It Depends: Lessons in Technology Leadership

By Kevin Goldsmith

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Category: Management

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Episodes: 72

Description

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

Episode Date
The Outsider's Audit: Due Diligence on Your Own Org
Sep 27, 2026
Paying for Nothing to Happen: Budgeting for Security, Compliance, and Reliability
Sep 13, 2026
The Agent Doesn't Know It's a Prototype: Team Autonomy in the Agentic Software Development Era
Aug 30, 2026
Build vs Buy When Building Got Cheap
Aug 16, 2026
ENCORE: Taking a thoughtful approach to the job search process
Aug 02, 2026
ENCORE: Protecting Your Team From Layoffs
Jul 19, 2026
ENCORE: Creating a Vernacular With Your Engineering Team
Jul 05, 2026
Managing Sideways: Everyone Nodded, Then Nothing Happened.
Jun 21, 2026
The Reliable Team Trap: Why Execution Excellence Doesn't Earn You Influence
Jun 07, 2026
The Conversation Before the Conversation
May 24, 2026
The Interesting Changes Aren't Happening in the IDE
May 10, 2026
Becoming a Business Leader
Apr 26, 2026
Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest
Apr 12, 2026
Don't Let Your Boss Do Your Job
Mar 29, 2026
Every Organization Is a System. Are You Designing It or Just Living in It?
Mar 15, 2026
The Director to CTO Path: How to Follow It, or How to Mentor It
Mar 01, 2026
Talking to Executives: That's Not a Derailment, That's the Meeting
Feb 15, 2026
The Shift to Managing Managers
Feb 01, 2026
Leading What You've Never Done Before
Jan 18, 2026
Success Makes You Dangerous: Why Comfortable Leaders Stop Growing
Jan 04, 2026
The Right Amount of Process: Finding the Balance Between Chaos and Bureaucracy
Dec 21, 2025
Technical Debt Isn't the Enemy: A Strategic Framework for Engineering Leaders
Dec 07, 2025
Demystifying Board Meetings: A CTO's Perspective
Nov 23, 2025
Crafting a Technical Strategy
Nov 09, 2025
Making Technology Choices That Last
Oct 26, 2025
The Hidden Architecture of Engineering: Practical Lessons in Organizational Design
Oct 12, 2025
Values → Culture → Everything: Why Company Culture Actually Matters
Sep 28, 2025
How to Handle Career Gaps and What CTOs Actually Do All Day
Sep 14, 2025
ENCORE: The Myth of the Startup in a Large Company with Kevin Stewart
Aug 31, 2025
ENCORE: Building a technical career path at Spotify
Aug 17, 2025
ENCORE: Addressing the challenges of partially distributed engineering teams
Aug 03, 2025
ENCORE: Becoming a CTO
Jul 20, 2025
ENCORE: Fail Safe, Fail Smart... Succeed!
Jul 06, 2025
Why I Wrote a Book: A Meta Episode on Self-Publishing and DIY Business
Jun 22, 2025
Answers That Depend: Tech Leadership Q&A Part 3
Jun 08, 2025
Answers that Depend: Tech Leadership Q & A pt 2
May 25, 2025
Answers That Depend: Tech Leadership Q&A Part 1
May 11, 2025
Succession for Scale
Apr 27, 2025
The Myth of the Startup in a Large Company with Kevin Stewart
Apr 13, 2025
Lessons From Creating The Spotify Technology Career Steps
Mar 30, 2025
Spotify Technology Career Steps
Mar 16, 2025
Building a technical career path at Spotify
Mar 02, 2025
Changing Hiring Practices to Build a More Diverse Technology Organization
Feb 16, 2025
A diversity challenge: tech start-ups have a great opportunity
Feb 02, 2025
Building a Management Training Curriculum at Avvo
Jan 19, 2025
Using Self-Selection to Create Journey Teams at Avvo
Jan 05, 2025
Thoughts on emulating Spotify’s matrix organization in other companies
Dec 22, 2024
The Spotify model: how to create, dissolve, and remix teams to be more dynamic and more innovative
Dec 08, 2024
Transcript of my speech from OPEX Week Summer 2018
Nov 24, 2024
Hiring Agile Coaches
Nov 10, 2024
Management and Systems Thinking
Oct 27, 2024
Writing Useful Performance Reviews: Delivering the Review
Oct 13, 2024
Writing Useful Performance Reviews: Making a Raise Recommendation
Sep 29, 2024
Writing Useful Performance Reviews: Evaluating the data and writing the review
Sep 15, 2024
Writing Useful Performance Reviews: Assembling the data
Sep 01, 2024
Twenty Questions For Your One-on-Ones
Aug 18, 2024
Addressing the challenges of partially distributed engineering teams
Aug 04, 2024
A Resignation Can Be an Opportunity
Jul 21, 2024
What do I look for when hiring an engineer?
Jul 07, 2024
Every Decision Creates a Policy
Jun 23, 2024
Protecting Your Team From Layoffs
Jun 09, 2024
The P Word (Politics at work)
May 26, 2024
Creating a Vernacular With Your Engineering Team
May 12, 2024
Becoming a CTO
Apr 28, 2024
How I Get My Focused Work Done / The Known Unknowns
Apr 14, 2024
Own Your Calendar / Work Deliberately
Mar 31, 2024
The Personal Strategy Off-site
Mar 17, 2024
When, why, and how to stop coding as your day job
Mar 03, 2024
Taking a thoughtful approach to the job search process
Feb 18, 2024
The challenge of top-down change and the Microsoft layoffs
Feb 04, 2024
Fail Safe, Fail Smart... Succeed!
Jan 21, 2024
Introduction
Jan 08, 2024