Upwork’s Zoe Harte and Han Yuan on Managing People and Products in a Distributed Company

Back in June, we had the pleasure of speaking with Stefan Kosriel, the CEO of Upwork, the world's largest freelance marketplace. Stefan laid out a compelling case for the distributed model as a way for talent-starved companies in expensive and in crowded cities to do business with workers who live in places with comparatively sluggish economies. But Upwork's not just thinking about this in theoretical terms. They practice what they preach with a distributed workforce of their very own. In this episode, we'll talk to two Upwork employees from two different practice areas who give us glimpses of how their company does distributed. First up is Zoe Hart, Upwork's Head of Human Resources and Talent Innovation. Upwork's legal, finance, and even HR departments are a blended mix of full-time and of freelance employees scattered across dozens of countries and cultures. Zoe helped to grow the company's workforce by 75% over the last 6 years, giving her a world-class perspective on how to expand and maintain fluid, flexible teams. After a great conversation with Zoe, I speak with Han Yuan, Upwork's Senior VP of Engineering. Han gives us an inside look on how his team's diversity of culture and thought becomes a powerful asset. He says diversity fosters curiosity and allows the company to tap into a wide array of perspectives and experiences. Alrighty, let's get started with Zoe Hart.

My name is Zoe Hart. I look after human resources and talent innovation here at Upwork. I've been here 6 years now. I started when we were oDesk prior to the merger of Elance and oDesk and have seen everything transform. I've been doing HR for almost 20 years at this point.

Wow.

Yes. And I spent, you know, almost a decade at Yahoo.

Tell me a bit about your HR team.

There's the traditional side of the house, right, which is we have recruiting, we have the HR business partners.

And how many people do we have?

We're about 20 in that world. And then we have, you know, there's another group of people who help do the onboarding for the talent innovation team, is what we call the freelancers who work directly back for us. And they help them with the onboarding, getting access to the Upwork systems in a compliant fashion, right? And provisioning them, making sure again their business documents and all of that are done in an appropriate way. There are also people in our organization who partner with freelancers who are working for our enterprise clients to help make sure that they're onboarded successfully onto the platform, getting access to those companies' data or whatever it is that they need. That's where making sure all the documentation about the independent business license and all of those things are done. Pretty varied in terms of what HR encompasses for us.

So about 20 for the full-time, so 450 full-time Upworkers. But how many for that sort of broader talent group?

That's about 4.

Oh, so that's pretty leveraged.

It's really leveraged. Wow. Yes, they would like to have a little more help there. But we also then use freelancers ourselves back to supplement that team too, right?

Our team— What sort of things do you use freelancers for in HR?

For everything. I mean, we use freelancers to help us design learning programs. We're moving some of our compensation to a different philosophy. We worked with a freelancer to do a video explaining the why and the how that impacts everybody. We work with freelancers when we're looking to bring in different skills or scale in our organization. So for example, when we were building out our Chicago presence and we were hiring a lot of salespeople, we needed to do a big hiring push all at once. I knew we didn't need a ton of recruiters full-time focused on that, but we needed a lot of sourcers to really dig deep into the talent network within Chicago. And so we did that with bringing people on in the platform. So that's like just a scale issue, right? And then for skills like video design, right, I can't do that, but this person made this video that's amazing and makes a complex thing that's coming out of our department easily digestible and clear.

I definitely live in the distributed work world, and until you started talking about that, I never thought about parts of HR being able to be something that be freelancing.

It all can, right? I mean, and that's one of the things I think that is so great about how Stefan has set us up here, is that the expectation is every single organization within Upwork is a blended organization that relies on freelancers as well as full-time employees. So legal, finance, all of us, even the organizations that you'd be like, that's hard, there's always additional stuff that can be done.

Yeah, and the third bucket you talked about was enterprise. You might need to define enterprise just super quickly on what that means in your business, and then how many people work on that?

Yeah, so for our enterprise business, that is out of our sales function. And so that's working with our largest accounts. So the biggest companies with whom we work, Fortune 500, Fortune 50.

So I might come to you and say, hey, I need 1,000 folks to do XYZ.

