• May 29, 2020 | Most Popular

    Ep. 1 - Remote Teams

    Episode Description

    On this episode, an Air Force General and the CEO of a fully distributed company discuss Remote Teams. Listen to Joel Gascoigne, CEO of Buffer, and Brigadier General, David Shoemaker (who is also Chief of Staff for the Pacific region), talk about their best practices for building remote culture and making people feel like part of the mission.


    • Joel Gascoigne, co-founder and CEO of Buffer
    • David Shoemaker, Brigadier General and Chief of Staff of Pacific Air Forces

    Episode Transcript

    Disclaimer: David’s views are his own and do not represent the United States government.

    Katarina: [00:00:00] I’m Katarina Jones, and this is OtherWise Insights: lessons in leadership and entrepreneurship from the intersections of life.

    Today’s episode talks about remote teams. Remote work was already on the rise in popularity, so much so that people called it the “future of work.” Now, with coronavirus spreading, many companies are trying to figure out how to manage their teams remotely for the first time, and while working remotely can offer a ton of benefits, like no commute time and flexible work hours, many companies still have questions and concerns about transitioning to an entirely remote approach. Which is why we’ve brought in a couple of experts with different perspectives to talk about what they have learned along the way. On today’s episode, we have Joel Gascoigne.

    Joel: [00:00:54] I’m Joel Gascoigne. I’m originally from the UK, living in Boulder, Colorado. I’m the co-founder and CEO of a company called Buffer, and we are about 90 people right now. We’re a fully remote company and we help small businesses with social media management.

    Katarina: [00:01:11] And an Air Force general.

    David: [00:01:13] Yeah. I’m a David Shoemaker. I’m a Brigadier general in United States air force currently working at Pacific Air Forces as the Chief of Staff.

    Katarina: [00:01:20] For context, as Chief of Staff, David is responsible for creating and communicating plans to make sure the Air Force in the entire Pacific region is operating effectively. So that covers about 46,000 active air men and women. In thinking about whose perspectives to compare and contrast for this episode, the military came to mind as an organization that has been working on distributed teams for a long time.

    They’ve had to figure out how to communicate and operate effectively across large distances and on a massive scale. And Buffer came to mind as a company that’s a hundred percent remote. They’re known for their transparent culture and for the content that they create to help other people understand best practices for remote work. So let’s see what they had to say.

    How can you tell if people are really doing what they’re supposed to?

    Joel: [00:02:06] The very fundamental thing is that I think there’s a shift that has to happen that some people have already made in their minds, even before they’re maybe thinking about remote work.

     It’s really, you’ve got to be focused on results not on time people are sitting in the chair. So that’s, I think one of the things that we’ve really focused on over time is being clear with each other about what are we trying to achieve as a team and what is each person individually doing as part of that, and what are the results that we’re striving for and the pace of progress and things.

    And so those are the things that will be checking in with each of them, talking about, and that’s the way we’ll approach accountability and not at all based on the time you’re putting in. I think once you have that, everything becomes easier then because you can understand whether people are being productive or not.

    And then that can be a prompt for a conversation if  things are moving more slowly.  The other aspect is in the way that we hire and the values that we have. And trying to find that alignment between, you know, personal values and the company values. And I think finding people that are self directed and very motivated is also key for us.

    I think we have found over time that the amount of structure people,  maybe are used to, it can be at first, it can be interesting, even between, you know, much larger tech companies that have built up a lot more structure versus I know smaller companies, may have a lot less structure.

    Just to, you know, how much guidance they need throughout the day. Because we can strive to provide a lot of touch points and guidance, but at the end of the day, when you’re working remotely, you do kind of have to be alone getting through problems, pushing through things or, being self motivated to like reach out to someone when you, if you do get stuck. So I think that’s key as well.

    David: [00:03:58] Yeah. Obviously Joel, our problem set is very different, but a lot of what you said is true and that’s we’re results-oriented. And if we’re getting the results, then again, trust goes both ways. I have to trust that the hours are being put in to get those results.

