Today is the day! My book "it depends: writing on technology leadership 2012-2022" is now available everywhere! amazon.com/Depends-Writing-T…

New ep of It Depends: "Leading Through a Crisis" When a crisis doesn't end, like COVID: "At some point, you have to tell people the emergency is over, even if the situation isn't." Until someone does, people stay in emergency mode and burn out. itdependspod.com/episodes/le…

It’s tempting to assume good work will speak for itself, but it rarely does. Your boss can’t recognize work they don’t know about, and they may not know at all unless you tell them. kevingoldsmith.substack.com/…

New It Depends: “Slight or Signal: Learning the Game at Work” If your boss really wanted to screw you over, why would they be so subtle? A lot of what feels like a slight is just something your boss never knew about. 🎧 itdependspod.com/episodes/sl… #techleadership

"We need to modernize the billing system" is hard for a CFO to weigh. "Two engineers, six months, about $200K plus whatever they won't build meanwhile" is easy. Price your legacy systems the way a buyer would. New newsletter: kevingoldsmith.substack.com/…

New ep of It Depends: "The Outsider's Audit: Due Diligence on Your Own Org" The longer you run an org, the less its workarounds look like problems. You remember every decision that got you here, so you've accepted them all. An outsider hasn't. itdependspod.com/episodes/th…

A SOC 2 report proves you can pass an audit. Whether you'd survive an attacker is a completely separate question. New issue on how to budget for the work whose only visible result is that nothing happened: kevingoldsmith.substack.com/…

Seven people was the right size for my security team at one company. Two at another. A fraction of one person at a third. No ratio would have gotten those right. The only thing that mattered was what a breach would have cost us. itdependspod.com/episodes/pa…

MVP isn't just about fewer features. It's about minimal infrastructure. A server handling 200 users behind a feature flag with telemetry is a legitimate MVP. The new confusion is that AI makes the distance to full production look small. kevingoldsmith.substack.com/…

New ep of It Depends: "The Agent Doesn't Know It's a Prototype" Autonomy is a reward for proving you understand its boundaries. 🎧 itdependspod.com/episodes/th…

We built our own MCP servers for vendors who didn't have official ones. The moment the official ones shipped, we switched. That was the plan. Build as a bridge, take the exit when it appears. The vendor is more motivated than you to keep it working. kevingoldsmith.substack.com/…

We built auth on an open-source component instead of buying it to save money. The savings were a wash once you factored in updates and security reviews. A month after the company switched to a vendor, that component had a serious vulnerability. itdependspod.com/episodes/bu…

New in the It Depends newsletter: driving change across teams you don't run. Borrowed authority buys agreement that lasts exactly as long as the pressure behind it. kevingoldsmith.substack.com/…

New It Depends: "Managing Sideways: Everyone Nodded, Then Nothing Happened." Early at Adobe, I forced a team to adopt our system. I won the argument and shipped it. They made me pay for it long after. Being right is the cheap part. itdependspod.com/episodes/ma…

Delivering well earns you more work, not more authority. You prove you can do the job, so you get more of the same job, not the next one. New piece on the trap that creates: kevingoldsmith.substack.com/…

New ep of It Depends: The Reliable Team Trap. Reliability buys you trust to execute. It does not buy you trust to decide. You can be rich in one and broke in the other. itdependspod.com/episodes/th…