpEx's failure-averse approach and Agile's embrace of learning through small, manageable failures. Through engaging anecdotes and lessons learned, Kevin emphasizes stepping outside your comfort zone to engage with professionals in different fields.

This episode offers valuable insights for leaders in technology and beyond. It explores how diverse perspectives can challenge assumptions and foster growth. Tune in to learn how principles of operational excellence can complement tech leadership while avoiding the pitfalls of over-applying rigid frameworks.

Don’t forget to subscribe to the accompanying newsletter and share your thoughts via the linked listener survey to help shape the future of the podcast!

Links to things mentioned in the podcast:

]]> Kevin Goldsmith, Chief Technology Officer and author of It Depends: Writing on Technology Leadership (2012–2022), shares a unique chapter from his audiobook in this episode of It Depends. Recorded on the road in Chicago, Kevin reflects on his unexpected journey into the Operational Excellence (OpEx) community, a world rooted in Six Sigma and Lean methodologies.

Kevin recounts his experiences speaking at OpEx conferences and collaborating with leaders in industries where quality is critical, such as manufacturing and hardware. He highlights the contrasts between OpEx's failure-averse approach and Agile's embrace of learning through small, manageable failures. Through engaging anecdotes and lessons learned, Kevin emphasizes stepping outside your comfort zone to engage with professionals in different fields.

This episode offers valuable insights for leaders in technology and beyond. It explores how diverse perspectives can challenge assumptions and foster growth. Tune in to learn how principles of operational excellence can complement tech leadership while avoiding the pitfalls of over-applying rigid frameworks.

Don’t forget to subscribe to the accompanying newsletter and share your thoughts via the linked listener survey to help shape the future of the podcast!

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 1463 24 full Hiring Agile Coaches Hiring Agile Coaches https://podcast.itdependsbook.net/e/hiring-agile-coaches/ https://podcast.itdependsbook.net/e/hiring-agile-coaches/#comments Sun, 10 Nov 2024 00:30:00 -0800 itdepends.podbean.com/7123e6ed-08b9-35ed-a7d2-c7312371a38a In this episode of The It Depends Podcast, host Kevin Goldsmith dives into the intricacies of hiring agile coaches—a role he discovered while working at Spotify and which has been transformative in his approach to building high-performing teams. Kevin shares personal stories of successes and challenges with agile coaches across different companies, reflecting on how this role can dramatically boost productivity and collaboration, although sometimes misunderstood. He also explores the current state of Agile and muses on what might come next for the industry. Tune in to learn about the nuances of agile coaching, the evolution of Agile, and strategies for demonstrating the value of agile practices beyond the engineering team.

Links to things mentioned in the podcast:

]]> In this episode of The It Depends Podcast, host Kevin Goldsmith dives into the intricacies of hiring agile coaches—a role he discovered while working at Spotify and which has been transformative in his approach to building high-performing teams. Kevin shares personal stories of successes and challenges with agile coaches across different companies, reflecting on how this role can dramatically boost productivity and collaboration, although sometimes misunderstood. He also explores the current state of Agile and muses on what might come next for the industry. Tune in to learn about the nuances of agile coaching, the evolution of Agile, and strategies for demonstrating the value of agile practices beyond the engineering team.

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 2114 23 full Management and Systems Thinking Management and Systems Thinking https://podcast.itdependsbook.net/e/management-and-systems-thinking/ https://podcast.itdependsbook.net/e/management-and-systems-thinking/#comments Sun, 27 Oct 2024 01:25:51 -0700 itdepends.podbean.com/cee2e848-3d1d-38b0-ad63-219150470c0a In this episode of It Depends host Kevin Goldsmith dives into the art of management through the lens of systems thinking. Using the metaphor of gardening, Kevin explores how leaders can “plant the seeds” for success by setting up the right environment, empowering teams, and stepping back to let growth happen organically. He shares practical insights on Kanban boards, the power of autonomy, and the challenges of fostering alignment across teams with different goals. Whether you're a seasoned leader or just stepping into management, this episode is packed with actionable advice to help you cultivate high-performing teams. 🌱

 

Links to things mentioned in the podcast:

 

 

