Welcome back to The Digital Workplace podcast. Today, our guest is Ali Greene. She’s the co-founder and co-author of Remote Works. Hey, Ali. How are you today?

Hi, I’m great. How are you doing?

Excellent, excited. This is going to be a fun conversation. I’m already gearing up for it. So I’ve been looking forward to this for a while. We’re going to get to know you in a little bit and learn more about your story and where you come from. But first, as always, we like talking to humans here. So your human question to make sure that you’re not a robot, Ali, what is your favorite smell?

My favorite smell is piping hot black coffee. You can just smell it coming through a house or a cafe and nothing gets me more excited to be alive than that.

Do you have a favorite roast or type of bean or anything like that?

No, but I will say I might get kicked out of Europe for saying this. The thing I miss most about the United States of America, because I’m an American that’s a digital nomad and spends most my time in Europe. I love third wave coffee shops where they have really fancy single origin coffee, and they take 15 minutes to brew you one single cup of black coffee. Nothing makes me happier in my life than that.

I love just waiting for the coffee to come. It’s good.

The anticipation.

Yeah, I love it. Love it. Good, great answer. Great response there. You’re a certified human. So let’s get in. You talked a little bit about your story in terms of being a nomad. But you have a lot of things in your background. So give us a little bit of the rundown of your history.

I’ve been working remotely since 2014. I was a remote worker turned remote. It was a bit of a cliche story. I love to say I traded in Madison Avenue for Machu Picchu. I was basically working in New York City, living that rat race lifestyle. It just didn’t make sense to me. I didn’t understand why we had to compete to get on the same subway line at the office by not even 9am, but 8am, to try to be our most productive and creative selves when people above us in an office environment dictated us to do so. Plus, I realized that despite thinking I was going to be this cool, like big city person, urban environments just are not for me. I was like, okay, well, if I’m going to leave this dream life, like I finally made it. I’m working on Madison Avenue. I live in Brooklyn. Like how cool am I? I need to do some more.

And for my young self that was going backpacking. And so I had this great plan to quit my job and go backpacking in South America. But what actually happened was the company I worked for didn’t necessarily want me to leave. And they opened my eyes to being a consultant. And so I took a break. I went to Machu Picchu, I hiked it. It was amazing. And then I started consulting and working remotely. It opened my eyes to, not just remote work, but a digital nomad lifestyle. Ever since then, I just can’t get enough of questioning different ways to live your life and how technology has enabled us as humans to design a lifestyle using technology to make our life better and more meaningful us to do our work faster and get more work done. That’s really what I’m all about is, yes, let’s help people be more efficient. But let’s also help people be more happy.

Yeah, absolutely. You’ve worked with some some large companies in the past, too, helping them managing their teams, too. Tell us a little bit about that.

I was the first people ops hire and the director of people for DuckDuckGo, which is a privacy company most famous for their search functionality. I helped them scale from just about 40 people to over 100 people in around four and a half years. What was amazing about DuckDuckGo is they were remote first and fully distributed. So we had employees that lived in Japan, Uruguay, all throughout Europe, US, and Canada. It wasn’t just remote work, people living in their homes in one town or a couple of states. It truly was a global organization. It was an incredible experience.

Shortly I moved on from that experience, I had an opportunity to consult with an amazing organization called Oyster that saw a problem with remote organizations not being able to hire like DuckDuckGo was able to hire and say, well, if we get into remote work, how do we make benefits easier for people? How do we make it easier for people to understand what are the compliance laws in different countries? And so now you see all these amazing global EORs that are remote like DO and Oyster was one of them. And so I had the opportunity to go and support them really early on. That was a really cool experience. I don’t even know how many hundreds of people work there now, but I got to see it when it was quite small. There’s something really so special about startups at that stage.

EOR meaning Employer of Record, right?

Yes.

