Phillip Faraone / Stringer / Getty Images
November 29, 2021 9:56 AM EST

We spoke with Slack CEO and co-founder Stewart Butterfield during our recent Workplace Summit, in a conversation that touched on how work, meetings, and Slack are evolving because of the extended period of remote work. We also asked him to respond to organizations’ concerns about activism and distraction among their employees in connection with their use of the service.

Here is a transcript of the discussion, edited for clarity:

I want to start by noting that you’ve had quite an eventful last year, including with Salesforce’s acquisition of Slack for about $28 billion. What have you yourself learned about leadership through this period?

I’m not sure if it’s new lessons or just reinforcing some stuff that I hadn’t learned enough yet. There’s a thing about how life just keeps on teaching you the same thing until you figure it out. But the biggest one was just people hate uncertainty. That’s not something that I didn’t know before. But I don’t know that I was prepared for this amount of uncertainty all at once.

Maybe late March 2000, I went to an ATM—and this was when we had no idea what was going on and everyone was super paranoid—and I got to the ATM and I was like, ‘Damn, I’m going to have to touch the keypad.’ I had a Kleenex in my pocket, so I took the Kleenex out and used that as a barrier on the keypad of the ATM. That was the experience that I think many people had in the very early days, just not knowing what was going on. Is this going to be a crazy horror movie pandemic? But then obviously the impact was really profound for a lot of people, either themselves or their family members getting sick. And there was economic uncertainty; the markets are going crazy. There’s probably less emotionally heavy uncertainty about ‘are we going to go back to the office?’ and things like that. But it also put people into a position of increased uncertainty in their own personal lives.

I don’t mean that necessarily in a negative way, but obviously the Great Resignation and the Great Relocation and all of that are the result of people reevaluating their priorities and thinking ‘given that I am now at a place that I’d never thought that I could end up in, what’s important to me and what I want in my life?’ So even if you don’t have all the answers, the big obligation of leaders in this time is to give what certainty you can. And the expression of just a plan is much more important than having the right plan.

For more on the future of work, sign up for the free Charter newsletter.

There are many things that people said with some certainty, precisely because they were trying to fill the need that people have for some kind of plan, that they then had to backtrack from. Like ‘we’re going to go back to the office in September,’ then ‘oh, actually it’s October,’ and then, ‘oh, actually it’s January.’ Or, ‘Oh, actually it’s never.’ How do you navigate that as a leader who’s trying to do the right thing, but is making plans in the context of a high level of uncertainty?

You definitely have to pick the domain. I don’t think anyone had a lot of anxiety around which specific date offices would reopen. So, back in April or May of last year, whether you said it was September or October was irrelevant. I don’t think the thing that was most weighing on people was that date. So I don’t mean certainty around that kind of information. I’m trying to think of a better word than retreating, but retreating to those things that are most foundational, like what’s the purpose of what we’re doing. What’s the mission? And what are the things that we can be certain of? The expression of solidarity among the people who are working together and the commitment to supporting each other is something that’s true, irrespective of vaccination rates or infection rates or office openings or any of that. It’s that assertion of things that might be in some sense, obvious, but in this kind of environment need to be heard.

Let’s talk about Slack the product for a minute. Have the product itself and your roadmap for it been influenced by the experience of remote work at a mass scale, and how?

It definitely has. In some cases, it’s a slight modification to something that we’ve thought about for many years. This year and next year we’re finally getting into all this stuff that we wanted to do in 2015 and 2016. But there’s definitely a huge impact of the epidemic. To some degree, it’s opportunism around specific features that people demand. In addition to flexibility about where people work, probably the bigger desire that became obvious is flexibility about when people work.

This is too long of a topic to get into, but that transition that happened in the 19th century from being paid for the output to being paid for the time, obviously had real consequences. If you think back to Organization Man in the 1950s, part of the pushback of the nonconformists (this is speculative) wasn’t just about ‘we all wear the same clothes and we all listen to the same music and we all read the same newspapers.’ It was about ‘we’re all on the same train in the morning. We all take our lunch break at the same time and we all go home at the same time.’ And there’s definitely a tyranny to that.

So, thinking about the product, what alternatives could we give people? Where’s a screwdriver and a plane and a wrench? I don’t know if I want to continue the toolbox analogy. But internally at Slack, the company, we asked ourselves, ‘What processes today are synchronous that could be made asynchronous?’ The manifestation of that in the product was, ‘What tools would we need to be able to do that?’ I’m still sorting through that.