     The results will be the first indicator that we need to have a chat about whether or not the right level of motivation and possibly the right amount of time is going into a problem set.

    Katarina: [00:04:23] How can you create a strong overall organizational culture and allow for local differences?

    Joel: [00:04:29] Yeah, absolutely. I think we’re an interesting case because we’re 90 people and about, I’d say about 60% in the U.S., but we’re really spread all across the world. We have someone in Sri Lanka, a couple of people in Singapore, we’ve had people in South Africa before and, all across Europe and South America and things.

     It is, you know, one person here, one person there. We don’t have maybe a hub that forms, as least not yet. There are a few remote companies that are at the kind of thousand person levels that probably start to have that maybe a group of people can gather in a co-working space in a different city, have to have enough people. We’re not really at that point yet. Like the only places we could maybe consider having co-working spaces for groups of people would be somewhere like London or New York or where we have maybe a handful of people. So, that means for us that we have to be pretty mindful of different cultures.

    I think we’ve given a lot of thought to have we ended up creating a set of values that actually doesn’t maybe align with different cultures. Are we like having a bias within those things where we’re making it harder for those people to work effectively and work in a way that’s natural to them as well?

    We’ve tried to give a lot of thought to those things and be open to adjusting things. I think one of the other things we do is really try and celebrate the different cultures. That’s one of the really neat things for us, it’s this opportunity for everyone to learn from each other, from totally different cultures.

     We do an annual company retreat once a year. It’s in a different place every year. We’ve done 10, 12, something around that number of those so far.  It’s always in a new place as well, and we’ve kind of put it to a vote in the team. And so we’re always as a team visiting for most people what’s a new place. Learning about that culture, and then also coming together and learning about each other’s cultures. And that’s a very special time. So then we’re just kind of breaking down those barriers.

     I think it is about maybe the values and culture we’ve put in place in the beginning as well. We’re trying to attract people that are very curious about that, very open to those different cultures as well. So, yeah, that’s, a key aspect for us.

    David: [00:06:38] Yeah. So, while while  we are again, all over the world, I don’t have the challenge that you have though of trying to pull social and  business cultures from all over the world together because,

    I’m still employing and commanding Americans, regardless of where they are. So, that’s really interesting to me. So obviously, one of my biggest things is I have, you know, commanded different places, is I don’t want to stop into somewhere and be little America. You know, I want to be sensitive to local culture, and we do have local nationals that work on our bases. So we do have to be really, really open to that. But as an Air Force, as a military structure you, it all starts, the Air Force level with our core values of integrity, service before self and excellence.  Those three things are the overarching values that then all of our cultures are built off of.

    And I would say in my piece of the military, and I’m in a very narrow wedge as a combat operator in the Air Force, that in my piece of the military that culture is built on a past success and heritage and, and all of that and nest together. You know, the Air Force identifies itself back to really World War One, although we weren’t a separate service until 1947. But when we talk about our culture, we talk about airmen making things happen and, and having, innovation in our DNA, and being fast and flexible and being able to move to the sound of the guns. When I talk about the Pacific Air Forces, we think a lot obviously about World War II and Korea and Vietnam and those places that the Pacific air force has made a difference.

    When I go down to one of my spokes, one of my outbases, remote bases, like where I commanded, before I came here, we talked about what that organization did.  An example of that culture I was the commander of the eighth fighter wing, which is known as the Wolf pack.

    And it has been since 1967. January 2nd of 1967 when Colonel Robin Olds got up in front of the crowd and said, “let’s go get them wolf pack.” And that day, he became the Wolf and the  wing became the Wolfpack.

    And so I was, I am the, I was the 57th Wolf. We keep numbers on who has been the Wolf, and at other bases, the youngest airmen of course, salute and call the commander Colonel and Sir. At the Wolf pack, you immediately tell the youngest airman that comes in the door, “I’m the Wolf. You call me ‘the Wolf.'” That’s a bigger sign of respect and then calling me, you know, Sir, or Colonel. That culture is so, it’s so set when people show up there, and the history and heritage of the wing. And then no doubt the single minded focus, when you see Patriot missiles pointed north on your base, you have a single minded focus. Everybody’s looking in the same direction, and that helps too. But it all starts at the very top. And all of those, all of those cultures of each organization, you go down the hierarchy have to obviously nest within that. So, the Wolf pack is nothing if it’s not integrity, service before self and excellence in all we do, because those are the core values of our organization.