]]> In this episode of It Depends host Kevin Goldsmith dives into the art of management through the lens of systems thinking. Using the metaphor of gardening, Kevin explores how leaders can “plant the seeds” for success by setting up the right environment, empowering teams, and stepping back to let growth happen organically. He shares practical insights on Kanban boards, the power of autonomy, and the challenges of fostering alignment across teams with different goals. Whether you're a seasoned leader or just stepping into management, this episode is packed with actionable advice to help you cultivate high-performing teams. 🌱

 

Links to things mentioned in the podcast:

 

 

]]> Kevin Goldsmith false No 1850 22 full Writing Useful Performance Reviews: Delivering the Review Writing Useful Performance Reviews: Delivering the Review https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-delivering-the-review/ https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-delivering-the-review/#comments Sun, 13 Oct 2024 01:52:06 -0700 itdepends.podbean.com/b843fd8e-ac5c-314b-b6d4-e1b25500b439 In this episode of It Depends, Kevin Goldsmith wraps up his insightful series on crafting and delivering effective performance reviews. Drawing from his extensive experience as a CTO and tech leader, Kevin discusses the challenges and nuances of giving feedback, especially for senior leaders who might not receive regular performance reviews themselves. He shares practical strategies for self-evaluation and growth, including the importance of building a personal advisory board and seeking feedback from direct reports. Tune in to gain valuable insights into navigating performance reviews at all levels of leadership.

Links to things mentioned in the podcast:

]]> In this episode of It Depends, Kevin Goldsmith wraps up his insightful series on crafting and delivering effective performance reviews. Drawing from his extensive experience as a CTO and tech leader, Kevin discusses the challenges and nuances of giving feedback, especially for senior leaders who might not receive regular performance reviews themselves. He shares practical strategies for self-evaluation and growth, including the importance of building a personal advisory board and seeking feedback from direct reports. Tune in to gain valuable insights into navigating performance reviews at all levels of leadership.

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 2241 21 full Writing Useful Performance Reviews: Making a Raise Recommendation Writing Useful Performance Reviews: Making a Raise Recommendation https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-making-a-raise-recommendation/ https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-making-a-raise-recommendation/#comments Sun, 29 Sep 2024 00:06:08 -0700 itdepends.podbean.com/7b60a816-6a14-394a-a56e-032cf6cb4007 In this episode of the It Depends podcast, host Kevin Goldsmith, an experienced CTO and technology leader with over 30 years in the industry, dives into the intricacies of making raise recommendations as part of performance reviews. Drawing from his book "It Depends: Writings on Technology Leadership" and a talk he delivered at Lead Dev Berlin in 2019, Kevin unpacks the often misunderstood processes behind salary budgeting and recommendations. He shares insights on how companies allocate salary budgets, manage compensation, and the importance of understanding cross-functional dynamics for CTOs and tech leaders. This episode is part three of a four-part series on writing performance reviews. It is essential listening for managers, leaders, and anyone navigating the complexities of pay raises and team performance in a corporate setting. 

Listeners will also gain valuable advice on preparing for job interviews, understanding the broader aspects of company leadership, and Kevin's reflections on alternative compensation systems like those used by GitLab and Buffer. Whether you're an aspiring leader or a seasoned CTO, this episode offers a unique perspective on a crucial aspect of leadership that is often left unexplored.

Tune in for actionable insights, real-world examples, and practical advice for anyone involved in making raise recommendations or leading a technology organization.

Links to things mentioned in the podcast:

]]> In this episode of the It Depends podcast, host Kevin Goldsmith, an experienced CTO and technology leader with over 30 years in the industry, dives into the intricacies of making raise recommendations as part of performance reviews. Drawing from his book "It Depends: Writings on Technology Leadership" and a talk he delivered at Lead Dev Berlin in 2019, Kevin unpacks the often misunderstood processes behind salary budgeting and recommendations. He shares insights on how companies allocate salary budgets, manage compensation, and the importance of understanding cross-functional dynamics for CTOs and tech leaders. This episode is part three of a four-part series on writing performance reviews. It is essential listening for managers, leaders, and anyone navigating the complexities of pay raises and team performance in a corporate setting. 

Listeners will also gain valuable advice on preparing for job interviews, understanding the broader aspects of company leadership, and Kevin's reflections on alternative compensation systems like those used by GitLab and Buffer. Whether you're an aspiring leader or a seasoned CTO, this episode offers a unique perspective on a crucial aspect of leadership that is often left unexplored.

Tune in for actionable insights, real-world examples, and practical advice for anyone involved in making raise recommendations or leading a technology organization.



Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 2321 20 full Writing Useful Performance Reviews: Evaluating the data and writing the review Writing Useful Performance Reviews: Evaluating the data and writing the review https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-evaluating-the-data-and-writing-the-review/ https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-evaluating-the-data-and-writing-the-review/#comments Sun, 15 Sep 2024 00:27:00 -0700 itdepends.podbean.com/5cf40fa1-6230-381c-84b8-f6079b50ea1d In this insightful episode of The It Depends Podcast, host Kevin Goldsmith delves into a critical aspect of leadership: writing effective and fair performance reviews. Kevin, an experienced CTO and author of It Depends: Writing on Technology Leadership, shares lessons from his own career spanning over 30 years, including his time at Adobe, Spotify, and Microsoft.

This episode, part of a four-part series on performance reviews, focuses on how to take the data you've gathered and craft meaningful, actionable feedback for your team. Kevin also reflects on his personal experiences with both successful and flawed review systems, offering advice on how to navigate various company processes. Whether you're a new manager or a seasoned executive, this episode is packed with practical advice and cautionary tales to help you master the review process.

Links to things mentioned in the podcast:

]]> In this insightful episode of The It Depends Podcast, host Kevin Goldsmith delves into a critical aspect of leadership: writing effective and fair performance reviews. Kevin, an experienced CTO and author of It Depends: Writing on Technology Leadership, shares lessons from his own career spanning over 30 years, including his time at Adobe, Spotify, and Microsoft.

This episode, part of a four-part series on performance reviews, focuses on how to take the data you've gathered and craft meaningful, actionable feedback for your team. Kevin also reflects on his personal experiences with both successful and flawed review systems, offering advice on how to navigate various company processes. Whether you're a new manager or a seasoned executive, this episode is packed with practical advice and cautionary tales to help you master the review process.

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 2074 19 full Writing Useful Performance Reviews: Assembling the data Writing Useful Performance Reviews: Assembling the data https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-assembling-the-data/ https://podcast.itdependsbook.net/e/writing-useful-performance-reviews-assembling-the-data/#comments Sun, 01 Sep 2024 00:17:06 -0700 itdepends.podbean.com/3def4340-edad-3fd1-9659-af6d5ca5c480 Join Kevin Goldsmith on the "It Depends" podcast as he explores the nuanced world of performance reviews in technology leadership. Drawing from his extensive experience and his book, Kevin offers actionable insights on making performance reviews more effective and less burdensome. This episode guides listeners through assembling relevant data and providing feedback that genuinely aids employee development. Tune in to transform how you approach performance reviews, making them a powerful tool for leadership and growth. Whether you're a seasoned manager or a new leader, this podcast promises valuable lessons in nurturing talent effectively.

Links to things mentioned in the podcast:

]]> Join Kevin Goldsmith on the "It Depends" podcast as he explores the nuanced world of performance reviews in technology leadership. Drawing from his extensive experience and his book, Kevin offers actionable insights on making performance reviews more effective and less burdensome. This episode guides listeners through assembling relevant data and providing feedback that genuinely aids employee development. Tune in to transform how you approach performance reviews, making them a powerful tool for leadership and growth. Whether you're a seasoned manager or a new leader, this podcast promises valuable lessons in nurturing talent effectively.

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 1582 18 full Twenty Questions For Your One-on-Ones Twenty Questions For Your One-on-Ones https://podcast.itdependsbook.net/e/twenty-questions-for-your-one-on-ones/ https://podcast.itdependsbook.net/e/twenty-questions-for-your-one-on-ones/#comments Sun, 18 Aug 2024 01:46:03 -0700 itdepends.podbean.com/b24eb0ec-385d-3bea-b9d5-34c1748a7d98 In this episode of the "It Depends" podcast, Kevin Goldsmith, a seasoned Chief Technology Officer, explores the importance of effective one-on-one meetings between managers and their direct reports. Drawing from his extensive experience, Kevin offers practical tips for making these meetings more productive and engaging, such as taking walks during the meetings or using tactile objects to encourage conversation.

He emphasizes the need for consistency in holding one-on-ones, particularly in remote work settings, and discusses how these meetings are crucial for building trust and ensuring that employees feel valued. This episode is a must-listen for managers looking to enhance their leadership skills and foster better communication with their teams.