Precisely. I need to translate these medical documents.

And I want you to manage it for me.

So we do do both, right? So we have some where it is, I want you to give me just the output, right? You figure out how to do it. And then we have others where they are more involved in the guidance themselves. And so they'll say, you know, for the marketing organization, we want a design initiative that's X, Y, and Z, and we'll do it this way. And so, like, Microsoft is a shining example of a company that's partnered really extensively with us and knows how to utilize freelancers in a wide variety of projects.

Are there other big clients you can talk about like that?

So companies like Dropbox and Pinterest are using us for a variety of different things as well. And then most of the bigger companies, you know, we've got at GE and other people like that who are really digging in within different functions organizationally, be it marketing or some of the writing organization or particularly web design and the technology pieces. Obviously, a lot of engineers can really be scaled. We do that here, I'm sure.

HR is so critical to being a distributed company. How should companies be thinking about this if they're starting to hire, say, right now?

Yep.

I have all my people in one office in Houston, Texas.

Right.

And now I want to start to engage and hire people in other places. Like, what do I need to think about?

I think you need to think about a lot of things. Like, is this going to be— I'm going to do this for one set of expansion, so I'm going to go to these 3 additional states, and then I know that's going to be pretty steady for X period of time. If that's the case, then I would argue, depending on how many people it is, it may be worth setting up nexus in those places. And so then you're beholden to pay the taxes there and set up all those kind of legal and financial things that you need to do. If not, and you're interested in saying, I am going to need 3 people in this place for the next 3 months, and then I want to explore the opportunity to have local translators in Brazil for X, Y, and Z reason, then I think you may benefit by exploring a freelance relationship with those people where you can dial it up or dial it down, and it allows both parties to really engage in a way that's very clear and communicative about these are the objectives of why we're doing it this way. Communication and transparency in terms of what the goals are, the deadlines, etc. But you're not then in a place where you need to manage all the tax implications, all the financial and all the legal ramifications of setting up businesses in a myriad of different countries, which can be hugely taxing— pardon the pun— but in terms of what you need to do organizationally, it can be such a distraction and so much overhead that arguably freelancers in that way can be much more efficient for a business.

Is there ways to manage some of this complexity? Because even in the US you have different workers' comp laws, you have different tax rates, you have so much stuff.

You do. I mean, firstly, I would say have a really good tax, like, person that you can use as a resource, whether that's somebody you contract with or otherwise. You can, obviously, if you're doing it the freelance way, like, I would be wrong to not say Upwork will do a lot of this for you, right? We can help with a lot of that. But I think in general it's about being mindful and intentional about it. I think Sometimes what happens is we fall in love with a person and a candidate and we think this person is perfect and you've already made some kind of oral commitment to them like, "I really want you to work with us on an XY project," and then you're like, "Oh, but man, they're in Massachusetts and the taxes in Massachusetts are a nightmare," or it's whichever state it is where you realize, "Oh, there's one of our biggest customers is there and if we set up nexus there, then we may have to look at our tax is differently because they're also there. And so, what do we trigger for both our customers and for ourselves? So, I think the biggest advantage we have, like, we have some great tax people here and it really helps us. And we've been very intentional about the places that we have full-time employees versus the places we're open to partnering with freelancers, which is worldwide, versus the places where we'll engage with least employees because that makes it a lot easier for us.

And had you been in a distributed organization before?

Personally, I mean, I've always had a distributed team, so I never have worked with a team that was solely in one place. It's funny, I hadn't actually reflected and made that connection that I'd never done it until I was thinking about talking with you about it. But I've always had that.

People probably think of, like, a Yahoo as being almost famously all in one place.

Well, now, yes.

Help people understand how maybe that org was really large.

It was.

It was sort of ginormous. I was there from '99 to 2008. And so the company was about 14,000 at its biggest during that time, but certainly grew and contracted various times.

That's a wild time to be at Yahoo, by the way.

