The Weekly Hagakure #2
On new beginnings.
Last week, I had an intro call with someone I admire, from whom I wanted to learn and get direction from.
Even though this chat was for my benefit, I wasn't well prepared, and I didn't have the right questions. As I stumbled through the half-assed explanation of what I had in mind for the next step in my career, my counterpart was the one who asked me the key question:
What is your promise?
I couldn't answer it. In that moment, I felt two things: first, a pang of "I don't have my shit together and I am looking like an idiot" type shame. Second, that I got handed the keys to the castle. I just had to find where the damn castle is.
That's what I have been doing over the last few days, in my now copious spare time: trying to figure out what my promise is. Here's what I know so far.
I have now spent over a decade working in Tech, the last 5 years serving in Engineering leadership roles. In that time, I have come to realize that how we work is, in many ways, broken. I don't have a large sample size of direct experience (nobody does) but I triangulated a lot. For too many people, it's not great. And looking at the data, I'm not far off the mark here. The more I think about it, the more I believe we haven't truly evolved past the (now hopelessly outdated) factory-type work paradigm. We have the technology but, in the end, it's how we humans relate to each other — and the biases we carry — holding us back.
So I decided to take a step back, in order to take two steps forward. I'm seeking better control of my time and space, to be able to focus on family and loved ones. And I want to contribute, for the rest of my life, to helping creating more humane (a word my counterpart in that call helped me find) workplaces in Tech. First, because better work leads to a better, more fulfilled life — and ultimately to a better world. Second, because on the long run it generates much better business results. I want to play long-term games with long-term people.
I don't know where this journey will take me or whether I can make it work. For now, I'm looking to take advisory/coaching/consulting roles, helping great people design the foundations of sustainable growth for their tech organizations. Creating environments that bring out the best in humans, putting people first, not paying lip service to it. Demanding 100% but holding the other side of the bargain as well. World-class practices beget world-class results (not the other way around).
Last week, I wrote that "building fundamentally better (real) companies, better teams, and especially better leaders is not optional". I want to put my money where my mouth is, and help as many people as possible in creating a better, kinder future. And to be successful in this, the first person that needs to be better is myself. It's a work in progress, and this newsletter is in part sharing that journey with you.
I'll get off my soap box, now. On to the main course. 😉
3 Articles ✍️
👉 Creativity Is the New Productivity
As we slowly but steadily automate the boring parts of every day work, what remains requires what no machine can (yet) meaningfully do: being creative. This is more evident than never before. In this thoughtful post, Scott Belsky explores the transition from productivity scarcity, to productivity abundance, and eventually to creativity — alongside the implications.
👉 Engineering Management: An Interview with Rich Archbold
Intercom easily ranks in my top 3 of inspirational companies. Everything they put out, including their blog, is supremely insightful and often funny as hell. This interview with their VP Engineering, Rich Archbold, is a treasure trove for anyone managing Engineering teams. One key lesson (of many): help people learn from their mistakes, rather than trying to prevent them.
👉 Distributed Work’s Five Levels of Autonomy
As the COVID-19-sponsored Great Remote Work Experiment continues, many have changed their mind about remote work, while others confirmed it’s not for them. The majority of companies have simply been unconsciously replicating their usual office practices, and realizing that Zoom fatigue is a thing (hint: default to audio only). Meanwhile, Matt Mullenweg, founder and CEO of Automattic — a fully remote company with more than 1000 employees — believes that enabling people to be "fully effective in a distributed fashion" is no less than a moral imperative for companies. In this post, he clearly outlines the way to get there. I think this is a critical conversation, and next week I'll be sharing a longer piece of my own on the topic.
2 Podcasts 🎧
👉 How To Build A Great Product: with Kevin Systrom & Mike Krieger
I have been thinking a lot about simplicity lately and Instagram always struck me as an example of that. Which shouldn't be surprising, since "do the simple thing first" became a mantra for how the founders approached each of the many problems they faced in building the company. This great episode contains a bunch of lessons, but a favourite of mine is that a product's reason for existing must be solving someone's problem.
👉 Increasing Your Team’s Capacity To Win
I came across Wade Chambers quite early in my engineering management career and this statement of his really opened my eyes: “Your job is to win and then increase your capacity to win.” It stuck with me ever since, and has shaped my focus in growing people, improving processes, and creating systems. Chambers is also incredibly articulate and concise, great skills for any leader to possess.
1 Book 📚
Ever heard of the 10,000-Hour Rule? Popularized by Malcolm Gladwell in his 2008 book "Outliers", it holds that 10,000 hours of "deliberate practice" are needed to become world-class in any field. It was largely debunked soon after, but that didn't prevent it from spreading like wildfire. To become world-class at something, focus on one thing from a very early age and deliberately practice it over and over.
Journalist and author David Epstein wasn't convinced, so he started picking the argument apart. Could deliberate practice be the key to greatness? Does it apply to any endeavour? As usual, reality is more nuanced — and perhaps more interesting for all us mere mortals. Deliberate practice can indeed lead to extreme levels of skill. But not all activities were created equal.
In “Range: Why Generalists Triumph in a Specialized World”, Epstein distinguishes between two types of environment:
Kind environments, made of repeating patterns, clear rules and mostly instant feedback (playing the guitar, for example).
Wicked environments, where things are fuzzy, rules are unclear or inexistent, and there are no obvious feedback loops (say, managing an Engineering team).
Life is mostly wicked. In fact, in particularly wicked environments, experience may perversely reinforce the exact wrong lessons.
So, if not through deliberate practice, how do you get really good at tricky stuff? Well, according to Epstein, it's by developing a broad spectrum of skills and interests. In other words, be a generalist for as long as it takes. Specialization can (and should) wait. Worked pretty well for Elon Musk, I guess.
A particularly interesting chapter in the book deals with the idea of analogical thinking. We make use of analogies every day and think none of it. But developing the ability to recognize conceptual similarities across multiple domains is a superpower:
“Successful problem solvers,” Epstein explains, “are more able to determine the deep structure of a problem before they proceed to match a strategy to it.”
It reminded me of an example, not featured in the book, but related to it. Rich Barton is not as famous as some other Silicon Valley moguls (perhaps because he insisted on living in Seattle instead), but he founded no less than three billion-dollar companies: Expedia, Zillow and Glassdoor. It's not his riches that I want to glorify here, though. It's that he understood the “deep structure of a problem” and over time architected three different solutions to it, all in wildly different industries. That problem can be summarized in one simple question: "What piece of marketplace information do people crave and don’t have?" For Expedia, it was prices for flights and hotels. For Zillow, what your house is approximately worth so you can avoid getting ripped off by an overly eager real estate broker. And for Glassdoor, it was employee reviews so you have a sense of what it is to work for a given company before you go there. As Barton is fond of saying, "Power to the People". If he had specialized in one market, technology or domain, odds are he wouldn't have connected the dots.
“Range: Why Generalists Triumph in a Specialized World” is a great read. And if you, like me, feel like you never got really good at any particular thing, well... maybe that's not such a bad thing after all. 😎
🙌🏽 Thank you for reading! I hope you enjoyed it, and until next week.
👉 You can follow me on Twitter @prla and subscribe to this newsletter here.