We’re going to play a really simple and really dumb game. I’ll explain the setup and the rules: Two one-person ‘teams.’ On a flat, boring surface, you draw two parallel three feet long white lines which are fifty feet apart. Teams choose one home baseline. The other line marks the opposing team’s home base. Team… more
I spend a lot of time listening. A non-trivial act for me because my mind… it wanders. However, I’ve got a system. Feet flat on the ground, slightly clenched jaw, staring you straight in the eyes. I am full body listening. You have my complete attention. I am not missing a word. We humans are… more
If you’ve had a 1:1 with me in the last decade you know that once we’re done with our planned agenda that there is good chance that I’ll stand up, walk to the whiteboard, and start drawing some version of the organization chart (“org chart”). I believe the org chart is one of the three… more
The majority of people-related disasters I’ve created originate with my choice to not say the hard thing. On my short list of critical leadership skills, the ability to “say the hard thing” is right after “delegate until it hurts.” I didn’t give feedback when behavior was off because the person was new and I told… more
At some point in your leadership career, you’ll need to care about performance management. My first bit of advice is the hardest: don’t ever let yourself think or say the words “performance management.” This is impossible, but aspirational. I will explain. My hard earned definition of performance management: a well-defined workflow that either leads to… more
Hi, welcome to the team. I’m so glad you are here at $COMPANY. It’s going to take a solid quarter to figure this place out. I understand the importance of first impressions, and I know you want to get a check in the win column, but this is a complex place full of equally complex… more
Wednesday afternoon. 3:30. Tanya and I walking through a complex political scenario involving Product and Engineering. Nothing devious. Just complex. Many moving parts. I’ve had some version of this conversation five times today. The whiteboard is my savior. I’m using it to draw a picture that anchors the core points of the situation. Those core… more
The quiet is my favorite attribute of a holiday break. My various Slacks are quiet, the house is quiet, and while it takes three days of quiet, eventually my head is quiet. Quiet creates reflection. I replay the critical parts of recent life and rather than living them, I observe them… at a distance. This… more
When you are asked as a manager “What do I need to get to the next level?” I suggest the quality and completeness of your answer is directly correlated to your effectiveness as a leader. Let’s start with the worst answer, “We’re a meritocracy where the best idea wins.” This is a bullshit cop-out answer.… more
The Old Guard is a set of humans who inhabit the early days of a start-up. As I’ve written about before, they define the culture in both obvious and non-obvious ways. Simply: the way they act and how they treat each other disproportionately affects the values of the company. The Old Guard gets to be… more