#117 The Truth About Remote Work - Ali Greene on being a remote leader, leaving the default path, stories and taking breaks, living in different countries, & writing a book (Pathless Path Podcast)

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Greetings everyone. Today I am talking with Ali Greene. She has been a remote worker for several years, even before the pandemic, starting in 2019, has been a longtime digital nomad, longer than me, so I'm excited to learn from her on that, has worked as a remote worker at several companies, including DuckDuckGo, where she helped run people operations and learned a ton about what do you do in terms of how to run a company remote and distributed, and excited to talk to you today about all of this. You're also working on a book called Remote Works, which you're going to launch next year.

Which talks about how to actually make remote work, I am guessing. So we'll talk a lot about that today. Welcome to the podcast, Ali.

[02:02] Ali Greene: Thanks so much, Paul. Super excited to be here.

[02:05] Paul: Question I'd like starting off with is around the scripts we grew up with. I'd love to just start with what was it like growing up as Ali Greene? What were some of the scripts and expectations you had about what you're supposed to be doing once you reach this magical adulthood?

[02:22] Ali Greene: Uh, so my script is really interesting. One, as a middle child, and two, as someone who experienced a lot of change in my early life but didn't necessarily correlate that change to questioning the status quo, at least until way later in my life. And so the script that I grew up with was always aspire to work really hard and to always want to succeed and, and climb that ladder for more. And so what that meant as a little kid was getting a B+ or an A- wasn't enough. Why didn't I get that A+? Or why am I in the regular class when I could be in the honors class?

And I was always really hard on myself, spending a lot of time studying, and that culture of working really hard will pay off in the end. but I never questioned what that payoff was. And that theme carried with me to university. I remember studying really, really hard and, you know, really just taking it above and beyond my peers to the point where I remember conversations with my parents being like, this is also a time for you to explore and have fun and socialize. And I was just so concerned about the next step if I don't do well. Here in this moment, what will it mean for getting a job?

If I don't get a good job right off the bat from university, how will I ever climb that corporate ladder and get to the top? But I didn't stop to think what that top meant until I was way late in that game. So, so to sum it up, I think themes of work hard, things will pay off in the end, and aspire to succeed without questioning what the word success could be defined as were the themes I grew up with.

[04:23] Paul: It sounds like me, similar to me. You didn't, didn't have like the parents actually pushing you. It was sort of soaked up from the environment around you. And I sort of look back now and I realize, oh, everyone was probably feeling like me and we all just sort of like agreed to not talk about, like, our deeper fears or like, why are we doing all this? It's just like, this is what you're supposed to do. It seemed so obvious at the time.

Is that sort of how you look back on it now?

[04:53] Ali Greene: Yeah, like, it's almost like I wish I could blame my parents and say I had these really strict parents and they pushed me really hard. They'll probably listen to this podcast and be like, that's not true at all. They pushed me for quite the opposite. And it wasn't until I was an adult where I actually listened to my parents. But if I wasn't getting this influence from them, where was I getting this influence from? And I really do believe that especially as an American, I can speak to my experiences in early education.

I'm not sure necessarily what it's like in other cultures despite my experience now traveling. In other countries and meeting lots of people in their environments. But we're socialized to believe in this American dream. And I think that starts at such an early age that we don't question where we're getting these messages from because we're getting these messages from everywhere. We're seeing these concepts in television. One of my favorite TV shows growing up was Saved by the Bell.

And you have these stereotypes of, you know, the person that works really hard, the character Jessica Spano, who works really hard. She's the best at, you know, being smart and she pushes herself. You have the person who's like popular and kind of a slacker, but they're always questioning like, okay, Zack Morris, like you're cool now. But there's these episodes where it's like, what's going to happen to you when you grow up? What does this mean for your future? And so In a really funny way, I look back at my childhood and I'm like, these concepts of who these people are going to turn out to be started really early on.

We saw it in television, we saw it in school, that almost dopamine hit every time I got an A+ and how sad I was when I came home with a B+ instead. Like, that was coming from inside of me, but it wasn't coming from my parents, it wasn't coming from my best friends, it wasn't coming from my siblings. It was coming from the system, and the system taught me to internalize it.

[07:01] Paul: Yeah, that's so powerful. It's, I think, I mean, for me, I sort of always got A's too. So I was almost even more blind to how deeply I had ingrained all this stuff. That's not to say like, oh, I had everything figured out because I was getting good grades. But like, literally, if you do well, in our society and culture, like nobody says anything to you. And this is what I realized in my career is like, as soon as I left the default path, people were like, what are you doing?

This is so crazy. This is so risky. How could you do this? Why would you do this? Don't you feel like you're wasting your potential? But you don't actually realize that's there until you've stepped off a path.

So I'm wondering if that resonates with you as well in terms of increasing your awareness of this?

[07:53] Ali Greene: Yeah, I think the first time I really became aware that I was doing something different was when I decided to take my first risk. I think when you talk about this concept, Paul, and I really like how you do this, you talk about prototyping life shifts, and I had no idea that's what I was doing at the time, but I got to a point where I was just so fed up in my current situation Yet I was still so wrapped up in society and how I could explain things to the outside world that I decided I'm really unhappy. I need to make a change. And at the time I was in my 20s, I was living in New York City. By everybody's definition, I was successful. Like, I had a very good job.

It was on Madison Avenue. I had an apartment in Brooklyn. I took the subway and did this commute every day. Like, I paid for bills by myself. It was, it was successful, let's say, whatever. I was at a really low point in my life and I wanted to make a change, but I felt that I couldn't make a change without having a way to justify it in a way that could tell a story to somebody else.

