- Speaker #0
a big part of strategy is knowing what you're going to say no to. Okay. And part of it too, is even if you can't say no, you can say not now. Right. And it's hard because it like, it's always been hard for me as a leader to, I always want us doing more, right. I always want us pushing further and going faster on stuff. And I'm a pain in the butt around that. But at the same time, you got to realize and recognize that at least you're going to get a lot more out of a team. If you can have clear, crisper, short-term goals, we then reassess and then pick up the next couple of things. And your, your next, next stuff list can sit over here off to the side while you actually accomplish the stuff you need to. But it's really, it's a hard conversation and you've got to wrestle it out as a leadership team. Cause that's part of the job is God from some decisions about what you're going to do and what you're not going to do.
- Speaker #1
Welcome to the Paid for World Society, where leadership is a continuous learning journey, and where knowledge is passed on to the next generation of leaders. I am Romain Jordan, and today my guest is Brian Elliott, a renowned speaker, advisor, and one of Forbes'Future of Work 50. With 25 years of experience as a startup CEO and executive at Google and Slack, Brian is uniquely positioned to guide leaders in building a better future of work. In this episode, we explore the challenges of leading distributed teams. Brian shares his insights on fostering trust, prioritizing effectively, and growing as a leader. He offers practical advice on creating a culture of transparency, celebrating successes, and discussing challenges openly. Whether you are a seasoned executive or a first-time manager, this conversation is packed with actionable insights to help you lead your team to success. So, let's pay it forward and learn from one of the best. Here is my conversation with Brian Elliott. All right. Hey, Brian, how are you?
- Speaker #0
Good. How are you doing, Roman?
- Speaker #1
Good, good. Thanks. Welcome to the Paid Forward Society.
- Speaker #0
Thank you for having me. Great to be here with you.
- Speaker #1
Yeah, I'm very glad to have you. So you were recommended by James, James Colgan, I had on the show a couple of weeks ago. And so thanks for the follow-up and being there with us today.
- Speaker #0
Very glad to do it. James and I go back to our days together at Slack, which wasn't actually that long ago, but sometimes it can feel like it.
- Speaker #1
Yeah, but... Of course, we know about you now, but would you share anything that you believe would be interesting for our listeners? And then we can delve into the leadership topic.
- Speaker #0
Yeah, no. So the quick and dirty, and we can get into sort of where I came from and what I did, is former consultant 25 years ago jumps headfirst into.com 1.0 bubble. So I spent about 25 years in technology companies. I was a startup CEO. I spent a fair amount of time. At Google, leading product and technology teams and small businesses within Google, small being a relative term for Google. and then Slack, where I both led the developer platform and then built out a think tank called Futureform. I spent the last four years basically studying what's working and what's not when it comes to flexibility in the workplace and how to build more effective teams. And these days, I'm just acting as an advisor, just acting as an advisor. A number of leaders, both startups, early-stage companies that are looking to leverage technology to build better ways of working for organizations. and I work with larger organizations that are grappling with like the changing nature of the future of work from both the demographic and technology perspective and how to, how to succeed while also enabling your people to do great stuff.
- Speaker #1
Yeah. That was quick. Thank you.
- Speaker #0
Yeah. I told that in a bit brief.
- Speaker #1
That's really cool. Thank you. Can you talk more about this think tank? I think the future of work is a future forum is very interesting to dive into. I think there are many questions, mostly after the four years of pandemic that we follow. I still count four years for some reason. I believe.
- Speaker #0
Yeah.
- Speaker #1
Yeah.
- Speaker #0
fully out of it yet but uh most of the pandemic most of the pandemic is behind us and we now treat it like the flu which is probably appropriate and yeah precautions now but it was four years ago so we're recording this in march of 2024 it was march of 2019 when pretty much around the globe all of us got thrown into this massive experiment you know and there are lots of horrible things about the pandemic quite obviously all of us were dealing with teammates and friends and family members who were ill, people lost their lives, lost loved ones. But we also had this massive sort of opportunity to reset a lot of our kind of understanding about the assumptions that we'd walked around with for literally decades, in my case, about nine to five, five days a week in the office being where work happens. And I think to the better for all of us, both for organizations and for people. So Future Forum itself was a think tank that Slack backed along with Boston Consulting Group, Miller Knoll, the office furnishings folks, and a group called Management Leadership for Tomorrow. It's a nonprofit that focuses on diversity, equity, and inclusion in the US. but those groups came together and backed us. Myself, Helen Kupp, Sheila Subramanian were my two co-founders in it. Jumping into this adventure early on in the pandemic when none of us were sure that, you know, this thing was in theory back in March of 2019, we all thought it would be over by May, maybe June. Ha ha, little did we know. So we did two things. We did a lot of research. So we spent... three plus years running research, primarily a survey of 10,000 office workers around the globe that we ran every quarter to understand what was working, what wasn't, and for whom. And then the other thing was diving deep with leaders, with executives inside of firms that were kind of using this as an opportunity to rethink a lot of their own assumptions about work and sort of think about how this is going to impact and allow them to rebuild their organizations. So, fantastic experience that I think a lot of us still carry around with us to this day.
- Speaker #1
All right. Perfect. Thank you. So, was it mostly about the balance between RTO, so return to the office, and hybrid and how people work together? Or was it broader than just this concept?