    Joel: [00:09:33] Wow. That was really amazing to listen to. I think what really stood out as well in that is the power of story and  shared history and things to sustain and drive culture and maintain culture over decades. Which is I think, really interesting. And it was just interesting to hear that because I think we do have a few, stories. We’re coming up to 10 years in business. So it’s just, it’s just interesting to hear like such a different scale. We’re at a much smaller scale and much earlier. But those things are also starting. There’s definitely parallels there, the different stories. You know, even coming into this conversation, coming into us being like, oh, you know, a level of imposter syndrome.

    Cause I’m thinking, wow. Like we’re just helping people send out tweets and Instagram posts, and it’s about defending country and things. But I think it was still those parallels, right, where we’ve had a few kind of incidents or stories or events that have happened. We were hacked, pretty early on.

    So we had an attack on our service, and we were only, you know, I think 12 people or something around that number at the time and it was very much this, okay, we’ve all go to knuckle down together. People were up all through the night to figure it out.  We weren’t sure what the source of the attack was and it was essentially just sending out spam content for every single user we had.

    And we had to kind of stop it and figure it out. Since then, that’s been a story that’s passed along, and we’ve actually kind of formally like, I do something called Buffer 101 for every new team member that joins and  that’s one of the stories I share, amongst many other stories of things that have shaped us over time.

    Stories that relate to, and are examples of our values.  And that’s really, really powerful. One of the things I’ve always thought about with Buffer 101, is that you can come into a team as a new team member and you come in almost saying the language you use can be, you know, different than once you’ve been in the team for a few years. Where you come in and say, oh, “they,” or you know, “I work for Buffer,” or instead of like, “I work with, I am part of Buffer, I am them.”  That’s one of the things I’ve thought about a lot with Buffer 101. One of my key goals for that is to help people come in, get a lot of the context, all these stories and things.

    And then transparency is a key component of that for us, where we, explicitly say, this is all, you can share everything, you can go to a conference, you can hang out with industry peers and share this all information to share as well. So I think that helps that person to feel I’ve been here one day, but I’m part of it.

    And they can almost feel like they were a part of some of these stories as well, which I think when you were sharing about the Wolf. And once that story is told you can feel like you almost part of that and you’re definitely part of it and going forward.

    Katarina: [00:12:19] I love that. The values are also reinforced by the stories, right? And recognizing that the company has a way of operating and then these stories really show that this is not aspirational, this is real, this is really how we operate. And then that mission really resonated with me too, David, that you were saying, it’s really clear what the mission is and being able to have the values to back up, like, we’re here for a purpose and this is how we’re gonna achieve that purpose and here are the stories to prove it. It’s really interesting to hear that, how that all works together.

    David: [00:12:50] One of the things that I’ve worked on for a while as a leader, and a lot of us do that I think in the military, is people need to feel like they’re a part of something bigger than themselves. And they need to know how what they do matters to the mission.

    Like Joel was just talking about when he does Buffer 101 bringing somebody in and you know, saying “coding this or doing that actually makes a difference, and here’s how.” For me it was how do I tell the guy that’s running my wastewater treatment plant on base what he does matters for the mission taking bombs north. Being able to teach those guys within one sentence, to be able to tell how they tie to that bigger mission, I think is really important. And Joel, I gotta tell you, I knew I was going to learn a lot today. I’ve already had one big aha moment and that is, you talk about your Buffer 101, we do a similar thing.

    But as I was listening to you talk, I think we focus too much on the processes of staff work and we need to probably take a step back and start more with the culture and heritage of PACAF before we get into processes. That was a great, great pointer.

