A Day in the Life of a Senior Leader

Chapter 16. Check Your Context

I didn’t much like Wally from the first time I met him. We worked in the same circles, but not on the same projects. I was aware of his work, but not involved or dependent on it. My initial reaction to Wally: “Complains. Nitpicks. Doesn’t act.” I made this judgment in a moment.

Months passed, and none of Wally’s observed actions changed this initial perspective. In conversation, he was the guy who pedantically and exhaustively pointed out flaws, but did not suggest the means by which we address the flaws. My impression was unchanged: “He believes identifying the problem magically fixes the problem.”

Several years after we first met, Wally and I were paired on the same project. I was the technical lead, and he was one of three engineers contributing. From the moment it was announced that we were on the project, I knew there would be a Wally situation.

To his credit, Wally didn’t Wally for almost six months. I figured there was something about the project or the team structure that prevented the endless critique, but I was wrong. Seven months in, the project went sideways, and the Wally flood began. The good news is that I’d been preparing my speech for him for just under a year. I knew what I wanted to say, and the moment the debate became unhelpful, I took him aside and executed my speech.

“Wally, it’s clear that you care about this project. So do I. It’s why they put you on this effort. You have experience. You work hard. You listen to the team. ...