- Speaker #0
Definitely broader than just the sort of hybrid and return to office battle type of thing. Matter of fact, in a lot of ways, that's the sort of... That's sort of the topic that we keep getting ourselves stuck on. It is an important one because workplace flexibility has real benefits for people, especially for historically underrepresented groups at work. Women more than men, caregivers more than non-caregivers, Black, Latino, Asian American office workers in the United States were able to pull data and look at and see that they have a stronger preference for flexibility when it comes to work location. and you can leverage that to both attract more distributed, broader sets and more diverse talent, as well as build more inclusive organizations if you actually leverage it. So there's a lot of work that goes into that one. The more interesting stuff in some ways is time matters more than place. One of the things that we've done over the course of the pandemic in some ways has made it worse because we've had the decade or two preceding that where technology allowed all of us to... you know, have a work device that's on us all the time, walking around with, you know, something that can go off with the random email from the boss, text message from the boss, Zoom, Slack, Teams, all the rest of it. And the other thing that happened during the course of the pandemic is meetings went through the roof because instead of tapping somebody on the shoulder to ask them a question, you block a half an hour and put a Zoom call on their calendar. And suddenly your calendar is Swiss cheese and you have no two-hour blocks for doing dedicated work. And focus time goes out the window and you're burnt out wandering through your day. So in the book that we wrote called How the Future Works as well, we get into two key elements. It's really not about... Office versus remote, it's about flexibility, because flexibility is time as much as place, and it requires teams to think through what their norms are. And then the other really big factor that's coming out of all this is teams are distributed. Like I've led organizations and teams that have worked in multiple cities for 22 of my 25 years in tech. right? And we didn't call them hybrid meetings. We just knew that the ones where some people were in the conference room and other people were trying to dial in from a remote office sucked, but all these problems, you know, pre-existed and they've only gotten bigger because post pandemic, most large organizations are way more distributed than they were before. Microsoft's a good case in point. At Microsoft in 2019, something like 65% of their teams were co-located in a city. In 2023, 75% of their teams are spread out among multiple cities. So it is literally inverted. And so all of a sudden what you find is that leaders and managers in almost all cases have to do something that I learned how to do two decades ago, which is lead a distributed team. Yeah.
- Speaker #1
So what are some of the best practices you have to share for people like myself? I mean, I run a very distributed organization with people deployed worldwide. Yeah. So what are some of the learnings that you could share?
- Speaker #0
Yeah. One of the key ones is around the fact that you just need to talk it out with your team and have this be an open conversation to get into the how of how you work together. Really, it's not about where, it's not about when, it's about how you actually operate as an organization. At the team level, there are these things called team level agreements that are really helpful in terms of setting your own operating norms. And there are some really fundamental things that you can do in that. and when you do it with a team that sort of has been around for a while, what you'll find is that a sizable portion of that team goes, oh yeah, of course, that's how we've always worked. And then someone will sit there and go, I had no clue that's what we were supposed to do, because you've never taken the time to really articulate it. So the key things in a team agreement tend to be things like, when and why do we get together, right? Back to using offices with a purpose. But... figuring out like what's the cadence at which we come together and for what reasons is a fairly big deal. And if you're in a sales organization that might be, you know, on Tuesdays, we have the weekly pipeline review, plus we do a show and tell. And so we want everybody together on Tuesdays to be able to do that. On a product and engineering team, it might be once a quarter, we get together for a week. and we do a ton of socialization and team building and bonding. And by the way, we do a lot of conversation about next quarter's, you know, sprint plan as an example. And so figuring that out is one part of it. But a team agreement also comes with a lot of other pieces, like how do we communicate with each other? Literally, which tools do we use for which purpose can help people understand what to do better? how do we share status and information about where projects are? Because God, we do not need more status meetings in our lives. We need tools and places where we can share that information with each other as broadly publicly as we can. And then there's also things you get into in terms of good habits around meetings and how we actually, you know, protect schedules. So there's lots you can get into in that, but things like talking about what your core collaboration hours are as a team. Everyone's expected to be available for meetings and for one-on-ones and for quick chats between 10 a.m. and 3 p.m. Monday through Thursday. So do us all a favor, schedule your doctor's appointments and your kid pickups after 3 or before 10 a.m. That way we're all available for each other. Those types of norms and working agreements. are really, for the most part, with the exception of when do we get together, are really sort of independent of that sort of where you work question. It's much more about being explicit about things that are often implicit about how a team actually operates.
- Speaker #1
Yeah. How do you make sure that people will get updated? I think one of the changes that I've been facing recently is that there's a big fatigue of individuals. having to catch up with docs or status or where to find information. So I think what are some of the best practices that you have developed on that front? And specifically, we tend to operate in a very US-centric manner. But when you have a very distributed team across many geos, that's even worse. That's even more difficult.
- Speaker #0
Yeah, it is. It is. And I got a couple of thoughts on that one. One, I'm a problem child on that one myself because I love soaking up information and knowledge. And so I'll go pretty broad as well as pretty deep, especially inside of an organization when I'm trying to understand what's going on. But that can make a lot of people pretty crazy too, right? Because there's no end to that, right? It never ends. You got to be careful about it. So I'll give you a couple of answers. One of which is... It's an open conversation you need to have with your team about swim lanes. This is one of the things that we did with the Future Forum team as well as part of our working norms, especially as we grew the team, was being really thoughtful about getting ourselves away from the sort of swarm ball tactics that happened with teams early on, right, where everybody has to be on top of everything. into figuring out, you know, what are the different areas of our operation? Who's responsible and accountable for those? Everyone else can be informed, but you don't need to be informed, meaning you don't have to keep up on top of it. And then what you do need to do is make sure that from a leadership perspective in particular, you're making clear what those items are that you think everyone needs to pay attention to. Like what are the most important things across the team for us to pay attention to number one, number two, number three, but also what's important information that's coming out of the organization more broadly that people need to be aware of in terms of business conditions or customer news or other things like that. And as a, as a leader, making sure that you're sort of helping people sort out what's actually important in all that noise is actually a part of the job. And so I think that that's kind of key. That way people don't feel like they have to stay on top of every single thing along the way.
- Speaker #1
Yeah, I agree. So what I experimented and I got... great feedback about that from my team members is the is having so at amazon we work a lot with docs so we have a ton of docs so uh so basically i've listed all the docs and and set priorities so like mandatory reading and giving a date and some that for your information and some that are important to know but yeah so and also having a tracker of whether or not people have read that. So each individual can check the box when they have read that. So I can see that we are all aware. And the feedback has been very positive because, oh, yeah, now I don't have to keep track of things. We have that, and that's the norm.
- Speaker #0
That's smart. I think what you've done is you've developed a norm around that, right, and a set of tools that people should expect to pay attention to. And I do think that one of the broader leadership challenges or managerial challenges that people face is. no one has good, if no one in your team has good habits around sharing information or requesting feedback, you know, if people aren't sitting there saying, Hey, this is important for the following reasons. I need feedback by next Tuesday. And here's the three people in particular that I want feedback from, you know, if instead of what you're doing is you're just throwing everything into, you know, a public Slack channel or a large email alias and saying, Hey, I'd love people's eyes on this. That's not very helpful. What's really helpful is give a sense of importance of it, give a timeframe under which you want the feedback or knowledge to be had and be really clear about why you're asking for feedback and from whom, right? If it's just, Hey, I'd love any, any general feedback on this versus no, Sally and Bob really need to read this because it might impact their project.
