It Depends: Writing on Technology Leadership 2012-2022, a book by Kevin Goldsmith

a copy of It Depends on a table

If you're an engineering manager, director, or aspiring technology executive, "It Depends: Writing on Technology Leadership 2012-2022" is a must-read collection of essays and articles by seasoned technology executive Kevin Goldsmith. With an impressive thirty-year career that includes leadership roles at industry giants like IBM, Silicon Graphics, Microsoft, and Adobe, as well as startups and unicorns like Spotify, Avvo, Anaconda, and DistroKid, Goldsmith shares his wealth of knowledge in this comprehensive book.

Within its pages, you'll find a diverse range of topics explored, including:

  1. Fostering a culture of experimentation and innovation
  2. Effective day-to-day management
  3. Advancing your career as a technology leader
  4. Building high-performing teams
  5. Practical advice for excelling in an engineering management role

Goldsmith understands that leadership dynamics vary from one company to another and from person to person. In "It Depends," he provides invaluable insights to help leaders craft solutions tailored to their specific company, team, and personal circumstances.

What distinguishes Goldsmith's writing is his ability to offer practical guidance and insights that many companies often overlook in their managerial training. He also delves into transitioning from leading a single team to managing multiple teams, shaping organizational structures, establishing career development frameworks, promoting diversity and inclusion, and optimizing the hiring process.

By immersing yourself in "It Depends," you'll acquire the knowledge and skills needed to become a more effective leader in the dynamic and ever-evolving technology industry.

Order e-book or print copies from:
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The audiobook in available from:
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Praise for It Depends
“It Depends is the PERFECT title for this book on engineering leadership. There is no exact blueprint for success in our field; everything is contextual. Goldsmith uses examples from his journey to provide the reader guidance on how to apply leadership tools and techniques to their particular situation. The combination of pragmatic coaching with a relaxed writing style makes this a highly enjoyable read. Recommended.”
- Kevin Stewart, SVP Engineering, Splice

"While technology is constantly advancing, the core challenges of running tech organizations often remain the same. Kevin's book, a compilation of his previous written work, offers a comprehensive view of the essential aspects of being a tech leader. He shares valuable insights from his journey, extracting essential lessons that are key to growing as a technology leader and building strong software teams and products.

Understanding your specific situation is crucial. In 'It Depends', Kevin uses engaging stories to show that the best approaches are based on a clear understanding of your current challenges and reflections from past experiences."

- Maria Gutierrez, VP of Engineering and Operations, Personio

"I've probably learnt more from Kevin than any other tech leader through our weekly calls while growing my company. His book condenses so many priceless lessons, would highly recommend it!"

- Kimeshan Naidoo, Chief Technology Officer, BX, Founder, Unibuddy
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You can subscribe to the It Depends Podcast to hear chapters from the audiobook with additional context and questions from the audience. Subscribe on your favorite podcast client or on Spotify, Apple, YouTube, Amazon or other apps.
Table of Contents
  1. Engineering Culture
    1. Fail Safe, Fail Smart... Succeed!
    2. The challenge of top-down change and the Microsoft layoffs
  2. Career Development
    1. Taking a thoughtful approach to the job search process
    2. When, why, and how to stop coding as your day job
    3. The Personal Strategy Off-site
    4. Own your calendar
    5. In 2018 Decide to Work Deliberately
    6. How I Get My Focused Work Done
    7. The Known Unknowns
    8. Becoming a CTO
  3. Managing Teams
    1. Building a vernacular with your engineering team
    2. The P-word
    3. Protecting your team from layoffs
    4. Every decision creates a policy
    5. What do I look for when hiring an engineer?
    6. A resignation can be an opportunity
    7. Addressing the challenges of partially distributed engineering teams
    8. Twenty questions for your 1:1s
    9. Writing Useful Performance Reviews: Assembling the data
    10. Writing Useful Performance Reviews: Evaluating the data and writing the review
    11. Writing Useful Performance Reviews: Making a raise recommendation
    12. Writing Useful Performance Reviews: Delivering the review
    13. Management and Systems Thinking
  4. Agile
    1. Hiring Agile Coaches
    2. Transcript of my speech from OPEX Week Summer 2018
  5. Leading Organizations
    1. The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative
    2. Thoughts on emulating Spotify’s matrix organization in other companies
    3. Using Self-Selection to Create Journey Teams at Avvo
    4. Building a Management Training Curriculum at Avvo
    5. A diversity challenge: tech start-ups have a great opportunity
    6. Changing Hiring Practices to Build a More Diverse Technology Organization
    7. Building a technical career path at Spotify
    8. Spotify Technology Career Steps
    9. Things We Learned Creating Technology Career Steps
    10. The Myth of the Startup in a Large Company
    11. Succession for Scale
About the author
photo of Kevin Goldsmith

Kevin Goldsmith is a seasoned technology leader with over three decades of experience in the tech industry. As the current Chief Technology Officer at DistroKid, the world's leading digital music distributor, Kevin plays a pivotal role in shaping the future of music distribution. He is also the Principal and Founder of Nimble Autonomy, LLC, where he provides expert advice and mentorship to emerging start-up leaders and managers.

Previously, Kevin has held several high-profile positions, including Chief Technology Officer at Anaconda, Onfido, and Avvo. He also made significant contributions as the Vice President of Engineering, Consumer at Spotify, Director of Engineering at Adobe Systems, and as a Development Lead at Microsoft. His diverse experience across these significant tech companies showcases his expertise and versatility in the field.

In addition to his corporate roles, Kevin is a well-regarded author and speaker. He has been writing the "Puppies, Flowers, Rainbows and Kittens" blog since 2004, a platform where he shares insights and opinions on various technology topics. His contributions extend to other notable sites like, the Spotify Developer blog, and the Adobe Developer Network. As an internationally recognized keynote speaker, Kevin has shared his knowledge and experiences in over 17 countries, making him a global thought leader in technology.

For more information about Kevin and his work, visit his website at His extensive experience and active engagement in the tech community make him a prominent figure in the technology world.

Please email for media or purchasing inquiries.