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

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

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

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

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

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

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

I asked DALL-E to draw a flowchart on how to make a decision. This is spot on.

Remember. Monday. It’s not Wednesday when everything is already blowing up. Monday is a blank slate before 9am; this is my chance to set the tone. While it is still quiet, get a fresh cup of coffee (I prefer black and strong). Not a coffee drinker? Great, try Chai or just a glass of water.… More

Do you remember your first job? Correction: not your first job, but the first job you wanted. This is my career. This is what I want to do. I don’t want to screw this up. I was a grocery store clerk, a butcher, a video store clerk, the guy who backed up the system onto… More