- Speaker #1
Yeah, that's true. The other thing that I think the mechanism that we're using is doc reads in meetings, which is very Amazonian as well. And at the beginning of the reading, we explain what type of feedback we're looking for. So depending on the maturity of the doc, if it is just a one pager about a new idea and we're looking for general feedback about that because it's very nascent. that helps to drive the discussion. But if we believe the doc is 70% ready, then it's a much larger conversation to have because stuff are in flux and maybe we took some, what we call one-way door or two-way door. So there's a level of complexity that adds up. So you don't need, you don't want to have... too many feedbacks as well. So being intentional about the reviews is important.
- Speaker #0
And the Amazon practices around that are ones that we used a lot at Slack. I actually used a number of them at Google too, around things like document reviews. The problem that I see in a lot of organizations, and I've certainly experienced this myself, is even if someone shares the content ahead of the meeting, you walk into it and you ask, and yeah, unless there's real enforcement from the top, which almost never exists, then no one's read the content before the meeting. And the worst of all possible worlds is, okay, we're here to have a debate or make a decision and we've got 45 minutes to do it, but I'm going to present to you for 35 minutes. now let's have a discussion. And that is just the worst experience. We've all been there. You get to the end of it and you're like, we're just starting to get into the actual meat of the conversation. Oops, we're out of time. So much better off. I mean, I'm a big fan of the written document over the presentation format because it forces an amount of like content to discipline. We'll come back to an issue with that one in a moment. but the second thing it does is it makes it much easier than to sit there and say things like, Hey, everybody, it's been the first five to 10 minutes reading the document mechanically, turn your camera off while you're reading, turn your camera back on when you're done. That way I can tell that you're ready. And as the moderator, you always have to call it at some point, you're seven meeting, you're seven minutes in, and there's only one person left out of 12 who hasn't turned their camera on, give them the one minute warning and then just get started. Right. So doing that can go a long way. The one caveat that I was going to give you is the written document can be a challenge for people for whom English is a second language. And so with international teams, which I know you have one, that can be a challenge at times, right? Because you're asking people to read verbose text in English. And so you have to be pretty disciplined in the writing style and what you're doing.
- Speaker #1
Agreed. And also, I think not only that, I'm talking about inclusivity, inclusiveness, never know. People with ADHD or on the spectrum of autism or with dyslexia, they have also different challenges to cope, to be able to understand. that amount of data of information and process it. So sharing the doc in advance is also something which is encouraged for other people. But we always need to have, as you said, we can't expect people to do it.
- Speaker #0
so having enough time for people to read is is important yeah and what you're really talking about is you're blending asynchronous and synchronous ways of working right you're giving people content ahead of time gives them the opportunity to think through it wrestle with it and undoes the extroverts advantage to be honest because the traditional you know let's have a debate meeting at work is, okay, let's assume it's a better run meeting. You've got 45 minutes and it's 15 minutes of presentation, then a half hour of debate. That format favors the extrovert, right? It favors the person who just wants to jump into it. It doesn't favor the person who wants to take a thoughtful approach and spend some time with it and turn it over in their head a little bit first before giving a response. And so I've always been a proponent of trying to find a way to blend those two practices. And this became a bigger deal during the pandemic too of How do you give people the time and opportunity to work on the content, which really is beneficial for all kinds of neurodivergent reasons, but also just basic personality differences? The other thing that it does is it prevents the groupthink filter that happens in a brainstorming session or a debate, which is if you ask people up front on something that you think is important to jot down their thoughts and then throw them all into a common document. when you start the meeting, you're going to get a wider range of ideas out of them than you would if you sat there and said, Hey, let's just, you know, throw it out. What's on the top of your head.
- Speaker #1
Yeah. Yeah. That's also the, I think the beauty of the dog reads where you can all comment on it. Yeah. And, and once you are done with all your comments, you can ship them. And now the. the dog owner has all the inputs and you have to figure it out and that's for sure but you can follow up on the different comments so that's quite powerful yeah it is it really is i think the the challenge though is it forces to be more vulnerable in the sense that it's not you as the owner which is criticized but it's it's your idea and and and and everyone is keen on trying to help improve the ideas or give some thoughts about why it's not going to work and that helps you to become better. But you need to be ready for that type of feedback.
- Speaker #0
Yeah, and it can be hard. And the biggest challenge in that, well, one of the big challenges in that is do you feel safe doing so, right? And so it comes down to psychological safety. But it also, all of that is really dependent on the leader. This is a leadership set of lessons that I learned kind of the hard way. I got taught early on in my career that I was to be seldom wrong, but never in doubt. Think about this from a perspective of being a professional management consultant. You know, you're in your 20s and you're being brought in to be a consultant for a major corporation. and you're dealing with 40 and 50 year olds who are deeply expert in their area. And you're all of a sudden expected to be, you know, highly capable and conversant. And honestly, what you learn is you learn to bullshit to some degree, you know, or certainly to sound like, you know, what you're doing. And I think the problem is a lot of leaders also get taught that, right? You're expected to have all the answers. And that's not only unrealistic, it's actually kind of a fatal flaw when it comes to building team engagement and building trust. Because you can, you know, you can undo a lot of it in that way. So I, I've had to learn how to like, let go of that. And I've also done a lot of counseling with leaders about like, it's okay. That doesn't mean that you don't paint the picture of, of the massive goals you've got for the organization. It doesn't mean that you lose your aspiration whatsoever. It just means that you're willing to say, Hey, look, we're going to climb this giant mountain. I don't fully know the path to get there. But we're going to get there together and you're going to, we're all going to figure it out together and you're going to invite them into that conversation. And the three most powerful words I think I learned as a leader was, I don't know. And they were hard to learn.
- Speaker #1
They are. Yeah. Yeah. It's always a struggle. But yes, indeed. I mean, having been also on the consulting path for several years in my early days. saying I don't know was even harder. Yeah. Yeah. Yeah. Because people were expecting from you answers.
