Management

The Ask

Coffee in hand, I sit down in the Cave. Any Tuesday during the work week, a sip, and I parse the calendar. 1:1 — he’s fine. Status meeting — listen. Staff meeting — read the notes from last week. Exec review — figure out the biggest fire, have a defensible opinion. Wait — Mark Team… more

May 25, 2026 4 Comments

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

Sometimes Your Job is to Get in the Way

The Head of Product, Customer Service, and the CTO of Slack were sitting in the front row at an important conference. This was peak Slack; we were all the buzz, the fastest-growing enterprise software company in history. The conference speakers were singing out praises, and at that precise moment, Slack was down. Again. I wish… more

April 27, 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

Three Bad Managers

I worked for each of these humans. They either hired or promoted me. I worked for them for many years. As is my way, I’ve vastly altered the details of each human, but the core issue I describe is the core issue. Also, each of these humans is very smart. No dummies. Here are their… more

February 9, 2026

I Hate Fish

I don’t like fish. “But Rands, have you tried…” Yeah, I tried that. I don’t like fish. “Wait, wait, wait, what you need to try is…” Tried that, too. A couple of times. I don’t like fish. “Rands, you haven’t had good fish.” Yeah, I’ve had good fish. Many times. Girlfriends, good friends, bad friends.… more

February 2, 2026 3 Comments

I’m Going to Dig a Hole

Many, many years ago, at my childhood house in the Santa Cruz mountains, I grabbed a shovel and started to dig a hole. Why? Unclear. I was six or seven. I’d seen what my Dad could do with a shovel, so one afternoon…. I started digging, and by the time evening approached, my Dad walked… more

January 19, 2026 2 Comments

The Wanderer

Manager at the first start-up. Solid guy. Significant experience. I know that I can learn from him. No doubt. All the correct operational 1:1 hygiene is there. We meet every week like clockwork; we fill the time, and I often leave with a healthy sense of productivity. But sometimes… he talks. And wanders. He’s a… more

November 25, 2025 1 Comment