I have to say, I can't say enough good things about it. We had various offices, right? So there was the large campus in Sunnyvale, but there was also offices. We moved our customer service organization up to Hillsboro, Oregon. You know, we had Broadcast.com, Mark Cuban's thing in Dallas, right? We were in LA and New York as well. And then of course, all over the world, there were Yahoo offices. So even when I was just managing one person as an HR manager, she was based in Oregon, I was based in California. You know, I mean, the other thing, towards the end of my time there, when I had left HR for a while, I was looking after the international customer care organization, and that was in 20+ countries.

Wow. So, and how many people was that?

That was about 300 people at that time.

Wow.

That was a really great learning opportunity, and it, you know, it also makes you mindful of time zones and different customs and different expectations about availability or responses over the weekend or what it all looks like and how different it is in different places.

If in the taxonomy of distributed versus all being in the same room, I guess I would call Yahoo or companies like that as multi-office.

Precisely.

There's offices all over the world across all time zones, but people would go into that office the majority of the time.

There was a lot less actual remote work like I'm in my home, you're in your home, somebody's in a coworking space.

So we just built a time machine. You can go back 20 years and talk to Zoe in 1999.

I know, she could be on it.

What would you tell her about what you've learned at Upwork and a massively distributed organization that you think would help maybe someone listening to this who's in a multi-office type place?

I think being precise and intentional about your communication cadence is probably the number one thing that you can do.

What's the cadence mean there?

So to me, that means saying, Okay, our entire organization will connect this many times a year in this many ways. There will be an all-department meeting once a month, once a quarter, whatever is appropriate. In that, we will cover these 3 priorities and broad progress and how it's impacting the business overall. Then the expectation would be that the smaller subsets of teams are meeting in this way, the leadership team is meeting in this way, and you as as sort of the overall leader, are connecting with your direct reports on this regular basis, and then making sure that you connect with every single person in your organization at least once every blank months.

Are there some things you think are unique to how Upwork's structured, or some processes you have like that, cadences that you have that you'd wanna share?

I think—

Some best practices.

Yeah, I think one of the things that is actually one of our greatest tools, which is a tool that I think, you know, everybody's got their own variation of it, right? Internally, we use Upwork Messenger, the Dash team, And there's just constantly the ongoing conversation that people have. So there's obviously a lot of work that gets done in that way, but there is also the check-in about like, hey, I know, you know, your daughter should be hearing back from colleges she applied to. Is everything going okay? Like, did she get into the one she wanted to get into? And just building that camaraderie and that understanding, you know, that's not something that's unique to us. It's something that is drilled into us that we will continually make sure that we are connecting on a personal level as well as a professional level within individuals.

Just from the culture or the tool does that?

From the culture as much as anything, and the tool really facilitates that for us. So for most of us, that's the first thing we do that's work-related every day. So like for my organization, we have a room for the leadership team, and the first thing we do every morning is check in, say good morning, like any personal updates, anything like, you know, the kids are fighting, so I'm going to be late to school and then late to work or whatever it is, right? And then it's like, here are the 3 things I'm going to do this day. And I need your help in this thing. And oh my gosh, you know, there's the meeting that we thought was a fortnight away is now next week. Can you help me get those metrics that I need earlier, right? And it just allows us to constantly be recalibrating the work that our teams are doing and connecting them back to the bigger, broader picture of what we're doing. You know, it's really simple. Like, I feel like I should have this massive words of wisdom for you and I don't. I think it's just talk more, communicate more, be clear about what you're asking and clear about when you need help.

Just because it's simple doesn't mean it's easy though.

No, that's true. I mean, it's really hard, right? And if everybody could communicate well, I think a lot of things could be different.

Is there something different you would look for when hiring someone to work in this kind of environment than you would if they were going to come into an office every day?

So obviously, it won't surprise you, like, are they a good communicator? Do they ask quickly for help and self-identify and see that as a strength that they're asking for help versus a threat or a weakness?

But how do you screen for that?

I mean, I'm a big believer in sort of behavioral interviewing and asking for really specific examples and then walking people through scenarios. And saying like, "Hey, this happens," and often it's something that's like literally happened the day before. What do you do in this situation?

I know that one thing that Upwork does is these meetups.

