Leadership

Why Your Strategic Planning Fails (And How to Fix It) I’ve seen more agile planning sessions derailed by politics than by any technical challenge. It always starts the same way. You get the right people in a room—Product, Engineering, Sales, Finance—and for a moment, it feels like a powerful alliance focused on building the future. A spy’s guide to strategy helped me realize these sessions unfold in three acts: Alliance, Competition, and Endgame. ...

I got into management because I saw myself as a player-coach. I could create software and make my teams more effective. The most rewarding part? Shielding creative people from bad direction and then watching them delivering results. Success gave me more influence to shape process and continue to help my teams be their best. Chris Dixon’s recent, high-profile shift from “Management” back to “Engineer” made me pause. He’s a true champion of the possible who had an outsized impact on my early career, and his move forced me to think about my own direction. ...

The legendary W. Edwards Deming once said “A bad system will beat a good person every time.” Playing Batman: Arkham Shadow recently, this quote kept resonating as I watched Commissioner Gordon - a dedicated public servant - struggle against Gotham’s broken system. This made me reflect on what effective executive sponsorship really looks like. Early in my career at Comcast, I experienced transformative sponsorship. Our development team needed Macs for coding (this was pre-WSL - yes, I’m dating myself here). Corporate policy prohibited Macs on the network. Instead of telling us to “make do,” or intentionally violating corporate IT policy, our executive sponsor recognized the systemic barrier and took action. They funded and built a parallel network infrastructure that enabled our success. Our team went on to deliver exceptional results because we were properly empowered. ...