Tag: failure

Barely Treading Water

Carolyn, my chief of staff, sat on the couch as I ran into my office. The Palo Alto building wasn’t built for tech; it’d been adapted to support the use case over the years. My office was in the center of the building, which had an inner atrium. Way too many windows. Maybe a salon?… more

May 19, 2026 1 Comment

The Slide

They don’t want to hear it. They don’t. It is legit good feedback. It is substantive, and it is 100% true, but they do not want to hear it. How do you know this? You’ve provided the feedback several times. Three different variants of the critical feedback, and each time, the response is one of… more

April 22, 2026

The Loop

Dream a Bit. Nothing innovative was created by committee. You have to stumble on that odd idea at 3:15a and recognize that you’ve never seen it before. Maybe no one has seen it. Let it bump around your head a bit. Stare at it from a couple of different angles. Do whatever you do to… more

November 19, 2025

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 4 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

The Coach and the Fixer

For this piece, I am going to simplify management a bit. Let us assume there are three different hats you wear as a manager. They are: the Leader, the Fixer, and the Coach. I will briefly explain each role and then explain how I’ve screwed up each. I’m going in reverse order because I’m building… more

September 26, 2022 4 Comments

Everything Breaks

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

December 10, 2018 2 Comments

Kobayashi Maru Management

Ted’s feeling pretty good. He sits across from me in the conference room and says, “Program launch is solid. We’ve been working on the details for almost a month. We vetted the concept with all the affected teams and made tweaks, and now they’re fine. The only step left is sending the announcement to the… more

August 8, 2018 5 Comments

Meeting Blur

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

February 8, 2018 4 Comments

The New Manager Death Spiral

The starting gun fires and when the starting gun fires, you run. You’re a new manager, and while the sound of gun firing is startling, you run because this is finally your chance. You’ve been promoted to the role of manager, you want this gig, and this is your chance to shine, so you run.… more

March 2, 2017 11 Comments