Yeah.

From an HR point of view, what are the pluses and minuses of these meetups?

That is a great question. The pluses are, you know, getting together. 9 out of 10 times, that is really fantastic. It's an opportunity to put a face to a name. It's an opportunity to share more personal stories, connect. To see how the work that you've done has made life easier for me and vice versa and all of those things and to brainstorm and just have more synergy, you know, I mean sitting around talking over a cup of coffee, you do tend to come up with different ideas than if you're in an official meeting. Challenges can be, it can sometimes be easier to relate to somebody via a screen. When you're in person, like maybe there is just something you guys don't like about each other, right? Like that can be hard. It also, I think, sometimes can feel forced or like it has to be absolutely brilliant or it's been a failure because they happen infrequently, they cost a lot of money, there's a big opportunity cost in terms of—

And y'alls are longer, right? Like, I heard 10 to 14 days?

They do tend to be long, so you're also going deep for a long time with a group of people that you're used to one very specific type of interaction with. And as much as, like, we have hangouts that celebrate people's birthdays or whatever it is.

Wait, say that again. So you'll have like a virtual hangout around someone's birthday?

Absolutely. I mean, we love a virtual hangout. You know, probably not the greatest HR example, but there are definitely virtual happy hours that happen with distributed teams around here.

Sure. Being in the same time zone helps that.

Yeah, it really does. That's when you're like, oh, 6 o'clock in the morning, no can do. I mean, the challenge is that it's a group of people, right? And you get any group of people together for X period of time, you know, think about Thanksgiving. Lots of pros for Thanksgiving. Also some cons when a family that's not always together is together for an extended period of time.

I think much like automatic, some Upwork meetups often happen, people stay at Airbnbs and stuff.

Yeah.

So that co-living is an additional variable. And by the way, you have to check the Airbnb sometimes. Yes. We've definitely had it where something they listed as a bedroom was actually like you had to walk through another bedroom to get through.

Oh yeah, yeah, yeah.

Things like that.

One of the big things that I personally advocate for a lot is making sure that all employees, but in particular women when they're traveling, never have to be at a place that has their bedroom door as a door to the outside. Just from a safety perspective, like an emotional safety perspective, like I want you, I want you to have a hallway. I want you to have somewhere, right, that feels safer than that. And just making sure that physical safety is something that you've been really clear about with everybody, like here are the expectations around that, okay? So, and being flexible. If somebody gets somewhere and it's like, I just can't, then you've got to have some wiggle room around that, right? And so like that may mean a buffer in your budget, which hopefully you don't need. Yeah, you need a separate hotel room, totally fine, I get it.

Probably want to avoid cross-gender sharing of those. Yeah, dishes and cleanup.

Dishes, yes. I feel like you have something to say about that. Apparently that just hits the sore spot personally, um, brings back bad roommate situations.

Tell me about dishes.

Yeah, right, like who's gonna clean up the mess? Is there a rotation? Is that clear? Is that part of it? And this certainly, I heard a story about this, like an expectation about who was doing the keynote was based on gender. Where there were two people with the same name, one was a woman who was a very senior leader, one was a relatively junior team man who was a man, and it was first name only on the thing, and one of them was doing the keynote, and one of the remote attendees was like, "Oh, I just assumed it was him." Hmm. Okay, well, A, whoops, you should know more about the organization to understand who is the leader in the situation. So I just think understanding that, but also understanding specific, like, especially gender roles in different cultures, right? You don't want to get into a situation where the expectation is, you know, that the woman's doing the dishes, right? Or whatever it is, or the men are taking out the rubbish all the time. You've got to make— just be intentional.

You just said something really key as well, which is across different cultures.

Yeah.

If you're distributed and coming together, there might be people from— 10 people from 10 different countries.

Right.

And it's easy to forget that people live differently in different countries.

Right.

So you almost need that defined for your company.

Yeah.

What are those expectations and kind of habits and culture of how you want to operate?