Even though I knew the story for myself was I am unhappy and I cannot be unhappy any longer. And so it took me almost a year to get the courage to quit my job. I quit my job and I decided to backpack South America and go to Machu Picchu. And it sounds super cliché now, but that trip was my way of justifying why I was making this big change. And when I told people this story, people fell into two camps. There was the camp that was like, oh, that's really great.

And when you get back from that trip, you can get another job because it's a pretty short trip. Trip and like you'll get this life experience and then you'll just come back and continue on your path. And there is this other group of people that started to really question my decision making. Why are you doing this? That's irresponsible. Are you sure that's a good idea?

And the more questions I got like that, the more thrilling this adventure became. Somehow I've never been rebellious in my entire life, and those types of questions started to help me question myself about when this trip does end, what am I coming back to? What is the life that I'm trying to create for myself, and how will I get there? And so I left for that trip with those questions resonating in my mind.

[10:33] Paul: That's such a powerful reflection. It's, it's so interesting too. It's so common in people that sort of take a leap or make a change, you, when you take a different path, often those people weren't actually super, like, they weren't actually worried about you. What they were doing is telling you their own insecurities, right? They're telling you, hey, I'm afraid of retirement or running out of money and you're making me feel uncomfortable. Aren't you worried about these things?

And then at the same time, like, I don't know if this was your case, but when this was happening to me, I didn't have a story. And it did force me inwards. But at the same time, I sort of had to like run away from that because it didn't make me feel good to be around those questions either.

[11:22] Ali Greene: Yeah, I think the second time I quit my job, so I've been through this twice now, I didn't have a story. And so it was a bigger moment for me personally the second time around. I, I left a really amazing job for no particular reason. It was February 2020. And so really quickly, my story didn't matter. And so I was kind of saved by the global pandemic in a way.

But while people stopped asking me why I quit this job and what I had lined up and why I'd didn't have any plans. I didn't get to ask those questions explicitly, but internally, I was going through that identity crisis myself because I left a role that I prided myself on. I loved having that title attached to my name. It made me feel a lot of emotions. It was during the pandemic. So for the first time in many years, I was forced to physically sit still.

And as someone who also identified as a digital nomad, that was terrifying for me. Who am I if I'm not traveling every month to a different country? So now I don't have a job, I'm not traveling the world, and I'm sitting here alone with my thoughts. And so that experience that you're speaking to happened for me many years later after the first time where I conveniently had a story.

[13:00] Paul: Yeah. And I think what my experience has taught me is that what you're experiencing in those moments is really this inherent uncertainty of being human. Right. And for me, I— that uncertainty is still there. It's just that I have a better relationship with the uncertainty rather than seeing like a job is like the cure for that. Has this been a similar sort of relationship with uncertainty for you?

[13:29] Ali Greene: Yeah, I, I think so. I think what it's made me realize is if I strip away all of these things that society tells us I should define myself as— so if I'm not going to define myself as my job, I'm not going to define myself as this really cool flashy thing that, that I like to tell people because it's exciting and it's different. Why are those things important to me? And if I ask myself why instead of what, then I get to a deeper answer. And so while the uncertainty will always come and go, you might always be changing jobs, you might always be in different life stages where you can latch on to a word that you can use to identify yourself, the underlying importance that you place on those things may always be consistent in your life.

And so there's a game I started playing, which was if you have to introduce yourself to somebody and you cannot say what your job is, you can't say where you're from, uh, how would you describe yourself only based on your values, only based on things that are important to you? And if you know those things are true, And for me, they still change. And so that's how I know that I'm still in this, this moment of uncertainty. And maybe they'll always be evolving since humans are always evolving. But the more that those values stay consistent, the more that I know I'm ready to face all uncertainty in the world.

[15:02] Paul: I love that. Yeah, it's, it's a continued learning process. I think one thing self-employment and just living in different countries has been great for is that you don't run out of challenges or discomfort or things you're learning about yourself. And it just, it's led me to just be a little more content and at ease with everything, even amidst the chaos. Did you find you were somewhat prepared for like the pandemic or was that a different situation for you?

[15:32] Ali Greene: Yes and no. So in terms of working, it was really funny. I felt like I was very prepared to live in a world in which I was socializing with people and not seeing them in person quite often, because as a digital nomad, I was often traveling around the world and learning how to stay connected to people I had formed relationships with while they were in other countries, or my community back in the United States while I was traveling. And so That was funny to me that I had friends express how challenging it was to schedule in time to stay connected to people they cared about. For me, it just seemed normal. If you want to build relationships and maintain relationships, you need to do that regardless of where you are in the world.

From a work perspective, except for the fact that I was starting a new path personally for myself in my work. I went from being a full-time employee to a consultant to an author, uh, during the pandemic. Tactically, nothing changed for me. And, and the pandemic actually was a strong motivator behind that change because I saw so many people just like doing things wrong and just getting frustrated with things that I forgot they would get frustrated by because I had lived it for so long and, and saw that it could be really easy. And, and so I felt this strong motivation to help people get the experiment correct, um, and so that they could experience all the benefits that I had had previously. So those things didn't change for me.

What I did notice, and this made me feel more connected to those core values that I defined myself by, um, was that I, I really struggled with my lack of freedom during that time. I, I spent the bulk of the beginning of the pandemic in a country where they had very strict restrictions, and I was only allowed to leave a studio apartment for 1 hour a day to walk within a 1-kilometer radius from my home. And I joked that I was like a caged lion and I had all this energy and I didn't know what to do with it. And I realized that my core values of having like freedom throughout my day to make very snap decisions on where I wanted to spend my time wasn't easily accessible to me. And that was something that brings me great happiness. I realized that my connection to nature was being taken away from me.

