Skip to content

17 posts tagged with “leadership”

Remote work really exploded when the Covid-19 pandemic hit. Everyone had to adjust to working from home, relying on Zoom and Slack and other collaborative tools much more. But beyond tooling, there’s also process. Matt Mullenweg, CEO of Automattic, has famously been a proponent of distributed work for a while.

Paolo Belcastro peels back the curtain to share how the 1,500 or so global employees of Automattic stay connected via two core principles:

There are two ideas that define our communication culture:

Radical Transparency: we default to openness, with every conversation accessible to everyone in the company. Asynchronous by Design: we don’t expect everyone to be “on” at the same time.

Everything is written down:

Our internal platform, P2, started life as a WordPress theme (it was called Prologue, later updated to version 2 and eventually shortened to P2) that lets people post directly on the front end of a site—fast, simple, and visible to everyone. Over time it evolved into a network of thousands of P2s for teams, projects, and watercooler chats (couch surfing, classified ads, house renovations, babies, pets, music, or games, we kind of have it all).

Every post, every comment, every decision ever made in the history of Automattic is preserved there.

As you can imagine, it soon becomes a volume problem. There’s too much stuff.

No one can read everything.

That’s why onboarding is designed to help people adapt:

  • Each newcomer is paired with a mentor from a different team, to give them a cross-company perspective.
  • They receive a curated list of “milestone posts” that map the history of Automattic, along with role-specific threads relevant to their work.
  • The Field Guide offers principles, templates, and advice about how to handle communication.

Somehow, they make it work.

Using chaos to communicate order

Using chaos to communicate order

How we communicate at Automattic

ttl.blog iconttl.blog

Building on Matthew Ström-Awn’s argument that true quality emerges from decentralized, ground-level ownership, Sean Goedecke writes an essay exploring how software companies navigate the tension between formalized control and the informal, often invisible work that actually drives product excellence.

But first, what does legibility even mean?

What does legibility mean to a tech company, in practice? It means:

  • The head of a department knows, to the engineer, all the projects the department is currently working on
  • That head also knows (or can request) a comprehensive list of all the projects the department has shipped in the last quarter
  • That head has the ability to plan work at least one quarter ahead (ideally longer)
  • That head can, in an emergency, direct the entire resources of the department at immediate work

Note that “shipping high quality software” or “making customers happy” or even “making money” is not on this list. Those are all things tech companies want to do, but they’re not legibility.

Goedecke argues that while leaders prize formal processes and legibility to facilitate predictability and coordination, these systems often overlook the messier, less measurable activities that drive true product quality and user satisfaction.

All organizations - tech companies, social clubs, governments - have both a legible and an illegible side. The legible side is important, past a certain size. It lets the organization do things that would otherwise be impossible: long-term planning, coordination with other very large organizations, and so on. But the illegible side is just as important. It allows for high-efficiency work, offers a release valve for processes that don’t fit the current circumstances, and fills the natural human desire for gossip and soft consensus.

Seeing like a software company

The big idea of James C. Scott’s Seeing Like A State can be expressed in three points: Modern organizations exert control by maximising “legibility”: by…

seangoedecke.com iconseangoedecke.com

Matt Ström-Awn makes the argument that companies can achieve sustainable excellence by empowering everyone at each level to take ownership of quality, rather than relying solely on top-down mandates or standardized procedures.

But more and more I’ve come to believe that quality isn’t a slogan, a program, or a scorecard. It’s a promise kept at the edge by the people doing the work. And, ideally, quality is fundamental to the product itself, where users can judge it without our permission. That’s the shift we need: away from heroics at the center, toward systems that make quality inevitable.

The stakes are high. Centralized quality — slogans, KPIs, executive decrees — can produce positive results, but it’s brittle. Decentralized quality — continuous feedback, distributed ownership, emergent standards — builds resilience. In this essay, I’d like to make the case that the future belongs to those who can decentralize their mindset and approach to quality.

