New episode of It Depends: "Working with the CEO."
You need to be close enough to influence, independent enough to be honest, and aligned enough to execute when you disagree. Most of us get one of those wrong.
itdependspod.com/episodes/wor...
My friend Omar Shahine recently shared his farewell message as VP of Microsoft Word. His leadership takeaways struck a chord.
I’ll admit I long underrated the value of kindness. Being perceived as a jerk puts a ceiling on your career growth unless you’re the CEO.
New newsletter: "Don't Let Your Boss Do Your Job."
If your boss steps in on something that was yours, they're not helping you. They're doing your job for you. And everyone sees it.
Signal, route, verify.
kevingoldsmith.substack.com/p/dont-let-y...
New newsletter: "Don't Let Your Boss Do Your Job."
If your boss steps in on something that was yours, they're not helping you. They're doing your job for you. And everyone sees it.
Signal, route, verify.
kevingoldsmith.substack.com/p/dont-let-y...
New episode of It Depends: "Don't Let Your Boss Do Your Job."
When an issue shows up, and you wait to respond, your boss doesn't see "I'm working on it." They see silence. And silence reads as "nobody's on it."
itdependspod.com/episodes/don...
Everyone knows that the key to "focus" and "simplicity" in User Experience is to shove all the unrelated things you've been trying into a single application.
New in the It Depends newsletter: how to develop systems thinking
I've been telling people to learn systems thinking for years without explaining how. This is my attempt to fix that, with a four-stage progression and practical exercises.
kevingoldsmith.substack.com/p/every-orga...
The nicest article about JPEG compression, by @sophielwang.bsky.social The moment there are color stats involved, I’m in.
It’s so well done it makes me think we need some kind of online library where articles like this get preserved.
www.sophielwang.com/blog/jpeg
New episode of It Depends: "Every Organization Is a System. Are You Designing It or Just Living in It?"
I've been telling people to learn systems thinking for years without teaching how. This episode is my attempt to fix that.
itdependspod.com/episodes/eve...
New newsletter: "The Director to CTO Path: How to Follow It, or How to Mentor It."
Three shifts define the path from Director to CTO. I break them down, plus how to mentor someone through them if you're further along.
kevingoldsmith.substack.com/p/the-direct...
I think "sorry, I am late. I was arguing with my LLM and lost track of time" is a totally valid reason for being a little late to a meeting in 2026.
New ep of It Depends: "The Director to CTO Path: How to Follow It, or How to Mentor It."
The job doesn't just get bigger. It gets fundamentally different. I map out what that shift actually looks like at each level.
itdependspod.com/episodes/the...
When an exec interrupts your presentation, they're telling you what the meeting is actually about. I've been on both sides of this and share what I've learned.
New issue of the It Depends newsletter is out. kevingoldsmith.substack.com/p/talking-to...
#ExecutiveCommunication
One could argue that this path might create a zillion vulnerable applications, but the non-deterministic nature of AI-generated code means each application would have different issues, which could mean fewer zero-days.
This is interesting. Folks have talked about how a prompt could replace a repository, but here is an actual, valid use case for it.
www.dbreunig.com/2026/01/08/a...
New episode of It Depends: "Talking to Executives: That's Not a Derailment, That's the Meeting."
When an exec interrupts your presentation, they're telling you what the meeting is actually about. I've been on both sides of this and share what I've learned.
itdependspod.com/episodes/tal...
The hardest leadership transitions aren’t about learning new skills.
They’re about unlearning the ones that used to work.
Managing managers means moving from decisions to context, from comfort to leverage.
kevingoldsmith.substack.com/p/the-shift-...
The hardest part of managing managers? Realizing that feeling indispensable is a warning sign, not a success metric.
New episode of It Depends: how to shift from being a decision-making bottleneck to providing context and leverage. itdependspod.com/episodes/the...
At some point in leadership, you outrun your own resume.
You’re responsible for systems, teams, and domains you’ve never personally worked in. Trying to stay the expert doesn’t scale. Ignoring the work doesn’t either.
kevingoldsmith.substack.com/p/leading-wh...
Did I just invent this, or did someone else already come up with this idea?
"Zoom Chicken": Show up to the meeting as late as you can without being the last one to arrive. Alternate rule: Show up as late as you can while still being the first to show up. Company culture dictates which rule you use.
Was planning my day tomorrow and may have come up with the title of my next book. "6 meetings before lunch: the job of the CTO"
New episode of the It Depends: Lessons in Technology Leadership Podcast - "Leading What You’ve Never Done Before"
Your scope will eventually outrun your resume.
The job isn’t to become an expert in everything; it’s to lead the system around it.
itdependspod.com/episodes/lea...
Experience makes the job easier.
That’s also when growth quietly stalls.
This week’s newsletter is about reflection as a leadership skill. Not journaling for journaling’s sake, but deliberate time to avoid running the same playbook forever.
kevingoldsmith.substack.com/p/reflection...
New podcast episode for the new year! Why a reflection practice is critical as you move into senior leadership (because no one else is going to be focusing on developing you). You can’t lead others to grow if you’ve stopped growing yourself.
pod.link/1724860326/e...
Most engineering orgs don’t struggle because they lack process.
They struggle because the process they have doesn’t match the problem they’re trying to solve.
This week’s issue is about treating process as a coordination, pruning it when it stops helping.
kevingoldsmith.substack.com/p/process-is...
Tech debt isn’t inherently good or bad. It’s information.
Some debt is a smart trade-off
Some is safe to ignore
Some is genuinely dangerous
Some is a warning that leadership systems, not code, need attention
The problem isn’t debt. It’s unexamined debt.
kevingoldsmith.substack.com/p/tech-debt-...
Registered for the #ATmosphere conference! See you in March!
