Leadership when the playbook is being rewritten

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Alfred Lin from Sequoia shared a David Brooks essay recently. The line he pulled from the Atlantic piece:

"The secret of life is to have a task, something you devote your entire life to, something you bring everything to, every minute of the day for the rest of your life. And the most important thing is, it must be something you cannot possibly do."

That is Henry Moore, the sculptor, talking to the poet Donald Hall about what a life of work feels like up close. The whole point is the doing itself, and the impossibility of finishing. There is no goal at the end of it. There is only the work.

It is also a working description of what good leadership looks like in this moment. The job is to keep showing up to a task that does not finish, especially when some of the things underpinning strong management principles (managing incredibly large teams, strong delegation etc.) are being challenged. The three operators I have been reading lately are sharing personal reflections under exactly those conditions: Tobi Lutke at Shopify, Brian Chesky at Airbnb, and Zeb Evans at ClickUp. Their starting points are different however the shape of how they decide and move the company forward is similar.

Tobi's view on experiencing the shop floor

Earlier this month, Lutke published a piece called Learning on the Shop Floor. The short version is that Shopify built an AI agent called River. She lives in their internal Slack channels, anyone in the company can talk to her, and she's written about one eighth of the new pieces of code their engineers shipped into the product. Also, River only operates in public channels as she refuses to respond to direct messages.

Most AI tools default to private. ChatGPT is a private window, Claude is a private window, Cursor sits between you and the IDE. Lutke made the opposite call and while the decision may have been controversial at the time, two months later, the share of River's code that was good enough to ship climbed from 36% to 77% without the AI model itself being upgraded. The improvement came from people watching River work, noticing where she got stuck, and writing down what she should have known. Every team's accumulated taste flowed into the agent.

The framing he reaches for is German. Lehrwerkstatt, literally "teaching workshop." The whole shop floor is the classroom. You learn by being near the work.

The load-bearing line in Tobi's piece:

"The speed of an organization is determined by the speed of its lowest-bandwidth communication channel."

Meetings are slow, email is slow, private DMs are slow while public conversations are fast, teachable, and they compound. The leadership call Lutke made was to bias the system toward what compounds, even when the short-term cost was friction. Most people at the company were used to private workspaces with their tools. Asking for help feels different when the whole company can see the question.

Chesky on leadership and the artist's instinct

Brian Chesky did a recent interview with Patrick O'Shaughnessy on Invest Like The Best (definitely recommend it if you haven't seen it). The familiar version of the story is the founder mode one. Chesky, post-IPO, over-delegated and was told by Sam Altman he should spend half his time on hiring. He didn't and as the company grew, was being a few layers removed from reviewing decisions, stopped sitting on details, and the company began building things he had not seen. He calls it his death blow.

The fix was reluctant and granular. He went back into the operations of the business and learned the craft of each function he was hiring for. He also spends two to three hours a day now on recruiting and argues your first hire should be a recruiter.

A few days after the interview aired, Alfred Lin posted his own observation on it:

"If you're a founder struggling to hire the right exec, you may need to do the job yourself first. Brian spoke to the best, learned the craft, and did the job himself until he understood it well enough to know what to hire for."

Lin's closing line: doing is better than guessing.

The other thread that runs through the interview is Chesky as a leader who thinks about his work the way an artist does. The clearest version of it is the story of hiring Hiroki Asai, Steve Jobs's former creative director at Apple. Hiroki taught him two principles from Apple that he carried into Airbnb: simplicity and craft. Inside that, Chesky quotes Steve Jobs directly:

"Design is the fundamental soul of a man-made creation that reveals itself through subsequent layers."

Chesky says here that great design is about distilling something to its essence. The second principle, in his own words: how you do anything is how you do everything.

The same instinct runs through the interview. He insisted on inspecting professional photos for early Airbnb listings himself because nobody else was going to do it at the level he wanted. He invented the eleven-star service exercise, the one where you design backwards from an absurd lens. Elon Musk takes you to space at eleven stars, a parade in your honour at ten stars, until six stars stops looking ambitious and five stars (think Uber five star ratings) is the default. The leader's job is to hold the standard for the thing itself, not to organise other people around the thing.

He closes the interview citing Rick Rubin: "an artist is an artist when they make it for themselves and they don't try to make something successful." He talks about adulation after the Airbnb IPO as a cup with a hole in the bottom, where you keep filling it thinking it's love and it just keeps coming out. The Hiroki story comes back at the end too as Hiroki told him that in the final weeks of Steve Jobs's life, Jobs was still showing him marketing, still looking at products. Chesky's read:

"They're working in the end because they did what they loved. Mozart, the great artists in history, did what they loved."

The leadership move he's making is to point himself at the work, not at the reward for the work. That sits closer to Henry Moore than it sits to most modern management writing.

Zeb Evans on transparency and making the tough calls

Zeb Evans is the CEO of ClickUp. Recently, he shared a post explaining a 22% reduction in his company's headcount. The opening line:

"Today we reduced headcount by 22%. The business is the strongest it's ever been."

The leadership move reveals itself within the initial headcount statement. Evans publishes his thinking in real time, while the decision is still fresh.

The contrarian counter to the consensus narrative:

"The common narrative is that AI makes everyone more productive. It doesn't. Many of the workflows of today, if left unchanged, create bottlenecks in AI systems."

His framing of where value concentrates inside functions:

"The great engineers, the ones who can orchestrate, architect, and review, are becoming 100x engineers. They're not writing code. They're directing agents that write code. The skill is judgment."

Finally, the line for any seat-in-the-middle question:

"Everything outside of managing systems, orchestrating AI, and reviewing output becomes a bottleneck."