    Joel: [00:13:50] That’s really neat to hear. It’s also probably one of the ways I lean as a leader and I’ve realized over time I need to make sure I have really strong leaders around process and operationalizing things. But yeah, for me, Buffer 101 has almost been just purely focused on, it’s  kind of story time and we all get on Zoom and, bring a coffee or drink and just hang out and I’m gonna share the whole story of Buffer and there’s been a lot of ups and downs and things. It also helps people understand the beginnings as well, which is really powerful.  Now that we’re 90 people and we’re profitable, it’s like you can lose some of those values around kind of being scrappy and taking risk and what went into some of those early days. So that’s also another way we can maintain that. But yeah, I almost feel like we should probably have more processes and things within it as well. So it’s probably, we each feel like we can go the other way there.

     Katarina: [00:14:44] Let’s talk about the role of transparency in remote teams.

    For me, transparency is really a way to build trust and as well as make sure people have what they need to operate effectively. Maybe Joel, you can talk a little bit about what you do in terms of transparency, because I know Buffer has an incredibly transparent culture. And then David, I’d love to hear from your perspective, like how does that compare or contrast to what you do.

    Joel: [00:15:07] So we set down and transparency as a core value very early on, when we were I think just about 10 people. And we phrased it as “default to transparency,” kind of have this belief that, the more we can make transparency the default and it should be the exception if something’s not transparent within the team, then we felt like that will be extremely powerful. And it really did come from that building trust aspect. But then, you know, starting at 10 people it’s quite easy to do. So it’s also been a real interesting evolution over time. I’d say in the early days it was very much just sharing everything, but trying to push boundaries, sharing all of our numbers within the team, but we even shared a lot of things externally as well. Kind of, I guess, unusual for a private company, we share salary. Salary information is completely public, so anyone can Google and find all the salaries of the people in the company, as well as our formula of how we approach that.

    And so a lot of that is definitely around building trust as well.  And also eliminating bias. I feel like for us, being transparent holds us to a higher standard as well, because we’ve got to have  clearly set down approaches to things if we’re going to be sharing them.

     And then over time, as we’ve grown, would realize it starts to break in places. So whereas in the early days, transparency was almost just achieved through everything being shared, over time, we hit certain inflection points, 30, 40, 50 people, and we realized this is kind of a fire hose of information now, that people can’t actually handle and it’s starting to actual to really negatively impact productivity. So then you start to think, okay, what information do we want to still try and maintain transparency around? Does it actually hinder some people to have too much information? Does it make people want to be involved in decisions where they don’t necessarily need to be, and you get too many people involved everyone kind of wants to have a say now because they’ve got that information? And we’ve really tried to maintain that transparency but it’s evolving.

    One of the ways we think about it is instead of push where it’s pushed to you, it’s like pull where you can find anything you need.

     We’re using Dropbox, Paper, or in all the different tools we use, we’ll try and make sure that the information is organized. But early on we used email a lot, and it was really like everyone would receive every email, no matter what team they’re on. And it would be kind of tagged so they could just archive it, but it would still be coming in their inbox.

    And over time we’ve shifted to, now we have forms of communication where it’s fully transparent in terms of anyone can dip in there and go and have a look and see what’s going on in this team. But it’s not like pushed to you, it’s not this fire hose that you have to be triaging and archiving and things. So, that’s the way we’re evolving it over time.

    I’m just fascinated by being more at the scale of tens of thousands of people instead. And, you know, you have to really be a lot more reflective and think okay, well what is this flow of information and things? 

    David: [00:18:12] Yeah. So Joel, first of all, I would offer you a job because you sound just exactly like a group of Generals sitting around the table.

    These are the exact things, even if it’s a larger scale in numbers, it’s the exact same issues and, but they’re very transparent. You can Google what I make too, and I think you will, you’ll be happy staying where you are. But with that, there are obvious red lines that you know and transparency when it comes to a classification in security that we can’t cross. But that’s not an excuse to say we can’t be a transparent organization, particularly transparency in decision-making and the discussion that you just had are the exact things that we talk about, how much is too much information and do we really want the the guy with two years experience that needs to be concentrating on turning wrenches, concerned with higher level policy making back in DC.

