5 Lessons from Stewart Butterfield of Slack

On community, selling saddles, and more

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5 Lessons from Stewart Butterfield of Slack

In the ninth installment of my 5 Lessons series, we have Stewart Butterfield, Co-founder of Slack, the company he sold to Salesforce for $27.7 billion in 2021.

I wrote a deep dive into Stewart’s story back in April 2023 and today I’m sharing some lessons from his journey.

1. Don’t Sell Saddles

A lesson from Stewart’s famous memo, We Don’t Sell Saddles Here.

That’s why what we’re selling is organizational transformation. The software just happens to be the part we’re able to build & ship (and the means for us to get our cut).

We’re selling a reduction in information overload, relief from stress, and a new ability to extract the enormous value of hitherto useless corporate archives.

We’re selling better organizations, better teams. That’s a good thing for people to buy and it is a much better thing for us to sell in the long run.

We will be successful to the extent that we create better teams.

Stewart Butterfield

2. Host & Guests

One of the keys to successful design.

The things that we did that were most successful were those things which made life more convenient for people.

And one of those was for example, typing your password on your phone is a pain, so we’ll send you a magic link that logs you in.

Or because, for complex reasons, most people wanted to have notifications for every message in Slack when they first signed up, so they felt comfortable and knew how it worked. But we didn’t think that was a good way for them to set their preferences long-term. After a few notifications, we would interject and say, “Would you like to switch to our preferred settings?”

And that kind of thoughtfulness or consideration, that kind of thinking of yourself as a host and the customers as your guests, is the secret, as it were, to good design.

Stewart Butterfield

3. Create a Community of Enthusiasts

Stewart used APIs multiple times for this.

I will say that in the early days of Flickr, one of the things that made us successful was we had APIs for everything.

You could just do anything you wanted and that excited people and they experimented. A handful of apps that people created out of the APIs, I think had genuine popularity and were useful, but mostly, it just created a community of enthusiasts.

In the case of Slack, it created 2,000 apps in the app directory and something like 900,000 custom integrations that are actively used by a customer. These are integrations that customers created themselves. That's like a mind boggling number. Had we not done that, had we kept it in a black box, I think there would've been a lot less utility.

Stewart Butterfield

4. It’s On You

A lesson on extreme ownership.

Leaders blame people all the time. Sometimes people are in the wrong role, but if they're in the wrong role, who put them there?

There's a lot of thinking or falling back on the idea that these people are too stupid or they have some other defacto problem that prevents them from doing the thing that your genius mind has envisioned them doing.

That's never the case though. It's on you to figure it out.

Stewart Butterfield

5. Tilt Your Umbrella

How to find good ideas.

There's this story I tell in our internal onboarding process of me and our head of project design going for a walk in Vancouver. And our office in Vancouver is in neighborhood that's really narrow, so I'd walk, sidewalks have sandwich boards from vendors out so it's very crowded, you kind of wind around, and so it starts raining while we're on this walk and maybe two-thirds of people had umbrellas with them and we didn't and people are walking towards us on the sidewalk and almost no one would move their umbrella out of the way so that the pocky things wouldn't get us in the eye.

Like I said, the sidewalks were very narrow so we had to keep on ducking. I can come up with many explanations for why this would be, but don't explain with malice that which can be explained by ignorance, so probably it wasn't just that these people have few avenues for exercising power in their lives and they were choosing but this moment to exercise some power, but then there's really only two explanations.

One is that they just walk through the world and they don't see that we're going like this to get away from an umbrella, even though inevitably they had that experience themselves, or they see that this is happening and they're like, "I just can't think of anything I can do to ameliorate the situation."

Despite the fact that it's this, it is tiny, like a hundredth of a calorie worth of effort and a tiny amount of consideration and the point of telling that story is that that's the way, this is a sad way of looking at the world, but that's the way that most people go through the world, they're oblivious to the problems that other people have and if they notice the problems, they're unable to come up with any kind of solution.

Two-thirds of the people just didn't tilt their umbrellas, which means that if you're the kind of person who's willing to tilt your umbrella, there's a whole world of opportunity out there.

Stewart Butterfield

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Justin Gordon

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