Slight or Signal: Learning the Game at Work
A leader is running an initiative, and at an executive meeting his boss gives three of his peers time to talk about it. He gets added at the end, almost as an afterthought. A few days lat...
It Depends
Lessons in Technology Leadership
Kevin Goldsmith brings you lessons and advice from decades in the technology industry.
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Recent Episodes
The Outsider's Audit: Due Diligence on Your Own Org
A CTO needs to hire more engineers, and the numbers are working against the argument. Engineering spend has fallen as a share of revenue because the company grew faster than the team, so...
Paying for Nothing to Happen: Budgeting for Security, Compliance, and Reliability
A vendor the security team wanted, budgeted two years in a row, and never actually bought. When Kevin Goldsmith finally tried to spend the money, his CFO asked what the ROI was, and he di...
The Agent Doesn't Know It's a Prototype: Team Autonomy in the Agentic Software Development Era
A developer builds a working replacement for an internal platform over a weekend using AI tools, then asks leadership why they can't ship it on Tuesday. The code is clean, the architectur...
Build vs Buy When Building Got Cheap
The spreadsheet says building is cheaper now, and the spreadsheet isn't wrong. A vendor's annual license on one line, a couple of developers and some tokens on the other. What that compar...
ENCORE: Taking a thoughtful approach to the job search process
Chapter 3 from It Depends: Writing on Technology Leadership 2012-2022
In this episode, we discuss my experience building an exercise to better understand what is important to me in a role or...
About the Podcast
"It Depends" explores the complex decisions and trade-offs that define technology leadership. Each episode dives deep into real-world scenarios, sharing practical insights from Kevin's extensive experience in the tech industry.
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