As Leaders Learn to Speak Machine, They Need to Speak Better Human Too

John Maeda
3 min readNov 10, 2020
Digital handwriting set in the amazing “Liebeheide” by typographer Ulrike Rausch

Long before the pandemic, I learned about “remote work” in Silicon Valley and I felt like it could be the future. That was five years ago, and I didn’t expect it to happen so quickly.

At the time, Automattic was the largest tech company operating fully remote, or more precisely “fully distributed,” and my good fortune led me to joining Matt Mullenweg’s prescient organization. As the pandemic has worn on, I have found that many of the “new” WFH tips that get shared today were pioneered long ago by Automattic. Things like the difference between the politics of a workforce that is partially distributed versus 100% distributed — the latter being the more effective option. And the fact that “asynchronous” unmonitored working is better than three-hour “synchronous” Zoom calls where showing presence is a requirement — but the former requires a great deal of trust that most bosses aren’t willing to easily extend. Perhaps the most revolutionary aspect of distributed work is the notion that talent does not need to be drawn from a hub like San Francisco or New York City, and can be just as easily sourced from Mexico City or Nairobi or anywhere in the world as an expanded dimension of the tech meritocracy.

I later came to realize that time zone differences, to start, tend to be insurmountable obstacles for working in a united fashion when everyone is distributed. And there’s also that English-is-the-universal-language issue that tends to get forgotten when you’re a native English speaker. Then there’s the fact that there’s so many conversations happening simultaneously at various density levels throughout the day. The only way to get a handle on what’s being said, of course, is to use algorithms to help bubble up to you what is the most relevant signal within all the noise. So as more and more of us WFH, we are adopting the norms of gathering all our information using systems that are akin to social media. These systems feed off of engagement, learn what we like, and optimize our feeds accordingly.

In the imminent future, being facile at speaking machine will require an even greater facility at…

John Maeda

John Maeda: Technologist and product experience leader that bridges business, engineering, design via working inclusively. Currently VP Design and A.I. at MSFT.