Ok. So, You Can’t Decide.

Even if you’ve checked your work, asked for all the help, and are moving gingerly, there will be decisions where you can’t decide. You’ve considered and reconsidered your pro/con lists, you’ve had endless debates with informed humans, but you remain mentally paralyzed. I have an observation regarding this paralysis, and then advice. First, the paralysis...

Sep 2021

Check Your Work, Ask for Help, and Slow Down

The quality of your decisions is the currency of leadership. It starts easy. The stakes are low. There is a legion of leaders around you who understand you’ve just begun, so when they see the decision in front of you, they proactively offer helpful advice. If the decision appears too complicated, excessively risky, or obviously high stakes, your manager...

Aug 2021

The Way I Heard It Was…

We’re a team. There’s a mountain that no one has ever climbed before, but you – in your bones – believe we can. More importantly, you can stand in front of us, point at the mountain, and tell us the compelling story of how we’re going to climb that impossible peak. You talk with your hands, you raise your voice at precisely the right times to...

Jul 2021

Ask for Help

In 2018, I wrote How to Rands, which seemed like a good idea at the time. Someone else came up with the idea of the manager readme, and the idea of writing a document regarding how I worked seemed like a helpful exercise1. I shared the document with the executive team at Slack, and the Head of People commented on this clause: I am an introvert and...

Jul 2021

The Hotel Giraffe

The 9th floor of The Standard located in Greenwich Village of New York City. Pre-pandemic. I wake up mid-day and a full-sized giraffe stands in the corner of my hotel room. The view of mid-day downtown Manhattan is obscured by a full-sized living breathing giraffe. This animal is staring at me. Blink. This situation makes complete sense, but I have...

Jun 2021

I Think in Flowcharts

The most valuable part of a long bike ride is the second 30 minutes. The first 30 are spent settling into a groove, finding the right pace, and clearing my head. I know this is done when random interesting ideas start showing up, as I’ve written about before. There are three categories of exciting ideas: Stop now. Instantly tell Siri to create a...

Jun 2021

Going Full Pascal

First-year of college at UCSC. First computer science class. Introduction to Programming. The language: Pascal. Failed it. Failed it badly. Knew I was going to fail it halfway through the class. This was my chosen profession. I’d been a grocery store clerk, a butcher, a video store clerk, the guy who backs up the system to tape drives on Saturday,...

May 2021

Feedback is a Mirror

You have an internal storyteller, and they are always telling you a story. Today the story is, “Almost done with all of my bugs. There were ten at the beginning of the week, but now I have two. One of them is hard, but I’ll figure it out. The other, I’m sure, will be a breeze. When these are done, I am going to spend some time working on my prototype...

May 2021

You are Going on a Quest

The most common conversation I’ve had during the last three start-ups was the growth conversation.Some version of: “Rands. I am here. How do I get there?”For leadership-minded engineers, there are four career paths available to you. I will describe three briefly, and then I’ll talk about the fourth one a lot.The first three career paths for leadership-minded...

Mar 2021

Doomscrolling at Scale

WARNING: The contents of this article might adversely affect your information consumption habits.A few weeks back, the sitting President incited domestic terrorists to storm the Capitol, so they did. For reasons I still don’t fully understand, this was a relatively straightforward process for the insurrectionists. It was also an incredibly well-documented...

Jan 2021