- Speaker #0
Yeah. There's a woman named Rodney Evans, who's the CEO of a group called The Ready, who I'm a fan of. And she, a podcast that they run, had this quip, must have been last year or so, that said something to the effect of, we wouldn't have imposter syndrome if we quit freaking trying to fake it all the time. Right. Which I think there's some truth to that, right? Imposter syndrome is a real issue for a lot of people, but I think in part it's because we put ourselves and our bosses put us in situations where we're expected to have all the answers as opposed to it being safe to say, I don't know the answer, but you know, I'll go try to find out.
- Speaker #1
Yeah. Yeah. true so going back to you your future of work and some of the learnings there so we went on the rto path and yeah so there are a lot of companies that are forcing the rto i mean amazon is one of them yeah and and and there are some good reasons for that there's there's i mean I think finding the right balance is hard. And that's probably why companies are forcing RTO because they don't have all the answers figured out yet. But one benefit is that you get to work with your teams. And if you don't have the supporting mechanisms or the agreement, as you explained, it doesn't really work. So what are some of the... the best practices for making that happen, because eventually we need more flexibility, for sure.
- Speaker #0
Yeah, because I swim in this data pretty much every week. Overall, the forced march return to office through a mandate doesn't really work. There's a couple of reasons why. Broadly, economically, you can see it actually hasn't changed anything in the past 18 months. Average office occupancy in the United States is roughly half what it was pre-pandemic. And that number has not shifted for 18 months now. So for every headline out there about an organization that's pushing people back into the office. there actually are a number of other companies that are actually going the other direction. So the average actually is moving away from full-time office work, either into some form of structured hybrid program or some sort of fully flexible thing. As a matter of fact, I just did a piece today on new data that we had out of one of my partners on financial services firms, which everybody thinks Wall Street's full-time back in the office, and they're not. But putting that aside, the problem with the mandate is it's a top-down, one-size-fits-all type of message. Yeah. And the one-size-fits-all doesn't work because of distributed teams in the first place, right? So if you say to people, you need to be back in the office three or four days a week to be with your team, but their team isn't in the same office, they understandably are going to look at you funny and say, I think you're doing this for other reasons. I think you're actually doing it because you want to monitor my performance. in a way that is pretty lame. You're going to monitor it through whether or not I'm showing up and sitting in a seat. And that does one thing and one thing only, it destroys trust. And that's pretty negative. There are really good ways to make this stuff happen though. And it does start with, you do have to do it at a function or team level and figure out what the things are that people actually care about doing together. Number one of those is always socialization and relationship building. there's absolutely a minimum pattern that comes up, which is even if your team is geographically distributed broadly, you need to find a way to get them together with each other and with their cross-functional peers at least three or four times a year. Yeah. You know, if that's whether that's regional or, you know, pulling people together across a continent or, you know, a smaller company, global offsite, you got to do it. And there's plenty of evidence to back up the fact that those, you know, quarterly gatherings have an impact on engagement and belonging that persists for four to five months afterwards. And they're actually also, by the way, most important for new employees and younger employees. Beyond that though, it's like figure out what the pattern is for your team. So I'm going to come back to like the examples of, I know a lot of people that have inside sales teams where, because inside sales is a pretty... rough job. People get beat up by cold calling customers, especially with newer employees and their managers. They say, hey, look, we are three days a week in the office. It's Tuesday, Wednesday, and Thursday. And we're going to have activities that are appropriate for the jobs that you guys are doing. And you're going to get a chance and opportunity to listen to one another. I also know people that have taken those programs and said, that's how we're going to run it for new employees for the first couple of months. Then once they've proven out, we let go of that to some degree, right? We let them have a lot more flexibility in where and when they work because whether you are doing inside sales or you're an insurance claims agent, the day in, day out, after you've been doing it for two or three months is pretty similar. One of the challenges in all this though isn't the fact that they're together or apart, it's how do they support one another? So I've seen this in a lot of organizations. you can have a fantastic manager who's very helpful and very available to you. But more often than not, you've got a manager who is also carrying their own individual load, right? And they themselves are struggling to stay on top of the work. So their ability to coach somebody on a minute to minute basis is pretty limited. What people need is the technical equivalent of the tap on the shoulder for somebody to take a look at something. And that should not be the... you know, let me book a half hour meeting with you next week. It's, you know, you use a huddle in Slack to say, Hey, can I get five minutes of your time? I've also seen people use a variety of open room formats. Like I know of an organization that's tested out having zoom rooms open. So the people who are, for example, claims agents and insurance companies can sort of like they would in a cubicle farm, sort of little bit here in on somebody's conversation without being fully immersed in it. and it just gives them an opportunity to step in and out of those virtual rooms and say, hey, anybody ever hear of this problem before? So those types of activities can go a long way towards making that type of thing work. But back to your question, the thing that gets people together is very much the connection, the relationship building, very much that sort of mentorship and training type of opportunities. and then it really depends on the habits and patterns of your team, right? Because again, the finance team probably should be together at the end of the month to close the books because it's a very intense time. The sales team at the end of quarter, but the inside salespeople on a more regular basis, and those are the patterns that I've seen work over and over again in organizations. And the other thing that helps is if you do it that way, you generally find that people do it because they want to do it, right? Because they get it. The average person actually wants to be in the office about two days a week because they want to be there together with their team for socialization and belonging. And if you support them in doing it and make it easy for them to do it and have a manager who knows how to sort of do an anchor day, as an example, then it's not a fight. It's an easy thing. But if the execs are sitting there looking at it going, two days isn't enough. We need four. Pick another battle, man. Really, there's much more important things going on than that one.
- Speaker #1
yeah i agree i agree i think what i've been struggling or and what i've seen other people struggling is that to replicate some of the the impromptu discussions so you know you cross the office and oh you you met that guy you exchange you say oh i have this idea what you think about it and then then you iterate on it and i've not seen a good formula well I don't know a good formula to replicate that in a very distributed way unless you create those quarterly meetings where you can have a discussion but sometimes quarterly is not enough and it's the speed of the business is much quicker than that.