Again, the more proactive communication you have about this, the better off you are, right? Because it's not just things like gender. Like, do you— does everybody eat meat, right? Are there religious, you know, ramifications for how meat is prepared? All of those different things. Like, are there people who pray before dinner, right? What are the expectations of this? Do you have somebody who is like a nursing mother who's going to need time to pump in between the schedules?

How about mentorship and learning and training? How do you do that, particularly across your full-time versus freelancers?

We have tended to focus on our full-time employees in terms of learning and development initiatives. One of the things about freelancers is by the nature of their work, they are reskilling at a higher level than the rest of us who are in these corporate jobs.

It's almost more Darwinian, like being in the open market.

Yeah, they're doing it constantly. They're much more aware of what is going on in terms of the influx of need for skills and things such as that. The research that we have done shows that the half-life of a skill is about 5 years right now.

Wow.

And so if you are an independent business who is working to garner your next project and the next client, you're much more mindful about, and as such, I should learn X new thing. So often we learn from that part of our community Oh goodness, we should be training on blank.

Diversity and inclusion is something that usually is covered by HR. How do you think about that in a distributed organization and a global organization like y'all?

We've done, frankly, a lot of self-reflection. We worked with Paradigm, who's a consultancy that have a lot of attention right now, to reevaluate every single full-time people process in the company last year, which is not a small thing in terms of just scope, but also not a small thing when you really think you're doing very well and you really, you care a lot and you're trying your best to realize all the places you're flawed and can do better. By the nature of how our organization is structured and the fact that it is a small portion of the people who are working to make Upwork Upwork that are full-time, we have a huge amount of diversity already due to the nature of the freelancers who are working with us at any given time.

As we kind of close out, Your biggest tips, like let's say someone new is joining and they haven't worked in a distributed manner before, what do you sort of point them to?

I point them to learning as much as they can about how our business works and the different roles that people have organizationally. I point them to really not being shy and just proactively communicating, like, "These are the 4 things I've been asked to work on. I understand these 2 really well." This one I think is like this, can you help me figure that out? And this fourth one, I've got no idea, I've never even heard of this before, who can help me? And then really making sure that they understand how their piece of the puzzle is impacting this incredible mission. I mean, I think every person who is associated with Upwork believes in our mission and our vision, and you feel it when you work here, and hopefully you feel it coming in and visiting us.

What is that mission?

Our mission is to create economic opportunities so people have better lives.

Yeah.

I've worked at many different places and you see values on the walls and you see a mission and people talk about it, but I've never been in a place where, like, the values are used to make business decisions at the executive staff level, right? It's really inspiring, and I think that makes everybody eager to do the very best that they can do while they're here because it's not just for us.

As we look forward, like from your HR point of view, you've seen how work has changed. 20 years from now, where do you think— what percentage of jobs do you think are distributed?

Gosh, I mean, 70? Like, I think a vast majority are going to be because real estate is so phenomenally expensive. The things that are just happening to make it easier even than it is already, and I would say it's really bloomin' easy right now to do it. It's going to be a non-issue. It's gonna feel like I'm here with you if you're in Singapore and I'm in Sydney. It's not gonna matter. I think the beauty of that is the world gets smaller and we learn more and we understand more. We have more diversity of experience in our day-to-day lives than, you know, I look at my grandparents who traveled a fair amount, but like the people that my children know versus the people that they know, their circle will be so much bigger. So much broader and they will have so many more inputs. And so that can only be positive for business, right?

That sounds like an amazing world for our current or future children to grow up in.

I hope so.

And thank you for being part of help create that.

Thank you.

That work and also with sharing your stories for the listeners here.

Thank you very much for having me. I appreciate it.

My name's Han Yuan. I'm the head of engineering for Upwork. I've been at the company for 3.5 years.

Had you worked distributed before joining Upwork, and how is engineering from a distributed or non-distributed view?

I have, um, under multiple contexts, I think, both from a, I'm at a company and we have multiple offices around the world, and also in situations where we had one or more agencies that we worked with directly and we collaborated in more of a— I would not say black box, but more like a white box way. So really engaging with agencies in a staff augmentation way. What's fascinating about Upwork is that we're pretty distributed. When we look at the engineering team, they hail from over 40 countries around the world.

