Their Fault. Still Your Problem

“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 […]

No Wind Is a Good Wind

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 […]

Can’t Read the Label From the Inside

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 […]

You Didn’t Hire a Slow Team

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 […]

Stop Lying to Your Cofounder

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 […]

Axioms of Effective Leadership

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 […]

Default to Lazy

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 […]

Nostalgia Debt

Remember the software craftsmanship movement? I used to walk around with those green “Clean Code” wristbands. Those were the days. But trying to hang on to a world that’s no longer there is futile. You and your senior engineers ought to come to terms with the new world. Yeah, we’re talking about AI again. The […]

Leadership as a Supporting Role

Do you find yourself huffing and puffing as a tech leader? Not sure how to keep all of those plates spinning? You, my friend, need to let go of your main character syndrome. The answer to the overwhelming load many tech executives report is rarely to work harder. Rather than piling ever more things on […]

CEO-CTO Therapy Part 4: What Are You Even Doing?

A major point of contention that often arises in relationships between tech executives and their CEOs is that the latter does not understand what the former are actually doing and where their time is going. They wonder whether things are doing fine and whether they ought to be doing better. They hear you describing a […]