It Depends: Lessons in Technology Leadership

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: Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends Newsletter

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: The Humanizing Work Show: https://www.humanizingwork.com/kevin-goldsmith/Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6The book: It Depends: Writing on Technology 2012-2022This chapter in the newsletterYour host: Kevin GoldsmithThe It Depends Newsletter

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: Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends NewsletterManagement 3.0Thinking in SystemsArchitecture and Organization

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends Newsletter"How do you keep growing when you are the leader of the organization" - my talk from LeadingEng 2022My "Management Books" Goodreads shelfThe newsletter issue with this chapter

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends NewsletterHow Does Salary Work? (LeadDev Berlin 2019The newsletter issue with this chapter

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends Newsletter

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends NewsletterThe Assembling the data newsletter issueLeadingEng NYC 2024 (use the discount code "Distrokid" for 10% off the registration price)

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: Manager Tools Podcasts on one-on-onesThe book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe It Depends NewsletterLeadingEng NYC 2024 (use the discount code "Distrokid" for 10% off the registration price)

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: Video and slides from Leading Distributed TeamsThe book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe newsletterLeadingEng NYC 2024 (use the discount code "Distrokid" for 10% off the registration price)

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.

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe newsletterLeadingEng NYC 2024 (use the discount code "Distrokid" for 10% off the registration price)

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe newsletterLeadingEng 2024

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe newsletterLeadingEng 2024

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: The book: It Depends: Writing on Technology 2012-2022Your host: Kevin GoldsmithThe newsletter

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: The newsletter with the text of the chapter: https://kevingoldsmith.substack.com/p/building-a-vernacular-with-your-engineering"It Depends: Writing on Technology Leadership 2012-2022" https://itdependsbook.netIt Depends newsletter: https://kevingoldsmith.substack.comQuestions/comments: contact@itdependsbook.net

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

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

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/

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

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: The book website: https://itdependsbook.net/My talk on the same subject: https://www.kevingoldsmith.com/talks/when-why-and-how-to-stop-coding-as-your-day-job.htmlHave a question you'd like me to answer? Send it to: contact@itdependsbook.netBuy the book on Amazon or bookshop.org