How Slack and Future Forum Redesigned Work for the Digital Age (with Brian Elliott, Founder, Future Forum)

Exploring Flexible Work Dynamics with Brian Elliott: Insights from a Startup CEO to Future Forum Founder and WSJ Bestselling Author.
Daan van Rossum
Daan van Rossum
Founder & CEO, FlexOS
I founded FlexOS because I believe in a happier future of work. I write and host "Future Work," I'm a 2024 LinkedIn Top Voice, and was featured in the NYT, HBR, Economist, CNBC, Insider, and FastCo.
September 27, 2023
min read

Brian Elliott spent 25 years building high-growth companies and leading teams as a startup CEO, a leader at Google, and then an executive at Slack and Salesforce, where he co-founded Future Forum, a think tank focused on redesigning work through data and dialog. 

Brian is the author of the WSJ bestseller,How the Future Works: Leading Flexible Teams to do the Best Work of Their Lives,” he’s been published in the Wall Street Journal, HBR, Bloomberg, the Economist, and other publications.

Today, we will discuss how Future Forum’s research helped Slack transition from in-person to hybrid remote work, all the lessons Brian learned during this time, and how you can implement them yourself, including: 

  1. When matters more than where. One of the key insights from Future Forum is that while we talk about location flexibility and how many days a week people should be in the office, time matters more than place. Giving people uninterrupted time to do deep asynchronous work boosts productivity more than location choice. 
  2. Online and offline connections. The second great insight from Future Forum is that even today, leaders don’t connect people well online and offline. When managing remote teams, getting people together and focusing on building relationships is critical, even if it’s just once a quarter.  
  3. Create an inclusive environment. The third insight from Future Forum’s research is to rethink how flexibility can drive inclusion in the workplace. As Brian shared, from their data, women and caregivers wanted flexibility more than men. He also noted vast differences between countries and their policies that drive the need.  
  4. Bring not just data but storytelling and practical ideas. Storytelling and practical ideas help build your case for flexibility better. Brian gives a great example of how we can gain the effect of a whiteboard session without being together offline. (Tune in to find out!)
  5. We can’t lift and shift. Instead of copy-pasting things that worked in an office, rethink them completely. Like meetings – do you really need all of them? What can be handled through online collaboration? Besides this, rethink mentorship, onboarding, and training. Think about the outcome you’re trying to achieve and the best way to get there without holding on to how we used to do things.
  6. Supporting managers. Whether you’re managing a team or managing managers, we need to rethink how we support managers. As Brian mentioned, managers are more burnt out than ICs and Execs.
    We need to give people who don’t want to be managers that opportunity and provide practical support for key management elements like asking good one-on-one questions, running virtual icebreakers before team meetings, and understanding each others’ personal user manuals
  7. Finally, on a more personal level, Brian shared two great personal lessons that we should all take to heart. 
  • There is no straightforward route to achieving success. It’s important not to become overly concerned with titles or the size of your team. Instead, prioritize your personal development and the tangible impact you can make.
  • Unlearn the idea that you need to know everything as a leader. The idea of ‘seldom wrong, never in doubt,’ isn’t true. Set ambitious goals but then make it a team effort, ask for help, and achieve it together.

For more Brian, follow him on LinkedIn.

We hope you’ll love this episode and can put these insights to good use. Subscribe on Spotify, Apple Podcasts and Youtube for the latest Future Work episodes. 


Daan: What should listeners know about your very impressive career?

Brian: Call it impressive, choppy, or whatever; I didn't start out with all that stuff. I started out as a grocery store clerk, short order cook, and industrial painter, putting my way through college.

After college, though, I was a math geek. I got into analytics, and Boston Consulting Group hired me right out of college. I spent a couple of years working for them. Then they put me through business school, which was actually fantastic and gave me a leg up there.

At Harvard Business School, I actually ended up being a case writer for a couple of professors in the technology and operations management group, and it was an opportunity to explore whether or not I actually wanted to go down the academic route myself and be a researcher.

The truth is, my ADD and being a professor really wouldn't mix very well. I didn't have the patience to go that route. So instead, I jumped back into BCG and then eventually into tech. I've been working in the tech world for 25 years. The startup CEO, after some great adventures, jumped from that to Google and Slack, as you noted.

