Redefining the Future of Work - A Conversation with Jennifer Tejada and Stewart Butterfield

Michael Rivo: Welcome back to Blazing Trails. I'm Michael Rivo from Salesforce Studios. And today we are continuing our special Dreamforce 2021 coverage. This year's Dreamforce theme is success anywhere and Dreamforce everywhere. And you can experience it everywhere digitally on the newly launched Salesforce +. So head over to salesforce. com/ plus to experience Dreamforce this year. You know, if you ask Stewart Butterfield and Jennifer Tejada what they missed most about working in the office, you'd hear the same answer that about 99% of us would give. And it's the people. Stewart, the CEO and Co-founder of Slack, and Jennifer, the Chairperson and CEO of PagerDuty, join moderator Michal Lev-Ram, Senior Writer and Editorial Director for Live Media at Fortune Magazine, to discuss how to foster meaningful remote relationships and the tools they use every day to stay connected. So let's jump right in and take a listen.

Michal Lev-Ram: Hi, everybody. Welcome to the session, redefining the future of work. I'm Michal Lev-Ram, Senior Writer with Fortune, and I'm going to introduce our speakers here. Stewart Butterfield is CEO and co- founder of Slack, which you may have heard is part of Salesforce now. And Jennifer Tejada is the CEO of PagerDuty. So thank you guys for being here and doing this and talking about a topic that we've all had a lot of opportunity to think about and talk about and ponder and constantly evolve. And I want to hear your thoughts on a number of different topics, but for starters, curious to know what is the one thing that you miss from office life?

Jennifer Tejada: People. No question. I miss my people. It's been so nice to be here at Dreamforce 21 and getting out and seeing Stewart. We haven't seen each other in a long time. Just being able to engage in person, see someone's whole person and be able to be together.

Stewart Butterfield: Yeah. I almost felt like that was a trick question for a second, because definitely the people. I was at one end of a hall from our GC and CFO. So anytime I had a break between meetings, I would just wander down, look and see who's in their office and what's going on. Probably really annoyed them, but I do miss it.

Michal Lev-Ram: It would've been kind of weird if you'd said the coffee machine or something like that, for sure. What don't you miss about office life?

Stewart Butterfield: The commute and the time. And I'm sure we'll get into this, but my wife and I actually had a baby during the pandemic. And it's very different because I came back from paternity leave and it was like the same as the day before, hung out with the baby for an hour before getting on the computer. And I think when people experience that, it's going to be tough to give it up.

Jennifer Tejada: I think that's true. The travel and the commute and the logistics of having to get to and from the office. I used to travel 60% of the time and I've been able to have dinner with my family almost every night for the last year and a half. And that is truly a gift.

Michal Lev-Ram: Yeah. Again, back to people, and time and quality and all of that. So, like I said at the onset, this has been an evolving and I'm curious at this point in time, what have you both said to your teams, to your employees, about what the future looks like for your respective companies? Stewart, can you start?

Stewart Butterfield: Sure. Actually, I'm a little curious, because I think what we've usually been saying is the date by which we expect offices would be open, but there's no expectation anymore that people will go into an office, unless their job is facilities manager or something like that. And I don't know the exact percentages, but we've been hiring many more people who they don't live within commuting distance of one of our office locations. I think that's probably the best way to say it. Which means that all those conversations about, we'll be in the office two days a week or three days a week, become moot if you don't live within community distance. And I think that the two days a week crowd are going to be disappointed because they're not going to have the flexibility to offer to employees and to give them what they really want. And also because the pool of potential talent is so much smaller, no matter how many offices you have.

Jennifer Tejada: I think we've sort of seen this shift from early in the pandemic where we were just trying to adjust from the original normal, and now we're realizing it's a totally new normal and that there are some huge benefits to you having a digital HQ, as Salesforce and Slack have coined it. Thinking about being a digital and distributed first company, which brings a lot of quality in some ways for people. There's no one location that is privileged over another location. We can engage with customers without having to invest significant time and money and travel away from our families. And at the same time, I think we've realized we have to build norms and set some standards and expectations on how we want to engage in teams, how we consider mental wellness and health, how we think about building relationships and connecting people to our purpose and mission. And some of those things are harder when you can't be in person and you can't demonstrate warmth and sort of physical empathy. And I think empathy is kind of the key word. You have to be empathy first. You have to think about the whole person, the whole customer, the whole employee and all of your stakeholders. And what in this different world can be better for them that we need to amplify, and what's going to be challenging, and how do we address those challenges?