And that was something that brings me great happiness. Um, to only walk within a kilometer of your home, you're not spending a lot of time unless you're lucky enough to live in nature, to be out in the trees, to see water, to hear animals. And those are life's little pleasures that I strongly value. And so I struggled with those things and felt that they were harder to explain, because while I was struggling with that, people were struggling with, how do I convince my boss that we don't need to be on this Zoom call? Or how do I, like, how do I, you know, function if I'm being told that I have to work from 9 to 5 but I'm just sitting at home all day and I'm exhausted and frustrated and I feel super lonely and isolated because I don't know how to connect with the people I love without being able to see them in person.

So on one hand, I was very lucky and grateful that I had the skill set already to conquer those things. On the other hand, I was learning new challenges that I didn't realize about myself.

[19:28] Paul: Yeah, the pandemic was an interesting experience. I lucked out. The day before lockdown, we moved into a massive co-living house So sort of got lucky that we had space to walk around like in the house and we had a little yard. Yeah. So we lucked out, but we were in the Canary Islands in Las Palmas.

[19:50] Ali Greene: Were you at Nines?

[19:53] Paul: No, we were at one of Nacho's places, Nacho Rodriguez in Las Palmas. But yeah, it was Pretty good. I'm sure we have some connections in common. We'll have to figure that out later.

[20:07] Ali Greene: But I feel like most people that spent time there really enjoyed it.

[20:13] Paul: Yeah, it was pretty good. I can't complain. But I'd love to shift gears and talk about the remote work stuff. So you quit your job the first time you go on this trip to Machu Picchu. Travel is sort of this cliché thing, but I also think it's this sort of like break from work that actually works with a high degree of success. And I think it works not because of the travel, but because of like the extended time away from work and you start just like reflecting and coming up with ideas.

So on that trip, like how did you start refactoring and rethinking about what the next steps were for you?

[20:53] Ali Greene: Yeah, so that first trip, I think it was part luck that led me to the next stage of my career, I happened to be in a situation where the reason I left my first job was not necessarily because I didn't enjoy the, the nuts and bolts of the job. I just didn't like living in New York and I didn't like working in an office. And there are all these extenuating circumstances that the world— I think I was a little bit too early in the world to explain. Why I wanted to leave that job. And now I think I can easily say to people, oh, there wasn't an option for remote work at that job, so I had to leave. But I didn't have the vocabulary for it then.

It just so happened that the company I was working for at the time that I was thinking about leaving, other team members of mine also were on their way to their next career stages. And so after a really lovely conversation with the VP of HR at that company, we decided that after this trip, you know, if I stayed in touch with them, if they couldn't find my replacement by the time I got back, that I could consult for them and help them with projects wherever I was until they could hire and ramp up the person that was going to fill my role. And so I remember sending a few emails and like the hostels that I was at, checking in with them, like, you know, just trying to keep one hand and one foot in the door.

And, and that was my first taste of what it felt like from an intellectual standpoint of remote work, because I was here having this amazing life experience, but also then was remembering to like check in and send emails and be thoughtful about like, oh, what about these types of projects or what's going on on like with this and, and just build that relationship and have that communication. And it felt really easy. It was like, okay, like this day we're not doing anything, I'm hanging out at the hostel, like I can easily send a few emails, no big deal. Um, and, and so that got sort of my interest piqued in, in what it meant to be a remote worker. It was also on that trip I had started to, to meet people for the first time that were traveling and working at the same time. And I was like, what is this?

Like, I didn't I didn't even know that was a possibility. And so as it happened, that's exactly what I did when I got back from that trip. I, I moved back to Michigan, which is where my family was, but I did do some consulting for that old company and continued to do projects that were interesting well beyond them finding my replacement as a partnership with that person. And I also was a waitress for a few weeks and I worked in a bakery and I did all these other things to just explore and like see what was going on. Um, and then I did another trip to South America and I backpacked again. And then I started to do even more consulting and take that aspect of life more seriously.

And so it was this very meandering time in my life where there were lots of things going on. And not a lot of direction, but a lot of life experiences until I finally landed in Philadelphia and I finally landed my first full-time remote role. And I can't pinpoint, and I'm sure you have similar memories, exactly what was the catalyst or what was the experience that led to the final kind of stepping stone. Of that ultimate full-time remote position. But when everything finally fell together, it felt like that was the next experience I was supposed to have.

[24:54] Paul: Yeah, it's so hard to pinpoint those moments. Everyone asks you in interviews, when was the moment you decided, right? And I think similar to you, I had this very meandering path. Was there something though, like a sense of like excitement or a sense of possibility that was like pulling you forward through all of that?

[25:12] Ali Greene: There was a question I kept asking when I was interviewing at companies because after my second trip to South America, I had decided that I probably should find a place to live again. I liked Philadelphia, I wanted to try it out. So I started interviewing at companies and I would ask them, is it okay if I come into the office whenever I want? As long as I'm getting my work done. Because I still didn't know that you could be a full-time remote worker. I still didn't know you could be a digital nomad.

So I thought the best I could get is I show up to the office whenever I want, I leave the office whenever I want, I have sort of this like high degree of flexibility. And if I find a company culture that aligns with that value, then I can design my life around that. And so I started asking in interviews trying to get a job, that question, a lot of companies would not hire me.

[26:13] Paul: Like, they were like, 2015, right? 2015, 2016, about, about that time.

[26:19] Ali Greene: They're like, you have to come into the office.

[26:21] Paul: Like, if you don't— it's like, they're like, yeah, you can show up between 9 and 10.

