Async, not avatars: Slack’s Stewart Butterfield on the future of work

Can a messaging app replace your office? Is that even the goal? Slack’s CEO takes us into what 2022 holds for workplaces everywhere.

Portrait of Stewart Butterfield

Stewart Butterfield thinks the office may never quite come back.

Photo: Slack

Stewart Butterfield has a lot of thoughts about how work should work. That’s not exactly surprising, given that he’s the CEO of Slack, and now works for Salesforce, two companies that are at the center of the digital workplace for businesses around the world. He’s seen what the shift to remote-first work has done to many companies, and how digital transformation has changed business’ conception of what “work” even looks like. It all sounds a little philosophical — and maybe it is — but it’s also the stuff companies everywhere are grappling with right now.

But 2021 was hardly an ordinary year. The way we worked and lived will (hopefully!) not be the way we work and live forever. So what trends should we leave behind, and which should we embrace? And maybe just as important, which are going to stick around no matter how we feel? The future of work doesn’t have to look like the present, but it doesn’t have to look like the past, either.

For our last Source Code interview of the year, we asked Butterfield to look back at 2021 and ahead to 2022, to try and figure out what the future of work might look like. Will asynchronous work become the norm? Will companies and employees gain a better work-life balance? Will all our meetings move to the metaverse? How should we set up notifications, build culture and create inclusive companies when everyone’s a rectangle on a laptop screen? Butterfield has thoughts and ideas on all of it, and lessons for everyone heading into another, hopefully much less chaotic year.

You can hear our full conversation on the latest episode of the Source Code podcast, or by clicking on the player above. Below are excerpts from our conversation, edited for length and clarity.

David Pierce: You’ve talked a lot recently about the idea of the “digital HQ.” I think what people imagine when you say that is, like, a virtual office where people gather similarly to the way they might in a physical office. Are you sure that’s the right metaphor for the future? Is that what you’re going for?

Stewart Butterfield: Kind of. I'm definitely not talking about the metaverse where we see cartoon avatars of one another walking around. Maybe the difference is, everyone has a digital HQ whether they recognize it or not.

I've used this thought experiment a couple of times, but if you imagine a parallel world where in March of 2020, somehow, we were all allowed to keep going to the office — we could commute, we could have working lunches, sit in conference rooms, all that — but we couldn't use any of the software, almost every kind of company would just disintegrate. It would last for 72 hours at most. So there's something that is like an infrastructure that supports productivity and collaboration that's common to all these organizations, that made it so that we could cut off the other side — flip it so that you don't commute, you don't go to the office, you don't have working lunches, you can't sit in conference rooms — and yet, work continued.

Digital HQ is kind of a branding and positioning. But it's also a little bit of a metaphor, I guess, to help people understand it in the same way that many individual employees, leaders, executives, have had all kinds of opinions about how offices should be set up to maximize productivity and collaboration. You'd have the stories about Steve Jobs in the Pixar cafeteria, trying to get people in different groups. But also going way back before that, to the first open office plans, or the predecessor to the modern cubicle, which was called Action Office. All these different setups. Reactionary ones, where people want to go back to a world where everyone has their individual office and they can think. There's a lot of effort and energy and attention that goes into that, and relatively little, in most organizations, into the digital side of it, and how we expect people to work together. And how we can make that more creative, more delightful, more collaborative, more productive. It's just kind of an afterthought.

DP: Part of that is also about asynchronous versus synchronous work. I know you've talked a lot about this, and it's been a buzzword for like a year and a half now. But my sense is that it hasn't really overhauled the way everybody works yet. You obviously have a pretty wide vantage point on a lot of this stuff. What is your sense of where we are in the push toward asynchronous work? And how far should that go?

I think we need a lot more, better tools. I’m trying to think — I guess I could just look at how many hours I work in a day and how many things are are actually booked in the calendar. But it's a pretty low percentage of my work that’s asynchronous, like, maybe it’s 20%.

DP: That’s a lower number than I would have guessed for someone in your position.

Well, yeah, I'm just trying to be realistic about how much stuff is on my calendar.

But I would definitely include reading and writing messages as asynchronous work, because your message might have been sent hours ago. Other things that come to mind are inserting comments in documents or presentations: asking questions, clarifying something, and hours later, someone answering them. There's all kinds of tools that support that. But I think they're not full-featured enough, and they're not easy enough.