Michal Lev-Ram: It's interesting, you're both kind of alluding to the fact that the question around office reopening and date is no longer really what's relevant. And I'm guessing you probably saw it because I know you're both buddies with Aaron Levie from Box, but he had this great tweet just a few weeks back, which was Office_Reopening_Dates. pptx is the most edited company slide deck in the history of capitalism. And I think you can probably both relate to that?

Jennifer Tejada: Well, two things. I'd say Aaron has an entertaining tweet on the daily. So, I'm a follower. But we actually got rid of slides entirely. We decided that slides actually are not a very inclusive way to communicate. So with everybody being distributed and being digital, we use narratives so that you can do async you can learn, you can scale information more readily and we're all having to relearn how to write. So for those of us that didn't pay attention in English, it's a little more challenging. But that's just one example of something that's had to change because the shift is not about the office anymore. The shift is about how are we going to work? How are we going to build a company? How are we going to build a culture? How are we going to build great products and services for our customers, when we can't stand in a meeting room together with a whiteboard?

Michal Lev-Ram: Tell me a little bit more about this concept of digital HQ. And Stewart, I want to hear, is Slack the new HQ? Is that what you guys are saying?

Stewart Butterfield: Slack is definitely the new digital HQ.

Michal Lev-Ram: I've heard that line uttered somewhere. So what does that actually mean?

Stewart Butterfield: Look at it this way. I think over the last 20 years, somehow, at some point, we kind of switched from a model where in- person communication as the means of creating alignment or collaborating was the principle way of doing it, and then digital supplemented that, to being the other way around. That digital was the primary inaudible of doing it and the in- person stuff supplemented it. And the proof of that is we all had to start working at home and everything worked. No, not every business was affected positively and not every company performed as well as maybe they did before. But then on the other hand, many companies performed as well, or even better. And if it had been the other way around, like you could still go to the office, but no one's allowed to use any software anymore, all these businesses would've disappeared in 48 hours. So that idea of being digital first and thinking about it as a digital HQ, that really comes down to one thing, which is putting as much time and thought into the digital tools that support productivity and collaboration as people do the physical. And I think about my own, the last decade of my life, I spent 10 X as much time on real estate leases, office buildouts, conference room design, seating plans, all of that. And that should definitely be inadvertent.

Michal Lev-Ram: What about you, Jen?

Jennifer Tejada: Well, we're big Slack users and PagerDuty's powering how well Slack operates all the time. And Slack and PagerDuty were both born in the developer community. And developers by definition have historically been more distributed teams than your traditional front line of business or back office teams. And so there's a lot we can learn from our developer community about how to work in a distributed way. And what they've taught us and what my developers taught me is that there's a lot I can do at async. There's a lot of empathy that you can leverage and communicate through emojis and icons and songs and gifys. I've seen a lot of gifys in Slack over the years. And at the same time, I think you have to really make this transition from using your platforms and applications as an adjunct to the way you work physically, to actually using them as the key platform and thinking about how those products and services can help you do your job more effectively, can help you do your job more efficiently, can help you build relationships with your teams more effectively. And so it is kind of to Stewart's point, turning everything upside down, because what I know for sure is gone are the days where you can just kind of swivel in your chair to the person next to you and get the quick answer that you need. And by the way, you might not know who has that answer. You might need help from machine learning or AI to figure out what is the problem? Who do you need to solve it? But Slack can be where you go to collaborate to get those things done. And that's kind of how PagerDuty and Slack are working together.

Michal Lev-Ram: So I want to hear a little bit more about some of the hacks and products, your own product, features and new things that you've done respectively to make this all work, because it has been a big shift even for both of your companies. And then I also want to talk about just more from a leadership perspective and empathy and inclusion and all that good stuff and how you've kind of managed through that. But tell us first about what tools have you had to enlist or to create in order to make this work better for you and your teams? Would you like to talk about clips and huddles?

Stewart Butterfield: Yeah, Sure.

Michal Lev-Ram: Excellent prompt.