That is the harder, more recent version of a much older idea. Frank Lloyd Wright said something almost identical decades earlier, in a line Chesky himself quoted in his interview:

"You manage people through the work. You don't manage the people."

Two voices on the same point, eighty-some years apart. Managers whose value lives inside the work survive. The seats that exist only to schedule, review, route and approve, sitting one layer above the work, may not.

Evans is also careful to name what does not get replaced. He calls it the front-liner carve-out:

"In a world that will become saturated with AI communication, the human touch will matter more than anything to customers. One-on-one meeting time with customers is something that shouldn't be automated."

That carve-out is the operative one for anyone in a customer-facing seat: advisors, accountants, retail business owners, anyone whose core work is directly customer facing or holding relationships through them. The work that reduces is the work that organises other work. The work that stays is the work that produces it, or the work that holds a relationship through it.

Zeb had the willingness to make the hard call publicly and name the trade-off honestly and own it.

A sightglass into leadership at Uber

I spent over seven years at Uber in San Francisco, working across strategy, product ops, as a chief of staff and more recently as a GM. One of the rooms where I learnt the most was with the c-suite as they worked through hard decisions under real pressure.

• Pricing trade-offs on the driver side of the marketplace in markets where the increase would hurt people relying on the income.
• Customer situations where partnering would get us to market faster, but with a potentially degraded experience. Speed to market was critical for our business, but equally we needed to hold the line on quality of experience.
• Regulatory questions were hotly debated, especially those where the framework had not been written yet.
• Then there was short-term vs long-term aspirations, which we called the objective function.

Sitting in these rooms taught me that many decisions that leaders inherently make are not based on a dashboard or a simple a > b outcome. It's a judgment applied under genuine constraints and trade offs, by people who have spent years (in many cases decades) getting close enough to the operating reality to be useful to it.

Uber had values that ran as working language for hard decisions under pressure. I'll share three of them with you:

• Go get it. The bias to action over deliberation, particularly when you had less information than you would have liked. You would go for it anyway, with the right mindset to succeed.
• Great minds don't think alike. The recognition that the strongest decision rarely came from a single point of view, and that disagreement well-handled was a feature, not a bug.
• See the forest and the trees. The hardest of the three in my opinion, to practice. You had to hold the strategic frame and the on-the-ground operational reality in the same head at the same time.

These might sound like slogans on a wall but in practice, they were how the senior operators I watched made some of the hardest decisions no model could have made for them. Data and recommendations from a tremendous amount of team members and analysis would land in front of them. The judgment was still making the tough call with real impact to our end users. Some of the leaders I saw in that room had a bit of artistry, shop floor experience and the guts to make the tough calls when it mattered.

What I took from those rooms is that leadership is the same kind of framework at any scale. Whether you are running a twenty-thousand-person platform or a five-person team, the question underneath every decision is the same. What are you doing? Why are you doing it? Who is it for? What does good look like? The size of the team changes the cadence of those questions and the stakes of getting them wrong. It does not change what is actually being asked.

Is good leadership today good leadership tomorrow?

Two threads in my own thinking have sharpened what I think those abilities are worth in the next five years.

1. The first is the judgment premium. As execution gets cheaper and faster, the scarce resource shifts to the decisions about what to build, why, when, and whether to do it at all. The roles that have a higher tendency for survival are the ones whose value was never pure execution in the first place.
2. The second is agency over skills. Skills are increasingly cheaper to acquire however the willingness to act on the world with what you have, to reach for the result directly rather than wait for the right instruction and the right approval, is the part you cannot make cheaper. The highly skilled senior operators I observed at Uber had agency more than they had any specific skill. That part of the job amplifies precisely as the skills get easier to come by.

When I came back to Australia last year and joined Jonathan at FGO Finance Group, I asked myself that same question - what would make me a good leader in the business? The team is smaller, the scale is different however when I distill it down to first principles, the questions are the same. What are we building towards? Who is it for and what does good look like? I write the posts you are reading rather than approving them in the past. There is no org chart to hide behind and I consider that my 'shop floor' experience.

Those questions are fulfilling on their own terms, and I hope the people we serve now and into the future are better off because of it. Having the aspiration to grow and scale a business from the ground up makes Chesky's instinct about distilling something to its essence, and holding the standard for the thing itself, land in a way it would not have when I was a few more layers from the work. I'm not saying one is better than the other but it didn't resonate as much with me then, but it definitely does now.

Connecting the threads together

Lutke's essay, Chesky's interview and Evans's manifesto are not telling the same story however they do share a setting. The world is changing faster than it has at any point in any of our working lives. The largest (and smallest) companies are producing outputs in ways that make traditional org charts look ornamental. The same technology lifting the productivity curve is also bringing data, knowledge and ideas to anyone with a screen at near-zero latency.

Both halves of the leadership job are getting harder at the same time. The premium on judgment at the top is going up while the pressure to stay close to the work, where that judgment is actually formed, is also going up. Truth be told, holding both is the hard part. None of the operators in this piece is suggesting you pick one. Lutke chose visibility but he is still the CEO of an incredibly large company. Chesky reclaimed the details but he is also still the public face of one of the largest travel companies in the world. Evans cut 22% and named the front-liner work as the part that compounds. Lin's whole observation is that doing the job yourself is how you eventually figure out what to hire for, not a permanent state.

For anyone in or near a leadership seat right now, the question to ask yourself is: what fraction of your week, this month, this year sits inside the work versus organising it? Both are necessary so perhaps the harder question is the proportion, and whether the calls you are making in either mode are the calls only you can make.

Henry Moore would have recognised the underlying point. The playbook can change, the tools can change and the org chart can evolve. How close leaders stay to the actual work being done does not. Perhaps that is the constant.

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