Ström-Awn offers multiple case studies, contrasting centralized systems with decentralized ones, using Ford, Amazon, Apple, Toyota, Netflix, 3M, Morning Star, W.L. Gore, Valve, Barnes & Noble, and Microsoft under Satya Nadella as examples.

These stories share a common thread: organizations that trusted their frontline workers to identify and solve quality problems. But decentralized quality has its own vulnerabilities. Valve’s radical structure has been criticized for creating informal power hierarchies and making it difficult to coordinate large projects. Some ex-employees describe a “high school clique” atmosphere where popular workers accumulate influence while others struggle. Without traditional management oversight, initiatives can moulder, or veer in directions that don’t serve broader company goals.

Still, these examples show a different path for achieving quality, where excellence is defined in the course of building a product. Unlike centralized approaches relying on visionary (but fallible) leaders, decentralized systems are resilient to individual failures, adaptable to change, and empowering to builders. The andon cord, the rolling desk, and the local bookstore manager each represent a small bet on human judgment over institutional control. Those bets look like they’re paying off.

Decentralizing quality

Decentralizing quality

Why moving judgment to the edges wins in the long run

matthewstrom.com iconmatthewstrom.com

Definitely use AI at work if you can. You’d be guilty of professional negligence if you don’t. But, you must not blindly take output from ChatGPT, Claude, or Gemini and use it as-is. You have to check it, verify that it’s free from hallucinations, and applicable to the task at hand. Otherwise, you’ll generate “workslop.”

Kate Niederhoffer, Gabriella Rosen Kellerman, et. al., in Harvard Business Review, report on a study by Stanford Social Media Lab and BetterUp Labs. They write, “Employees are using AI tools to create low-effort, passable looking work that ends up creating more work for their coworkers.”

Here’s how this happens. As AI tools become more accessible, workers are increasingly able to quickly produce polished output: well-formatted slides, long, structured reports, seemingly articulate summaries of academic papers by non-experts, and usable code. But while some employees are using this ability to polish good work, others use it to create content that is actually unhelpful, incomplete, or missing crucial context about the project at hand. The insidious effect of workslop is that it shifts the burden of the work downstream, requiring the receiver to interpret, correct, or redo the work. In other words, it transfers the effort from creator to receiver.

Don’t be like this. Use it to do better work, not to turn in mediocre work.

Workslop may feel effortless to create but exacts a toll on the organization. What a sender perceives as a loophole becomes a hole the recipient needs to dig out of. Leaders will do best to model thoughtful AI use that has purpose and intention. Set clear guardrails for your teams around norms and acceptable use. Frame AI as a collaborative tool, not a shortcut. Embody a pilot mindset, with high agency and optimism, using AI to accelerate specific outcomes with specific usage. And uphold the same standards of excellence for work done by bionic human-AI duos as by humans alone.

AI-Generated “Workslop” Is Destroying Productivity

AI-Generated “Workslop” Is Destroying Productivity

Despite a surge in generative AI use across workplaces, most companies are seeing little measurable ROI. One possible reason is because AI tools are being used to produce “workslop”—content that appears polished but lacks real substance, offloading cognitive labor onto coworkers. Research from BetterUp Labs and Stanford found that 41% of workers have encountered such AI-generated output, costing nearly two hours of rework per instance and creating downstream productivity, trust, and collaboration issues. Leaders need to consider how they may be encouraging indiscriminate organizational mandates and offering too little guidance on quality standards. To counteract workslop, leaders should model purposeful AI use, establish clear norms, and encourage a “pilot mindset” that combines high agency with optimism—promoting AI as a collaborative tool, not a shortcut.

hbr.org iconhbr.org

Cap Watkins, Head of Product Design at Lattice, was catching up with a former top-performing designer who was afraid other designers were mad at her for getting all the “cool” projects.

What made those projects glamorous and desirable was her and how she approached the work. There’s that old nugget about making your own luck and that is something she excelled at. She had a unique ability to take really hard or nebulous problems (both design and team-related) and morph them into something amazing that got people excited. Instead of getting discouraged, she’d respond to friction with more energy, more enthusiasm. In so many ways, she was a transformative presence on any team and project.