Stewart Butterfield: I can do that pretty quick. We do a lot of Zooming. And I think some of the more interesting stuff has been and more techniques that people have to bring teams together. You're never going to get the same quality or imediacy of experience that you get with in- person, but trying to reconfigure how we use existing tools to do a better job. And that hasn't been, probably to our shame is too strong of a word, but to our disadvantage, I guess, but it hasn't been coming from the top down. That's been frontline managers who I think have had a much more challenging experience and a much more difficult position during the pandemic. And it's kind of a shame because I think we should be investing a lot more in how we communicate managers, executives, spend a hundred percent of their time on communication, but most any job is 50% or 60% or even 70% communication. And we don't do a lot of training and the rare counter examples really stand out. So Amazon's six page memo format everyone knows instantly because it's one of the few organizations that's actually said, this is how we want to do it. But yes, I will say about clips and huddles, the bad part about Zoom, big fan, important partner, Eric's a friend, all that stuff, but the hard part isn't so much the well, in addition to being on camera it for eight hours a day, which is just psychologically very strange, it's that what would have been a swivel to ask someone a question is now like 30 minutes, but we can't schedule it until Tuesday. And so everything's half hour. It's like the minimum increment of work. So huddles were a reaction to that to try to recreate a little bit of the serendipity and spontaneity, but also to make something a 90 second conversation when it could be, instead of a 30 minute conversation. And then clips, same thing. Is just really trying to look at the meetings that we do critically and saying which of these could be handled asynchronously? And one of the challenges I think people had with kind of migrating the meeting from synchronous asynchronous was thinking that we're going to have to write this all in documents and it's going to be like term papers. And we're all going to be like professors reading in other people's documents and then requires a thoughtful response. And sometimes a video is a much more effective way of getting that done. So yeah, I'd love to see more, and I think we will see more experimentation about how people make use of the tools to take best advantage of them.

Jennifer Tejada: We've seen very similar things. One of the things that we built our platform around was the concept of swarming and empowering a person closest to the issue to make the best possible decision in the moment. That's really the definition of incident response. The challenge is, and even in a physical world, but in a distributed world, it's very hard to manually detect an issue. It's hard to move that issue to the right teams, the right skill sets in the right places to diagnose that issue and resolve it. And with the acceleration of digital transformation that we've seen where digital has become the main game, as opposed to kind of the nice to have, or the emerging business for the largest enterprises in the world, they need SaaS platforms that are really easy to use, really intuitive, and help them manage this new kind of work, which tends to be unpredictable, unstructured, time sensitive and mission critical. And booking a meeting in two days to solve an issue that is taking down your entire shopping experience, ain't going to cut it. And so PagerDuty's been investing a lot in helping development teams, IT teams, security teams, et cetera, and more recently, customer service teams because the call center is gone. Everybody's in their homes, and yet customers need to be able to manage a case from the time they learn about it, which sometimes unfortunately is from the customer, all the way through to that case being resolved and that end customer being happy. And they can leverage PagerDuty and the AI and the machine learning to do that in conjunction with Slack. In fact, Slack's team uses PagerDuty for customer service, or also in conjunction with Salesforce. And so this is the way our platform has evolved. But what hasn't changed, which I think is really important, is it's easy to use. You can deploy it in minutes. It doesn't require significant training. It integrates to everything. More than 600 applications and services. And the old enterprise software platforms that are out there don't do that. They're not interconnected. They're not easy to integrate. They're not easy to learn. They require lots of consultants and dollars to make them work. And so we used to call this the consumerization of the enterprise, but the fact of the matter is, workers are more like consumers every day. They want instant gratification and they're on a time clock. They've got to handle these challenges and opportunities quickly.

Michal Lev-Ram: So I'm curious, you're talking about incidents response and swarming and that makes a lot of sense for your product and what it enables IT teams to do, right? What they need to do, their jobs. What about surfacing and making sure that problems that employees have are bubbling to the surface in a world where you're not having these organic interactions. And I don't know, maybe those problems were actually harder to surface when you were more in person and face to face. Maybe people have an easier time bubbling them up to the surface now, but how have you guys approached that?

Jennifer Tejada: I think Slack has democratized the way employees can... I have employees reach out to me on Slack no problem.

Michal Lev-Ram: More people are reaching out directly to you, the CEO, now than before?

