Frustrated that you don’t get time to work on tech debt and improving infra? Working at IBM was my career’s peak no-business-contact. I had a blast working on internal tooling, and without any business demands, was left to do what I pleased. Naturally, as a young engineer, I filled the time with tech perfection and […]
The senior engineering staff was in a meeting with stakeholders. Everyone from engineering was exhausted after handling a nightmare of a week with a project that blew up. It was a project that was specifically spun off the regular work as a task force, so the VPE wasn’t in charge of it. Not his mess. […]
I sat down with a CTO for the first time. Their co-founder and CEO was worried and wanted to support the CTO. We had a nice chat. I asked a few questions. We parted ways without any drama. A few days later, the CTO was out. That’s a good thing. They made up their minds […]
“Why did that take so long?” Cue the blame shifting. “Product wasn’t ready on time/Sales overpromised things/Customer Success didn’t answer our last email asking for explanations.” Every fact there might be true. Perhaps you can even produce the relevant Slack threads and meeting notes with dates. That doesn’t make it not your problem. Minding Your […]
The CTO was pretty proud of the org’s velocity. I asked what the company’s vision was. Without hesitation, he started listing things like shipping a major feature, landing an enterprise client, SOC2 compliance, etc. “That’s the roadmap; I asked for the vision.” Silence. He could name everything built, but not what it was for. Funny […]
When our kids started at their new school when we moved to Rome, they were stunned. They didn’t imagine things could work this differently. They never complained about the old way, because they couldn’t picture another. But once their eyes were opened, they couldn’t imagine anything less than that. You can’t miss what you’ve never […]
Work without a clear outcome, finish line, appetite, or milestones expands until it consumes the quarter. “Why isn’t it live yet?” “It turned out to be more complicated,” the CTO says. Or another priority got in the way. The conversation quickly becomes about urgency. Nobody said what outcome the feature should create, what that outcome […]
It’s sprint review. A team “pulls out” work finished a couple of weeks ago, presented as fresh. Everyone in the room half-knows. That’s how teams deteriorate fast, and startups become political. Let’s create a healthier org. Fake It Till You Break It Startups run on promising things that don’t exist yet. CEOs sell features that […]
Everyone’s acting like AI rewrote the leadership playbook. It didn’t. Some tactics have shifted, but the core practice of leadership remains. Here are some axioms for effective tech leaders I’ve collected over the years. They’ve stood the test of time and are well worth your attention. How well do you have them sorted? Executive Leadership […]
Larry Wall, creator of Perl, famously said that laziness is one of the three main virtues of a programmer. Being effectively lazy is highly useful for ICs as well as for leaders. An organization with a culture of healthy laziness can actually cover ground faster. The Danger of Not Being Lazy People who aren’t lazy […]