But the things that are in common across all that, for me at least, are that I'm just curious about how things work in a bunch of different ways, and I would move on when I found that I wasn't really learning anymore when I was bored with the job because it felt like it was too routine and too repetitive.

I also found ways in almost any situation, even when times are really tough in the startup phases, to find what brought me joy in the job. Usually, that had something to do with people—getting people aligned and motivated and helping them grow their own careers. But I also learned that once those things that brought me joy were overwhelmed by the things that brought me down—corporate bureaucracy and admin trivia—it was time to move on.

I guess there's two things that I'd pass on to anybody out there, which are that there's no linear path that necessarily fits with how you get there. The jungle gym analogy works really well—at least it did for me—which is that sometimes you have to move sideways to get a new learning experience to move back up. Sometimes you have to move down and don't get hooked on titles or the size of your team.

I've been a startup CEO where I had a team of 300 and some odd people. When I first went to Google, I had a team of 2. One of them quit on the first day. When I left Google, we had 350 people on the products and engineering teams. We had thousands of contractors working on the project I was doing.

I jumped to Slack, where there were roughly 50 people on the platform. It was just a fantastic move because I had a great experience doing that. I did it again at Slack, though, when the pandemic started and we had the opportunity to build something different.

Future Forum was just three of us getting it off the ground, and each time it was much more about thinking about, like, what are we going to learn? Where can I have an impact? Letting myself get too hooked up on the title, the size of the team, and all that mess that tends to nag us

Daan: Can you describe Future Forum specifically? What is? What was its goal? What made you start it? Perhaps you pitched Slack internally. How did that go?

Brian: There are a couple things on that front. One, it ties back to my research in data geek aspects, because really what Future Forum was about, at the heart of it, was research-driven insights combined with habits and practices we're seeing companies do that were really better for people.

But it was also borne out of a couple of things. One, as a startup guy, I got the consultant knocked out of me pretty early, and what I learned was through the school of hard knocks that that old phrase culture eats strategy for breakfast was really true. If I wanted my team to succeed, I needed to spend a lot more time building relationships with people, building trust, a sense of belonging, and a sense of purpose in the team.

That was really something that I wanted to espouse more broadly and bring out into the world. The pandemic then created this massive opportunity for a lot of us to rethink how work was happening. What happened in early 2020 at Slack was that myself and a number of others found ourselves in conversations with executives at other companies. We're all wrestling with much more profound issues: how do we care for our teams, but also how are we going to make major shifts and changes in policy? 

So, I pitched Stewart Butterfield on something that was honestly his idea years ago that never came to fruition, which is that Slack should have its own think tank around the future of work, and I said, "Hey, Stewart, I'd love to pick this up and run with it. Can you give me a couple of people I could recruit into this and give us six months and see where we can take it?"

And I had two fantastic co-founders along with me, Helen Kupp and Sheela Subramanian, who were just really amazing people that I've known for years. I hadn't worked with them directly, but I knew their skills and capabilities. I knew that we thought alike in a lot of ways, but we were also very different people who would bring different things to the equation.

At the end of the day, what it was, was a labor of love that turned out to be a lot bigger than any of the three of us, I think, expected going into it. Something that could have been a six month and you're done project became a three-year adventure that I think has had a lasting impact.

Daan: It definitely has. What are some of the things that you do with a team? The people you were with were from outside of Slack.

Brian: No, Sheela and Helen were both at Slack. Sheela had been on the marketing team and had led Slack's Enterprise Marketing International expansion, among other things. Helen had been a strategy leader in the organization and had worked on pricing, international expansion, and growth. She was actually a product manager who was leading part of the platform team. I helped talk her into taking this grand leap.

Both of them were at Slack along with me. We did, though, go out and recruit partners externally, so we didn't want this to be just about Slack and just about digital tools. So Deborah Lovich at Boston Consulting Group, Ryan Anderson at MillerKnoll, and Tina and her team at Management Leadership of Tomorrow were fantastic partners who brought different perspectives about space, global leadership, diversity, and inclusion and could bring in perspectives that we wouldn't necessarily have.

It was really that grouping of a dedicated core that we're building what we're doing in Future Forum and partners who were really going to help push us in new directions.