You’ve had a fascinating experience. And like you said, starting back in 2014, is great. We were just talking earlier on an earlier podcast about the difference between looking at the whole system of flexible work and seeing that some people really lean into that flexibility of where you work. Some people lean more into the flexibility of when you work. You seem to really have latched on to that where being able to travel around, do a lot of nomad stuff, be in lots of different places. I’m sure also taking advantage of the when as well. For me, it’s been mostly a when. I love being able to have control of my schedule and know when I want to work, if I want to go out and take a walk, or go and play with kids or whatnot, it’s just a fun thing to think through.

I love that. I think flexibility should be all of those things. In our book, we talk about this energy tracker. So there’s really different Chrono types, and some people naturally are an early bird or a night owl. I am a camel. I have two peaks. They both happen to be in the afternoon. I always joked I’m an afternoon person. And it wasn’t until we interviewed this professor at Stanford where she confirmed that’s truly a real thing. Some people are afternoon people.

That’s a thing.

Yeah, that’s me. That’s been me my whole life. I like to go to bed early, but I like to sleep in late. I get all of my work done in two peaks in the afternoon. Once people started to understand when they like to work, it’s also do you like to work with music on? Do you like to work around people? Do you need to be in your silent cave? If you actually combine all of those factors, that is the definition of real flexibility in my mind. It’s the how you work, who you work with, when you work, where you work. If you’re only focusing on one of those puzzle pieces, you’re missing the big picture.

Your book is exciting. I’m excited to read the full version when it comes out. But we’re going to play a little game here, Ali, where we’re going to talk about some parts, I’m going to give you, hopefully, we’ll get through all five of these, five statements about this new world of flexible work. You just give me a quick agree or disagree. We’ll try to get into some good debates between the two of us. Hopefully, these are provocative statements. So let’s get started with this. First one, employees do not need managers in truly distributed teams. What do you think?

I disagree with that. What about you?

I will agree because I’m going to take the old definition of what a manager is. So you tell me first why you disagree.

I like your caveat. I think that with this new world of working and distributed teams, we need to redefine what a manager is. So manager no longer has to be the person dangling a carrot or a happiness stick waiting for employees to comply with the when, where, how, and the value of your work. In our book, we define a manager using four different personas. So we talk about a project manager, this no longer has to be a role you’re hired for. Everybody at work a project manager, because they need to talk about and think through the dependencies and complexities of the tools they’re using, the skill set to run a project and manage the different milestones asynchronously, and without being able to check in with people just by walking over to their desk. So everybody needs to learn how to become a project manager.

People management I think is incredibly important in distributed teams. These people act as your wayfare, helping you navigate an organization, helping make sure that they someone in the organization truly knows and cares about you and knows your career goals and can help you structure your goals and connect with the right people in a distributed organization to make sure you’re getting what you need to be happy and to succeed. Then we also talk about a cultural leader, someone who can really, not leadership, not like the CEO, not even the HR people, but someone who can critique meetings, critique how people are spending their time, humanizing the environment. That cultural leader is a manager, and a strategic leader, someone who’s challenging the thought processes, challenging the status quo, and making sure you’re using the tools efficiently and effectively.

That’s well said. I think that that role of manager will split from just becoming primarily that project manager or the task leader. There are so many things to do in any kind of organization. Like you said, all the things you listed are important. Just in general, just taking care of humans and figuring out how they’re going to work best and setting them up for that, that’s going to be an important role in the future. Yes, I think we ended up agreeing on that statement. But obviously, there’s a lot more to figure out there. Statement #2: teams should delay working out most conflicts until they can be in person.

I disagree.

All right. I’ll go ahead and agree with this. I feel like, and I’ll go first, some issues, if you try to handle them over a text thread, it’s just going to make it worse. There’s certain level, maybe it’s just a maturity level, too, of the people involved in it. But if you have a really sticky thorny issue, a big conflict that’s come up in a team, man, I would say, hey, guys, we got a visit plan next month, let’s just wait and handle this. Come back at me. Change my mind. What do you think?