    So with that, we’ve actually come up with a solution a lot, like what you talked about. Under my current  commander of Pacific air forces, we’ve come up with a solution where we hang information, and depending on the classification, we have different systems at different classifications.

    So if you have that clearance, you have that system, you can go out and you know where to find the information. So it’s all there. We’re not pushing it. You can think through what you think you need as somebody down the chain. So there is still, you know, again, how much is too much?

    Those are the discussions we have all the time. And if you ask 10 different officers, you would get 11 different answers on, on where the line is on getting that information now. When we can, you know, we kind of operate in two modes. The line is fuzzy that we operate in two modes and one is just “steady state operations,” what we do day to day. And that’s more like a corporation, like a large corporation. But we have to be able to flip the switch and do a contingency mode or a wartime where things are a little bit different. So where we can really can be more like a corporation, the more we’re transparent in those times, the more when we have to flip the switch and I don’t have time to tell you why I made the decision I made, you just need to do it. We build that trust in the times that we can through transparency and then when it’s time critical, we can’t have you asking why, we just need you to do it, that trust is there. 

    That’s, that’s kind of how we detected that. It was interesting to hear you as you talk to you that we’ve had those exact same discussions, I would say in the last few months around the table.

    Joel: [00:20:28] Wow. That’s incredible. One thing I’d be curious to maybe touch on here as well, in terms of a different way of building trust. I’m curious if it is necessarily different in military, but I think one of the things we’ve also been leaning into a lot in the last few years is the  idea of vulnerability and like bringing your whole self to work.  Transparency has been incredible way to build trust.

    I think another way is managers working with their team members and trying to build up that ability to be vulnerable, both ways, in a way. You know, if the manager is actually being vulnerable about something, it builds that trust as well. You know, if someone’s thinking about leaving, or if someone has something going on in their personal life that really is challenging and will affect their work, like these are things that we’ve tried to break through and know about earlier so it feels like it’s better for both sides, rather than being like, oh, I can’t go there and talk about that. Or if I’m starting to think about leaving, you know, then they just give us that two weeks notice it’s much, less useful for us than if they are able to share that two months in advance or share when they’re starting to look for other opportunities. Then I think about it as like, can we even help them with, you know, finding different opportunities, a better fit for them or things. So, that’s an area we’ve thought a lot about. Yeah, so vulnerability. I’m kind of curious if that is something that happens or works in military or not?

    David: [00:21:55] It is, and in fact, our catch word of the day is resiliency. You’ll hear that when you’re hearing about the military services, and it really started as an effort to combat suicides, or suicidal ideation that really reaches into all of the things you just discussed. And personally as a leader, you know, I’ve always felt that each independent case, it isn’t about that independent case.  If you have an employee that’s looking for other opportunities, once they’ve made that decision, they’ve made that decision. You get to the point where there’s nothing to say that this is going to keep them in that organization.

    How do you treat it at that point? That is crucial for the rest of the organization. So if you make that person dead to you, then the rest of the organization hears that loud and clear. Versus if you say, how can I help you and I can I help you get a job with the airlines? Can I harvest some of your experience by helping you get into the reserve while you go to the airlines? What can I do to help you out?

    And that’s why I’m clear to those guys that are on the fence, those people that aren’t too sure if they’re going to stay or go, when they see how you treat that person who’s already made your decision. So absolutely.

    We talk about all the time, retention is a big deal for us, and resiliency is a big deal for us.

    Joel: [00:23:03] Yeah, I was just going to mention that. I don’t know if it’s necessarily something else, but you kind of earn that trust over time, right? You build that up through sharing the mission, the values, and operating based on those and, all kind of being aligned as a team. In the times where we can be more transparent in the way we work, we can then earn that trust and build that up so that when we need to, we can just make things happen and not wait. Luckily for us that happens less often. Hopefully it will allow people to ask a lot of questions. But yeah, we’re still need to move at a certain pace with things and make things happen. So that really resonated.