[26:26] Ali Greene: Yeah, they're like, that's not how work works. Like, flexibility, sure. Like, uh, you can go for lunch whenever you want, Um, but like the level of flexibility I wanted just didn't exist until finally I met the CEO of DuckDuckGo and he was like, yeah, like most of the people don't even live in Philadelphia that work here. Like you can do whatever you want. I was like, yes, like finally someone who is like a CEO of a company believes what I believe and is actively hiring a people ops person to continue to build and grow this culture. And so the moment for me wasn't a positive moment in the sense that it was— I mean, it was in the sense that I met Gabriel and all of a sudden I was like, oh, this company is doing something really innovative in terms of company culture.

But it was a pain point leading up to that, which was interviewing at all of these other companies and being told that I was— had unrealistic expectations or that I was being entitled or whatever the reason was that I wasn't a good culture fit, you know, things like that.

[27:33] Paul: It seems like you had this hunch that like you had this taste of, okay, I'm working remotely, this different life. I don't want to give this up. I'm going to like try and find something that might be able to. And then like DuckDuckGo comes along and you're like, oh, I was, I was like missing this whole world that existed. Now this is possible. Then you get the job.

Did you start there right away in people operations?

[27:58] Ali Greene: So I worked with them as a consultant for a really long time. I can't remember the exact details. I feel like it was 6 months before we finally, like, committed to each other. I loved that whole, like, process of interviewing and consulting with them before making the leap to employee status again. Um, I also worked remotely for them, but lived in Philadelphia for a year before I became a full-fledged digital nomad, which was another interesting thing. Like looking back, I had went to university in Montreal.

I had done all this moving around growing up. I lived in Washington, D.C. I lived in New York. I lived in New York a second time in my 20s. I had done all this moving around. And so by the time I got the job at DuckDuckGo, like, I think any other person that knew me could have told me that I would have traveled and worked full-time, but I think I needed that year to really hone in on a remote work skill set before I brought travel into the mix.

And I'm— glad that I had that experience of living in a city and working remotely because now as someone who advocates for remote work in lots of different setups, I'm happy to have experienced doing it close by to an office location in a pretty normal routine as well as living this digital nomad life.

[29:36] Paul: What does a remote work skill set mean?

[29:40] Ali Greene: To me, it means being really bold about setting clear expectations and not being afraid to clarify what your boundaries are. I think that takes a certain level of self-awareness, trust, and confidence that a lot of people don't learn entering the workforce because they're being told always what time to show up to work, how to work, when to leave work. And so you have to relearn all these things about yourself and all these preferences about how you like to get your work done that you wouldn't know otherwise. And then you need to also learn how to communicate it in an assertive but non-threatening way to your team and your peers in a way that makes everybody feel included and respected. But also getting everyone's needs met, which isn't always possible, especially working across time zones. So that's a huge one.

Secondly, a shift to asynchronous communication and patience, and you're not going to get all of the answers immediately, and you need to write down your thoughts, and then you need to focus on a different set of work or take a break and get back to it. So this disjointed workday and how to feel comfortable Navigating that is an important remote work skill set from my perspective. And then the third one I think is really this mixture of like tools plus empathy. It's how do you interact with the tools that you use to optimize them to get your work done and then understand the human element behind the person that's using that tool. And have empathy for when mistakes are made and that people are probably also just rushing to get things done on their end because they have lives outside of work.

[31:32] Paul: Yeah, I love that. It's a lot of people's first dose of remote was what I've been calling pandemic remote, which is basically just a dumpster fire of hacking things together. And what most companies settled into, which was quite disappointing to observe, was basically this let's just try to recreate office life on the internet, which doesn't actually optimize around some of the benefits you can have from being remote first, which is increased time to kind of work in more deep work stretches, asynchronous communication, all this. What was it like watching some of the organizations sort of make all the same mistakes that maybe you had learned years before?

[32:22] Ali Greene: I mean, that was my biggest fear for life. Like, that sounds super dramatic, but that was my biggest fear for life. Um, when I started working remotely, I pushed that remote work was going to be a thing for a subset of people always moving forward. I had never imagined that we would be talking about remote work in the way that we're talking about it today. But I look back at my career and because of the internet, because of things being saved to the cloud, we have always had the ability to work remotely since I have entered the workforce in terms of the technology has existed. For me, it's always been about societal norms control, like how we're shifting what it means to think about work and the way that work should be portrayed in our life.

And that's a really hard thing to shift. That takes possibly generations to move the needle on. And so I always felt extremely frustrated by this. Which is why I wanted to be a digital nomad. It's why I wanted to travel the world and work. It's why I wanted to work at odd time zones and, and really flip the script on everything I was doing.

And so when I saw the shift to the pandemic happens, it was two instant, like, instantaneous thoughts. One was, finally people are talking about remote work. And then, oh shit, if everyone's talking about remote work, and they all do it in a way that fails, we will never get a chance to prove to them that there is a right way to do this. And if we cannot prove to them that there's a right way to do this, then future generations of knowledge workers will not get the chance to experience the true benefits that I have gotten in my life. And that made me really sad and really pissed off and really scared and then also really motivated, which is why I ended up writing a book to help managers and companies help their teams get better at remote work so that they don't have to sit in front of their computer from 9 to 5 every day waiting for people to ping them and waiting to join Zoom calls.

Because if you're just attached to your computer all of the time, you're missing out on so much of life and also of work, but more importantly of life.

[35:03] Paul: Yeah, it's so hard to pull apart what people are actually talking about, right? So a lot of what I write about in my book is we don't really have a definition of what work is, but what some people mean by work is basically performing like a ritual and sacrifice as part of their life. So for some people, work is not actually the content of what they're creating. Right. It's the performance of a role in society. Right.

They're showing their commitment to this work job thing. You commute as part of that. You go to an office as part of that. And it's almost like borderline religious how people are like stuck and tied to this. Whereas like you go all the way to the other end of the spectrum is like it's just this, this work. You're just producing output, right?

