We had an internal culture of counting the passage of time from Day 0, the day (in California) we started working on the project. We made the first calls and published our first vaccine availability on Day 1. I instituted this little meme mostly to keep up the perception of urgency among everyone.

We repeated a mantra: Every day matters. Every dose matters.

Where other orgs would say, ‘Yeah I think we can have a meeting about that this coming Monday,’ I would say, ‘It is Day 4. On what day do you expect this to ship?’ and if told you would have your first meeting on Day 8, would ask, ‘Is there a reason that meeting could not be on Day 4 so that this could ship no later than Day 5?’

I started every meeting and status report to the team by reminding them what Day it was. Our internal stats dashboard had a counter of what Day it was. I had a whiteboard in my apartment showing what Day it was. I wrote that every morning as soon as I woke up, and updated the other two numbers right before I went to sleep. Those were: the number of locations we had published to Californians where they could currently get the vaccine, and the number we knew about elsewhere across the United States with the vaccine.

The latter was zero at this point, of course. I brushed my teeth, wrote my emails, ate my meals, did media interviews, called my family, negotiated with funders, and said my prayers with the zero where I could see it.

From The story of VaccinateCA.

A lot of people think of Twitter as a public utility, a public trust, “the town square,” a company with an important social mission that many of its users and employees and Elon Musk care about deeply. And its CEO and board of directors essentially can’t bring themselves to talk about it. When employees asked him about what was best for the company, Agrawal could talk only about the shareholders. Elon Musk is not at all embarrassed to say that Twitter has an important public mission, which is why he’s buying it. But its current management can’t say that, which is why they’re selling it.

I want to be clear here that I am not saying that it was a bad decision, for Twitter’s product or users, to sell to Elon Musk. I have no idea; that’s not the point. The point is that the board seems to have put almost no weight on these questions. … I have written this before, but the basic problem with Twitter’s management and board of directors seems to be that they do not care about Twitter, as a company or as a product, so they are left to care about shareholders. This seems bad for everyone, including shareholders.

There are a lot of tech companies whose CEOs do not think this way. They are not all companies with “other legal mechanics,” as Agrawal said: Tesla Inc. and Amazon.com Inc. do not have dual-class stocks, and Elon Musk and Jeff Bezos have exactly the same duties to their shareholders as Agrawal has to his. But what Tesla and Amazon have are executives and boards who believe in what they are doing, and shareholders who trust them to pursue a long-term vision. If you ask Elon Musk about his decision-making, he would never say “Tesla is a public company owned by shareholders and I just try to maximize their profits.” He would talk about his master plan to decarbonize the world, he would talk about self-driving cars and rockets and tunnels. He cares about the product, not the shareholders. That’s why Musk’s shareholders are rich, and why Bezos’s are, and why Twitter’s are selling at $54.20.

From Matt Levine, Twitter’s Board Gave Up.

As an engineering leader, it’s important to remind your team that moving fast doesn’t mean working harder, or longer, or on the weekends. And it definitely doesn’t mean releasing a perfect product from day one. It requires cutting scope, iterating over time, and being more at ease with putting out a feature that’s not fully baked in order to learn what customers want.

You’re not going to get everything right from the outset, and that’s okay. The goal is to learn as you go: formulate a hypothesis, establish metrics, derisk, gather feedback, iterate, rinse, and repeat. Once you embrace the uncertainty, working on finding product-market fit isn’t just a challenge, but a thrill.

From Planning in the Dark: Planning for Product-Market Fit - Increment.

The already classic scene in which Paul wrenches the chorus to Get Back out of himself shows us, not just a moment of inspiration, but how the group pick up on what is not an obviously promising fragment and begin the process of turning it into a song. In the days to follow, they keep going at it, day after day, run-through after run-through, chipping away, laboriously sculpting the song into something that seems, in its final form, perfectly effortless. As viewers, we get bored of seeing them rehearse it and we see only some of it: on January 23rd alone they ran it through 43 times. The Beatles don’t know, during this long process, what we know - that they’re creating a song that millions of people will sing and move to for decades to come. For all they know, it might be Shit Takes all the way down. But they keep going, changing the lyrics, making small decision after small decision - when the chorus comes in, where to put the guitar solos, when to syncopate the beat, how to play the intro - in the blind faith that somewhere, hundreds of decisions down the line, a Beatles song worthy of the name will emerge.