Links to things mentioned in the podcast:

]]> In this episode of the "It Depends" podcast, Kevin Goldsmith, a seasoned Chief Technology Officer, explores the importance of effective one-on-one meetings between managers and their direct reports. Drawing from his extensive experience, Kevin offers practical tips for making these meetings more productive and engaging, such as taking walks during the meetings or using tactile objects to encourage conversation.

He emphasizes the need for consistency in holding one-on-ones, particularly in remote work settings, and discusses how these meetings are crucial for building trust and ensuring that employees feel valued. This episode is a must-listen for managers looking to enhance their leadership skills and foster better communication with their teams.

Links to things mentioned in the podcast:

]]> Kevin Goldsmith false No 1404 17 full Addressing the challenges of partially distributed engineering teams Addressing the challenges of partially distributed engineering teams https://podcast.itdependsbook.net/e/addressing-the-challenges-of-partially-distributed-engineering-teams/ https://podcast.itdependsbook.net/e/addressing-the-challenges-of-partially-distributed-engineering-teams/#comments Sun, 04 Aug 2024 02:40:11 -0700 itdepends.podbean.com/1ac6b160-340b-3808-a961-8d56a7437617 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:

]]> 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:

]]> Kevin Goldsmith false No 1985 16 full A Resignation Can Be an Opportunity A Resignation Can Be an Opportunity https://podcast.itdependsbook.net/e/a-resignation-can-be-an-opportunity/ https://podcast.itdependsbook.net/e/a-resignation-can-be-an-opportunity/#comments Sun, 21 Jul 2024 00:10:00 -0700 itdepends.podbean.com/9ee8d195-9e7e-320b-a4d2-e8f44b456e3b In this episode of the "It Depends" podcast, host Kevin Goldsmith, a seasoned CTO and tech executive, explores the valuable lessons that can be gleaned from employee resignations. Drawing from his extensive experience and insights from his book "It Depends: Writing on Technology Leadership 2012-2022," Kevin delves into how a resignation can actually present a unique opportunity for growth and improvement within a team.

 

Kevin discusses the emotional and professional impacts of resignations, the pitfalls of unhealthy retention, and the importance of fostering a dynamic team environment. He shares anecdotes from his career, including experiences at Adobe and Spotify, highlighting how to handle resignations constructively and turn them into opportunities for positive change.

 

Listen in to learn how to transform the challenge of losing a team member into a strategic advantage, improve your management skills, and create a more resilient and innovative team.

]]> In this episode of the "It Depends" podcast, host Kevin Goldsmith, a seasoned CTO and tech executive, explores the valuable lessons that can be gleaned from employee resignations. Drawing from his extensive experience and insights from his book "It Depends: Writing on Technology Leadership 2012-2022," Kevin delves into how a resignation can actually present a unique opportunity for growth and improvement within a team.

 

Kevin discusses the emotional and professional impacts of resignations, the pitfalls of unhealthy retention, and the importance of fostering a dynamic team environment. He shares anecdotes from his career, including experiences at Adobe and Spotify, highlighting how to handle resignations constructively and turn them into opportunities for positive change.

 

Listen in to learn how to transform the challenge of losing a team member into a strategic advantage, improve your management skills, and create a more resilient and innovative team.

]]> Kevin Goldsmith false No 1839 15 full What do I look for when hiring an engineer? What do I look for when hiring an engineer? https://podcast.itdependsbook.net/e/what-do-i-look-for-when-hiring-an-engineer/ https://podcast.itdependsbook.net/e/what-do-i-look-for-when-hiring-an-engineer/#comments Sun, 07 Jul 2024 00:00:25 -0700 itdepends.podbean.com/d764bc46-d6e2-3bad-be25-059d7c1e3827 Welcome to the It Depends podcast with your host, Kevin Goldsmith! Kevin is a seasoned Chief Technology Officer with over 30 years of experience in software development, having worked in both colossal companies and budding startups. In each episode, Kevin delves deeper into the chapters, offering more context and behind-the-scenes stories.

 

This week, Kevin revisits a chapter from 2013: What Do I Look for When Hiring an Engineer? Tune in as he discusses the evolution of hiring practices in the tech industry, shares personal anecdotes from his days at Microsoft, and provides valuable advice on navigating the ever-changing landscape of job interviews.

Links:

]]> Welcome to the It Depends podcast with your host, Kevin Goldsmith! Kevin is a seasoned Chief Technology Officer with over 30 years of experience in software development, having worked in both colossal companies and budding startups. In each episode, Kevin delves deeper into the chapters, offering more context and behind-the-scenes stories.