There’s a strange—not quite an irony, but in the same way that people eat more candy than they should and do other things that are ultimately unhealthy—when you have the choice on the one hand between a careful articulation of your thoughts in written form edited for concision and then reading other people’s stuff and thinking carefully about it and offering written feedback, or having a 30-minute meeting, the meeting is the candy—like, ooh, that’s easy. So you can end up having 13 meetings over the course of nine weeks or something like that for something that with a little bit more vegetable eating could have been accomplished much quicker. So, how can we help people get to the point where those two alternatives seem equivalent in effort or desirability?

Some companies are actually even going meeting-less, or fully asynchronous. Do you think that’s where more of us are headed and do you see any trade-offs? Some people cite potential downsides for workplace culture….

Spending time together is really important. I wouldn’t advocate at all that people should give up meetings because I think they play an important role. Many people over the last 20 years at various points have been like, ‘Email is stupid and email is killing us, and we shouldn’t do any email.’ ‘Meetings are stupid, meetings are killing us. We shouldn’t have any meetings.’ ‘Slack is stupid. Slack is killing us. We shouldn’t use Slack.’ It’s a pretty natural and understandable reaction.

But I think it’s being more thoughtful and judicious—because there’s this weird, not quite paradox—you ask any executive, maybe I’ll ask you. Charter is like fresh and new and shiny. So you probably don’t have problems that have kind of accreted over the course of many years…

We’ve yet to have our organizational barnacles.

Maybe at Charter, but certainly over the course of your career, would you say that with the right kind of discipline, the right kind of format, the right kind of coaching and enablement and education, you could increase the average efficacy of meetings at your company by 25%? And every single person will say yes. And zero people do anything about it. Because it’s a gnarly problem.

The reason every person on this call probably has heard of the Amazon six-page memo format is because the examples are so few for people even trying to make an impact there. We obviously can’t change the way that people choose to work, but we can offer tools that create a few more different possibilities.

I’m not going to go on a promotional rant about the tools themselves. But the idea of the ‘huddles’ features that we launched a little while ago was ‘imagine a call didn’t start and then stop, but it was a place that you could enter and then leave, a little bit similar to walking over to someone’s desk.’ And if you could recreate some of the spontaneity and serendipity of those conversations, then you don’t have to say the only tool is the 30-minute Zoom, and we can’t have one until next Thursday because that’s when everyone’s calendars are free. Then what might have been a 90-second conversation turns into a 30-minute conversation because whoever stops the call early? Things go for their allotted time. If things like that work—we’ll launch some, other people will launch others—the tool set will evolve and people will figure out what works best for them. My hope is that we end up in a much better place, irrespective of whether we end up back in offices or not. We just have a better set of fundamentals.

What are you yourself most impatient to fix/change/upgrade about Slack, the product?

There’s an infinite series of little—we call them ‘paper cuts’— that I’m eager to fix. None of them individually is that important, but on aggregate it’s the flavor of the experience. The big one is taking what we’ve done with Slack Connect and generalizing it to let people create their own networks. Early in the pandemic, Jen Tejada, the CEO of PagerDuty, hosted a dinner. This is mid-February 2020. The email thread for that dinner—because there was a bunch of SaaS company CEOs—became the de facto discussion group for, ‘Hey, are you actually thinking about shutting down your offices?’ This is during early days. That turned into what we inside Slack call a multi-org shared channel, a shared channel with a whole bunch of participants from 17 or 18 different organizations. There’s one for CFOs, one for CEOs, one for chief people officers, one for heads of marketing. There’s all these questions then like, as a people leader, what do we need to do to support employees? Or what should the policies be, everything from insurance to sick days and absenteeism. For CFOs, it was how are we going to model the impact of this and what are we going to tell investors? It’s incredibly powerful. The one used by the group of CEOs is still in very active use. And I’d love to generalize that and make it available to different networks or communities.

The other one is the platform. So I think we have one of the best-used platforms in the world. There’s 900,000 custom integrations that customers have created that are in active use. But there’s still a very, very high degree of friction. The dream for me is this collaboration between professional software engineers on one end and IT and biz tech people in the middle, and then the end users at the other end of the spectrum. Because a salesperson or an accountant knows best the workflows and kind of friction that’s in their way when it comes to closing a deal or closing the books for the quarter or whatever it is that they’re trying to accomplish. And that’s just something that doesn’t exist. Software is still very rigid and flexible.