There's all kinds of tools that support [async work]. But I think they're not full-featured enough, and they're not easy enough.

But I think there's actually a bigger problem, which is like, here's your two options: Option A is to carefully and concisely write out your idea or your proposal, and then edit it for clarity, and include supplementary information and data and stuff like that, and then distribute it to everyone, and then carefully read their responses and incorporate blah, blah, blah, blah, blah. Option B is let's have a meeting for half an hour. And it's a little bit like, would you like some vegetables, or would you like some candy? We're gonna choose the candy every time. And I'm absolutely guilty of this.

And I think many times we can trick ourselves into these hyper-realistic work-like activities that consume a lot of time, but it's not the efficient way to do it. Because you might end up with 16 meetings over the course of 11 weeks or something like that, to get to a place that you could have got to in several hours of real preparation and attempts to articulate the proposal or whatever it is.

DP: I like the vegetables metaphor, because you can make a pretty convincing case that doing it in that careful way is better in all ways, including ultimately for the efficiency of your business. But dear God, do I not want to do that most of the time.

There are absolutely times where I think it is preferable to get on the phone for two minutes or three minutes because it's just daunting to think about how you even would type something out. Most of us are better at just freeform speaking. But the tools, it’s not like the only problem is they're lacking features. The other thing is, how can you make that option A as attractive as option B? Or at least much less less attractive than option B? Because you want to encourage people to think, “Oh, that's, that's my preferred way to do it, because I'm going to save all this time.”

Lizzy Lawrence: Another thing with the asynchronous movement is Slack is often depicted as the villain or the antihero within that movement. It's sort of the poster child of constant communication. And I was curious what you make of that, and if there's a way to use async communication and Slack effectively.

Yeah, I definitely do. That's mostly how I use Slack, is asynchronously.

I think a lot of stuff gets really conflated, because there is a whole bunch of work where real-time communication to coordinate a bunch of people is the heart of the work. So if you think about incident management or network operations engineers, or security teams or something like that, or for that matter, marketers launching a new website, people working on the event, streaming services: All this different stuff requires that back-and-forth communication. There's many areas of modern work that don't require that constant communication. And I think it requires some discipline to configure notifications and break the habit of compulsively checking.

The same things that people say about Slack today, they said about email and BlackBerry in like 2000-2001. Let me put it this way: This is not a PR-department-approved way of saying it, but humans aren’t always immediately effective with new forms of technology. You think about the early days of the Industrial Revolution, in cities like Boston and London, the rivers would catch on fire. The Charles River or the Thames would just literally catch on fire. And over time, we've figured out how to reap the benefits of the technologies of the industrial revolution without lighting as much stuff on fire.

Similarly, we evolved over hundreds of thousands of years to seek all these social signals and approvals and recognition and acknowledgement and all kinds of stuff. And now you can post a photo of a 7-month-old, you can post a photo of your kid, and like instantly have 500 people say, “Oh my god, so cute,” or add the heart reaction or something like that. We can't handle that. We're not good at budgeting or consuming an appropriate amount of those interactions, which I think is why we have all these challenges around social media and just scrolling your phones.

It's almost like we’ve had hundreds of thousands of years to seek sugars and fats and calories, and now we live in a world of effectively infinite free calories, and so a lot of people get diabetes. And similarly, I think at an intellectual level, a lot of people end up with a kind of cognitive diabetes. All of these signals, which were meant to be rare and precious, are hyper-abundant. And it's harder for us to control ourselves.

I think at an intellectual level, a lot of people end up with a kind of cognitive diabetes.

I hope that doesn't come off as me saying people are using Slack wrong!

LL: How will the nature of that workplace communication evolve as we move from mostly in person and spoken to now mostly remote and written?

I think we'll still see a lot of spoken, just not necessarily in person. We've been living in a world where a switch has occurred, from digital technologies supplementing in-person communication as the means of facilitating collaboration and productivity to the other way around — the in-person supplements the digital. And the thought experiment I talked about earlier, where we were allowed to keep our offices but weren't allowed to keep our software, illustrates the importance of that.