Daan: With that group, you started researching the Future Forum, and obviously, Slack was transforming from a chat app or communication tool to the new digital HQ. What were some of the findings over those three years that really stood out to you?

You said something about the culture's eating strategy for breakfast and the fundamentals of what makes good teams.

Was there a lot of new insights, or was it also confirming that the age-old pillars of good leadership and good management still hold true?

Brian: Great management is really key and essential to building high-performing teams. There's plenty of research that has been out there for years that points to a lot of the same things we found.

I think there were a couple of big differences. We did actually gain some new insights, and the world was much more open. Leaders were much more open to questioning conventional wisdom and rethinking the assumptions we had.

For example, at Slack itself, the product changed, but we were not a remote first company by any stretch of the imagination. I mean, part of my job wasn't just leading Future Forum; it was helping us discover our own path forward because Slack was less than 3% remote pre-pandemic. It was an office company.

Offices were where and when work happened. I had an engineering leader who worked with me out of Denver, Colorado, Mike, who would come to San Francisco. He came to San Francisco 23 times in 2019. He did it to be "in the room where it happens." Because there would be some senior review with Stewart and Cal, who's our CTO, and Tamar, our chief product officer.

And Mike didn't want to be trying to dial in from Denver, unable to get a word in edgewise, and Mike's got five kids. It was really painful. We had this debate at Slack for years prior to the pandemic about whether we should spin up a remote team because it was so hard to recruit designers, product managers, and engineers into San Francisco, New York, Vancouver, and Melbourne.

We never did it because we'd never done it before, so we didn't know how to do it.

Daan: That sounds like such a huge challenge that you're trying to get the best people to design and build Slack, and you're so reliant on the people in the immediate vicinity of the office.

Was the pain just not big enough to go out and say, "Okay, we got to go remote?" There's no other way.

Brian: Apparently not! We opened the Denver office and hired Mike to be the leader there. We're opening up a Toronto office for an engineering and product design team there as well. We did the same thing in Dublin and in other parts of the world, and it was just easier to replicate what we had done before in the same place rather than try to think through all different ways of working.

What shifted was that we got 3–4 months into the pandemic, and Cal Henderson, our CTO, said this is working a lot better than I expected. The fears we had about productivity were unfounded, other than the horrible conditions some people were in, especially the team that I was overseeing in India. 

Innovation, creativity, and spark were still clearly there. We were being driven to build new capabilities really well, and so all of that was part of it. Go back to your question, though, which is that we were also seeing things in the research that Future Forum was doing that helped drive some of that. So I'll give you three quick examples.

One is that we talked so much about location flexibility and how many days a week people should be in the office or together somewhere else. And the research showed super quickly that time matters more than place; giving people big blocks of focused time during the workweek in 2 to 3 hour chunks was a much bigger benefit to their productivity than location flexibility.

Clearly, the two are tied because, by the way, if you force them to commute five days a week, you lose some of that, and so that led to a lot of things that we were doing internally around how do you give people focus time? It also led to a lot of things from a product innovation perspective. How do you share information asynchronously so you can kill off unnecessary meetings? That's number one.

Number two, Slack got this one pretty well, but a lot of other organizations don't. A lot of senior leaders still don't know to this day that the connection inside a team is as much digital as it is physical. There is a core role, and a really important one, in getting teams together. I would never work with a team that I lead, manage, or am part of that doesn't get together at least once a quarter for a week to build belonging and meals together.

There are so many ways in which people can stay connected digitally with one another. Socially, we can build global connections within an organization. There aren't two generations of digital natives in the workforce. I'm in my fifties. I didn't grow up with all of this. I've had to learn it myself. But digital builds connection as much as real life builds connection at this point.

The third one that was less obvious to me as a senior white male and non-primary caregiver executive was that there's just a huge opportunity to rethink inclusion in the workplace that flexibility brings to all of us. So, we saw this in the data early on. Women, more than men want flexibility. Caregivers, especially women with children, needed it more than men.

We could see global trends that were pretty much tied to how good the country's infrastructure was around caregiving. The U.S. was far worse than any other developed country when it came to primary caregivers' needs for flexibility because the U.S. does not have good maternity leave policies and does not have a good prekindergarten childcare infrastructure. Australia was better. The UK was not far behind the U.S. Germany and France looked pretty good. It's just one of those things where you kind of look at the data and go; there's an issue here.