    David: [00:23:43] Taking the idea of trust and putting it against our problem set, with our remote locations. With all of our wings and number of Air Forces that are out there across the Pacific, I think the number one thing for us looking at a sub-organization is acknowledging the fact that – this is a way to build trust – acknowledging the fact that we don’t have the information or understand the situation on the ground like they do. And it’s made even more clear having a headquarters in Hawaii. If I swoop in from Hawaii and tell somebody in Korea how to do their job, that’s met with the resistance and the trust goes right out the window.  If I act like I understand the situation where they are like they do.

    A way to combat that beyond allowing, the transparency in decision-making and maybe even some help in the decision making, is just actual presence. The army has a saying that  virtual presence is actual absence.

    So if I’m going to help build that trust, if I’m going to, you know, walk in and give somebody an order on a base that’s 4,000 miles away, they better see me at that base 4,000 miles away at some point, asking the right questions, and then, you know, get my hands dirty with them. Again, I know it’s different than your remote workers, but, something that we looked at for trust building.

    Joel: [00:24:57] It certainly resonates. Within remote work in tech there’s a big debate and discussion around fully asynchronous working versus being synchronous.

    There are some remote companies out there that it’s all written communications, no video calls.  It can be even fully asynchronous.

    It’s not even a synchronous conversation in a chat or anything.  It can just be someone’s writing their progress update on something and then someone else could write at any other time later. It doesn’t matter that it’s has to be one after the other. And then all the way to the other end, which is, actually meeting up in person and for us we’ve been trying to constantly figure out what that what’s that balance.

    Obviously the more we go to async, the more freedom people get and it can work and kind of flow around their lives, which is really powerful and really interesting. But there are certain things that you definitely lose. I mean, I was just mentioning that I had two people in the leadership team in Boulder where I live for the last few days, and so that’s, unusual for a fully remote company. But the amount we can get done in a few days and the amount of trust we can also build, it’s about also sharing personal stories and serendipitous moments that much harder to recreate in a fully remote kind of video call environment.

    And that’s something that we’ve really tried over time to be very thoughtful about as well. I think at the end of the day, it’s hard to beat being in person for some of those things. I think if you’re in person all the time, then there’s other things that can suffer, you know, I think it can actually be, have a negative impact on productivity or, and things you can’t get into your flow state and get work done.

    But for us, it’s really, we try and think about, okay, what’s that balance?  We’ve even tried things like having remote, casual chats so we’ll just get on a zoom call and and chat in small groups and and say, what’s going on in life? Like, what are you up to right now?

     Those are the things that took us a while to even think that we were missing or that we needed to add in. Because those are things that when you’re in person in an office, they happen naturally. You get lunch together, you chat about those things. It’s a combination of trying to recreate and have some of that remotely versus acknowledging the power of being in-person and having that as being absolutely essential.

    So we have a whole company annual gathering for one week per year.  And it is really important that people attend that. And then we also have on-sites as we call them, where people get together in the individual teams, but in the same location and meet face to face as well. So I think it’s that combination of all those different things that they can make it all work.

    Katarina: [00:27:37] So there you have it from the experts. A few key takeaways for me were: Build trust in the good times so that it’s there when things are most critical. In order not to overwhelm people with too much information, but still maintain transparency, focus on a system that allows people to find the information they want rather than sending everything to everyone.

    A few ways to build trust on a remote team include: transparency, valuing the expertise of the people on the front lines, dedicating time to get to know your team members the same way you would if you could grab lunch or coffee together, vulnerability, and the occasional in-person meetup to strengthen virtual bonds.

    And finally building remote culture. You can do things like have a clear mission and values to live by shared history and storytelling and explain to every team member how what they do matters to the bigger picture. A huge thank you to Joel and to David for taking the time to share their wise insights with others.

    If you liked this episode, please subscribe to get our upcoming conversations. I’m Katarina Jones and this has been OtherWise Insights.


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