Second Time Lucky: Failing Fast (and Rising Strong) with Slack’s CTO Cal Henderson

We ask Slack’s co-founder and CTO, Cal Henderson, about mastering the fast fail and rising strong in its wake.

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As the fastest-growing business application in history, Slack (and the team behind it) has to be doing something right.

The sleekest and most playful work-based messaging service on offer was created in the wake of failure – the 2012 closure of online game Glitch. The founders spent a solid month finding jobs for all of the employees they were forced to let go by creating a portal site for their résumés, before turning their attention to the chat platform they’d created to help them build Glitch in the first place.

It’s this kind of forward-thinking that has led Slack, now worth US$2.8 billion, to grow a supportive, empathetic staff culture for its 365 employees, making the company as strong internally as is its client base externally (a roster which ticks off Pinterest, the US Department of State, NASA, Harvard, Time magazine and The Wall Street Journal).

Fresh from opening Slack’s fourth global office in Melbourne, co-founder and chief technology officer Cal Henderson (who is also trying to make the web more accessible for fellow colour blindness sufferers in his spare time) found time to talk to Collective Hub about the evils of email, knowing when to stop working and why having lunch is a perfectly reasonable workday highlight.

It’s still very strange to think about how successful it’s been. When we were first building the product, we were like, ‘Uh, maybe other teams like us would find it useful’. We didn’t see this coming like, ‘Yes! This is a thing! We’re going to ride this wave!’ It was luck. I think, if we weren’t here at this time, somebody else would’ve been. I mean, email is such a bad tool for team communication, it’s just been around for so long – it’s the cockroach of the internet. We’re not going to be able to kill it for a long time but, if you’ve been on a 30-40 person ‘reply all’ chain, you’ll know that email is a pretty terrible tool.

One of the most important things that we learned from [the failure of Glitch] was that it’s important to quickly build something that you can prove whether it’s going to be successful or not and then iterate upon. When we started building the [Slack] product, I think we started in January of 2013 and then in mid-March, so 10 weeks in, we switched our company over to using it as our only method of communication. And whilst that was very painful, it also very quickly made us address all of the things that were an actual issue. So we got to a product that, by April of that year, we thought it was useful enough to get some other companies to try out.

The big advantage we have at Slack that you don’t necessarily have in every sector is that we use Slack every day for running the company. I’m sure, if you’re a company that makes expense reporting software, you don’t use your software every day. You use it, at most, once a month and you probably hate that experience. Like any other kind of business software, you’re probably not using it every day and you’re probably not the primary customer. That was a big advantage for us.

For the first couple of years, if you visited, you probably wouldn’t have been able to tell what it was we did. We had a super [basic] homepage that didn’t explain everything. After that, we had to not only get you to sign up but get you to send invitations to other people on your team to get them started and we just didn’t invest enough time in that initial new team user experience and that’s where most of the product finesse needs to go. Once you get over the hump of trying it, it’s either useful or it’s not and then the product will fail on its merits but up to that point, getting people through the door, the whole team at once, is really difficult.

I work a lot but I try to be really good about ‘work ends at this time’. One of our internal mottos is ‘work hard and go home’. Be present when you’re in the office, work intensely, focus on your work and then go home and have a life. I’ve seen a lot of start-ups in San Francisco and Silicon Valley burn people out with crazy working schedules, and that works great for six months or a year, but that’s not sustainable.

We’re really just trying to build a place we want to work at. Not just today but a place that will still be enjoyable to work at a decade from now and that’s very different as a company grows. When we shut down the previous product and started Slack, we were eight people in a small office and everybody knew what everybody else was doing, so there was a very different feel to now.

[When] a company grows as quickly as we have, everything that you do today gets thrown away and gets replaced with a new process [and] the job you have today is very different to the job you’ll have in six months. But figuring out what it was that we wanted to keep constant about working there versus what can be thrown away has been really important.

When we were eight people [and] only four or five of us were in San Francisco, we used to all eat lunch together every day. It was easy when there was only a few of us, [but] we still do that to an extent.

We all eat lunch together in the cafeteria [or] people go out for food and then bring it back. There’s a big culture of everyone sitting together and that’s a lot of the way I meet new folks. A lot of space in the office is dedicated to just being able to sit and talk with other people.

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