That's like almost just as toxic as well, right? Because it sort of takes apart the human element. And says it can be automated and turned into like these systems and processes. But it's like basically we need to tease all that apart. And it seems every company is sort of making this decision. The smart companies are saying like, what is the best possible way for like our people and our company to thrive?

And then they can work backwards and say, well, how do we actually design our systems, our processes, and our people organization to achieve these results? And then other companies are still just stuck in that frame of, okay, work is this ritual, ritualistic, like performance. And they're like stuck in this weird hybrid, like mishmash of a bunch of different things. And like, people are so frustrated at these companies, but it does seem to be working out. Like, it does seem like companies are stuck. It seems like a majority are either hybrid or fully remote.

And are having to slowly figure out, oh, okay, we need to redesign our processes and operations. Are you optimistic now in what you're seeing?

[37:06] Ali Greene: Yes and no. I think it stems to your first point. I actually don't care where companies fall in their definition of work. If a company is fully committed to it being a ritualistic process for them, I don't necessarily want that in my life, um, but I respect that as long as they can be very clear and very honest in their definition that to them that is what work means. They can clearly state what rituals within the work process they value and they pay against, and you can transform some of those rituals into things that fully align with a remote work culture.

And so instead of a commute to show how dedicated you are, a remote work company that really values themselves on the rituals of work can have a culture in which they have documentation where when people see something out in the world throughout their daily life that reminds them about how to make a company process better or how to make V2 of a product better, that people are submitting ideas into that portal and there's constant influx of that. And the more influx you have, the more dedication you have, the more of a ritual and tie you have to work. I'm not saying that's good or bad. I'm not saying that's a place I would work or not, but I'm saying that's how you can show a value of dedication and a value of ritualistic work, if that's important to you. On the other hand, you can be a kind of company that says, hey, all we care about are these outputs. Here are the KPIs.

Here are the dates that it needs to get done. Do whatever you want whenever you want, as long as asynchronously, like once a week, you show us progress towards these KPIs. And like, if that's true, um, that could also work in an office or not. Where I have a problem with companies and with work is when what they say and what they do are not aligned. And that becomes increasingly important in remote work because you have less opportunities to mimic people you see in the office. And so you need to be sure that what people say, especially at the leadership level, especially at the management level, and what the company values in terms of promotions, in terms of written documentation, sharing knowledge and information so you can get your work done.

All of those things in action need to be the same as their words. And so hybrid, remote, not remote, do whatever you want. I just think all companies still need to be way more intentional about that skill set.

[40:09] Paul: Yeah, it seems like remote is a big opportunity to sort of make the implicit explicit. Like, I think back even to my time in consulting, there are pretty clear paths, but you had to be in the office and sort of like catch up on the gossip to figure out like what was really happening. How do people really get promoted? Like the truth behind like the higher level ideas of like how promotions happen. What, what did you do at DuckDuckGo in terms of doing some of these things? I know writing is a big thing for a lot of remote and distributed culture, but what were some of the other things that you guys either did well or tried to get better at or struggle with and some of the tradeoffs you might have had to deal with?

[40:59] Ali Greene: Yeah, one project that took me— it was an evolving project, so it took me my whole career there. ongoing iterations that I was really proud of and think they did well was the explicit expectations based off of your role in the organization and not role in terms of are you a designer or are you a developer, but more so if you're an independent contributor making this type of salary at this certain level, this is what we expect of you. In terms of your project management capabilities. This is what we expect of you in terms of your ability to ask questions in the organization and to make processes better. This is, or what we don't expect of you rather, at the case of a junior level independent contributor. Um, and it was very clear down to the point of like once a week you share status updates, um, in written format in this particular Asana thread.

So they're as detailed and as explicit as that. And everything we did went back to those shared expectations that everyone in the company held. And so you would get promoted based off of those expectations. Anybody in the company could, in a kind way, call you out on those expectations in the sense that if you're a you know, working in people ops like me, but you were super interested in design, which is also true about me, and you were curious about the project of a new campaign that was going on. If there wasn't an update on Friday, it was acceptable to ask like, hey, what's going on with this project? I'm really curious about it.

Like, I'd love to learn more. And that was like a trigger that somebody wasn't living up to the expectations of being, you know, a corporate citizen in a way. And I think everyone sharing those things and having them be explicit took away from a lot of things I've seen in other organizations in terms of politics, in terms of people getting their feelings hurt, in terms of potential microaggressions about who's asking you questions and why, or feeling like your toes were being stepped on. It let you realize that people were asking you because they're genuinely curious in that project. and I thought that was really cool and just kind of easy. I knew that I had to do a certain set of things and I, it took the guesswork out of it.

[43:30] Paul: What are the meta processes like for talking about the process, right? So you have like, here's how we do things. And then I think the biggest mistake I see companies make that have shifted to remote is they literally have no one responsible for like talking about the process of how they work. So what was that like? Were you in constant dialog with the CEO, other people? Was there a team dedicated to this?

[43:55] Ali Greene: It depended on the situation and depending on the skill set needed. But there was always someone directly responsible for whatever the project that was happening. But to bring it to a more current example, even in a team of just two, me and my coauthor right now are doing that exact same process. For ourselves. And what's really funny about creating processes to work remotely with two remote work experts, uh, like using that term kind of with the quotations around it, is that I came from a background of this very like kind of strict, uh, regime of using Asana in a very particular way. My co-author comes from Automattic where they use their like internal blogs in a very particular way.

And so we both are very confident with asynchronous communication. Both of us are very clear on the importance of documentation, and both of us love a good process, but agreeing on what that process should look like from two completely different worlds is a project. And so for remote companies, like what we're learning is we thought we could just organically have it happen because both of us were so comfortable and we were on the same page with the importance of it. The, the bigger decisions of like weekly updates, uh, asynchronous as much as possible, meetings to build relationships and to brainstorm, but not just to do status updates. Those are kind of these sacred rules of remote work and we believe those and we teach about those. But when it came to the two of us getting the work done for the first time, we couldn't just assume it would happen because when we did that, we failed.