In other words, this designer cared and made the best of all her assignments.

Make things happen

Top designers aren’t handed “cool” projects—they transform hard, unglamorous work into exciting wins. Stop waiting. Make your work shine. Make things happen.

capwatkins.com iconcapwatkins.com

Sonos announced yesterday that interim CEO Tom Conrad was made permanent. From their press release:

Sonos has achieved notable progress under Mr. Conrad’s leadership as Interim CEO. This includes setting a new standard for the quality of Sonos’ software and product experience, clearing the path for a robust new product pipeline, and launching innovative new software enhancements to flagship products Sonos Ace and Arc Ultra.

Conrad surely navigated this landmine well after the disastrous app redesign that wiped almost $500 million from the company’s market value and cost CEO Patrick Spence his job. My sincere hope is that Conrad continues to rebuild Sonos’s reputation by continuing to improve their products.

Sonos Appoints Tom Conrad as Chief Executive Officer

Sonos Website

sonos.com iconsonos.com

This post has been swimming in my head since I read it. Elena Verna, who joined Lovable just over a month ago to lead marketing and growth, writing in her newsletter, observes that everyone at the company is an AI-native employee. “An AI-native employee isn’t someone who ‘uses AI.’ It’s someone who defaults to AI,” she says.

On how they ship product:

Here, when someone wants to build something (anything) - from internal tools, to marketing pages, to writing production code - they turn to AI and… build it. That’s it.

No headcount asks. No project briefs. No handoffs. Just action.

At Lovable, we’re mostly building with… Lovable. Our Shipped site is built on Lovable. I’m wrapping hackathon sponsorship intake form in Lovable as we speak. Internal tools like credit giveaways and influencer management? Also Lovable (soon to be shared in our community projects so ya’ll can remix them too). On top of that, engineering is using AI extensively to ship code fast (we don’t even really have Product Managers, so our engineers act as them).

I’ve been hearing about more and more companies operating this way. Crazy time to be alive.

More on this topic in a future long-form post.

preview-1752160625907.png

The rise of the AI-native employee

Managers without vertical expertise, this is your extinction call

elenaverna.com iconelenaverna.com

Read past some of the hyperbole in this piece by Andy Budd. I do think the message is sound.

If you’re working at a fast-growth tech startup, you’re probably already feeling the pressure. Execs want more output with fewer people. Product and engineering are experimenting with AI tooling. And you’re being asked to move faster than ever — with less clarity on what the team should even own.

I will admit that I personally feel this pressure too. Albeit, not from my employer but from the chatter in our industry. I’m observing the younger companies experiment with the process, collapsing roles, and expanding responsilities.

As AI eats into the production layer, the traditional boundaries between design and engineering are starting to dissolve. Many of the tasks once owned by design will soon be handled by others — or by machines.

Time will tell when this becomes widespread. I think designers will be asked to ship more code. And PMs and engineers may ship small design tweaks.

The reality is, we’ll likely need fewer designers overall. But the ones we do need will be more specialised, more senior, and more strategically valuable than ever before.

You’ll want AI-literate, full-stack designers — people who are comfortable working across the entire product surface, from UX to code, and from interface to infrastructure. Designers who can navigate ambiguity, embrace new tooling, and confidently operate in the blurred space between design and engineering.

I don’t know if I agree with the fewer number of designers. At least not in the near-term. The more AI is embedded into app experiences, the trend—I predict—will go in the opposite direction. The term “AI as material” has been floating around for a few months, but I think its meaning will morph. AI will be the new UI, and thus we need designers to help define those experiences.

preview-1751840519842.png

Design Leadership in the Age of AI: Seize the Narrative Before It’s Too Late

Design is changing. Fast. AI is transforming the way we work — automating production, collapsing handoffs, and enabling non-designers to ship work that once required a full design team. Like it or not, we’re heading into a world where many design tasks will no longer need a designer. If that fills you with unease, you’re not alone. But here’s the key difference between teams that will thrive and those that won’t: Some design leaders are taking control of the narrative. Others are waiting to be told what’s next.

andybudd.com iconandybudd.com

Bell Labs was a famed research lab run by AT&T (aka “Ma Bell” before it was broken up). You can draw a straight line from Bell Labs to Xerox PARC where essential computing technologies like the graphical user interface, the mouse, Ethernet, and more were invented.

