Professional

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. ...

I was reviewing an older repository during a production incident the other day and couldn’t figure out what sections of the code were doing or what the overall system looked like. It’s so frustrating to be in undocumented code. Software documentation is a mature pillar of engineering these days. The tools are there, the patterns exist, the documentation standards are well-established. We just… don’t do it. Why don’t we when there is documented correlation between high performing engineering teams and open and accessible codebases? ...

Does my marriage need more FHIR? I read this as being solicited to spice up my marriage. Wildly inappropriate for LinkedIn 😂. (FHIR is pronounced “fire”) Originally I added my ‘Marriage to Jen’ in my LinkedIn work history as a private joke. Almost immediately it was effective in filtering sales and recruiting calls to let me know they had actually read my profile. I’m keeping it because now it’s helping me find the bots. ...

My 89 year old Dad got beat by a younger team of 70 year olds. Dad called me today. His team, Ponza United got bested by Denver at the Florida classic. He said Denver had lots of people on the young side and “They could run” Genetics definitely play a role in his continued ability to compete (Thanks again Mom for my celiac and asthma!) but he was a lifelong advocate of never missing a game. From the time I was young he trained multiple times a week and I even remember an argument when my sister wanted to get married on game day. His priority was to maintain a lifelong habit of training, and I watched that habit become stronger through the decades. ...