Wow, like currently living in 40 countries? Right. And that's of the 350? Right. But we're in an office right now in Mountain View. So tell me about that.

Typically, we try to make sure that all of the key meetings happen between 9:00 to 5:00, West Coast time.

Do you have many people in kind of the Asia-Pacific time zones?

We do not.

Makes sense because those core hours would be tough to keep there.

Right.

Most of our personnel is somewhere between South America, Europe, and Eastern Europe. We also find that because we have an agile organization, the leads of those agile teams are oftentimes not here in Mountain View. And since they do have the authority, or they're expected to recruit and hire for their own teams, there is a tendency to hire within 1 or 2 time zones of wherever they happen to be. Geographic dispersion of our team is probably partially organic in that sense.

You come into this Mountain View office about how often?

I come in about 4 to 5 days a week.

Oh, yeah. It's pretty good.

I still come in pretty regularly.

What do you like about it?

I think I like the routine a little bit. And some of it is just my own personal situation where it's harder for me to work like at home. We also happen to have most of our product managers happen to be, you know, on-premise. And so collaborating face to face with product managers, designers is a key part of my job. And so I do tend to come to the office pretty regularly.

How do you keep the folks who aren't here as in sync?

I think that's a really good question, and I think that's probably one of the greatest challenges of leading a distributed team. And I think it breaks down to a couple of things. One is, how do you maintain a consistent culture? I think that's a very difficult problem.

And what does culture mean to you right then?

In a lot of cases, it has a lot to do with how both the big and small things regarding how people interact and communicate with each other on a day-to-day basis and what their expectations are. So for me, it's being very, very explicit in certain cases what— what people expect from each other. So for example, how long can you sit on a pull request? Can you sit on it forever? Can you sit on it for 1 day, 3 days?

Mm-hmm.

Without that Coda in place, different engineers from different parts of the world have, you know, potentially different points of view on what is being responsive to a colleague. And so we spend quite a bit of time documenting and being very explicit about what we expect in terms of behavior from our engineers. And hopefully, to the extent that we're consistent, we reward and we also, you know, give feedback for behavior when it's inconsistent. But I think that's a key part of it.

Yeah.

The second thing I think is more of a practical thing, which is we generally bias towards hiring people who have strong written communication because we want to do things as asynchronously as possible. In order to do that, being able to write well is very important. I think Chat is less interesting to us in general because it's a little bit synchronous in nature. And so we want to encourage our engineers and our team to really put things down thoughtfully and clearly. And then along those lines, as an organization, we spend a lot of time trying to create transparency within this sort of working operating system of how we build the site. And so a big part of that is making sure that when there are issues, everybody understands it, even from the executive standpoint, the engineering executives. And then also having the ability for teams to propose and communicate innovation at all levels of the organization or recognize people at all levels of the organization. And so we have various mechanisms to achieve that.

You mentioned kind of like if I were going to make a proposal, you want me to kind of write it out and really present it. How about when there are those technical agreements? Two great engineers, maybe on different teams or maybe the same team, have a difference of opinion for which way they should go? How do you work that out, especially when you can't get people around the whiteboard or in the same room?

In a distributed organization, there's a tendency, and rightfully so, right? You have to have some structure where you say, hey, you are the CEO of this problem. And so there are times when, let's say, I may come to an engineer, or engineers come to each other and say, hey, can you make this change? I'm really worried about this thing that you built. You should make this change. And as the owner, of course, you could say no. But in that sense, the decision-making is very clear and absolute. But we have seen situations where the decision was the wrong decision, or multiple people came to that decision maker and said, I really think you guys are doing a bad idea. And they said no multiple times. And so over time, in order to flag these issues, what we encourage teams to do is as soon as you have come to a place where you disagree You follow our proposal process, which is the same format. State your problem, state each other's point of view, and then bring it to the adjudicating body, which in this case would either be an architecture review or we have a different body called Eng Staff, which is the top 30 senior people in the engineering organization to adjudicate over this.