The three reasons I disagree, well, definitely for in-person, because I’m detail oriented, so in-person, waiting to actually be with each other, that could be weeks, months, or we’ve seen in the past few years, years. So if you’re waiting for that, it can, number one, delay a resolution. It could be something that is just an honest miscommunication. If you can resolve it quickly, why let those feelings linger and delay a resolution? It can let things fester. So if you’re waiting and you’re not talking about the conflict, then it can impact trust. Trust is such a core value for remote work. It can create silent disengagement. So people have easy ways to hide in remote work. They can join video calls with their cameras off. They can disengage from things like the online water coolers. If it’s because there was a personal conflict and they feel uncomfortable, it’s harder for others to know that that has happened and to come up with the resolution.

And to your point on maturity, I would say the number one lesson that I have learned throughout remote work and that I teach others is to approach things with the ideology of most respectful interpretation. If you’re writing back and forth to each other asynchronously trying to resolve conflict, in your head, be gracious and think what is the most respectful interpretation. It’s not that this person hates you and thinks your ideas are stupid. It’s that their kid was downstairs playing and making a lot of noise. And they wanted to quickly finish to go join them and play with them because it sounded like they were having a lot of fun downstairs. That’s a more respectful interpretation of why the message sounded short and uninterested in what you had to say.

I definitely agree with the fact of there are certain situations where you just can’t wait, if your next offsite is planned for 11 months from now, do you really want to go through 11 months of just holding this thing out to the side and wondering about that.

There’s so much to get in here, too.

Yeah, I think there’s a case, too, if there’s a really serious problem, then that’s just like, hey, I’m buying your plane tickets, we’re getting together, we’re going to sort this out in-person over meals and drinks and work on this. Because there is something that in-person provides that just next level of fidelity that we get to feel each other’s energy. We get to see things. If we’re eating together, that can break down some barriers, too. So I will hold some space there to say I do think that being in-person is a way to really fully deal with issues that you can’t in other spaces, maybe.

I do honor that caveat. I will say we could have a whole conversation just about this. There’s a lot of differences between friction based on person, and are you having conflict with this person, and do you need to build a relationship. That’s great to do in person. Or are you having conflict because of the work, and there’s friction and ideas? In which case that conflict is actually really healthy. And you should lean into that conflict because you can get a better solution for the work product.

Good one. I like that discussion. It was good. Number two was a winner. Statement #3: teams often waste time when they write up documentation for every tool. Just trust people to be adults.

No. Disagree.

This is a tough one for me, because I am a documentation freak. I love to say, look, use this one specifically for these things and do this. But I also feel like everyone ignores me when I put that together and they just use it the way they want to. And 80% of the time it works out. So I sit in the middle of this one. I really don’t know. I would love to say, yes, but I also feel like we do kind of go too far in it a little bit. So tell me your side.

I think documentation is so important. People aren’t used to doing it so they don’t think about it as part of their workflow. I think people need to think about documentation as cleaning up while they cook, not cleaning up after they cook in order to better enjoy the meal. The benefits of that meal are things like it makes onboarding easier. When you have a new employee, they have one place they can go to learn everything and read the history and really immerse themselves in the company. They don’t need to track down all these people and have all these different synchronous meetings. If someone leaves the company, they’re not taking away all of the knowledge with them from the company. So there’s no single source of failure. Transparencies then baked into your company culture, because you’re documenting things. It can help with decision making, because you can quickly learn why you made a decision, what thought processes you used, what got you here. It makes asynchronous communication easier, because things are already written down in part of your workflow.

Do you think documentation can go too far? Is there a limit to somebody being just obsessed with it?

