Kevin Goldsmith
@kevingoldsmith.com
This is my account for technology leadership posts and announcements. For personal stuff, https://bsky.app/profile/kmg.bsky.social. Author of "It Depends: Writing on Technology Leadership 2012-2022" CTO @ DistroKid https://kevingoldsmith.com
New It Depends episode: “Slight or Signal: Learning the Game at Work” Your boss may hear about your team secondhand and only talk to you once a week. Sometimes what looks like a slight is just something they never knew about. 🎧 itdependspod.com/episodes/sli...
Good numbers hide fragility. Efficiency metrics reward running thin until something breaks, and by the time incidents pile up, you're already in trouble. New in the It Depends newsletter: auditing your own org the way an acquirer would. kevingoldsmith.substack.com/p/the-outsid...
New episode of It Depends: "The Outsider's Audit: Due Diligence on Your Own Org" An acquirer doesn't expect you to be clean. They expect you to know where you're dirty. itdependspod.com/episodes/the...
New: hackers say they have personal data on all FBI employees and spouses. I got a sample of 5,000 alleged employees, including name, physical address, phone number, and in some cases spouses. Could be a massive national security and counterintelligence risk www.404media.co/we-hacked-th...
‘We Hacked the FBI:’ Hackers Say They Have Data on All FBI Employees
A sample of 5,000 alleged agents seen by 404 Media includes names, addresses, phone numbers, and details on FBI employees' spouses.
404media.co
A quick test of your budget: has a security or reliability line item been approved and then quietly raided for two years running to cover an overrun somewhere else? That pattern tells you what the company really believes, no matter what the budget says kevingoldsmith.substack.com/p/paying-for...
My New Project: Tips for Managers & Leaders! - practical advice from my journey as an engineering manager. Give it a read: https://medium.com/@severin_bruhat/my-new-project-tips-for-managers-leaders-f2ce75cf2eae #SoftwareManagement #CareerGrowth
I budgeted for a security vendor for two years running and never bought it. When I finally tried, my CFO asked for the ROI. I didn't have one, and I lost the argument. 🎧 itdependspod.com/episodes/pay...
Your developers, who are introducing the most tech debt right now, think they're cleaning it up by using something newer and better. New newsletter on why AI-powered speed is breaking team autonomy models and what to do about it. kevingoldsmith.substack.com/p/the-agent-...
The Agent Doesn’t Know It’s a Prototype
Team autonomy in the agentic software development era
kevingoldsmith.substack.com
New episode of It Depends: "The Agent Doesn't Know It's a Prototype" When the agent builds something that looks finished, the hardest discipline is remembering you haven't decided to ship it yet. 🎧 itdependspod.com/episodes/the... #engineeringleadership
Here's the one question to carry into the build-versus-buy meeting: Who patches this in year three? If nobody can answer, the decision hasn't actually been made yet. It's just been costed. kevingoldsmith.substack.com/p/build-vs-b...
Nobody regrets a build decision in the first quarter. That's the whole problem with it. Building got cheap. Owning what you built costs what it always did. New episode on build versus buy in the AI era. itdependspod.com/episodes/bui... #techleadership
SignalFire’s analysis indicates tech hiring has stalled at 75% of pre-pandemic levels. While engineering roles at the big tech have held up, design, product, and marketing have taken a hit as has hiring of new grads. That AI can replace non-tech roles is actually more strongly believed than coders.
New in the It Depends newsletter: how to drive change across teams you don't run. You can be completely right about the better way and still completely stuck. Being right and getting another team to change turn out to be almost unrelated. kevingoldsmith.substack.com/p/managing-s...
New It Depends: "Managing Sideways: Everyone Nodded, Then Nothing Happened." Everyone agrees on the better way, then nobody moves. How to drive change across teams you don't manage. 🎧 itdependspod.com/episodes/man...
Managing Sideways: Everyone Nodded, Then Nothing Happened. - It Depends Podcast
A room full of managers agrees on a better way to do something. Everyone nods. Six months later, every team is still working exactly the way it did before. The idea was sound. Nobody had to change, so...
itdependspod.com
Delivering well earns you more work, not more authority. You prove you can do the job, and the reward is more of the same job, not the next one. New piece on the trap that creates: kevingoldsmith.substack.com/p/the-reliab...
New It Depends episode: The Reliable Team Trap. Reliability buys you trust to execute, not trust to decide. Different currencies, and you can be rich in one and broke in the other. itdependspod.com/episodes/the...
New It Depends newsletter: "The Conversation Before the Conversation." For years, I told myself I was being patient. Most of the time, I was just being slow. kevingoldsmith.substack.com/p/the-conver...
I know, I know, I have some kind of severe ascii fluid sim addiction but I'm trying to build the once-and-for-all version and god damn this shit lookin good.
New episode of It Depends: "The Conversation Before the Conversation" The conversations I regret as a manager were never the hard ones I had. They were the easy ones I kept postponing until they got hard. Here are five signals that a conversation is already overdue 🎧 itdependspod.com/episodes/the...
The Conversation Before the Conversation - It Depends Podcast
Most leadership advice is about how to have a hard conversation. Far less of it is about when. In this episode, Kevin Goldsmith argues that the when is usually where things break, and that the convers...
itdependspod.com
I've been breaking AI adoption into four layers: tooling, process, structure, judgment. Most companies are stuck on layer one. The other three are where the actual leadership work lives. kevingoldsmith.substack.com/p/the-intere...
The Interesting Changes Aren’t Happening in the IDE
What I'm still figuring out about AI and engineering teams
kevingoldsmith.substack.com
New ep of It Depends: "The Interesting Changes Aren't Happening in the IDE." If you're looking for the AI transformation in your company, don't look at the IDE. Look at the org chart. 🎧 itdependspod.com/episodes/the...
Your CEO hired you, hoping for a business partner, not just an engineering leader. Stay in the technical lane, and you're quietly disappointing them, even when your teams ship well. That gap ends a lot of CTO tenures early. New piece on how to close it: kevingoldsmith.substack.com/p/becoming-a...
New episode of It Depends: "Becoming a Business Leader, Not Just a Technical One." The ceiling between a senior technical leader and an executive isn't technical. It's business fluency. And most people don't see it until they've hit it. itdependspod.com/episodes/bec...
Four people I mentor brought me the same problem in one week: how do you actually work with your CEO? New article on the four foundations of that relationship, what erodes trust, and when it's time to go. kevingoldsmith.substack.com/p/working-wi...
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...
Don’t Let Your Boss Do Your Job
What Your Organization Sees When You Go Quiet
kevingoldsmith.substack.com
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...