You had something really key in there I wanted to ask about. You said make the other side's argument. Tell me about that, because that's not a normal thing to do. Normally, if I'm proposing something, I just make my argument.

We really want to encourage empathy in general. And so a key part of empathy is being able to try to see the other person's point of view. And in an organization as distributed as ours, where people come from all around the world, we view it as an essential ingredient to developing deep and meaningful collaboration.

What do you think is the main benefit of what you do that couldn't be accomplished if you had sort of a traditional office approach like you did in prior jobs?

I think there's a bunch of practical things that people would often say, like, oh, we can do 24/7 development, or you can have access to talent. And I think those are valid.

Mm-hmm.

But if you were to ask me, I think the most important thing is diversity of thought. And I think that has a lot to do with different people from different backgrounds in different parts of the world who have experienced different things and have worked on different things. And that, I think, is quite powerful. I think when nurtured well, creates the conditions for things like creativity, empathy, collaboration, and things like that. And I think that's very valuable.

Can you share an example where that came into play or you felt like that improved the outcome?

It happens oftentimes in big and small ways. For example, because people are very aware that they come from different places, they, they tend to ask more questions, which I think does elicit a little bit more thought from other people. And I think it also forces people to normalize their communication, their language, their reaction to things that, that's a little bit more neutral. But these are like very subtle things. Like diversity of thought comes from the place of actually interacting with somebody who isn't very familiar with how you do things.

Are there any commonalities or practices of the highest performing engineering teams? Like, do they do daily standups? Like, what's the sort of things that they adopt?

The highest performing teams actually have much smoother communication between the product team and them. There's context setting that I think the transmission of context is just cleaner because when, when that happens, the engineers are brought into the solution space. Not just in the implementation space.

Yeah, so let's say I was leading an engineering team that you perceived kind of bottom quartile in the company, wasn't doing as well. How would you coach me to have a better context setting or connect better with my colleagues to be more effective?

For all of our groups, we have them document what their vision and values are for that team and align around what's important to them. So for some organizations, for example, if you're on a platform team, you may value very, very clean code, maintainable code, and you may value doing things very well over speed. For teams that are working on things that don't have product-market fit yet, we encourage them to, you know, break things, um, write things a little bit on the side, and it's fine. And they can go ahead and say, hey, this is what we're going to do, and explain why we're going to do it.

How about in-person versus remote? So let's say I was this weak engineering manager in Houston. I was like, hey, there's this product person in Mountain View I'm just not connecting with. Like, would you encourage us to get together physically, or are there meetups? How does that work across, particularly with the full-time and non-full-time people?

In almost every case, team performance has improved after they've met face-to-face once. Now, the gains that you get from meeting up twice, 3 times, 4 times, 100 times tends to fall fall off quite a bit.

Diminishing marginal utility.

Exactly. But the first time, the gains are huge. And so we typically fly groups of 30 or 40 folks on meetups. And since we're so distributed, it tends to be some kind of random city on the planet that's more or less geographically accessible to those teams.

And those would be freelancers and full-timers? Yeah.

Cool. And then they, these meetups can last for a week to 2 weeks. And so that's usually enough enough face time for people to get a feel for how I work.

Yeah, you had mentioned you find it hard to work from home when we started. So tell me a bit more about what you find challenging working from home or not.

I think this is a personal quirk that—

Yeah, totally.

—propose nobody else, but I really like to partition when I'm working and when I'm not. And then to your point about isolated time, even during the workday, I have not had this in 6 weeks, but historically, I try to block off at least 3 hours. When I write code, code, and I still do from time to time at home, not at work, I've done a bunch of performance studies on myself and I know that I can only generate about 4.5 hours of solid code.

I'm curious how you knew when it started to drop off. So if you really want to know, this is what I did to myself.

I would measure blocks of time of 30 minutes and then set a timer. And every 30 minutes I would tick off on a scale of 1 to 3 whether or not I did what I thought what I was going to do in those blocks. When I start the next block, I tell myself, this is what I wanna accomplish. And then— Very Pomodoro-like.

It's very Pomodoro-like.