 

This week, Kevin revisits a chapter from 2013: What Do I Look for When Hiring an Engineer? Tune in as he discusses the evolution of hiring practices in the tech industry, shares personal anecdotes from his days at Microsoft, and provides valuable advice on navigating the ever-changing landscape of job interviews.

Links:

]]> Kevin Goldsmith false No 2033 14 full Every Decision Creates a Policy Every Decision Creates a Policy https://podcast.itdependsbook.net/e/every-decision-creates-a-policy/ https://podcast.itdependsbook.net/e/every-decision-creates-a-policy/#comments Sun, 23 Jun 2024 00:01:00 -0700 itdepends.podbean.com/477a5d83-9f27-3531-9dd8-880ea53b08fb In this episode of the "It Depends" podcast, host Kevin Goldsmith delves into the complexities of decision-making in management and its implications on organizational policy. Titled "Every Decision Creates a Policy," this chapter is particularly significant, highlighting common managerial pitfalls and their long-term effects on company culture and consistency.

Kevin shares his extensive experience to illustrate how seemingly simple approvals can set precedents, inadvertently shaping future policies. He explains scenarios where inconsistent decisions led to perceived favoritism and ultimately necessitated the imposition of strict, rigid policies that curtailed previously enjoyed freedoms. The episode emphasizes the importance of consistency and transparency in managerial decisions to maintain trust and morale within the team.

Listeners will gain insights into the nuanced impact of their decisions and learn practical strategies for aligning individual managerial actions with broader organizational values. This episode is crucial for managers, leaders, and anyone interested in understanding the ripple effects of their choices in a corporate environment.

 

Links:

]]> In this episode of the "It Depends" podcast, host Kevin Goldsmith delves into the complexities of decision-making in management and its implications on organizational policy. Titled "Every Decision Creates a Policy," this chapter is particularly significant, highlighting common managerial pitfalls and their long-term effects on company culture and consistency.

Kevin shares his extensive experience to illustrate how seemingly simple approvals can set precedents, inadvertently shaping future policies. He explains scenarios where inconsistent decisions led to perceived favoritism and ultimately necessitated the imposition of strict, rigid policies that curtailed previously enjoyed freedoms. The episode emphasizes the importance of consistency and transparency in managerial decisions to maintain trust and morale within the team.

Listeners will gain insights into the nuanced impact of their decisions and learn practical strategies for aligning individual managerial actions with broader organizational values. This episode is crucial for managers, leaders, and anyone interested in understanding the ripple effects of their choices in a corporate environment.

 

Links:

]]> Kevin Goldsmith false No 1844 1 13 full Protecting Your Team From Layoffs Protecting Your Team From Layoffs https://podcast.itdependsbook.net/e/protecting-your-team-from-layoffs/ https://podcast.itdependsbook.net/e/protecting-your-team-from-layoffs/#comments Sun, 09 Jun 2024 00:03:00 -0700 itdepends.podbean.com/2f3124cd-5ea4-3fbe-893d-65a497950bf4 This chapter discusses what you can do as a manager to protect your team from layoffs: Ensure the team is aligned with company goals. Raising the visibility of the good work of the individuals on the team. Managing performance. All of these things will help when someone is trying to decide if anyone from your team should be laid off. This episode adds more information for individuals and talks about how managers are judged more by the work of their team and less by their own individual contributions.

Links:

]]> This chapter discusses what you can do as a manager to protect your team from layoffs: Ensure the team is aligned with company goals. Raising the visibility of the good work of the individuals on the team. Managing performance. All of these things will help when someone is trying to decide if anyone from your team should be laid off. This episode adds more information for individuals and talks about how managers are judged more by the work of their team and less by their own individual contributions.

Links:

]]> While nothing can guarantee you will never have to lay off someone from your team, ensuring the team is aligned with company goals and that the team’s good work is visible will help protect them. This episode includes specific tips to help. Kevin Goldsmith false No 1745 1 12 full The P Word (Politics at work) The P Word (Politics at work) https://podcast.itdependsbook.net/e/the-p-word-politics-at-work/ https://podcast.itdependsbook.net/e/the-p-word-politics-at-work/#comments Sun, 26 May 2024 00:01:26 -0700 itdepends.podbean.com/d7e0f82d-6531-310d-bb3a-0c5e402200ed Politics! The word has such a negative connotation when discussing work and corporate culture. Political tactics or maneuvers aren't inherently bad. It is the intent behind them that makes them so. You can leverage those same tactics for good instead of evil.

