Growing engineering organizations face a communication problem that more meetings won’t solve. When you’re small, decisions happen naturally. Everyone knows what everyone else is working on. You can sit around a table and discuss problems and solutions. But as you add engineers and teams, that breaks down. You start seeing the symptoms: conflicting architectural decisions …
Someone on your team is using an AI tool you didn’t approve. Your solutions engineers built a custom data ingestion pipeline without telling anyone. A pre-sales engineer spun up a demo feature that customers are now asking about. Your instinct might be to enforce the policy and shut it all down while reminding everyone about …
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 …
Most strategic planning focuses on protecting what you already know is valuable about your business. You’ve identified your core competencies, you’re investing in them, you’re keeping the knowledge in-house. Check. The harder problem is recognizing when something you’ve been treating as plumbing has quietly become the thing that customers are buying and actually differentiates you. …
Most outsourcing decisions are easy to justify. Reduce costs, ship faster, let the team focus on what matters. Individually, they’re often the right call. The problem is that the impact of these decisions compounds. What starts as offloading commodity work can quietly become ceding the thing that makes you different–not through one bad decision, but …
I’ve watched companies outsource their competitive advantage because “the vendor was cheaper.” I’ve seen engineering teams spend months building authentication systems from scratch because “we’re a technology company, we build things.” Both mistakes stem from the same root cause: failing to distinguish between core competencies (what makes you unique) and core capabilities (what you need …
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 …
For the last decade or so, I’ve been collecting questions. Good ones. Weird ones. Chaotic ones. Questions that make people stop and actually think instead of giving the usual autopilot responses. I started out calling them my “Tinder opening lines” because that’s where the idea came from, but they’ve become so much more useful than …
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 …
I’ve been doing a lot of hiring lately. So I’ve been thinking about how people can differentiate themselves from the pack. It’s an interesting proposition when there are so many people out there with great work and life experience that can help them contribute to and enhance a team. One of the trends I have …
