I keep hearing a version of the same question: how do I get people to make more decisions themselves? There are plenty of reasons people don’t make decisions. Analysis paralysis. No time to think. Unclear authority. Not wanting to own the outcome. But even when someone is willing and allowed to make a decision, they …
Every management book, every “how to run better meetings” post, every leadership-tips list tells you: start your staff meeting by asking each person for a win. I do it. I’ve done it for years. But I noticed that the write-ups usually stop at the prompt. And, while important, I think the prompt is the least …
Your calendar looks the same as it did a year ago. The same standups, the same one-on-ones, roughly the same number of meetings with roughly the same amount of stuff said out loud. But far more work is getting done in the gaps between those meetings, and more work getting done means more decisions getting …
A two-day hackathon looks like a gift to your team. Two days off the roadmap. Two days of building whatever they want. If you’re a CRO wondering when the feature to help close the deal will be deployed, it looks like you just lit a match on a week’s worth of productivity (because you’re also …
SaaS is in a rough stretch. Companies are cutting, consolidating, fighting to keep the lights on. The Saaspocalypse is being felt at varying stages depending on the market. And when organizations are under pressure, something deeply human kicks in: they start hoping for a hero. Not necessarily a specific person. Just someone — from engineering, …
You can’t memo or force your way to AI adoption. I’ve written before (Strategy Isn’t Strategy Unless Repeated) about why communication alone doesn’t change behavior. Adoption is a behavior change problem. You need mechanisms of change, not just announcements. Two that have worked well for me for AI adoption specifically are: hackathons and local champions. …
Engineering leaders spend years learning to build fault-tolerant systems. We design for failure. We instrument everything. We think carefully about what happens when a node goes down, when traffic spikes, when dependencies become unreliable. Then we walk into a meeting about team structure and don’t apply those same lessons. The highest-leverage work for most engineering …
Unless you’re an AI vendor, you don’t need an AI strategy. You need an AI adoption strategy. This distinction matters. “AI strategy” implies a comprehensive vision for how AI transforms your business—a roadmap, a framework, maybe even a consultant or two. That’s the right frame if you’re selling AI products or reimagining your SaaS business …
Your job as a senior leader isn’t always to make decisions — it’s knowing when to make them and when to ensure others do. People talk about ’empowerment’ all the time, but empowerment without context is just abdication. Empowerment with control is just micromanagement wearing a friendly T-shirt. What actually works is giving smart, senior …
Over the course of my more than 15 years as a CTO, I’ve learned many technical lessons. But the lesson that has mattered the most, and has had the greatest impact on the teams I’ve led, is this: strong teams are built by strong managers leaders. That idea didn’t come from the world of tech …