Yeah, when it becomes to the point where you’re doing more work about work, and your day is filled with admin, and your day is not filled with thinking creatively and creating your work output, then documentation has gone too far. So I do think that it’s a spectrum. But right now, I think most companies are not good at and don’t embrace documentation. It sounds like both of us are documentation lovers. I just think people are scared of it. There’s no need to be afraid of it if it’s part of your standard workflow. Or if you’re treating knowledge like an asset, my co-author, Tamara, talks about this, in the same way that you wouldn’t just leave money scattered around your office building, you shouldn’t leave ideas just scattered around in people’s brains.

I totally agree with you. I feel like this, for most 90% of companies out there, you need to do more documentation than you’re doing right now. Most people need to do that. Most teams need to do more than they’re doing now. But I do hear those people who are frustrated with people like me that are just like, hey, I wrote up this report yesterday, everyone needs to look at it and figure out what we’re doing. There’s also an element of control. I feel like because there are those of us who are more used to that and like it more then we tend to dominate those discussions, too. And the person who writes up the documentation is the one who has the power of how it goes. And perhaps somebody else that wants a better voice, but either just doesn’t write as well or is busy with other things, maybe doesn’t get as much of a voice in that. Have you ever seen that come through?

Actually, that is me. And that was the most challenging part of growth into leadership early on in my remote career. I thought things had to be perfect before I shared them. We used Asana as our project management tool. And I would obsess over do my ideas come across clearly? Is this written in the most intelligent way possible? Is my grammar and formatting correct? And the CEO of the company sat me down one day and was like, Ali, just stop being a perfectionist because you’re wasting your time with documentation and you’re not being listened to. You’re getting left behind in conversation because you’re waiting too long. Again, if you embrace most respectful interpretation, and that’s baked into your company culture, and you allow people to get their ideas out there fast, then you allow people to participate in the conversation without being perfect. Again, you also need to have benchmarks where you say, stop, the stakeholders that are most important to this project haven’t had a voice yet. And don’t move until they’ve had time to participate. I think that’s the most important scenario, especially across different time zones. Identifying those stakeholders and everybody’s role up front will really help with inclusion.

I felt there’s a lot more we could do with that one, but definitely good discussion around documentation. Statement #4: establishing when a team works together, when their synchronous time overlaps, is more important than where they work from, whether it be from home or as a nomad or from an office or a co-working space. What do you think?

I agree.

I’m also agreeing on this one. For me, it’s definitely I don’t really care where you’re working from for the most part. There are a few situations where I do want people to get together. But on a day to day basis, it’s all about the time and it’s all about when we have that overlap and when you’re expected to be there.

Yeah, I would say the one caveat for the where, and this is me putting my HR hat on, is if you don’t have a remote work policy or a digital nomad policy in place, you might want to consider it because it’s important for things, like knowing what employees are allowed to expense, how your company is setting themselves up for compliance and tax. But otherwise, I would say team norms and setting expectations for things that impact one another is way more important than you making decisions on things that are only going to impact you and how you show up to your work the best. I would take it a step further, though. I would define what and why you need the synchronous time for. What is the unique value of being together at the same time? What’s the goal? And how are you going to reach that goal? But I’m just a big stickler for asynchronous.

I ask guests this question. What do you think is the optimal amount of time on a day to day basis that you would want to be on a synchronous schedule with your teammates? Like how many hours in a day would you want to be able to have a decently at the same time conversation?

I mean, I can’t answer that, because I think the answer goes anywhere from zero to two or three hours a day, depending on level of experience with remote work, fluency, and acumen level of experience in the role, confidence and trust in yourself, what type of work you’re doing if your internal or external facing. At this point in time, I can go days on end without having any sort of synchronous meeting. But I’ve working with someone who the two of us combined have 20 years of experience with remote work, and we’re often only interfacing with each other.

So for sure, I would agree. I do, like you said, that three-hour mark, I feel like if you are exceeding that three-hour mark every day, something is not quite right.

Yeah, after three hours, I think you’re going to burn out. After three hours of synchronous conference, when are you actually getting your time to get your work done, and do your life?