A good song or album - or novel or painting - seems authoritative and inevitable, as if it just had to be that way, but it rarely feels like that to the people making it. Art involves a kind of conjuring trick in which the artist conceals her false starts, her procrastination, her self-doubts, her confusion, behind the finished article. The Beatles did so well at effacing their efforts that we are suspicious they actually had to make any, which is why the words “magic” and “genius” get used so much around them. A work of genius inspires awe in a lesser artist, but it’s not necessarily inspiring. In Get Back, we are allowed into The Beatles’ process. We see the mess; we live the boredom. We watch them struggle, and somehow it doesn’t diminish the magic at all.

From The Banality of Genius: Notes on Peter Jackson’s Get Back.

A recurring bug in many leaders’ operating systems—including mine—is overlooking just how much useful context a leader can have than folks on their team.

A regular practice I’ve adopted is sending a brief, five-minute weekly video communication to my team. The weekly comms, in fact, has been a long tradition in my org predating me that I have continued. Having been on both the receiving and sending end of the regular weekly comms, I’ve come to believe that this is a critical leadership activity on a growing team.

Information dissemination is a core responsibility of a leader. Leaders have access to a huge amount of information that most individuals on the team do not. Why is Sales hiring so much? Why did we decide to work on X instead of Y? What exactly is Marketing working on? By communicating habitually with my entire team, I can tell them what is going on, why it is going on, and critically, reinforce core cultural values.

The format

My weekly comms consist of an informal 5-8 minute video and transcript, published internally and announced on our internal all-company listserv. I record a video for a few reasons:

1. There are people willing to watch a video but not read an email.
2. It feels more personal and creates a bit of face-to-face connection on a distributed team.
3. It is easier.

The last bit is surprising. It surprised me, at first, and would not have been true a year ago. But now I am practiced at talking to a camera and have a good video setup that I use every day. Another factor is some excellent software called Descript that makes it simple to edit video and create transcripts. It feels like a magical advance in video editing.

I’m someone who obsesses over word choice, so I’ve found it easier to bang out a video script because I don’t worry as much about polishing it to the same extent as a stand-alone document. In the past, I tried to write a weekly email in the same format, but I was never consistent. It always felt like too much work. Recording a video is more sustainable.

I record in one take.

In practice, about one-third of the team watches the video, and one-third read the transcript, for about 2/3 total penetration.

What I talk about

• Welcoming new team members.
• Acknowledging major, company-impacting accomplishments.
• Acknowledging significant accomplishments that can fly under the radar of the business. Things like open source contributions, technical debt paid off, continuing iterative improvements after a big-bang launch.
• Announcing new policies.
• Connecting revenue numbers with project initiatives, site traffic, major closed deals, etc.
• Project team spin ups and spin downs.

A regular weekly comms is a great way to get a consistent message out to the entire team at once.

The habit

The key to making this work is forming a habit. If I wait until Friday morning to sit down in front of an empty text editor, I create lots of head-scratching and not much writing.

So on Monday, I create an empty document for the week that will serve as a script and transcript of the recording. I leave it open all week. On the side, I keep a running document of possible, non-time-sensitive topics to cover or topics that didn’t make it into the previous week.

Throughout the week, as I learn things from leaders on the team or hear of any information that needs to be flowed down, I capture that in the script as a quick bullet point.

On Friday morning, I write a quick draft and often send it to a few people for a quick review. Their feedback is critical—it’s a quick check to make sure I’m communicating what I mean. It is especially important to ensure I acknowledge the right people for accomplishments and don’t leave anyone out.

Then I record, almost always in one take. My assistant edits the video, exports, and then I Slack and email it to the team.

I dedicate 1.5 hours to my weekly video. Is this a lot of work? Yes. Is it worth it? Also yes. It is a chance to acknowledge efforts that could go unnoticed. It is a direct conduit to people on my team. It also makes me a better listener. Consistently creating a weekly comms puts me in a mindset of asking questions like “Is this important?” “Is it important for the team to know?” And critically, “what culture values can I communicate and reinforce?” It gets me out of my own head. It makes me a better, more informed leader.

What you talk about is what gets thought about

The weekly comms is a nudge. Done well, it can consistently and subtly shift the conversation in a positive direction. The weekly comms is an opportunity to create a story around the team and give it purpose.