In this episode, Kevin delves into 'The P Word' and discusses the good and bad sides of politics in the workplace based on his own experiences. Whether you're navigating corporate hallways or startup pathways, this one's packed with insights you don't want to miss.

 

Links:

]]> Politics! The word has such a negative connotation when discussing work and corporate culture. Political tactics or maneuvers aren't inherently bad. It is the intent behind them that makes them so. You can leverage those same tactics for good instead of evil.

In this episode, Kevin delves into 'The P Word' and discusses the good and bad sides of politics in the workplace based on his own experiences. Whether you're navigating corporate hallways or startup pathways, this one's packed with insights you don't want to miss.

 

Links:

]]> In this episode, Kevin delves into ’The P Word’ and discusses the good and bad sides of politics in the workplace based on his own experiences. Whether you’re navigating corporate hallways or startup pathways, this one’s packed with insights you don’t want to miss. Kevin Goldsmith false No 1760 1 11 full Creating a Vernacular With Your Engineering Team Creating a Vernacular With Your Engineering Team https://podcast.itdependsbook.net/e/creating-a-vernacular-with-your-engineering-team/ https://podcast.itdependsbook.net/e/creating-a-vernacular-with-your-engineering-team/#comments Sun, 12 May 2024 00:14:00 -0700 itdepends.podbean.com/9bffabd0-1d9c-3978-8715-88fd02aeac2f Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team works together and to make it easier when onboarding new members.

 

Links:

]]> Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team works together and to make it easier when onboarding new members.

 

Links:

]]> Teams create their own languages organically, which is essential to team bonding and belonging. Understand this and use it to improve how your team works together and to make it easier when onboarding new members. Kevin Goldsmith false No 1280 10 full Becoming a CTO Becoming a CTO https://podcast.itdependsbook.net/e/becoming-a-cto/ https://podcast.itdependsbook.net/e/becoming-a-cto/#comments Sun, 28 Apr 2024 00:30:00 -0700 itdepends.podbean.com/b03913bb-167b-302d-be49-7215f0fe02d6 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.

More information about the book is at itdependsbook.net Questions/comments? contact@itdependsbook.net The newsletter: kevingoldsmith.substack.com Your Host: Kevin Goldsmith

]]> 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.

More information about the book is at itdependsbook.net
Questions/comments? contact@itdependsbook.net
The newsletter: kevingoldsmith.substack.com
Your Host: Kevin Goldsmith

]]> 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. Kevin Goldsmith false No 2062 9 full How I Get My Focused Work Done / The Known Unknowns How I Get My Focused Work Done / The Known Unknowns https://podcast.itdependsbook.net/e/how-i-get-my-focused-work-done-the-known-unknowns/ https://podcast.itdependsbook.net/e/how-i-get-my-focused-work-done-the-known-unknowns/#comments Sun, 14 Apr 2024 02:50:47 -0700 itdepends.podbean.com/eb15f56d-6c7b-3b08-b54d-eee4e8d4545d Once again, two shorter chapters in this podcast from the book.

How I get my focused work done: When you are a manager, constantly interrupted, how can you get focus time to devote to your projects?

The Known Unknowns: Understanding the mastery curve.

Links: Book/Podcast/Newsletter website: https://itdependsbook.net/ Questions/Comments/Suggestions contact@itdependsbook.net

 

]]> Once again, two shorter chapters in this podcast from the book.

How I get my focused work done:
When you are a manager, constantly interrupted, how can you get focus time to devote to your projects?

The Known Unknowns:
Understanding the mastery curve.

Links:
Book/Podcast/Newsletter website: https://itdependsbook.net/
Questions/Comments/Suggestions contact@itdependsbook.net

 

]]> Kevin Goldsmith false No 1416 8 full Own Your Calendar / Work Deliberately Own Your Calendar / Work Deliberately https://podcast.itdependsbook.net/e/ownyourcalendar/ https://podcast.itdependsbook.net/e/ownyourcalendar/#comments Sun, 31 Mar 2024 00:15:00 -0700 itdepends.podbean.com/e6c75165-956d-3b2d-b959-3e4b58c9ce4a Two chapters from the book this week! Discussing a deliberate approach to managing your calendar and tracking how you actually are using your time, and then how to approach your work with thoughtfulness and decisiveness instead of just making decisions based on instinct. More information about the book: https://itdependsbook.net/

Ask a question or request a signed copy: contact@itdependsbook.net

The newsletter: https://kevingoldsmith.substack.com/

]]> Two chapters from the book this week! Discussing a deliberate approach to managing your calendar and tracking how you actually are using your time, and then how to approach your work with thoughtfulness and decisiveness instead of just making decisions based on instinct.

