Management

The Plane on the Crane

If you want to teach a Californian kid about cold, have him fly out to New York in January. Have him pack poorly and then have him walk out of JFK airport at 3pm with aforementioned poor packing, and watch what happens. Wait until the sliding door opens. Wait for it. And watch. I did… more

October 9, 2025 2 Comments

One Compliment

An idea just comes to me. I’ve been writing for a long time, so the ideas come partially formed. Not written but formed into the beginnings of a familiar shape. It is critical in the next hour that I write this idea down somewhere accessible because it’s just an idea, and failure to capture it… more

September 22, 2025 3 Comments

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,… more

September 3, 2025 2 Comments

The Product Engineer

If you work for a company that builds primarily consumer software, there are, hopefully, three groups of humans who believe they are accountable for the product. They are: Engineering. They build the product. Design. No, they build the product. Product Management. No, really… they build the product. Do you see the issue? You have three… more

March 17, 2025 11 Comments

Ok. So, You’re Failing

Years ago at Borland. My first real gig. I was poached from an internship into a full-time QA gig. When I accepted the offer, they sent me a box of Borland schwag, t-shirts, notebooks, and pens. I was elated. No more hourly wages, I was full-time. Six months in, my manager sat me down at… more

March 3, 2025 3 Comments

Managing Up

My problem with the phrase “Managing Up” involves a hard-earned historical observation regarding its weaponization. The helpful version of this practice is a clear understanding between you and your manager that there are uncommon, intriguing, or worrying developments that you — without hesitation — share with your manager. Isn’t that their responsibility, as well? It… more

December 30, 2024 2 Comments

Poets and Police

I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack… more

October 3, 2024 5 Comments

Words on Founder Mode

I’ve worked at three successful start-ups and one failure. I’ve also worked at post-IPO successes such as Borland, Netscape, and Apple, which means I’ve seen a lot of different founders who, if you measure success financially, were quite successful. My backstory aside and with deep respect, most founders fail. You’ve heard of the stories of… more

September 8, 2024 4 Comments

Late Again

Awkward. Seven of us now. Sitting around the table. Five minutes since the start of the meeting. We’ve used up our chit-chat allowance and wonder if you will show. In the scheme of things relevant to a company’s success, showing up late to a meeting is not the end of the world. When it happens… more

August 19, 2024 2 Comments

Seven Conversation Hacks

Say their name if you think they aren’t listening. In a meeting with five or more humans, it’s ok if someone checks out of part of the conversation. Not every topic is of equal interest to all humans. When you know the conversation is steering back to a human who isn’t listening, say their name.… more

June 20, 2024 1 Comment