Jennifer Tejada: I think Slack is a lot more inclusive and inviting. And likewise, we have customers that use PagerDuty for employee relations, crisis management, onboarding, offboarding. There are use cases that go well beyond crises. Even when we had outbreaks earlier in the pandemic and making sure that we could keep people safe, et cetera. But I do think that this democratization of how you almost use digital solutions to flatten the organization, there may still be actual hierarchy in terms of reporting lines, but there's a lot more transparency with a tool like Slack. So I can look into a channel and kind of get a sense of how employees are feeling. And I think that makes my job easier in a lot of ways. In Zoom, I experienced my first Zoom earthquake yesterday. I was on a call with the Australian team, the APJ team, and the earthquake, the boxes in Melbourne started shaking first. And then the boxes in Sydney started shaking. And our crisis management leader reached out and my chief of staff answered back," Oh, they're all fine. We just saw them. We saw it. Everybody's good. We know where they all are. They're in all hands. It's okay." That would've never happened previously.

Michal Lev-Ram: What about you Stewart? Anything to add on just how you're making sure that your finger's on the pulse of how employees are feeling? I know you guys have at Slack done a lot of research also around this.

Stewart Butterfield: A lot of asking people, and there's a lot of great tools. And I think probably every company at this point, certainly during the last 18 months, has done more, I can't remember what the category of software culture is an example of.

Jennifer Tejada: Serving, pulsing, testing.

Stewart Butterfield: Yeah, so there's a lot of that. And there's a lot of really specific reaching out. There's also a lot of synthesis of the issues that do bubble up and encouraging managers. Again, going back to the frontline managers, to take the time to check in with their team, because I bet they have the natural inclination, but sometimes feel a pressure that they're supposed to accomplish X by whatever date. We have this objective, they're going to be evaluated by that. So telling them to step out of that, to check in more with their teams and get that feedback. And obviously it's very appreciated. The one thing that I think is a universal among every employee, every company now, is now that they've had this taste of freedom, maybe overstating a bit, but I think people are really realizing how much they value the flexibility. And that is according to the future inaudible research we've done. Second only to comp in thinking about evaluating a new job. So I think we're going to see a lot more of that and also just a lot more market demand for roles that have a lot of flexibility.

Michal Lev-Ram: So you kind of think into the future, like five years out, you're talking about digital HQ, flexible, hybrid, all this stuff. How do you make sure that we don't revert and regress back to what we still know as the norm? Or worse, that some parts of your employee base do and others don't, and it creates this sort of inequitable playing field? Are there rules that you're putting in place that you can talk about that make sure that it's still going to be as level of playing field as possible?

Jennifer Tejada: It is a big challenge. And I think like any big challenge in a business, you want to come up with a hypothesis and a strategy, put some goals in place, and sort of measure how things are going. So Stewart mentioned sentiment testing, like constantly checking in. And the questions evolve over time as we understand some of the issues that our employees have. Putting in place work agreements. So, starting with norms, how's the team going to work together? How often, if at all, are they going to get together in person? What is the expectation if part of a team is together in a location and part of the team is remote? We have the expectation that there's one square per person in that scenario, so that you don't leave someone out looking at those little pin heads in the distance, in the big room on one square and having their head life size in the other. And I think really just being intentional about what it is that we've learned through this crisis that we want to embrace and bring forward into the future. And likewise, what we're going to let go of and give up that wasn't working for us before. So I think you mentioned meetings. We are a meeting driven culture. And when the crisis began, you could literally go 14 hours straight of Zooms and want to just kill yourself at the end. And no one is having an original thought by the 10th Zoom, for sure. Some of them not after the sixth. And so we started doing things like setting the defaults in calendar so you cannot book an hour long meeting. Or every meeting ends at the 25 minute mark and the 50 minute mark to give people bathroom breaks, to allow parents to make lunch for their children, to do the things that we have to do. And those improvements are staying with us even on the days that we might be co- located. Also just making sure we're still doing all the things that we need to do, like putting sustainable programs in place to ensure representation, to ensure an inclusive environment. And I think belonging is such a hard one. I mean, think of all the people you onboarded over the last year that you never met in person. I'm going to put myself at risk and hug all those people the first time I see them because they don't get to experience our culture the way people who were here before when we were all physically together. And so how do you create those touch points in a measurable way to make sure those are still going to happen? What are the parts of your culture that are really meaningful that you want to make sure new employees experience, and what new ones are you going to build? So being intentional about that too.