You can see the same thing when it comes to people with disabilities and racial and ethnic differences, especially in the U.S., where you get the data. Those research findings were the type of thing that we would then try to make sure that we helped executives understand as they were thinking about their own approaches.

They didn't do it just from the perspective of, Here's what worked for me when I was going through the system, because, let's face it, a lot of our employees who are digital natives who are not white males, non-primary caregivers, face a much different world than we did at that point.


Daan: Definitely. When you then bring these insights to companies and to leaders, what gets adopted easily and what is maybe even to this day still quite difficult for people to kind of get their heads around and to actually put into practice.

Brian: The thing that doesn't work is to just give them the data. I love the data. I love the research and the insights. But if all you do is give them the data, you're going to hit a roadblock very quickly, because unfortunately, when you've never experienced a different way of working, it is too hard of a bridge to cross to try to invent it out of whole cloth. What you need to do is combine the data with storytelling and tactical examples.

When it comes to creativity and innovation, the thing that I've heard probably 100,000 times at this point is that we should need to get the whiteboard back in front of a whiteboard and do some brainstorming so we can come up with creative ideas.

The research will tell you the majority of whiteboarding sessions in front of our groupthink, because the thing that happens is that someone who talks a lot like me is the one that's grabbing the pen at the front of the room and they're commanding that pen. And they're writing things down, and they're the most senior person in the room who's been around for a while. 

If you're new or not in the majority or have a different opinion, if you're really daring, you might share it, but you might also just sit on your hands and not share it at all. That insight might be helpful to leaders, but what's more helpful is to then say, "Okay, let me give you a different tactic" in a way that you can actually tackle this, which is like this concept of brain writing.

You've got a problem you're trying to solve as a team. You've got some information about it. You give the prompts. Here's the problem we're trying to solve. Here's the information we've got for the team. You give them three days or a week to put them together. Not a full write-up, but I just want your three bullet-point thoughts and what we might try to do around this.

Give me 3 to 5 ideas. Write them down. Spend time on this before we get together. And when we come together, all of us toss all of our ideas at the same time into a Google doc, a Microsoft doc, the chat, a whiteboard app, wherever it happens to go. And what that does is just get more ideas out on the table.

It avoids that pre-filtering that happens when it says, "Oh man, Brian's holding the pen or Daan's holding the pen. I'm not about to toss this out because I want to hear what they say first." And you just get a lot more ideas that way.

That's a redesign of how we work. That's a lot better than the groupthink process around whiteboards or relying on a random chance encounter with a water cooler.


Daan: This is part of the bigger idea that we need to redesign and rethink how we work rather than just take our in-office practices and put them online. Because I think we've seen that it doesn't work.

Brian: Yeah, what we've done too often is just lift and shift. By the way, we've just sort of taken what the vast majority of companies and organizations did in 2020 and 2021. We had the same meetings. As a matter of fact, we had more meetings. We just did them all digitally on Zoom, and we got burned out because we were facing ourselves all the time and we didn't really step back and say,

We're going to fundamentally rethink our approach to mentorship. We're going to redesign our onboarding process. We're going to think about how we train new employees and how we can be more intentional about things like how we pair them up with people they should be in contact with to help them build networks.

There are so many things that we could do if we just pick a problem, pick an area, and think about what outcomes we're trying to accomplish. How might we both experiment but take practices from other companies and try stuff out that might give us a better outcome than simply taking what we've done for the past 20 years and trying to do it on a video call?

Daan: Absolutely. That's one way to explain that to leaders and executives in companies. Another is to get this to become the new way of working at all levels of the organization. 

We released research around what hybrid and remote employees think about their direct managers, and the way they rate those direct managers on how good they are at embracing some of these hybrid and remote best practices is not too good. They're not too positive about their leader's ability.

How can we also get managers, especially newer managers, who are probably digital natives, to think in this way and to work in this new way?

Brian: I'd love to hear more, even in terms of what you guys saw too, in terms of the habits and practices that the good ones do adopt. We ran into this ourselves within Slack, the organization, and I've heard it from so many of the executives that we worked with, which is the pinch point for all this: your frontline managers.

