Working with the CEO: Close Enough to Influence, Independent Enough to Be Honest
The CTO-to-CEO relationship is the highest leverage relationship in your career as a technology leader, and it's the on...
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
Don't Let Your Boss Do Your Job
Your boss doesn't step into your area because they want to micromanage. They step in because nobody said "I got it," an...
Every Organization Is a System. Are You Designing It or Just Living in It?
Have you ever felt like you're solving the same problems over and over, just in different forms? That's usually a sign...
The Director to CTO Path: How to Follow It, or How to Mentor It
The path from Director to CTO isn't a single ladder. It's a gradual expansion across three dimensions: your focus widen...
Talking to Executives: That's Not a Derailment, That's the Meeting
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,...
The Shift to Managing Managers
Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders strugg...
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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