The path from Director to CTO isn't a single ladder. It's a gradual expansion across three dimensions: your focus widens from your team to the company to the industry, your orientation shifts from execution to operations to strategy, and your technical breadth grows from narrow specialist to broad generalist.

In this episode, Kevin maps out what that progression actually looks like at each level, drawing on his own career through Adobe, Spotify, and multiple startups. He shares practical ways to develop the skills you need before you need them, from taking finance people to lunch and shadowing unfamiliar teams, to aligning your team's work with company strategy, even when the company is moving in a direction you didn't expect.

Kevin also covers the mentoring side. If you're already a VP or CTO, how do you identify high-potential leaders and intentionally develop them? He talks about delegation, transparency, and giving feedback that's aimed at the next level, not just the current one.

Whether you're a director trying to figure out what VP-level thinking actually looks like, or a CTO thinking about how to grow the leaders behind you, this episode gives you a concrete framework for both.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)

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, Kevin talks about executive communication from both sides of the table. Early in his career, he learned the hard way that being right doesn't matter if you're not being understood (a Microsoft VP made sure he never forgot that lesson). Now, as a CTO, he watches people make the same mistakes he did.

Kevin shares a practical framework for communicating to executives: the Four C's of Clarity, Context, Consequence, and Control. He also talks about why executives interrupt, why they sometimes just get up and leave, and why protecting your credibility matters more than protecting your ego.

Whether you're presenting to senior leaders for the first time or trying to get better at it, this episode will help you walk in with more confidence and a better understanding of what's actually going on in the room.

• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)

Moving from managing individual contributors to managing managers requires a fundamental shift that many leaders struggle with. In this episode, Kevin shares lessons from his own difficult transition, where staying too close to the work actually limited both his team's growth and his own.

The core challenge isn't autonomy versus control. It's leverage versus comfort. When you focus too far down into your organization, you become an information bottleneck, your managers lose ownership, and your own leadership growth stalls. The job fundamentally changes: your leverage no longer comes from making decisions, but from providing context.

Kevin covers the warning signs of overmanaging (managers escalating decisions that clearly belong to them, work slowing when you're unavailable), practical frameworks for delegating effectively, and why feeling indispensable is usually a red flag, not a success metric.

A key test: Could you step away for two weeks? Would your managers make good decisions without you? If not, you might be the problem.

• Using Agile Techniques to Build a More Inclusive Team: https://www.youtube.com/watch?v=Atfxtk2Q90k
• Every Decision Creates a Policy: https://itdependspod.com/episodes/every-decision-creates-a-policy/
• "Turn the Ship Around!: A True Story of Building Leaders by Breaking the Rules" by L. David Marquet: https://amzn.to/49XH2Ty
• Delegation Poker from Jurgen Appelo: https://medium.com/@jurgenappelo/unclear-team-responsibilities-use-delegation-levels-985537dbea38
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)
• ConFoo 2026 (https://confoo.ca/en/2026)