And it wasn't until we learned from our own teachings and we said, we need to treat this as a project. So I'm going to be the DRI for thinking about how we look at project management and create a project management system.

[46:02] Paul: What is DRI?

[46:03] Ali Greene: And DRI being like a directly responsible individual. So of the two of us, if one of us isn't in charge, neither of us is in charge. So me, Ali, I'll design how we come up with project management and you'll come up with how we do our brainstorming and then we'll get back together and we'll talk about it and agree on it so that we have clear expectations. And that was a sprint that we did with each other because we realized we can't organ— even the best people at remote work can't organically come up with processes if we don't sit down and treat it like a project. And so that was something that we did recently.

[46:40] Paul: I just want to pause you there. So you're saying stuff I'm familiar with when you say like, this is a sprint we did together. Can you just sort of bring a little more color to that? So you're working with her on this book project. Like, how do you define a sprint? Do you have multiple sprints going at once?

How do you time How do you timeline these?

[47:00] Ali Greene: Yeah, these are great questions. I could get into so many small details. I'll try to save your listeners and be as concrete as possible.

[47:08] Paul: Let's go into it.

[47:09] Ali Greene: Okay, let's go into it.

[47:10] Paul: I love bringing alive the detail because a lot of people just talk about these things like we should do asynchronous work, but how do you actually implement that? I think that is really interesting and sort of underexplored. So I'd love to hear more detail.

[47:26] Ali Greene: Yeah, so we specifically decided, um, certain rules of thumb. So writing the book together, uh, we didn't need to do any of this. It happened so organically that by the time we, we got to the point in the book writing process where we wanted to launch projects, um, this is where this came up, where we were like, oh, okay, we need to start using our best practices of remote work. Like, let's get a project management tool in place, um, let's get a process in place. All of these things that we know we should do, even though we're just a team of two, like, let's do it. And so we sat down and we decided we are going to have asynchronous stand-ups, is a good example, which means instead of meeting where we go through what everybody's working on and give updates, we're going to do it in written form.

What that tactically looks like is that, um, she's a few time zones, uh, earlier in the day, so I kick it off when I wake up on Mondays. I fill out what my top priority, my most important thing is of the week, looks like. Um, because there's only two of us and we both really believe in like the freedom and flexibility of remote work, generally like what our work schedule looks like for the week. So for example, I'm notorious for this. I love going hiking on weekdays when nobody's out on the trail. And then I work on weekends because everything's really busy on weekends and it's hard to find parking and restaurants are loud.

So tomorrow, for tomorrow's Wednesday, I'm going hiking. I'm not going to work. So I would like say something like, oh, it's going to be really sunny tomorrow. Like this week, plan for Wednesday. I'm not going to work. So my heads down days are these days.

If we need to brainstorm or have meetings, here's my availability for the week. And I'll lay out all those details and she'll do the same. We talk about all of our ongoing other commitments, uh, things like this podcast, things like I've committed to updating our website, what are the next steps there, and then ask for help. These are the things that we need help with from each other. And when do we expect to get a response from the other person? And is that feasible?

Is that too much work for the other person that week? And so we do that all on writing on Mondays. And then on Fridays, we close it out with a recap of how far we've come or not. And so that's like our process of how we work with each other. And then we have one dedicated space where throughout the week, if anything comes up, that's not related to a specific project, if we don't know where to put it, we put it in that task and it's just our hub to communicate. And so that's one tactical way of how we get things done.

Another example is we also use Google Docs a lot for collaboration. And there used to be a Google Doc that she would make and it would have a lot of details in it. And then I would make a separate Google Doc. This is our process, taking all of her details, um, and making the high-level direction. So that's something that is more in line with my strengths. And then together, this is for like kicking off a new project.

So an example recently that we've done is we're building a new website. And so hers would have a lot of information about the, the, the branding. What kind of designs we should do, what information should be in there, um, aspiration and inspirational websites that we love, the look and feel of them, why we like them. Mine would be, we need to create a wireframe. Here are the 5 sections that are the most important. Here is the breakdown of the deadlines, like very strict project management stuff.

Um, So you can see how these two brains then come together. And then our process is once these two documents come together, we both read each other's, we'll have a meeting and we'll have this meeting be very like open and free flowing. We'll talk about things, we'll evolve the conversation. And during that meeting, a third document is written and that third document becomes like the state of law. And those are all of the final decisions we make and things that we're committed to. And then we have an area in our project management tool that's that third final document and then the two archive documents of like, how did we get to these decisions?

So if in two weeks I forget, why did we decide this again? I can go back and look like this and this topic led us to this final decision. And so that's a really unique way that works for us, but we sat down and during, uh, a sprint, which is a week where we just sat down and figured out how do we best work together? What does our process look like? We decided that is the way that we like to work together. And that's how it was born.

[52:40] Paul: I love this. So much good stuff in what you just said. And I think one powerful thing, which you sort of downplayed a little, is that how most people use meetings is people use meetings as like figuring it out time. It's like people use a meeting for like, we'll just talk out and then like figure out what we're doing. But I think when you're using remote work best and basically what you're describing is like you do all your thinking, like the work you do best, like the high-level structuring, the synthesizing, on your own, and then you show up to the meeting and then you're taking action on things moving towards that next document. Why, why are most— I'm sort of setting you up here in a direction, but like, why are most meetings in Zoom now wasted by many companies?