- Speaker #0
Yeah. And I think part of that is, think about the times when you do that, but we put a lot of mythology around water coolers. You got to think about like, was that because that was someone literally random that you'd never met before and you had this fantastic conversation that generated a brand new idea? Or was it because there's a series of people that, if you run into them once a month, you know you're going to have an interesting conversation because there's different ways of handling and tackling that. The water cooler thing is interesting because it turns out that it only actually works for people that live within a 20-meter radius on a floor. So the odds that you actually run in, you run into the same people over and over again. And by the way, they're the same people you run into digitally over and over again. And the chance meeting of two humans that generates a thing is pretty low. There's even academic evidence that what was once true, which is co-location and proximity. resulted in more new and novel ideas. changed right around 2010. And in fact, it actually inverted. And now distance is actually a slight benefit. And the reason for that is obviously like broadband communications, but it's also because you can connect people from more diverse disciplines. from broader parts of your organization together. So I do think you need to do both. Like, so for example, when I'm talking about gatherings, I really do promote for people to think through like, what two things, two or three different flavors of it. One is when you're doing the flying people together to do the big thing, it should be cross-functional in nature and should be larger parts of your organization. but the other is think about what are you doing to actually promote those connections on a local basis. So a lot of organizations are thinking about things like the monthly social hour for whoever happens to work in Austin or Atlanta or Boston or wherever else, because you don't have to be on the same team. You're part of the same organization and we want you to cross collaborate. And then the third one I'll give you is digital actually does play a really interesting role in this. I'll give you an example. There's a... A guy I know who told me the story of working in a large organization. He worked out of the New York office and prior to the pandemic, he's a sneakerhead, right? He collects Jordans. Okay. And he knew who his sneakerhead buddies were in New York and they would show off their stuff to each other. So like six months into the pandemic, they started up a channel called Sneakerheads for the five of them. But then they each invited five more people. And then within a week, there's 150 people. And within a month, there's 1,000 people in this organization. They're sneakerheads in offices all around the globe sharing what it is that they're wearing or there's a big release coming out or have you seen this thing? And that builds a little social connection, but it does another thing that's actually really, really cool, which is I may not know. I'm out of New York. I'm on the sales team. I'm looking for somebody in marketing who knows where we are on, you know, the next round of enablement sessions for the product I'm working on. I don't know anybody in marketing. Oh, wait. Yeah, I do. Because Sally who's in the sneaker heads channel, I think she's out of San Francisco. I'll just reach out to Sally and see if she knows what's going on. You made a weak tie through that. You just, you know, you've connected these things together in interesting ways. that all of a sudden span geographic boundaries that they didn't before. And so it's really that sort of blending of both that I think is going to continue to sort of shift some of our thinking and approaches to this that help people pick up.
- Speaker #1
Yeah. No, I love that. Great. I do belong to some of those groups, not on sneakers, but on cars. And that's cool. That's cool because sometimes you say, hey, what do you do actually? Yeah, exactly. And so that's really good. That's really good. It's the equivalent, I guess, as parents and you meet with other parents at the school and say, okay, what do you do? And then, oh, you…
- Speaker #0
Yeah, exactly. And eventually those networks, especially the longer you're in an organization, those networks build up, right? And what you find too is that inside of organizations, there are these people that are super connectors. They are the people that touch a lot of different things, right? Because they play that sort of spider web role inside of an organization. And that's where you got to think about how you leverage and think about those folks. I've run programs where we've intentionally involved a lot of those people early on in the thinking about like, hey, how do we approach flexibility in the workplace? Because. they're going to have more insight into the challenges and the opportunities. And honestly, they're going to also drive a lot of the engagement and get people doing things. So like enlisting those, those internal, you know, super connectors and change agents. And by the way, if you're a leader, you probably have one or two of those either in your team or adjacent to it. And you know who they are. Yeah. So don't hesitate to tap them on the shoulder and say, Hey, I feel like we're struggling with whatever we're struggling with. And what, you know, any thoughts?
- Speaker #1
Yeah, totally. I've been using that indeed. Very useful.
- Speaker #0
Yeah.
- Speaker #1
All right. Switching gears a bit. So when we met the first time, you said that, I mean, there was an interesting topic that I wanted to tackle with you. It's how do you use culture and team alignment to deliver results?
- Speaker #0
Yeah.
- Speaker #1
That's a big topic, but I feel specifically in a very distributed environment, I think culture is very important. Yeah. and the alignment as well.
- Speaker #0
Yeah, and part of it is really understanding what drives and builds culture in the first place, right? And the slogans on the wall aren't really what drives culture, it's the behaviors inside the organization and what gets prioritized, what gets resources, who gets rewarded, that type of thing. but I think like, think about like a couple of foundational elements that most people really want, which is you want, you want trust and you want focus on the customer and you want, you know, focus on delivering results. Those things actually all line up really nicely in some ways, but it means you got to figure out how you build trust in the first place. And how do you build trust in distributed teams? Right. Okay. That can be hard. And that's why I'll come back again to like being a firm believer in the sort of minimum quarterly gathering for people. because three days spent together where at least half of it is social in nature, at least half is meals together, volunteer activities, personality test exercises, you know, karaoke, pick something, you know, Lego building, like let's do, let's do some stuff. Those types of things help break down barriers in the first place. there are habits and practices you can exhibit as a leader. I've been a fan since my Google days of personal user manuals. Personal user manual is a description of what I'm like as a person and as a worker. I'm a morning person, not a night person. It's not necessarily your astrological sign, but it is your habits and practices. I consume written content honestly better, and I have more fun with it than I do video. and that's just my specific way. I've got, you know, at this point, two kids who are out of the house, so it's not as relevant, but at once upon a time, it was like, hey, by the way, you know, I've got the following commitments on Thursday afternoons that you should be aware of. Those types of things can help people, you know, sort of understand that, and the social aspects can play into your week-to-week too. Like, I think we think that all meetings now have to be hyper-efficient. and honestly, your staff meeting should be wickedly inefficient at times, right? Because it should be the sort of thing where you're just, I would always kick off staff meetings with a social icebreaker question. Like, what's the worst haircut you ever had? You know, where do you stand on pumpkin spice latte? But fun stuff that gets people talking, right? And I've had people say, but yeah, we then wander around for 10 or 15 minutes. I'm like, yeah, that's a great 10 to 15 minutes because you're getting to know one another and you're having some fun. but then the other side of that is trust means you deliver. It means you deliver results, right? It means you've got to have clarity of purpose for your team. Why does what we're doing matter? It means you got to have clarity about how we're going to measure results in this, in this team or in this organization. It's got to mean you are transparent and sharing how you're doing on that. It's got to mean that you're willing to talk about the things that aren't working as well as the things that are. And yeah, you celebrate the successes, but you also sit there and are real about like, hey, we let this customer down in the following way, or we missed this quarter's goal and here's why, and here's what we're going to do about it. But that's what really builds that sort of nice recursive circle of you build relationships, you build trust and relationships around intention. You build trust around small victories so that you can have bigger victories. You build trust around being focused on the results, not on the appearance. And that to me is the embodiment of culture, right? When it works and when it sings.