Aeroform, writing for 1517 Fund:

The reason why we don’t have Bell Labs is because we’re unwilling to do what it takes to create Bell Labs — giving smart people radical freedom and autonomy.

The freedom to waste time. The freedom to waste resources. And the autonomy to decide how.

preview-1749165348692.png

Why Bell Labs Worked.

Or, how MBA culture killed Bell Labs

1517.substack.com icon1517.substack.com
Closeup of a man with glasses, with code being reflected in the glasses

From Craft to Curation: Design Leadership in the Age of AI

In a recent podcast with partners at startup incubator Y Combinator, Jared Friedman, citing statistics from a survey with their current batch of founders says, “[The] crazy thing is one quarter of the founders said that more than 95% of their code base was AI generated, which is like an insane statistic. And it’s not like we funded a bunch of non-technical founders. Like every one of these people is highly tactical, completely capable of building their own product from scratch a year ago…”

A comment they shared from founder Leo Paz reads, “I think the role of Software Engineer will transition to Product Engineer. Human taste is now more important than ever as codegen tools make everyone a 10x engineer.”

A winter panoramic view from what appears to be a train window, showing a snowy landscape with bare deciduous trees and evergreens against a gray sky. The image has a moody, blue-gray tone.

The Great Office Reset

Cold Arrival

It’s 11 degrees Fahrenheit as I step off the plane at Toronto Pearson International. I’ve been up for nearly 24 hours and am about to trek through the gates toward Canadian immigration. Getting here from 73-degree San Diego was a significant challenge. What would be a quick five-hour direct flight turned into a five-hour delay, then cancelation, and then a rebook onto a red-eye through SFO. And I can’t sleep on planes. On top of that, I’ve been recovering from the flu, so my head was still very congested, and the descents from two flights were excruciating.

After going for a short secondary screening for who knows what reason—the second Canada Border Services Agency officer didn’t know either—I make my way to the UP Express train and head towards downtown Toronto. Before reaching Union Station, the train stops at the Weston and Bloor stations, picking up scarfed, ear-muffed, and shivering commuters. I disembark at Union Station, find my way to the PATH, and headed towards the CN Tower. I’m staying at the Marriott attached to the Blue Jays stadium.

Steve Jobs

Putting a Dent in the Universe

I have been a Mac user since 1985, when I was in the seventh grade. For months I lusted after the Mac on display at Computerland on Van Ness Avenue in San Francisco. I'd go there after school just to play with MacPaint. It simply captured my imagination. Finally, after many weeks of begging, I got my dad to buy me a 512K Mac. Thus began my love affair with Apple.

Imagine how lucky I felt when I actually began working on the brand and on Pixar in 2001-2002. It was such a privilege to be so close to the magic and to Steve Jobs himself.

The Steve Jobs I knew was human. Not a god. Not someone who could distort reality. Just a man.

The Need to Breathe

“1000+” should be a familiar number for Google Reader users. My RSS feeds have been neglected in past months. Emails from AdAge.com, Creativity-Online, and links from friends go unread and unclicked. I’ve just been running 100 miles per hour at work. This is not to slam my current employer (because I truly like working here), but more of an observation.

If we creatives are always so busy with projects, and never take the time to look up, take off our headphones and find inspiration, our work will suffer. Our work will stagnate. Our work will suck.

So this is a reminder to myself (and to other creatives) to take a bit of time each day to remain inspired. Surf the web. Watch TV. See a movie in a theater. Listen to new music. Read a magazine or a book. Go to a bookstore. Go to a museum. Go hiking.