Let's face it, we've not done a good job for decades now of giving them much training or support. Your frontline manager is somebody who just happened to be the most senior, experienced individual contributor on the team who wanted a promotion, got a promotion, and is now a manager with very little training or support. There are a couple of things that we can do to unpack that.

Let's just start with the fundamentals. Not everybody wants to be a manager, really. And so what I've been a big proponent of is in as many situations as you can think about how you have two tracks for employees where you've got the manager track, but you've also got an expert track that goes up, preferably as high as VP level in an organization.

Engineering teams have been doing this for a long time now. We did it at Google. We did it at Slack. The architect, who can get paid as much, gets as big of a title as a VP in an organization, but is leading through expertise, not through managing people. I've seen it done in design, product management, and content teams within marketing. 

I think there are a lot of places where we could apply. Because you really want people who want to lean into the job of leading people through management, teaching them, and training them.

The second huge one is that we've got to give them support and tactical experience. So some of what we did even in the early days at Slack, and we've done this with other companies too, is a couple of things.

One, make sure that they've got support networks of other managers that they can talk with. Start off by facilitating those groups. Your people team can help do this to get it off the ground, but you want them to find people they can go to and ask for help. But you've also got to get super tactical, like, how do you run a good one-on-one with your team? What are the three questions that you should ask every single week?

Things like, "Hey, what do we say we're going to get done last week and how did it go? What are your priorities for this week to make sure that we're aligned, and what's blocking you? What can I help you unblock to get out of your way?"

Giving managers super tactical "how-to" examples is really going to give them a leg up in how they manage and lead their teams.

You can't just be giving them euphemisms like, Hey, you need to be an emotionally capable, vulnerable leader to be good. You have to show them what that means and give them concrete tools they can use to do that.


Daan: Which is, by the way, one of the best practices that employees rated their managers lowest on? In terms of being empathetic. Are they understanding? That was one of the things where we actually saw the lowest scores.

We basically saw pretty high marks on things like flexibility and adaptability. Our managers are able to embrace this new way of working and balancing, working together while a lot of things are changing externally.

We also saw some pretty good scores on setting clear expectations. Providing guidelines, deadlines, and performance goals You have a lot of work to do even when you're not sitting together with your manager. So that's pretty important.

But then, the thing where we saw really low scores beyond empathy was inclusion. So, inclusion was actually the one that scored the lowest.

Are managers really thinking about everyone on the team and making sure that everyone has equal opportunities? Onboarding was very low.

Is there a good program in place? Is the manager equipped and able to bring new team members on board in these remote and hybrid contexts and document? You just said something that we used to do, which was sit around the whiteboard.

I think some people have kind of transplanted online, and now we sit around the online whiteboard. But like you said, is there a document afterward? Are people able to input on that, maybe even if they're in a different time zone? So that's where we saw some of the low marks.

And then you really think about what companies can do to enable these managers to upskill in those areas.

Brian: Yeah, that's great insight, Daan, and thanks for going into it on that specific set of areas because you can't just teach empathy. You've got to give them tools for showing empathy and how to do that. I've got some empathy for managers because they're the pinch points in the organization, in our research and others, too. They're the most burnt out.

Middle managers are more burnt out than the executives, by far. They're also more burnt out than the individual contributors. Often, they're sharing their own individual load as well of work they need to get to do as well as care and feeding of the team. It's a hard spot to be in. 

And so it's often hard for them too to show that vulnerability. There's a couple of things you can do, though, that sort of help you take steps in getting there. Tactically, things like the weekly staff meeting that's got an icebreaker question at the beginning of it. It can be a silly question. We're entering fall in the U.S. so it's pumpkin spice latte season.

Where do you stand on pumpkin spice Latte? It happens to be my favorite seasonal question.


Daan: That sounds too controversial as an icebreaker question. There could be a three-hour debate.

Brian: It was. My team went off on this for about 15 minutes one day. And it turns out, by the way, I didn't know this either, but there's no pumpkin or pumpkin spice. It's just the spices. I learned that one teammate who shall remain nameless hates orange vegetables. It's all the stuff that you get into when you learn and do this.