Shifting to the question of workplaces and the role of Slack, some business leaders have gone so far as to say they regret installing Slack because of employee activism—sometimes called ‘slacktivism’—that it has enabled for workers. They feel like they have more headaches, workers are less focused on their actual tasks and more focused on mobilizing each other and getting each other all riled up. What is your response to them?

I think that Slack plays a role. But this is the result of a whole bunch of different factors all put together. One of the companies that has had the most challenges in this area obviously is Google. And while there are parts of Alphabet that are happy Slack users, it is forbidden inside of Google. So exactly the same challenges can easily arise irrespective of the tools that people are given. Having said that, I think there’s a lot of subtlety and there’s a lot of kind of unintended consequences and a lot of thought needs to go into setting up both the product and a particular organization’s usage to maximize the benefit. This is not a perfect analogy, but if your job is to dig ditches and you have a shovel, and then someone gives you a backhoe, that’s a lot easier to do the ditch digging. You can do a lot of accidental damage with a backhoe and you can’t really do accidental damage with the shovel. It’s just hard. And that’s been humans’ relationship with technology since the beginning. In the Industrial Revolution, you had the Thames and the Charles River just lighting on fire periodically…..I see that with digital technology too….

Sign up for Charter's newsletter to get the handbook for the future of work delivered to your inbox.

So you aim to add features to Slack that actually maximize the benefits and minimize the wandering nonproductive part?

Some of it’s features and some of it’s guidance on the usage. But Slack does lack a lot of the administrative or community management features that become really necessary for open public networks and tools. So there’s definitely some aspect of that. We need to figure out—and it’s not incumbent solely on Slack—we need to figure out what the best guidance is to give people.

At this time, it’s especially tricky because it’s hard to pull apart all the different factors here. Some people are very eager to get back into the office and it’s certainly possible that they feel that way because they’re going bananas trapped in their house. You don’t necessarily have to physically work from inside of your home in the future.

Conversely, other people think that they’re never going to go back to an office when the alternative is presented as offices that are plexiglass covered, you have to wear a mask, you can only go down one corridor, there’s no energy, there’s no people, there’s no snacks. When the real alternative is there, they might think differently. So it’s really hard to predict from where we are today which feelings, which inclinations, which trends are ultimately with us for the long run and which ones are just the result of the circumstances of today.

Acknowledging that, do you have thoughts on how work will be different five, 10 years from now than it is today?

We don’t know that the labor versus capital power balance has shifted permanently, but there’s definitely been a pretty big shift. And it’s tough to take things away once people have them. Like once people got Saturdays off, all those coal miners were not going to start working on a Saturday again. Once you have the flexibility, it’s very difficult to imagine it being taken away completely. By flexibility, I mean around where you work and to some degree—and hopefully more of a degree—when you work.

So I think it’s very unlikely that we’ll go back to a world where there’s a strong expectation or requirement among employers that you’re in an office nine to five, Monday to Friday. For some people that might end up being like a four-day workweek or the expectations around when you’re working are reduced. You still have some period where you get the synchronicity, but the rest of the time is much more flexible. It’s hard for me to imagine both the labor side and the employer side agreeing that they still want to do the same thing, which is you have this big office building and you’re going to devote 80% of the square footage to what’s effectively like factory farm chicken housing for people to sit and use their laptops all by themselves and not talk to each other. That part you could do anywhere. Now, as a place where you convene people to collaborate and to do creative stuff, it’s hard to come up with an alternative that’s better. But I think fewer offices, more flexibility and definitely a little bit of a permanent shift in the balance of power towards workers and towards flexibility.

What’s your short answer to the question: what kind of leader do I need to be now?

This is not a trick answer, but: a leader. That is expressing the certainty where you have it or the confidence that solutions will arise. Even just, ‘we’re gonna get through this,’ is an important message for people to hear. Because the degree of anxiety, fear, uncertainty is pretty extreme. If I have 10 more seconds, I think a leader who uses this as a time of opportunity to be creative and to invent the future that they want. Because we didn’t realize we could get this far off the track that we were on before. But, given that we can, what else is possible?

Watch the video of our conversation.

Read more from Charter
EDIT POST