And this was back when I was, I would argue, gainfully unemployed where I was kind of working on my own thing. I ran this over 10 hours a day, 7 days a week for about 12 to 18 months. Wow. And so I had significant data on how I work. And I found out that generally speaking, my prime hours are somewhere between 11:00 7 and 3. And so once I figured that out—

I— morning or night? During the day. Yeah.

Once I figured that out, I was like, okay, in the afternoon I'm gonna go hang out, work out, do other things. And so I, um, as a result, I, I feel like at least for myself, I have a few hours that are good and most of it's not so great.

That is utterly fascinating. First, what other variables did you find?

So sleep was really important too. So when I started to correlate number of hours that I slept, that was really important.

How much do you need there?

I typically need 6.5 to 7 hours.

I do want to talk about tools a little bit. What are the tools that you use when you like share this writing or these proposals or, yeah, what do you rely on there, particularly in engineering?

Sort of day-to-day collaboration, I would say our most important tool is actually the G Suite. Being able to co-author documents in real time, comment, assign action items, it is a game changer for us. Especially when it comes to assembling information very quickly. When we have site incidents, for example, we really need to make sure that a document is written quickly so that it's fresh on the top of people's mind and that we run the postmortem. That level of tooling is critical. We have a messaging client on our platform, which we use for day-to-day business, but the challenge is that when the site's down, oftentimes our messaging system is also down because it's part of the same platform. Yeah. And— What's your fallback? Yeah, so our fallback is typically Slack, and so Slack is still very important. In order to reduce mean time to response, our tech ops team and site reliability teams always collaborate on Slack, and so they're basically online on Slack. I think related, we also use Hangouts quite extensively just for video collaboration, but also during site incidents, Hangouts are important because you can—

I'll spin one up.

We will spin them up just because we have found that chatting back and forth is usually not fast enough. Hangouts also give us the ability to see what's on each other's screens. And so during those kinds of events, it's actually more important to watch an engineer type versus look at their face, their panicked face. So I think that level of collaboration is very, very critical, and that's when we need to go forward. Real-time but remain distributed. Everything else is probably like standard tech stack stuff, like Git's important, things like that. Jira, GitHub, what's the kind of— We use Jira and then essentially all the Atlassian stuff like Bitbucket, so on and so forth. We don't dictate what the engineers do on their own machines. We have a very sort of loose bring-your-own-device policy. And so people use different kinds of tools. Favorite thing about distributed work?

The people you meet. Yeah. Least favorite thing? Miscommunication. Mm-hmm. Especially across cultures and languages, right? Yeah. Final one. Say 20 years from now, what percentage of jobs do you think will be distributed?

I think almost all cognitive labor can be distributed. I don't know how many companies or what percentage of companies will be fully distributed. Mm-hmm. And I think there'll probably be a spectrum of fully distributed companies, like Automattic, and partially distributed companies.

So pick a number overall, then we can check it in 20 years.

I would say most companies will be partially distributed. And that maybe 20% of the companies will be fully distributed.

So that would be like 35% of jobs? Yeah. Cool. Well, I really appreciate it. That was Han Yuan from Upwork. Before that, you heard Zoe Hart, also from Upwork. You can follow Zoe on Twitter @ZoeSHarte. That's Z-O-E-S-H-A-R-T-E. Han's not on Twitter, but he's pretty active on LinkedIn. Just search for Han Shen Yuan. That's H-A-N-S-H-E-N-Y-U-A-N. S-H-E-N-Y-U-A-N, and you'll find them. As the world's largest network of freelancers, Upwork has a big opportunity to define what distributed work looks like in a big blended company. I'm glad they have such thoughtful people throughout the organization who are thinking hard about how to create economic opportunity and great work experiences. Next time on The Distributed Podcast. We'll be speaking with someone who I've been working with for a few years now. John Maeda is an author and certified design guru— if there's such a thing. He also happens to be the global head of computational design and inclusion at Automatic, and will be joining, uh, Publicis soon. We're going to talk about how the distributed model impacts design teams and about the tools and processes he's using to foster creativity among them. Thanks again for joining us, and see you next time. Yeah.