References and further reading

• Week in Review Leadership Comms | Lara Hogan
• Sending weekly 5-15 updates. | Irrational Exuberance

Groups of technically oriented people often want to optimize the work process to those activities needed for the technically oriented output, and overlook those that are focused on the needs of humans and groups of humans working together. Yes, you can have a standup and not get any value from it. You can also not have a standup and avoid providing a convenient mechanism for taking advantage of the differences in observation, interpretation, and significance made by the entire team.

If you’ve got a really good team facilitator, they’ll likely notice this and help bring it out. If they’re really excellent, they’ll convince the team to work in a fashion where it can more easily come out without them acting as a middleman to make it happen. They might use a simple technique such as a daily standup to create such an opportunity.

From George Dinwiddie’s blog » Daily Stand-Up Meetings. Reflects my background suspicion of the efficacy of Slack “standups.”

… most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow. Plus, either way, you need to be good at quickly recognizing and correcting bad decisions. If you’re good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure.

Yes, I’m quoting Jeff Bezos’ 2016 Letter to Amazon Shareholders again. This quote is referenced in Working Backwards, which I’ve added to my recommended reading for engineering managers.

Pair with Making the decision right.

• Clayton Christensen, The Innovator’s Dilemma. I resisted reading this for a long time because it’s so much a part of the fabric of working in tech. I’m glad I did. Cost structures matter. Recommended.
• Ta-Nehisi Coates, Between the World and Me. I listened to this as an audiobook, read by Coates himself. Short but powerful.
• Eric Berger, Liftoff: Elon Musk and the Desperate Early Days That Launched SpaceX. If you want to know why SpaceX can do so much in so little time, this is where to start. Great story.
• John le Carré, The Night Manager. A lot of people love le Carré; I am not one of them.
• Colin Bryar and Bill Carr, Working Backwards: Insights, Stories, and Secrets from Inside Amazon. You can find a lot online about “how Amazon works.” This is the clearest distillation I’ve found.
• Brad Stone, The Everything Store: Jeff Bezos and the Age of Amazon. Broad, not deep. That said, I’m looking forward to the next installment. A summary.
• Arkady Martine, A Desolation Called Peace. Solid sequel to A Memory Called Empire.
• Rick Perlstein, Nixonland: The Rise of a President and the Fracturing of America. I hadn’t realized just how chaotic the late 60s early 70s were. This book filled in many gaps for me on where many of the political divides leading up to the Trump era originated. The book is overlong, and the author maintains an ironic detachment that grows tiring.
• Kim MacQuarrie, The Last Days of the Incas. Recommended. In the end it reads likes a morality tale as the original conquistadors of the Incas, almost to a man, fall to violence and betrayal.
• Ted Widmer, Lincoln on the Verge: Thirteen Days to Washington. A strange little history book that makes a lot of connections.
• Erik Larson, The Splendid and the Vile. Engaging, but ultimately not for me.
• Barack Obama, A Promised Land. What you think this book is exactly what it is.
• David McCullough, The Wright Brothers. Really enjoyed this. I would have appreciated more about the business and patent fights of later days. You can see the Wrights slipping behind in the industry but, this is scarecely commented on.

As companies get larger and more complex, there’s a tendency to manage to proxies. This comes in many shapes and sizes, and it’s dangerous, subtle, and very Day 2.

A common example is process as proxy. Good process serves you so you can serve customers. But if you’re not watchful, the process can become the thing. This can happen very easily in large organizations. The process becomes the proxy for the result you want. You stop looking at outcomes and just make sure you’re doing the process right. Gulp. It’s not that rare to hear a junior leader defend a bad outcome with something like, “Well, we followed the process.” A more experienced leader will use it as an opportunity to investigate and improve the process. The process is not the thing. It’s always worth asking, do we own the process or does the process own us? In a Day 2 company, you might find it’s the second.

Another example: market research and customer surveys can become proxies for customers – something that’s especially dangerous when you’re inventing and designing products. “Fifty-five percent of beta testers report being satisfied with this feature. That is up from 47% in the first survey.” That’s hard to interpret and could unintentionally mislead.

Good inventors and designers deeply understand their customer. They spend tremendous energy developing that intuition. They study and understand many anecdotes rather than only the averages you’ll find on surveys. They live with the design.

I’m not against beta testing or surveys. But you, the product or service owner, must understand the customer, have a vision, and love the offering. Then, beta testing and research can help you find your blind spots. A remarkable customer experience starts with heart, intuition, curiosity, play, guts, taste. You won’t find any of it in a survey.

From Jeff Bezos’ 2016 Letter to Amazon Shareholders. The whole letter is clear, precise, and worth reading.