[53:34] Ali Greene: Oof. I mean, a lot of them don't need to be meetings. Like a lot of them, I think, follow— they follow a script. And there are scripts that they're used to having because it feels comfortable. It's, um, and it— no harm to them. It's based on best practices that people have taught, myself included at one point, about what makes a good Zoom meeting.

One is everybody should participate. The easiest way to get everyone to participate in a Zoom meeting is to let everybody speak. The easiest way to do that is to give everybody a chance to give a status update about their project. That's boring. Nobody cares. Like, you can read about that asynchronously.

Um, a more interesting way to get everybody updated, or to get everybody to participate rather, is read each other's status updates. What's one question you have for somebody else that will like push their project forward or get them to think about their project in a new way? That project has, that That kind of meeting has a lot more value because you're challenging each other. People don't necessarily like to be challenged. I think that's when teams and managers get a little scared. They're afraid it's going to mean conflict and tension.

And we talk about this in our book. We talk about the difference of like people tension versus task tension. And I think really healthy remote teams recognize their differences. Like me and my co-author, I know that she has this amazing like creative brain and she can get into this like meat and details of stuff. And then I can pull it out into an outline and have it be really structured. If I start from my structured outline, I will sit there for days trying to make it more detailed and I will get frustrated and annoyed at myself that I've made zero progress.

And so I need her. Um, and we need to come together and have sometimes this creative tension of like, okay, How do we take this structure and add more detail? Or how do we take this detail and add more structure? Like these are two opposing forces coming together for good. And if you build trust, which is possible remotely, like when we started writing the book together, we hadn't seen each other in person in, in years. If you have enough trust and you can be honest with each other, you can criticize each other's work because you're making questions, you're making constraints.

About how to make things better. And it's not about the person at all. It's about we believe so much in this end goal. We believe so much in what we can produce as a team and what this company is doing to better society or the mission or the widget we're producing that we want to make this the most awesome widget possible. The only way to do this is to challenge each other to make it even more awesome. So why don't we make our team meetings— this is just one idea about questioning each other's work or offering feedback, but to just give a status update like you can read that, that's a waste of time.

[56:36] Paul: Yeah. And this, this like obsession with excellence and kind of high standards, to me, that's sort of independent of remote or not remote. I've worked in companies in office that are great at this and not great. But I think the stakes get larger if you go remote without that culture because there's going to be more friction, right? And people are just going to give feedback less. What have you learned about increasing the flow of communication and high-quality feedback in a remote culture?

[57:10] Ali Greene: Ask and know about yourself how you prefer to get feedback given to you and what your natural tendencies are. I think that takes a long time for people to be really aware of. So something to know is, do you prefer to see the feedback written down for the first time and have private time to absorb it and then be able to go back and ask questions? Or do you want to have a conversation and have that back and forth immediately with the person you're talking to so you can have that human element right away? If you're working with someone remotely for the first time and you're not asking these questions, how do you like to receive feedback, you've already made mistakes. If you're working remotely and you don't know about yourself these answers to these questions, you're making mistakes.

And, and there aren't mistakes that can't be solved. Of course they can. Think about a time where someone gave you feedback off the cuff, how did that make you feel? Like, were you prepared? Did you like it? Did you roll with it and have a nice conversation, or did you shut down and feel the need to defend yourself?

Why or why not? These are ways that you can start learning about yourself so that you can start to guide other people on how to best interact with you remotely. And then again, think about that tools plus empathy equation. There's written, obviously, as a format to use. There's limitations to the written word. It's very direct.

If you're someone who just wants to be direct and you're okay with that, throw in a few emojis, like, whatever. But you can also incorporate things like Loom and really show empathy and facial expressions, walk someone through the work and show them the types of feedback that you're trying to give visually. And let them listen to it and watch it on their own time. And that's where, again, the world continues to open up because of the tools that we're using today.

[59:12] Paul: Yeah, there's been so many good tools. I love using Loom. That's helped me so much in just working with like contractors and other people. What— talk to me about your book. How, how's it going? How are you enjoying writing a book and what sort of themes are emerging?

That maybe surprised you or have been interesting threads to follow?

[59:35] Ali Greene: Yeah, writing the book has been amazing. So as I mentioned, me and my coauthor were writing it. We're two different time zones apart, an ocean apart. So it's really been practicing what we preach from a remote standpoint. What's been awesome about watching the book unfold is just seeing it come to life from First, our frustration and our fear that people weren't going to get remote work at the pandemic, uh, then it shifted into how can we help them and inspire people to do this in a way that really works for them. And so not prescriptive at all in terms of do exactly these 5 things and you'll be an amazing remote worker.

And so What was awesome in my collaboration with Tam is not only did we tell our personal stories from our time working at remote companies, but we also interviewed, um, over 30 other experts at remote companies, um, that were remote before the pandemic, during the pandemic, after the pandemic, all these different varieties of people to see what was working well for them in their remote processes. And we realized while people oftentimes had the same goal, how they implemented that goal could be different. And so my favorite part of the book is that it's like a management workshop that you can do without having to schedule a workshop. You get the book and there's lots of activities that you do with your team to figure out what the tailored right answer is for your unique company.

There's reflection questions that you can have to either think about independently as a manager or to bring back and discuss with your team. And so really through reading this book, by the end of it, you'll have a roadmap of how to operate as a remote team that's completely unique to a different team reading the book because of the results of these workshops, these reflection questions, um, the activities and things of that nature. Also, there's just a lot of, you know, really relatable and funny stories in there as well. And what I was always missing as I was trying to climb that corporate ladder at the beginning of my career was books that I felt were for me in the management space. And I always felt they were— the books that were written about business were so unreachable. And so one of my goals was to just make this one a little bit funny.

There's, there's a few random puns in there. but to just make it fun so that people could learn and laugh at the same time.