Last one, #5: objectives, talking about goals and objectives and things, they change so often in some teams that creating productivity output metrics is counterproductive.

I disagree.

I really don’t know what to say in this. I’m going to listen to your reasoning first, and then I’ll give you my answer.

This sounds like an excuse to me. It is so hard, I will acknowledge and give so much credit to teams and managers and leadership up with objectives. It is always a long process. Things can change. And you have to pivot your business. But if you can’t think critically about what productivity output metrics you’re going to use to define done, then I think you’re evaluating employees work on things that are not clearly defined or too long term. How I think managers and leaders should approach this is break objectives down into projects where projects have clear definitions of done and success metrics attached defined upfront. That way you know, are we hitting these certain milestones? Are things on track? When are we actually going to call this project completed?

The alternative to that is the status quo is we work 40 hours a week. But what does that mean? What is productivity in that scenario either? I think that is worse. Two really great examples here, a company called Doist, who I really admire, they have clearly defined projects. They call them do-s, and they work on cycles. And so you have a project that is a cycle long. I believe their cycles, they’re what can you get done in these four weeks. Define it up front. Similarly, at DuckDuckGo, we did 10-week check ins. And if things aren’t moving along in 10 weeks, let’s have a meeting. Let’s redefine the objective and talk about it. But let’s not set goals, because we’re afraid that we’re going to have to redefine the goals, that seems silly to me.

You did a good job of covering the spectrum there. I’m much more like, I love objectives. I love the idea of these output metrics. Because like you said, the alternative is just saying, hey, they showed up every day, they responded to all my messages I sent to them. They seem like they were working hard. That’s not a great way to judge somebody’s productivity. I have been on teams, though, where it does feel like we put in an enormous amount of effort into trying to come up with some kind of objective that then changes in a month. And then we have to do the whole process over again. That weighs on people and they get frustrated. They’re like, oh, we got to do this all over again. So I feel like there is some level of maybe, like you said, focusing on, hey, we’re going to do this project one way or the other. We’re going to get this done. We’re going to do it. Then as the team matures, as this project matures, and the objective becomes more clear, then we’ll lean more into that. But yeah, there has to be some kind of output and metric for teams to hang their hat on to see if they’re being productive or not.

Yeah, and I think if you define statements of work, then you can clearly identify this is what I’m doing. This is what you can judge my value and how I’m contributing to the company, which also helps with things like motivation outside of just productivity and salary and things like that. And so it’s really showing what you’re providing for the effort that you’re doing.

Yeah, like you said, otherwise, we just fall back to do I like you, do I feel like we work well together. These are all very subjective metrics, or they’re the objective metrics we don’t want, like how much work are they putting in? Did they give up their family meetings so that they could be at this event? Those aren’t the things we want to honor and reward. Excellent, I had fun with that. Those were five good issues I feel like are pretty get into the weeds of someone like you who’s been in this world for a long time and has seen lots of things. So thanks for playing our game. You’re a winner. I don’t know what that means, but you won.

That was really fun. I could go deep in any one of those. So it was really challenging to share the message really quick and fast. And I hope that all of the listeners come up with their own agree or disagree and share back to us what they think.

Yeah, absolutely. So Ali, tell us about when is the book going to come out? Where can people go to learn more about it?

Yeah, it has quite a journey ahead. But please feel free to follow along in our journey. You can visit remoteworksbook.com. We’re actually currently giving away a free version of our energy tracker if you join our mailing list where you can see some fun behind the scene pictures and monthly reflections of what it’s like to write a book remotely from two different continents and our thoughts on remote work. And the book will be available in bookstores February 2023 and for preorder copies at the end of 2022. So if you want to stay tuned, and actually remember those dates, also, feel free to connect with me on LinkedIn.

Wonderful. We’ll have those links on our show notes. Ali, thanks so much for being a guest on the show.

Thanks so much. Have a great day.