Stewart Butterfield: Yeah. When we think about five years out, I think there's one big question mark is, do we get to the point where we're able to kind of negotiate the risks associated with COVID in a way that has us, it's more like the flu or it's more like the other risks that we take in our life, like driving automobiles and stuff like that. And if we do, then I don't think there's any real risk of drifting back. And that's mostly because it took the pandemic to get us from there to here. I think it would take something pretty dramatic to get us to go back. And I'm worried that I'm coming off as anti being in person. I'm actually very pro being in person. And here's an optimistic take that really requires you to think rather than the future is this one thing is different, but everything else is the same and my frame of reference is February 2020, it's many things will be different and my frame of reference is today. Because we have to move from the actual present that we're we're living in. So most organizations comprised principally of knowledge workers did okay. So that's the baseline, did okay. And then you got the amenities of normal life returning, like you can go get your nails done or go to a theater or have a dinner with friends in a crowded restaurant, all those kinds of things.

Jennifer Tejada: Breathing all over each other.

Stewart Butterfield: We'll see the extent to which people want to, but the option is nice. So things are okay and then life is better. And then we get in person collaboration, communication back in the toolkit as one of the things that's available to us. And if you look at it that way, A, it's a pretty positive thing, but it's really hard for me to imagine what reason people would have to ever choose between two options in their career. And one is, cool company, I'm happy with the compensation, this is good for my career goals. They have a policy that says we can use the office or in person get together as much as we want, but we don't have to be in the office. And this one is all the same attributes, except I must be in the office nine to five, Monday to Friday. Who would ever take the second option? Just the option of being able to have that control and determination over how you spend your time is going to be so valuable to people that it's impossible for me to imagine. And the last thing I would say is ultimately, we as CEOs and our colleagues can say whatever we want, this is going to be a market driven decision. In other words, the group of employees in total will decide what the answer is, just like the way that we determine compensation. You can't just decide, at my company, we only pay our software engineers$ 30,000 a year, because you just won't be able to hire them. So yeah, people can say whatever they like now, and then when the market speaks, they'll have to listen.

Michal Lev-Ram: Okay. I'll ask you again in five years.

Jennifer Tejada: Maybe on Zoom.

Michal Lev-Ram: Sorry, what was that?

Jennifer Tejada: Maybe on zoom.

Michal Lev-Ram: Yeah, on Zoom. So one last, very quick question for both of you. I think we've all had to tap into new skill sets over the last year and a half and just in this new way of working. What as leaders do you think is the skill or characteristic that's most helped you as a leader through the last year and a half?

Jennifer Tejada: I'll have to ask my team that, but I do think it's my ability to connect and to demonstrate authentic care for people, no matter what we're talking about in the business. And I used the word empathy before, but I've always been a big fan of walking one- on- ones, because people will tell you things when you're walking around the block that they won't tell you staring across the table. It's just a different mindset and frame of mind. And what I found when the pandemic started was that we didn't do those anymore because we couldn't walk together. So we started walking virtually and the first 15 minutes are really like, how are you doing? How are you going? Et cetera. Well, that's great one on one because you're seeing people in their living room, you're connecting. But one to many with the much broader organization, you have to be more intentional about thinking about how am I connecting these people to the mission and to our purpose and to what our customers need? Because Stewart mentioned it, flexibility is going to be table stakes. Anybody who's not giving employees flexible options I don't think survive in the future. So we all have to do that. But what are we going to do to differentiate ourselves? That's going to be purpose, mission, vision and culture. The feeling of the place, even if you're not in a physical place.

Michal Lev-Ram: All right, Stewart, you get one word. Is it brevity?

Stewart Butterfield: Empathy.

Michal Lev-Ram: Empathy. Empathy. All right, I'm sorry we have to wrap. Jennifer, Stewart, thank you so much and thank you to everybody.

Michael Rivo: That was Stewart Butterfield, CEO and co- founder of Slack, and Jennifer Tejada, the chairperson and CEO of PagerDuty, speaking at this year's Dreamforce. If you liked this episode, be sure to subscribe wherever you get your podcast, and be sure to check out this year's Dreamforce on Salesforce+ at salesforce. com/ plus. Thanks for listening today. I'm Michael Rivo from Salesforce studios.