[01:02:15] Paul: I love that. What, what are the smartest, most forward-thinking leaders get right that have impressed you?

[01:02:24] Ali Greene: So the best leaders get right in not thinking they can manage for every situation the same and not managing every person the same. And what I mean by that is You have to think about the term manager different. So in the old way of working, a manager was someone who responded to PTO requests and said if you could leave work earlier or not and delegated projects to other people. And in a remote environment, a manager can be a connector and someone who's helping people learn how to connect to company culture, to a network of people, who to know for what, they help build culture. A manager can be someone who project manages and who executes work very well and very efficiently. And so you want to learn from them because they have this really unique skill set at a tactical level.

Um, and so there's all these different situations and different hats managers need to wear. And then also each person is different. And so you have remote workers like me who thrive on different situations. They need to travel. They like working at different time zones. They want to take Wednesdays off and work on weekends.

and so that person might need less of a personal check-in throughout the week, but will always potentially need help if they want to improve on a project or if they're personally struggling versus someone who's really new to remote work, who doesn't yet know how to take these little experiments with changing around their work week, who might feel isolated working remotely, and that type of manager might need a little bit more of a personal touch with that employee as they're getting started. And so the, the best leader in a remote workforce will know that each person is different and each situation is different, and they will adapt accordingly.

[01:04:15] Paul: So a couple rapid-fire questions. The first one I want to start with is, who is a path role model? Somebody you look up to on a similar path or somebody that's inspired you on your journey?

[01:04:29] Ali Greene: This answer may be like clouded by judgment, but I would say my partner. He threw the standard checklist out the window and now inspires other people to do the same and has definitely inspired me along my path.

[01:04:47] Paul: Awesome. Yeah, I'm very inspired by my wife as well. So it's great to have somebody like that to inspire you close by. What is a book, piece of content, something that's inspired you in the last 6 months?

[01:05:03] Ali Greene: My whole entire life, actually, the book The Giver. And it's a book that I constantly reread. And every time I read it from childhood to adulthood, pick up on things that make me look at the world differently.

[01:05:16] Paul: So this question might not be a rapid one, but what's wrong with the 4-day workweek?

[01:05:22] Ali Greene: Oh, so, uh, for me, the 4-day workweek is a form of golden handcuffs where it's saying to people, um, look, you're getting more freedom and flexibility with your time. You only have to work 4 days. But if you actually pull the veil away, it's not giving people freedom and flexibility because it's telling people they have to work 4 days a week, and maybe some people prefer to work all 7 days a week. They just wanna work less hours every day. And maybe some people want to work 2 really long days a week because they like to have very intense sprints and then need long periods of rest. So assuming that everybody will benefit from 4 days, whether it's 32 hours or 40 hours, is assuming that everybody works the same way.

And everybody needs the same type of input in order to get similar outputs, which is a false assumption.

[01:06:23] Paul: Yeah, I love that answer. I think I was very captivated by the 4-day workweek at first, but eventually realized this is just going to have the same problems as the 5-day workweek. Though I do wonder if just like the extra day of space might expand the imagination. So it's almost like a step A of like, more steps along the way. But yeah, I'm a little skeptical too. Like, I'd rather just have one month off at a time and still work intensely other parts of the year.

[01:06:54] Ali Greene: I'd rather just everybody choose for themselves what works best for themselves, even if it makes it more complicated to figure out with the team. But yeah, that's why I'm here fighting the good fight.

[01:07:05] Paul: Yeah. And I think that's what's so amazing about today's environment, and I think we dove into a lot today, which is like there isn't really a remote versus in-office debate. That debate is about like societal values. And like, in my eyes, it's more or less settled that like remote work is here and it's an option for many, many millions of people around the world. Now, companies have chosen, people are taking different paths. It's just that the stakes or the responsibility for the individual, it's way higher, right?

Because you have to sort of decide like, which path are you going to take? But the remote person office, like, to me, it's settled. There's many options. The majority of companies are either hybrid or remote. And if they're in person, you want to be in person, it's great because those companies still exist too.

[01:07:58] Ali Greene: Yeah. And now people have even more questions to ask themselves. So I was recently at a co-living and people still like, I was like, this is so cool. People are traveling and they're open-minded and, and they are so free, but they still worked so hard Monday to Friday and then crammed their weekend full of activities for themselves. And I was like, well, why don't you just do some of those activities during the week? Because I'm like selfishly a huge advocate of that as we talked about earlier.

Um, and like I got some blank stares and it really bothered me. And then I had to think about why it bothered me. I still don't know the answer to that. I'll let you know later. Um, but I just feel like now is the time for everyone to ask themselves questions about what's important to them. How do they want to live and be very intentional about like exactly as you said, like what path do they want to live?

But like explicitly, what does that look like? Like what is your Monday to Friday? Monday to Sunday look like? What is your 8 AM to 8 PM or whatever hours look like? Like, what does your life look like? And more importantly, why?

[01:09:06] Paul: Yeah, I love that. I, I mean, I wrote a book about this, so I'm a, I'm a fan of, uh, thinking about these things. But I think some of the discomfort is just that these scripts we're living out, like work Monday through Friday, are handed down like multiple generations now, and we're sort of disconnected from the culture it arose from. It arose from factory work, and we're not working in factories, we're working on screens now. So it's like we're still sort of performing this way of working, but it's not quite connected to the way we're working. I sense that's some of the discomfort, and I think we're still at the early stages of like awakening to this.

[01:09:48] Ali Greene: Yeah, I wish I had like a magic ball to see what exactly happens, like 20, 30 years out because I'm a little impatient.

[01:09:58] Paul: Yeah, well, I appreciate the work you're doing and I think it's great. What— where can people learn more? Where should they stay tuned about the book you're going to be launching next year?