Management

I’ve watched talented engineering teams burn out not from working too hard, but from working without direction. The pattern is always the same: leadership announces a new strategic pivot every quarter, teams scramble to adjust, morale craters, and your best people start updating their LinkedIn profiles. The problem isn’t the changes themselves. It’s that without a guiding vision, every shift feels like a complete reversal rather than a necessary course correction. ...

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. ...

Is the Economy derailing your Agile Transformations? Economic uncertainty hits. Layoffs are all over the news and productivity suffers. Every time, I see people wanting to blame the loss or productivity on budget cuts and layoffs. That is the short term impact, but I see longer term harm playing out. Teams that were thriving on collaborative decision-making suddenly go quiet. The same people who were debating sprint priorities and pushing back on requirements start waiting for marching orders from above. ...