Net-Positive Mistakes

Leaders fixated on outcomes treat the path as just friction, a hassle. In reality, the journey is where compounding growth lives: in the errors, corrections, and patterns you either notice or don’t. To help your team grow, stop focusing on avoiding a specific mistake. Aim to make those mistakes count. What “Net-Positive” Actually Means Every […]

You Taught the Company to Overload You

As the person who keeps telling tech leaders to stop being so negative and shoot down everything (the infamous “CT-No”), I feel obliged to address the other extreme. The VP of Engineering who tries to accept everything eventually reaches the same dead end from the opposite direction. Learning how to push back effectively is a […]

Stop Firefighting Better

When a CTO tells me they just barely saved the day, I annoyingly don’t pat them on their backs. Instead, I walk them back to why they were ever in that position. The hero moment is usually evidence of a prior failure. The impressive thing isn’t rescuing the team. It’s building a team that doesn’t […]

Auto-Pigeonholing Tech Leaders

A CTO who runs a flawless engineering org with clean architecture, a happy team, and great velocity, while Product is a mess, Sales is flailing, and the company is quietly dying? Now more than ever, it’s clear that tech leaders are often only as limited as they make themselves. Many have already realized that the […]

CEO-CTO Therapy (Part 3): Prioritization

The sitcom-worthy moment: CEO barges into the room with three new “must-haves” for the current version. The CTO, with ruffled hair and bags under the eyes, pleads for a breather. “Oh, you’re always complaining,” the CEO mutters on the way out. Roll credits. You’ve lived this scene. Probably more than once this quarter. Note: You […]

Manufacturing Creativity

Do you feel like your team isn’t really creative? Not coming up with any initiatives or ideas? Or when they do, is it all limited to tech fluff? You end up feeling like it all comes down to you (and, if you’re lucky, a couple of reliable people)? No wonder. How can they be creative? […]

From Sinking to Shipping: Tackling Your Org’s Debt

Do you look around your org and see a pile of problems? Untested legacy code, knowledge silos, tooling gaps, recurring fires. Perhaps you know what needs to change, but the list is so long it feels insurmountable. You feel defeated before you’ve taken the first step. Don’t get overwhelmed and “freeze.” It Doesn’t Have to […]

Internal PR: Fix Your Team’s Reputation

For myriad reasons, your organization might be suffering from a bad rep. I’m sure you’re working on addressing the issues. But you have to do the PR as well. Unfortunately, most tech leaders see this as beneath them or dirty. They’d rather wait for people to notice improvements than actively shape perception. That hesitation is […]

Suffering Isn’t Leadership

I recently chatted with a CTO who said things were personally abysmal at work for a couple of years, but now were “finally improving.” Of course, it’s good when things are getting better, but experience shows that these long stretches of frustration aren’t inevitable. They’re usually a combination of martyrdom mindset and pessimism. This is […]

Tech Leadership Right Now: Experimentation, Not Answers

We’re in a genuinely different moment. The pace of change means that what works today might not work in a couple of months. Let alone what worked so far in your career. This isn’t the usual “things are changing” platitude. Things are actually shifting substantially. What should you do as a tech leader? Stop Trusting […]