But that's humanizing. It helps, and just reminding people that it doesn't have to be the question that starts off with, How was your week at work last week? Or what did you do this weekend? You can find ways to explore what kind of Olympic skier you want to be. What was the worst haircut you ever had?

Just get to know people. Personal user manuals are one of my favorite things. It can sound super cheesy, and you can make them super cheesy about, like, what's your astrological sign? But the really important stuff is, like, how do you like to communicate? Are you a morning person or an evening person? What's your life setup? What do I need to be aware of as a boss?

And the thing that you got to do as a manager that I tell people all the time is that you got to go first. It's your job to set the tone, share yours out there, and tell your team. You know what some of your own feedback points are in areas where you're looking for development, help, and support, and sort of being open and vulnerable around doing that.

Then, to your other point about how you know what a team's norms are, there's no better thing than a team-level agreement, and a manager doesn't have to do the upkeep on all this stuff. There are always people on your team that want to make the team a better place to work because, let's face it, the old people don't leave companies; they leave managers; they really leave teams.

If you can have people volunteer, raise their hand to help you craft things that are in your team-level agreement, which are things like what tools to use to communicate off-hours so that you don't have to monitor, such as Slack plus Teams plus email plus Zoom plus PagerDuty plus five other tools. How do we make decisions?

There's just so many things that are the norms and habits of a team that if you're doing that, when somebody new joins, they get the document and review it. They can also start asking questions and saying, "I don't know what that even means, so help me out. 

It's just a much better starting point. Too often managers think that all this stuff falls on them when there's almost always somebody in your team that please doesn't abuse them for this, but who's willing to pitch in and help shepherd this through and help build in better habits and practices because maybe someday they want to be a manager too.


Daan: How would you find that person on the team if you're a manager sitting there thinking, "Well, that sounds great. I can offload some of this stuff to someone else."

Brian: Ask for help, ideas, and volunteers. I do think this also goes back to the opportunity question. You've also got to look around and not keep reassigning it to the same person all the time. Please be aware of gender differences. The note-taker shouldn't always be the only woman on the team; that's a horrifying place to be.

You need to think about things like: what are the leadership and growth opportunities for members of your team? But you've also got to move them around within your team over time to make sure that they're not all landing on someone's back, number one, and they're not being disproportionately given only to the people who look like you, or worse yet, that feel like administering trivia tasks that are being handed to people that don't look like you.


Daan: We could definitely talk data, stories, and ideas for a lot more, but we're almost at the end of our time.

One final question: After all of this, what is your big wish for humanity? Something you could put on the billboards and share with the world.

Brian: I think the biggest thing that I'd like to see people continue to do is just be open to new ideas and to listen to your own teams in order to find them, especially for executives and executive leaders.

I had to unlearn this myself. We're all expected to have all the answers. We're expected to be seldom wrong and never in doubt, which is a phrase that got burned into me when I was in my twenties. And I had to unlearn over the course of decades.

But you know what that does? It just sets you up for failure because all that's doing is saying you have to be smarter than everybody else in your organization, and there's no way that's going to be accurate.

At the same time, when I say that to people, they get back in return, but then how do I motivate the team? I really want people to be able to do two things at once. You should have massive aspirations, giant mountains that you want to climb as a leader, point towards those goals, but also invite people along for the journey and say, "Hey, look, we're going to climb that mountain; we're going to do it together. But I need your help in finding the right path for us because I know I can't do it all by myself."

If you can do that, the engagement of your team and of your employees goes up dramatically, and they will then share with you thoughts and ideas that maybe you didn't have. That might be where you run into some problems, but there are also some ways in which you might get up there faster together. So listen to your team. You don't have to have all the answers. Aspiration; nothing wrong with it, but be open to new ideas.

Daan: Beautiful. It speaks to that sense of curiosity that you were talking about in the beginning, which has always driven you in your career. You don't need to have all the answers, but you do need to be curious about what's possible.

Brian: I still hope that I can always get there, and some days I do and sometimes I don't.


Daan: Wonderful, such is life. Okay, Brian, thank you so much for being on. 

Brian: Thank you, Daan. Appreciate you having me.

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Future Work

A weekly column and podcast on the remote, hybrid, and AI-driven future of work. By FlexOS founder Daan van Rossum.