More information about the book: https://itdependsbook.net/

Ask a question or request a signed copy: contact@itdependsbook.net

The newsletter: https://kevingoldsmith.substack.com/

]]> Kevin Goldsmith false No 1632 7 full The Personal Strategy Off-site The Personal Strategy Off-site https://podcast.itdependsbook.net/e/the-personal-strategy-off-site/ https://podcast.itdependsbook.net/e/the-personal-strategy-off-site/#comments Sun, 17 Mar 2024 00:31:15 -0700 itdepends.podbean.com/30a8f292-111e-3129-8eaa-e0929072e917 Taking a day, once, twice, or even four times a year to reflect on how things are going and think about where you want to go next is a valuable practice. This episode includes how to approach this practice and get value from it. This episode also includes Chapter 5 of the audiobook "It Depends: Writing on Technology Leadership 2012-2022" by Kevin Goldsmith. 

It Depends Book website: https://itdependsbook.net/

CTO Podcast link: https://pod.link/1356275803/episode/7a88eac00279eb4bd3172b9a59d21ab7

Jason Cavness Experience Podcast Link: 

https://www.youtube.com/watch?v=aoUR0bj9BGQ&list=PLh4aquRHsHCZfVVGNO7IY9-5Z0IF8XgwZ

Have a question you'd like me to answer? Send it to: contact@itdependsbook.net

Buy the book on Amazon or bookshop.org

]]> Taking a day, once, twice, or even four times a year to reflect on how things are going and think about where you want to go next is a valuable practice. This episode includes how to approach this practice and get value from it. This episode also includes Chapter 5 of the audiobook "It Depends: Writing on Technology Leadership 2012-2022" by Kevin Goldsmith. 

It Depends Book website: https://itdependsbook.net/

CTO Podcast link: https://pod.link/1356275803/episode/7a88eac00279eb4bd3172b9a59d21ab7

Jason Cavness Experience Podcast Link: 

https://www.youtube.com/watch?v=aoUR0bj9BGQ&list=PLh4aquRHsHCZfVVGNO7IY9-5Z0IF8XgwZ

Have a question you'd like me to answer? Send it to: contact@itdependsbook.net

Buy the book on Amazon or bookshop.org

]]> Kevin Goldsmith false No 1351 6 full When, why, and how to stop coding as your day job When, why, and how to stop coding as your day job https://podcast.itdependsbook.net/e/when-why-and-how-to-stop-coding-as-your-day-job/ https://podcast.itdependsbook.net/e/when-why-and-how-to-stop-coding-as-your-day-job/#comments Sun, 03 Mar 2024 07:00:00 -0800 itdepends.podbean.com/5709b65d-b662-3108-8298-0ddcd60eea87 One of the questions I most frequently get from engineering leaders or aspiring leads is "how much coding do you do?" or "How do you handle coding and managing?" One of the hardest things for me in my development journey was letting go of developing features on the products I worked on. This episode is all about that. I include Chapter 4 of the audiobook for It Depends: Writing on Technology Leadership 2012-2022, which is all about this step in your development as a more senior engineering leader.

Links:

]]> One of the questions I most frequently get from engineering leaders or aspiring leads is "how much coding do you do?" or "How do you handle coding and managing?" One of the hardest things for me in my development journey was letting go of developing features on the products I worked on. This episode is all about that. I include Chapter 4 of the audiobook for It Depends: Writing on Technology Leadership 2012-2022, which is all about this step in your development as a more senior engineering leader.