But if you've worked at a big company, there's great odds that there's 50 people on your floor or 80 people on your floor, and you don't really work with any of them. In fact, you don't even really work with anyone in this office campus, but a different office campus across town and a different time zone. People who aren't physically present with you anyway. If we're able to provide the right tools — I don't mean just we, Slack, I mean the industry — then hopefully, we will see a switch towards more asynchronous forms of work. But it's probably going to be a minority. And there will be plenty of video calls and other forms of real-time communication to make the whole thing operate smoothly.

DP: We've passed this point where it's like, OK, we can all get work done remotely. Now the question is, how do we build a company that people are happy about and proud of and want to work in, and where they know their colleagues? And my dear hope is that the age of Zoom happy hours is ending. But it does seem like these digital tools you're talking about have an obvious big role to play there. What is your sense of kind of where all that's going? Are Zoom happy hours here to stay? Please say no.

I mean, you can do them more effectively. There's definitely models for facilitation that I believe that people use, when they think about people doing World of Warcraft raids and being on the audio chat. It's a recreational activity, not getting to know your co-workers, but people can have fun hanging out with friends where the interaction is mediated by digital stuff rather than vibrations in the air because I happen to be in the same room.

DP: See, an office-wide WoW guild is something I'm extremely into.

Yeah! You just have to switch it from Zoom to WoW.

But I think there's two things going on. This isn't really what you're asking about, but this is the Great Resignation, and the reevaluation of priorities and thinking about what work you do and you want to be meaningful. The huge shift, from my perspective, is the balance of power to labor from employers. I've always been a believer in some version of the “culture eats strategy for breakfast” thing. So it was always important, but it's more important now.

I think our team at Slack, the company, has been phenomenal at building onboarding programs that help people feel connected, and that they belong, and that there’s some enculturation and shared understanding. But it's a huge amount of effort that's dependent on the leader. Most of the time, that's most of the reason the CEO gets up in front of the company at some kind of all-hands presentation. Whether it's positioned this way or not, it’s cultural. It’s getting people aligned, getting people to a point where they have a shared consciousness and set of beliefs and all that.

I think that things got much, much harder, because the importance of it just increased, given the Great Resignation. And the fact that we don't have the in-person time, or have much less of that. It's fascinating to watch, and I think it takes a while for cultures to really drift. But I would expect that unless there's a real 180, we all end up back in offices Monday to Friday, 9 to 5 in the next six months. Then over the year that's coming up, I think we'll see more and more organizations where they haven't invested in culture sufficiently start to really suffer.

DP: We have a few lightning round things for you. No specific questions, just want to get your thoughts. First: the metaverse as a work thing. Thoughts?

I think there are all kinds of industrial applications I can imagine that would be fantastic. Repairing the inside of the subway tunnel with virtual goggles on and stuff like that. The hanging out does not seem very attractive to me. Maybe for the purpose of one specific meeting? But I can't imagine anyone hanging out in the metaverse all day at work.

LL: What about geography-based pay? As you know, the workforce is spreading out. What are your thoughts on that?

It's a really tough one. Because there's a fairness angle no matter which way you decide. Compensation, historically, always has been determined by the market, and people got paid more in places where the cost of living was higher, because that's what you needed to pay them in order to get them to come work for you. I had thought that we would more or less inevitably move towards single compensation bands for roles irrespective of geography, because it is a marketplace. And if enough companies decide that that's what they're going to do in order to compete, we all have to do it. But that hasn't really materialized. So it's a little tough to predict.

DP: Last one: Work-life balance, as a thing that is possible to achieve.

I absolutely believe so. And I personally found it so much easier during this pandemic era. Because it's very easy to wander away from my computer after a meeting and do something completely different: play with my 7-month-old or practice classical guitar, or go skiing or something like that, which would have been impossible if I was wandering away from my meeting in a conference room inside of our office. Obviously, I'm in an incredibly fortunate position. But I think this makes it much, much easier.

With the organization we started called Future Forum, we've done all this research, and flexibility is the second-most-important consideration after compensation for most people today. And the desire for flexibility around where you work is very, very high — north of 70%. But the desire for flexibility around when you work is much higher. And I think the tyranny of time-based compensation for hours worked that arose during the Industrial Revolution, hopefully will kind of subside towards something with a little bit more of a compromise. So you're not required to just be present, like Stanley in “The Office,” until it hits 5 o'clock, and then you can go home. That sucks for the employer and the employee. It's not productive for anyone. And if we can move towards a world where it’s your contribution or the output or the impact, that is what you're compensated for, we're all better off.


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