- Speaker #1
Yeah, true. It's so easy to tell about it, to talk about it, and somehow very difficult to implement in real life.
- Speaker #0
Oh, yeah. It is. It's really hard. I don't know if you and I talked about this, but I'll share it with you. In my early days in startup land, when I left consulting, I got my butt kicked. I was a pretty shitty manager and not the greatest partner either. I was arrogant because I had back to seldom wrong, never in doubt, that attitude. And I got pulled aside by Mariah DeLeon, who's my people partner, and told, you're kind of an asshole. and she was right, except it was more than kind of, but that I also saw it for myself, right? I saw that I was not getting anywhere in my relationship with, with a couple of people and, you know, it got me to step back and think about like, okay, how do I understand different, different people's perspectives, right? As a consultant, I'd hired a bunch of people. as a consultant. They all looked and operated and thought the same regardless of their race, gender, ethnicity, but they're all the same type. I was suddenly in a position where not only were gender, race, ethnicity, parenting very different, but so was your orientation around why you were there in the first place and how you thought. Salespeople are vastly different from engineers in some ways. That's a little typecasting, but you learn that not everybody's a type A consultant. And that took time to figure out and for me to learn and kind of grow into. But once I did, that's when you start figuring out, okay, if I can start building actual trust-based relationships with these people, then we're not worried over whether or not somebody's going to mess it up for you or not. You're worried about the business. You're worried about the customer. You're worried about the thing that's out there, not the thing that's inside the four walls of our organization. But that takes, man, it takes experience and learning. And it also can get really, in big companies, it can get really messy, unfortunately.
- Speaker #1
Yeah.
- Speaker #0
very true that's why I like startups
- Speaker #1
I think James told me that you were behind the implementation of the W framework at Slack for the prioritization of work and how the flow of information goes between leadership and the different teams so can we talk about that?
- Speaker #0
yeah so I've I've done this a few times in my career, even in my startup days. So going back to when I was doing that, we had a mechanism we called the blue sheet, because believe it or not, this was, oh my God, late 1990s. We would literally print out our top 10 list on a blue sheet of paper that people would pin up in a cubicle. But this was a monthly exercise just to rank what were the top 10 most important projects in the company. And the company was maybe a hundred people. to be able to say what was the deliverable, you know, right. Very, you know, a lot of ways the precursor to something that looks like an objective and key result type of program, but what's the objective. It's gotta be measurable. It's gotta be attainable, you know, smart goal type of thing. Who's the, who's the group of people responsible and who's the directly responsible individual for it. so that you would know and understand that if someone asked you to work on a project that happened to be number nine on the list, but you actually had an important deliverable for number three, you could say to them, I'm sorry, I'm working on number three right now. And I'll get to that later. And that process carried forward. We did a lot of the same things at Slack. When I first came in. We had a Monday operations meeting, which a lot of organizations and companies do. Ours consisted of, at the time when I joined, I think about 65 people out of the product design and engineering team, spending an hour and a half going through JIRA and saying whether their project was on track or not. this is a fairly bad way to use 65 people's time, right? But we've all been in those meetings and experienced this thing. That got re-engineered and redesigned in a couple of ways to be a lot crisper. You know, Slack implemented objectives and key results itself about a year later. We got a lot cleaner and clearer about what, you know, the priorities were in the organization. And not just me, but a number of other people tightened up that process considerably in terms of building out something that was a lot more like, let's take the status updating and do that asynchronously broadly. We're still going to have that Monday morning meeting because the important conversations are the resource contention ones that always happen, right? Like, hey, these two projects, yeah, I know they may be ranked one slightly above the other, but we have a real issue that's from a customer perspective where we need to pull. you know, Andy off of project A and Beth off of project B and swap them into this thing. And we're gonna have to wrestle it through. Right. So, but the process should be one that sits there and goes, okay, how do we pull out those critical decisions, right? Those roadblocks and things that need to be escalated. out of otherwise a fairly mundane status update process, and then have the hard conversations about them on the basis of prioritization. And then how do we make sure that we take that same information? Because by the way, a lot of those people, 65 people wanted to be in that room because they wanted to hear what was going on. How do we make sure there's all the transparent sharing of the decisions that got made back out to the teams? So the people aren't sitting there going like, but I have to be in the meeting because I'm not in the meeting. I'm not going to know what happened. So. A lot of this involves processes around what maybe seem like simple things, but which are really building as much transparency as you can into the decisions that you're making as an organization. And the other thing that really requires is some pretty hard leadership conversations about what are the most important things. you know, certainly worked in organizations where everything is important. Right. And you read the OKRs and you're like, you could put anything into this, every single project in the company, you could point to one of those things and say, this is tied in with that somehow. And if that's the case, you're not doing it right.
- Speaker #1
Yeah. So how do you filter out those ideas?
- Speaker #0
You gotta be like, this even goes back to my strategy consulting days. A big part of strategy is knowing what you're going to say no to. Okay. And part of it too is even if you can't say no, you can say not now. Right. And it's hard because it's always been hard for me as a leader to, I always want us doing more. Right. I always want us pushing further and going faster on stuff. And I'm a pain in the butt around that. But at the same time, you got to realize and recognize that at least you're going to get a lot more out of a team if you can have clearer, crisper. short-term goals where you then reassess and then pick up the next couple of things. And your next stuff list can sit over here off to the side while you actually accomplish the stuff you need to. But it's a hard conversation and you've got to wrestle it out as a leadership team because that's part of the job is, God forbid, make some decisions about what you're going to do and what you're not going to do.
