I blinked away the tears.

I was halfway up the four-story vertical ropes course, when my course partner at the leadership retreat decided she couldn’t continue any further. We agreed she would energetically cheer me on as I continued. I kept climbing and nearly got …

Prioritization is a perennial challenge when building a product roadmap. How do you decide what to work on first?

“You’ve Got Mail” via Giphy

hh5800/Getty Images

Do you consider yourself “a doer”?

This was first published on my mailing list The Looking Glass. Every week, I answer a reader’s question.

Image from here

This is the final part of a 6-part series of blog posts based on a talk I prepared called Successfully Derailed Product. It’s about the ways in which we define and talk about “success” influence what – and how – we build. See part 1, part …

The Story of Five Points

I recently published Chavah Messianic Radio, a Pandora-like music player, as a Progressive Web App and submitted it to the 3 app stores (Google Play, iOS App Store, Windows Store).

A Chaos Day is a dedicated team day focused on using chaos engineering to reveal weaknesses in your system. We’ve all heard of hack days and hack weeks, where you focus on building new features. Well, a Chaos Day is focused on building more …

I thought it’d be useful to share out some of the tools and resources that I use as part of my workflow as a manager. Below is a link to a number of Google docs, which if it sounds interesting to you I encourage you to copy for your own …

EX-99.1

I was recently tagged into a conversation on Twitter. The thread started with this summary of findings about open plan offices:

The first time I took on a tech lead role early in my career, I had little clue what I was doing.

First principles thinking, which is sometimes called reasoning from first principles, is one of the most effective strategies you can employ for breaking down complicated problems and generating original solutions. It also might be the …

When Ernest Cline’s Ready Player One was published in 2011, the reviews were ecstatic, beatific. It was an “enchanting,” “accessible ” “nerdgasm ” full of “fascinating social commentary ” that one critic claimed was “the best science …

Recently, the Strava Engineering team took a weeklong break from regular product work to focus attention on our core technology platforms. We coined this effort Guild Week. Before explaining Guild Week, it’d be useful to understand what a …

Who was the best manager you ever had?

Photo by Zachary Spears on Unsplash

Today we are excited to share Patreon’s revamped Engineering Leveling Guide. In Patreon’s early years, we had little in the way of objective criteria for leveling engineers. We’ve come a long way since then, and our engineering organization …

One of the most frequent questions I hear as I coach managers is, “How do I handle how tired I am as a manager?”

The telegram was a breakthrough in communication technology, which Vannevar Bush imagined could evolve in unprecedented ways.

A long time ago, my manager sat me down to inform me of my next year’s salary. I was receiving a reasonable raise, it should have been an easy conversation. Once we finished the conversation, I left the room and immediately started reaching …

You spend years trying to learn new stuff but then look back and realize that maybe like 10 big ideas truly changed how you think and drive most of what you believe.

Hi, everyone! A lot of stuff has happened since I was writing all those blog posts about Aeron chairs 18 years ago. Some of those blog posts are old enough to go to college.

Many years ago, I worked at a five-person startup.

This was first published on my mailing list The Looking Glass. Every week, I answer a reader’s question.

Power has a way of flowing towards people managers over time, no matter how many times you repeat “management is not a promotion, it’s a career change.”

I once downloaded a speed-reading app that would flash individual words across my phone. I aggressively set the rate to 400 words per minute and braced for the onslaught. I used this system to parse essays, primers, and long-form …

Introduction to the model – SSCC

Whether you’re dissecting Adam Smith’s The Wealth of Nations or relaxing poolside with 50 Shades of Grey, reading is, for many of us, a regular source of joy, perspective, and ideas, which enable us to grow personally and professionally. …

A tool for gaining a shared understanding of responsibilities

The modern web contains no shortage of horrors, from ubiquitous ad trackers to all-consuming platforms to YouTube comments, generally. Unfortunately, there’s no panacea for what ails this internet we’ve built. But anyone weary of black-box …

The simple of idea of putting a mission statement together for the team makes most managers tremble in fear. It’s a sad situation we’ve gotten ourselves into when leaders fear to express the purpose of an organization (and employees snicker …

Illustration by Laura Wright

We know Engineering interviewing can be stressful, and stress can often make interviews a poor sample of what you can do at work. We want to create an interviewing environment where you can show who you are and what you can do. Hopefully …

I feel like an idiot while doing my job. A lot.

Workplaces have adopted internal social tools—think stand-alone technologies such as Slack, Yammer, and Chatter, or embedded applications such as Microsoft Teams and JIRA—at a staggering rate. In an ambitious study of 4,200 companies, …

Software companies should put careful deliberation into their engineering job levels, and make available a job ladder explaining what is expected of employees, the distinction between roles, and areas for career growth.

I sent this to my personal email list of 25,000+ founders, but thought it contained enough value to share on Medium too. Edited for brevity.