I’m Slack CTO Cal Henderson, and This Is How I Work
Cal Henderson is the co-founder and CTO of Slack, a leading workplace messaging platform that Henderson’s team invented while trying to create an online game called Glitch. This wasn’t the first time Henderson and Slack co-founder Stuart Butterfield set out to create a game and ended up building a startup. In the early 2000s, Henderson joined Butterfield’s team to create Game Neverending, which spawned the photo-sharing site Flickr. He programmed (and kept a blog on iamcal.com ) 15 years.
We spoke with Henderson about how he works, how he works at Slacks, and what it’s like to be a huge hit twice.
Location: San Francisco Current Workplace: Slack CTO One word that best describes how you work: Relentless Current mobile device: iPhone 7 with an ugly battery Current computer: 11-inch MacBook Air, but running Windows
Tell me a little about your past and how you became who you are today.
I started doing computers at a fairly young age; It started when my older cousin got a Texas Instruments TI-99 when I was about six years old. Like most computers at the time, it came with a BASIC interpreter, and I was fascinated. After a few years, I decided that programming is what I want to do when I grow up. Since then, I’ve been very obsessed.
I’ve lived in San Francisco for 12 years, first coming to San Francisco from Vancouver after Yahoo acquired Flickr. While at Flickr, I spearheaded a number of technologies that are still widely used, including APIs, oAuth, and oEmbed, and wrote O’Reilly’s bestselling book, Building Scalable Websites . I worked on Flickr at Yahoo for 4 years before leaving in 2009 to start an MMO [Massively Multiplayer Online] called Glitch with Stuart Butterfield, Eric Costello and Sergei Murakhov, all from Flickr.
How is your workplace arranged?
I have a table at our headquarters, but I rarely go there. I spend most of my time in meetings. Considering that our office area in SF is 50,000 sq. Feet, I can do most of my 15,000 steps a day during work hours.
However, when I am found at my desk, you will notice that my desk is usually a whole bunch of junk. I use a very small laptop (11-inch MacBook Air, RIP), but connect to external monitors whenever I can. I am also a fan of mechanical keyboards and currently use Varmilo without ten keys with blue switches Cherry MX. It is very loud and sounds very loud. a bit like a typewriter.
What’s your best time-saving shortcut or life hack?
Listen to audiobooks at 2-3x speed. About 5 years ago, I almost completely switched to audiobooks, so I could combine walking with reading, but the choice of speed was a real incentive.
How do you replenish? What do you do when you want to forget about work?
Listen to books or podcasts at 3x speed while playing games on iPhone; Bit City is the last one to take root in the office. Or spend time with my 3 year old son. Nothing makes you refocus your attention like a toddler.
What is your sleep pattern?
I have a very regular sleep schedule: I usually go to bed at 10:30 and fall asleep at 11:30. I usually spend 30-60 minutes at the end of the day relaxing listening to science fiction books. I wake up at 7:30 every day.
You and your colleagues have developed Flickr and Slack when developing video games. What were these reversals like? What changed the second time around, Slack vs. Flickr?
The turns were tough – no one is going to fail. You do not know when you are closing a bankrupt company, on the other hand, there will be a good result.
What has changed this time is the growth and maturity of the Internet as a platform: there are 100 times more people on the Internet every day. When we started Flickr, the idea of putting your photos on the Internet was fairly new. Now the idea to place them somewhere else is weird.
Another big shift is infrastructure and cloud development. The bar to get started has gotten lower and lower, allowing you to spend less time setting up servers and more time working on what you’re trying to build.
What are some of the things you do best in everyday life? What’s your secret?
It’s a bit full. I was told that I have a tremendous capacity for goal-oriented work and high productivity, but what allowed me to become a CTO in an organization the size of Slack is my 15-year history of team management and the reward I find in the human aspects of work. There is a very common stereotype that engineers are socially inexperienced, but this is not the case. Interpersonal communication is an absolute requirement for leadership and leadership in all functions of a company, and not least in engineering. This is a team activity.
What apps, software or tools can’t you live without?
- Job: Lethargy
- News: BBC, Twitter
- Family: WhatsApp, Snapchat
- Entertainment: Audible, Reddit
What’s your biggest workplace problem?
Probably prioritizing my time. As an organization grows in size and complexity, it is easy to react. One more thing always comes to you that needs attention and that needs to be done right now. But taking a step back and strategizing on what you’re focusing on is really important.
What do you listen to while you work?
I spend most of my workday in meetings, but when I work from home I get hooked up to Spotify – there was a mixed Kanye and (UK trip-hop group) Sneaker Pimps this week.
What are you reading now or what do you recommend?
I recently completed Ada Palmer’s Terra Ignota series , which I highly recommend. A look at humanity after scarcity and what it takes to bring society together.
What’s the best advice you’ve ever received?
I’m not sure where this advice came from, but the idea is to find a group of people you enjoy working with, not a perfect project. We didn’t set out to start Flickr or start a Slack company, but finding a group of people you trust and love to work with means you enjoy what you do, even when you switch to something completely different. …
And drink plenty of water and exercise regularly.
What’s the best idea you’ve had that you wouldn’t want to bring to life?
I still think that what we were trying to do with Glitch (a multiplayer online social gaming space in which to build and collaborate) is a great idea. We didn’t manage to turn this into a successful business and I don’t think I will try to do it again, but the gist of the idea was great. If someone manages to do what we were aiming for, I would kick the shit out of him.
What is your Slack etiquette and how does it fit with the rest of your team? For example, how much Slack do you use outside of business hours? Have you ever done a major misstep, like sending a confidential message on the wrong channel?
I think I make this mistake more often with email than with Slack, probably because I use it less often. Although I read Slack all the time, I try not to text people in DM late at night. Forcing people to react quickly can make people think they need to be in touch. Making a queue of messages to be sent in the morning makes people know that my questions can wait.
You’ve done some great tricks like the Who Looks Like Manager game at Yahoo. [Henderson’s game asked Yahoo colleagues to guess which of the two people was higher in the company based on their photographs alone.] What role have side projects played in your career?
I really liked the first internal Hack Days at Yahoo, showing that it was possible to create interesting projects that were not just a user-centered product feature.
Playing Game Never Ending (predating Flickr) was what I did in my spare time when I was in my early 20s, but “ hacking ” the system to better understand how the game works is what ultimately led to that Stewart recruited me. come work for Flickr.
Fill in the blank: I would like _________ to answer these same questions.
Jay Parikh (VP of Engineering at Facebook)
What else would you like to add that might be of interest to readers and fans?
I’ve always loved how you can use software to just create things and quickly put them in people’s hands. If that’s what you love, now is a great time to get into the industry. There are many opportunities to create things that people will use every day. As an industry, we still have a long way to go, but now is the time to pursue a career in software development; you don’t need to study computer science at a prestigious university or have “typical” software development experience. People from all walks of life who are passionate about what they do have a lot to accomplish.