- Speaker #1
Yep. I fully agree with that. I think those are a difficult discussion but i like what you said about having short goals and and the transparency i think short term helps people to get the sense of achievement because we all need that and then move to the next next next thing and i feel that one area of of growth for me is also taking the time to celebrate you you know, those achievements on a regular basis, you know, because we drive so much big things, but it takes time to progress. And so being able to turn them down into a smaller, smaller chunks and then say, okay. we achieved this. Let's enjoy that moment before we move to the next thing.
- Speaker #0
Yeah, no, that's a great point. And it is something that really is important that I've sometimes forgotten about also, which is how do you give kudos for, you know, the accomplishments that you've gotten already? And how do you make sure that people have the chance to every once in a while celebrate and also step back and look at, you know, how far they've come already? And yes, there's a lot for there to go.
- Speaker #1
Yeah. All right. There was another topic that I thought would be very important, you know, in the context of prioritization and so on. There's also sometimes when people don't fit anymore. So I think you are helping leaders to... I think quotes, counsel people out, as you said. So it would be interesting to discuss about that.
- Speaker #0
Yeah, there's a lot underneath that. It's hard. It's really challenging work. I've always found it's easier for me to counsel out someone whose how is the problem as opposed to their what, right? The toxic behavior inside of a team. Because you know it and you know when it's happening and you know you need to deal with it. the broader challenge is like ensuring that you're building this up along the way and that it's not, no one's being surprised. You should never have the case where the annual performance appraisal process is the thing where you deliver a bit of news that says, I don't think this is the right place for you anymore. Right. That should have been a conversation that was building up over the course of months, if not longer. But yeah. From a frontline manager perspective, there's a lot that we need to do to support them, even in things like how do you conduct a weekly one-on-one, right? A big part of managing people and helping them understand whether they're meeting or exceeding or way behind the goals for the position is. every week you're having the conversation, right? And it's, it's not like it's a formal review of, you know, them, but it is a conversation about how did it go last week? What got done? What didn't get done? What are this week's priorities? Let's make sure that we're aligned. And what do you need? What do you, what would help you be able to go faster? You know, what can I do to help out or can others do if that's the set of issues, if you're having that conversation every week or even every two weeks, then, and you're being reasonably disciplined about it as a manager. which means that you're willing to say, hey, look, this part's not working, right? And that's hard. Then you're not going to have the same surprises further down the stream. There are times when people, when the job eclipses them, they weren't the right fit. or when the environment around them changes, right? And that's less likely to happen at an individual contributor role. It's much more likely to happen with leaders, including myself, to be honest. Like there have been times when, give me an example, I was leading the developer platform team at Slack and got to a spot where my own level of interest in proper formulation of an API may not have been what it once was. I just looked excited about some of that stuff than I had been. The opportunity to do something different had presented itself. And we also had started talking with a couple other people about bolstering up the team and came to the conclusion, as did my boss, that, hey, it's time for me to do something different. And that can be a learning opportunity, right? So you got to recognize it in yourself too, that we all grow by taking on new and different challenges. And sometimes after, especially if you've been at the same thing for a few years, it may be time to switch up anyway, right?
- Speaker #1
Yeah.
- Speaker #0
The harder part is making sure that, you know, this happens in startups all the time, right? Which is the organization, the business is growing dramatically. Some people scale with that. Some people don't. And that may mean that they stay with your organization, but in a different role, or they stay in the organization, but with a higher level boss. But especially if you're working in startups, you kind of come into it understanding that that may happen to you.
- Speaker #1
Yeah.
- Speaker #0
And if you are the boss, and I've been in that position, you need to not wait too long to have that conversation. You should have it up front with anybody you're hiring in a lot of ways. And then you need to keep having that conversation every few months too, about like, hey. we're now hitting this next level of inflection point. I think, I think these, tell me about how you plan on, you know, rising to the new set of challenges and what you're going to need, you know, is it mentorship? Is it outside support? Is it, you know, you've never been a CFO before and you're a VP of finance. but let me get you some board members that you can talk to that can help counsel you on this. You do want to find ways to support people in doing that before you simply counsel them out.
- Speaker #1
Yeah, totally. I think your example is a great example of self-awareness, which is lacking for a lot of people, and it's not easy. So do you have any advice to become more self-aware?
- Speaker #0
look part of it is age may have helped me on this to some degree i do think it's the easier part early on in my career is if you're getting especially for me if you're getting bored in your job right it is time to then it is time to move on or if you feel if you're in a point where you're in continual contention with your boss right like you think that they're being continually unrealistic and the goals they're setting for you it probably is time for you to move on. And your boss may be right. Your boss may be wrong, but it doesn't really matter to some extent because that is your boss. And, and so, you know, when you're getting that signal on a continuing basis, it's probably time to figure out what you're going to do next. If you've, you know, attempted, you know, rise to the occasion already and this is not working. So a little bit of this is like, there's only so long you should try to beat your head against a wall. Another part is just like talk with people. My own experience has been, you know, if I look back, I made a number of shifts and changes that are sort of the equivalent to the Sheryl Sandberg. Your career is a jungle gym, right? Where you sometimes go down to go up. I left as CEO of a startup that had like 300 employees and took a job at Google where I had two employees. I left a job at Google a few years later where I had roughly speaking 500 employees to take a job at Slack where I had roughly 50. I switched roles within Slack from something that had a couple hundred people to something that had three of us. Like, don't be afraid to take something that you might feel like something that you have done already or couldn't have done a decade ago. If it gives you the opportunity to do it in a new setting with people that you like working with, with a new opportunity, that's something that's going to stretch you in new ways. because if there is a formula for my own success, it's been focusing on continual learning and sort of pushing myself a little bit.
- Speaker #1
Yeah, love that. And it's not about building empires.
- Speaker #0
No. No, I've never been a fan of that, to be honest. I can see there's some appeal to it. And certainly big corporations essentially drive off of that, right? Which is you get promoted on the basis of too often the size of your team or the size of your budget as opposed to what you deliver, which is a little absurd when you think about it from a business value perspective. But therefore, that's what creates a lot of the issues with big companies also, which is. it becomes much more about hierarchy and resources managed than it does about, you know, what's the outcome of that thing that you're leading.
- Speaker #1
Totally. Totally. All right. I think we are hitting the end of the episode and your free time. So thanks a lot for, for everything that you shared so far. Did you have, before we go into the closing questions, any, any other thoughts that you would like to share?