Links:

]]> Kevin Goldsmith false No 1608 5 full Taking a thoughtful approach to the job search process Taking a thoughtful approach to the job search process https://podcast.itdependsbook.net/e/taking-a-thoughtful-approach-to-the-job-search-process/ https://podcast.itdependsbook.net/e/taking-a-thoughtful-approach-to-the-job-search-process/#comments Sun, 18 Feb 2024 07:30:00 -0800 itdepends.podbean.com/20a95849-52ed-3785-99d3-2882932aa4d5 Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022

In this episode, we discuss my experience building an exercise to help me better understand what is important to me in a role or company and then how I used the results to help prepare for job interviews. I also discuss some of the mistakes people make when interviewing for roles in a downturn with how they present themselves in job interviews. If you're currently looking for a job, or thing you will in the future (we all will), this episode will be helpful.

Some links:

 

]]> Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022

In this episode, we discuss my experience building an exercise to help me better understand what is important to me in a role or company and then how I used the results to help prepare for job interviews. I also discuss some of the mistakes people make when interviewing for roles in a downturn with how they present themselves in job interviews. If you're currently looking for a job, or thing you will in the future (we all will), this episode will be helpful.

Some links:

 

]]> Kevin Goldsmith false No 1612 4 full The challenge of top-down change and the Microsoft layoffs The challenge of top-down change and the Microsoft layoffs https://podcast.itdependsbook.net/e/the-challenge-of-top-down-change-and-the-microsoft-layoffs/ https://podcast.itdependsbook.net/e/the-challenge-of-top-down-change-and-the-microsoft-layoffs/#comments Sun, 04 Feb 2024 08:10:00 -0800 itdepends.podbean.com/f8c57a43-d5da-3923-b26f-ad2ebf42ee25 How can top-down culture change be effective? Looking at Microsoft and Yahoo as examples.

 

Links:

It Depends book: https://itdependsbook.net

Questions/comments: contact@itdependsbook.net

]]> How can top-down culture change be effective? Looking at Microsoft and Yahoo as examples.

 

Links:

It Depends book: https://itdependsbook.net

Questions/comments: contact@itdependsbook.net

]]> Kevin Goldsmith false No 1258 3 full Fail Safe, Fail Smart... Succeed! Fail Safe, Fail Smart... Succeed! https://podcast.itdependsbook.net/e/fail-safe-fail-smart-succeed/ https://podcast.itdependsbook.net/e/fail-safe-fail-smart-succeed/#comments Sun, 21 Jan 2024 00:07:06 -0800 itdepends.podbean.com/fa061929-bd30-378d-a89d-9925cee8cfdc We discuss how critical failure is to innovation and how to handle failure well. We talk about how software used to be written, Clippy and why it was bound to fail, how Spotify uses the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more...

links:

  • Newsletter: kevingoldsmith.substack.com
  • Book: itdependsbook.net
  • Videos of the talk: kevingoldsmith.com/talks/fail-fast-fail-smart-succeed.html
]]> We discuss how critical failure is to innovation and how to handle failure well. We talk about how software used to be written, Clippy and why it was bound to fail, how Spotify uses the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more...

links:

  • Newsletter: kevingoldsmith.substack.com
  • Book: itdependsbook.net
  • Videos of the talk: kevingoldsmith.com/talks/fail-fast-fail-smart-succeed.html
]]> We discuss how critical failure is to innovation and how to handle failure well. We talk about how software used to be written, Clippy and why it was bound to fail, how Spotify uses the Think It/Build It/Ship It/Tweak It framework to build fail-safe products, and more... Kevin Goldsmith false No 3430 2 full Introduction Introduction https://podcast.itdependsbook.net/e/00-introduction/ https://podcast.itdependsbook.net/e/00-introduction/#comments Sun, 07 Jan 2024 22:01:03 -0800 itdepends.podbean.com/5672d498-02d9-3017-aa31-d94ec0b085e6 Welcome to the podcast! This episode introduces the podcast and includes the introduction to the book "It Depends: Writing on Technology Leadership 2012-2022" by Kevin Goldsmith.

 

Links:

Book info https://itdependsbook.net/

Blog https://blog.kevingoldsmith.com/

 

 

]]> Welcome to the podcast! This episode introduces the podcast and includes the introduction to the book "It Depends: Writing on Technology Leadership 2012-2022" by Kevin Goldsmith.

 

Links:

Book info https://itdependsbook.net/

Blog https://blog.kevingoldsmith.com/

 

 

]]> Welcome to the podcast! This episode introduces the podcast and includes the introduction to the book ”It Depends: Writing on Technology Leadership 2012-2022” by Kevin Goldsmith. Links: Book info https://itdependsbook.net/ Blog https://blog.kevingoldsmith.com/ Kevin Goldsmith false No 498 1 full