WordPress was my first introduction to the idea of distributed work — we didn’t need to live in the same place or work in the same office to build something that changes the world. So when I started building Automattic in 2005, we took the exact same approach. All you needed was good WiFi and a dream.
Fast forward to 2019, and Automattic remains a fully distributed company, with 900 employees working from 68 countries and no central office. Now that we’ve been working this way for over a decade, I wanted to create a podcast to tell the story of distributed work — not just sharing everything we’ve learned at Automattic, but speaking with other companies, executives, and creators who are pioneering the future of work. We’re going to learn about the practical application of distributed work in our daily lives, but also answer the bigger questions about why it’s important.
Forward-looking new series about distributed work from the founder of WordPress and Automattic (my employer).
Confidence isn’t optimism or pessimism, and it’s not a character attribute. It’s the expectation of a positive outcome.
I’m inspired by Rosabeth Moss Kanter’s work and philosophy on change management. The consistent message in her writing—many of her essays are in Harvard Business Review—is that a leader’s job is to “provide the tools and conditions that liberate people to use their brainpower to make a difference in a world of constant challenge and change.”
In a brainstorming exercise with my group at the altMBA, I expected to dive deep into the work, tuning our understanding of business models while working under pressure to create as many ideas as possible in a short time. We did just that, relishing our creativity and ingenuity.
Yet the most satisfying outcome wasn’t how deep or wide we ranged as much as the practice of creating the right space for it to happen. Allowing discovery, allowing the best work to shine through. The moment created by the creative space was the true prize.
In our session there grew a playfulness and a natural building up of ideas as serendipitous intersections occurred where a concept, channel, or stream could be cloned to adapt to a new business idea. Growing, it created momentum and provided a sense of space — room to roam.
The diversity of the team made for richer output as we kept exploring. Ideas born from one member cloned rapidly into new ones by tapping into our backgrounds, affinities, and environments. Though we started together pitching and editing out loud, it was slow going. The pace accelerated only after a 45-minute switch to brainwriting, writing solo to bring more life to the list. We successfully avoided the problem of “one loud voice” by taking turns narrating and typing.
Creating the space to run together started with finding a format that built enough structure without slowing us down. We later dubbed this the napkin sketch for its simplicity.
The napkin sketch technique produces a great number of ideas without too much detail. Just enough to explain a business idea or “micro” business model to a friend in plain English.
Here’s how it works:
Outline and pitch the business idea.
Detail the basics only: value proposition, market, costs, and revenue.
If you feel a spark, clone the sketch and adapt it.
Repeat until you run out of ideas.
If you freeze an idea too quickly, you fall in love with it. If you refine it too quickly, you become attached to it and it becomes very hard to keep exploring, to keep looking for better. The crudeness of the early models in particular is very deliberate. — Jim Glymph, architect
Jim Glymph (Gehry Partners, architects 1990–2007) explains the value of crude early models—what my altMBA group called “Napkin sketches.
Originally posted on Medium—and if Matt’s reading this, it’s required for the course. 🙃
If you want to be an effective strategic leader, you can’t settle for a regimen of reading board books and showing up for quarterly meetings. You must engage fully on your organization’s mission; seize opportunities to observe frontline work; and, at each board meeting, take every chance to confront the big, long-term issues by asking tough questions.
After checking the gauges, you’ll know what to do next: keep effective performers, remove laggards, and ask the tough questions and demand answers.
This advice for board members applies equally to an executive team member in a business setting, leading teams at Automattic. In short—do the work, be open to the burden of responsibility, and seek out direct connections.
We are rewarded for the answer. Not another question. It’s beaten out of us from kids, and later in work it can be hazardous for your career. —Warren Berger
Via the Farnam Street podcast I loved this cultural insight. An honest assertion that our business culture rewards quick-hit answers instead of rewarding the act of slowing down to find the right question.
Why a Flat Organizational Structure will Fail as You Grow is an insightful and thought-provoking study from Lighthouse, a software tool for managers. Keeping in mind when considering any decision that someone else — somewhere before — solved the same issue. From my personal workflow, to team processes and habits, all the up to key decisions on company structure.
There are a few advantages and many disadvantages to a flat organizational structure as you grow. We share how growth breaks a flat organizational structure
…if you think it’s a good use of your time to try to innovate in employee on-boarding, performance feedback, quarterly reviews, promotions or weekly all hands meetings, you are mistaken at best and destroying your company at worst.
Call ten friends who work at great companies and crowd source the best practices. These best practices are widely understood and broadly implemented, and the differences are minimal or arguably irrelevant.
What makes a company or product unique? What makes it exceptional? Even though we should continually seek to improve, a strong legacy most likely won’t come from rethinking the 1-1 check-in chat, how we process payroll, or even our technical toolkit.
By modeling organizational excellence on what is already known to work everywhere else we can focus our creativity and innovation on improving the product experiences that help our customers succeed.
Note: My colleague Cate points out that the origins of most technology company practices are outlined in Andy Grove’s classic book High Output Management (1983), describing how to build and run a company.
Via Wikipedia, a canonical bookmark for the business phrase “table stakes” that I’ve heard a few times recently.
In business, table stakes are the minimum entry requirement for a market or business arrangement. They can be price, cost model, technology, or other capability that represents a minimum requirement to have a credible competitive starting position in a market or other business arrangement.
For example, to be a wireless service provider, the table stakes are the basic features you need to have in order to be in that business to achieve foundation capability: network, handsets, a data service, a mail server, etc. Beyond that, real competitive advantage comes from additional nimbleness and cost or product differentiation.
A reference to poker and other gambling games where the “table stakes” represent a limit on the amount a player can win or lose in the play of a single hand.
Note: I’m learning lots of new business terminology, so if you have more insights or examples to illustrate this one — please leave a comment.