- Speaker #0
No, I think, you know, find, I guess the one that I would say is. find your own mentors, your own coaches out there. I actually am a big fan of coaching programs like leadership coaching programs. My wife happens to be an executive coach, but I also think finding even peers that can be sounding boards for you and preferably some peers that are outside of your organization. And then do the same in reverse for other people, because one of the things that I've found, especially as I step more outside of the companies that I was in is. even no matter how much you've been beat up internally within every organization and everybody gets beat up at some point in time, you know, a lot more than you think, you know, that's actually valuable to other people. So it's a little bit of a give to get right. Like act as a advisor or signing board for someone else to get the same thing back in return. And that act of like listening to what they're saying and what they're wrestling with and reflecting on it with them is really valuable.
- Speaker #1
All right. Sounds like. the paid for what society so yeah yeah that's yeah exactly i guess it is all right so um let's go with our exciting closing questions so how do you keep learning and growing as a leader you said continuous learning so how
- Speaker #0
how does it work it's a big part of that is even what i described as my as my kind of career journey which is being willing to step off of the track that you're on to put yourself into a new situation right so an adjacent, you know, company slash market slash position is a, is a great way to do it. And through that sort of learning through experience and school of hard knocks. The other is listening to other people, like sort of describe that sort of peer level thing, but also your own team, your, your peers inside the organization, like really listening to them, asking them for feedback and insights, describing what you're wrestling with. even with your own team in terms of, Hey, you know, I've gotten feedback that I need to work on, you know, my communication style. And so here's what I'm going to try to do, but I would appreciate, you know, feedback and insights from you on it. And then, you know, if you, if you're open to it and you actually show that you're doing something with it, we'll give you, we'll give you help.
- Speaker #1
Love that.
- Speaker #0
so what are the two or three pieces of content that you recommend the most that one's impossible man i we talked earlier about i said earlier that i'm a voracious consumer of information but i read a lot listen to a lot so tons of podcasts i'm a carouswisher fan tons of news type of stuff but two my favorites that are a little more smaller audience one is a thing called search engine by a guy named PJ Vogt, V-O-G-T. I think he's a former New York Times. He does, I think it's like about a weekly drop. It is in depth on a topic. The topic may be, are the monkeys in the zoo sad? Or the topic may be, what's the future of the media industry? But it's fantastic. And then the other one is a thing called At Work, which is, I mentioned Rodney Evans earlier at the ready. She's the CEO. She and Sam Sperlin do a... a semi-regular podcast about work and work habits that falls very in line with my own like question of conventional wisdom thinking. So it's just a good one to listen to. Books, classics, or things like Stanley McChrystal's Team of Teams, it holds up really well. And a recent favorite from sort of a work and creative perspective has to be Rick Rubin's The Creative Act. Okay. Role of meditation and thoughtfulness in... in creative work. And by the way, it does a great job of helping you understand that all of us do creative work. All of us have, you know, creative problem solving things. It's not just people who make records.
- Speaker #1
Okay. Perfect. So what's your favorite interview question you, you, you ask candidates?
- Speaker #0
You know, I'm not sure I've got a favorite question. I was wrestling with this one in my head a little bit. I do tend to get into what are your superpowers and what's your kryptonite, right? what are the things that you just, you know, dramatically excel at and are great at? And what's the thing that makes you crazy at work? Not the thing that you're bad at. I don't want to hear the thing you're bad at. I want to know the thing that makes you nuts, that just gets under your skin and annoys you. And the other thing is I will, I will almost always try to do something that gets us interacting. Like let's build something together. Let's do something together. Let's solve a, you've been in this position before. Let's try, let me give you a hypothetical. And how would you and I, how, you know, how would you and I solve it together?
- Speaker #1
Nice. Yeah. Okay. Love that. How can the audience find you and be useful to you?
- Speaker #0
Yeah. So you can find me on LinkedIn pretty easily. I'm Brian Elliott. I post there on a almost far too regular basis. I probably do four to six posts a week of research or case studies that I find interesting around the future of work in particular, largely around flexibility and generative AI. but largely rooted back in human behavior and what, you know, what drives, what builds a better world of work for people, for humans. So that's where you'll find me. And that's the stuff I'll do. And I would love to have people share with me what they're learning and what they're seeing and what they find either insightful or problematic.
- Speaker #1
Oh, perfect. Yeah. I will, I will try to follow what you say about gen AI, because that's the big topic at the moment. Yeah. I'm deep into it. So yeah. So, so.
- Speaker #0
yeah yeah all right and last question what other leaders should i interview next you might reach out and i can connect you with my old partner at future forum helen cup helen is fantastic as a as a leader as as a human she now has a new thing that she's building called women defining ai they're aiming to close the gender gap in adoption of generative ai tools between men and women she's also building out programs that help people with a sort of from a hands-on learning perspective learn how to use these tools in ways that aren't they don't feel quite as imposing as your boss says you need to learn it right okay yeah she's got a she got another venture called almost technical that's that's that's really good so
- Speaker #1
helen's fantastic and then it'd be a great place to start perfect yeah thank you
- Speaker #0
I'll give you one more. There's a ton of people I've been thinking about recently, but another one that came up even yesterday, again, in a conversation with CMO of a company, a woman named Erin Grau, G-R-A-U. She's the co-founder of Charter out of New York. She and Kevin Delaney started up a media organization focused on the future of work. And Erin is just an extraordinarily thoughtful leader and human being.
- Speaker #1
Perfect. Thank you. Thank you so much. Very interesting. So thanks for spending this hour with me and sharing your thoughts. I learned a lot and I need to dive deeper into a few things now. So very, very useful. And yeah, thank you for your time.
- Speaker #0
Well, Roman, thank you. It's been a pleasure. Really enjoyed it.
- Speaker #1
Cheers.
- Speaker #0
Thanks.
- Speaker #1
You stayed until the end. Thank you for listening to this episode of the Paid Forward Society. If you enjoyed it, please subscribe and share it with at least two people who would benefit from this discussion. Your support helps me reach more people and make a greater impact. You can also help me get discovered by leaving a five-star rating and a review on your favorite podcast platform. I appreciate your support and look forward to continuing this journey with you. Bye.
