The following is a transcript of our podcast conversation with Ali Greene. You can listen to the full episode on Spotify or Apple Podcasts.
Sarah
Hello and welcome to Humans Beyond Resources, an HR podcast by Reverb where we cover topics from culture to compliance. Reverb believes that every decision a leader makes reverberates throughout the organization, From hiring your first employee to training your entire workforce. We believe in building healthy, inclusive cultures that engage your team. I’m your host, Sarah Wilkins. We’re excited to be talking about remote work and remote work fluency with Ali Greene in today’s episode. Ali has been working remotely since 2014. She was previously the director of people operations for DuckDuckGo and was the former head of culture and community at Oyster, where she hosted their distributed discussions podcast. Ali was named a top 50 remote accelerator in the 2022 and 2023 remote influencer report. Ali’s mission is to empower people and companies, helping them thrive and making work and life better. Welcome Ali. Hello, thanks so much for having me. Great, yeah, I’m so excited to hear about this because I absolutely both love remote work and the balance that it brings and the flexibility. And also I am a person who really appreciates getting in person with people. So I’m excited to talk about kind of both of those topics with you today. So first, will you share a little bit more about you and your book on remote work.
Ali
Yeah, so you gave a great professional overview of what I’ve been up to in my journey for remote work but it also is incredibly personal for me. So very early in my career, I moved to a different state for my first job. And I had this experience of what it was like to really shift around everything I knew my friends, my community, my daily life, my home for a job. And then a couple years later, I relocated once again for a job to New York City and thinking that, this is what success looked like. And I really got disenchanted quickly. I had an over hour commute to get to an office by 8 a.m. I had to walk to a subway to take another subway, feeling like a sardine with every loud, smelly other person in New York City, and I hated it. And I finally gained the courage after one year to let go of my lease and to quit my job. I felt that desperate that I couldn’t do this rat race anymore. And it just so happened that luck stepped in and there was an opportunity to stay on with my company but not live in New York anymore. And so that was my first taste of what remote work could look like. I transitioned to more of a consultative role with them. And I backpacked South America because I needed a cool reason to leave New York City. And while I was backpacking South America, I met some people that were doing work on their laptops before a hike to Machu Picchu. And it was interesting because I had been finding hostels with Wi-Fi so that I could connect and keep in touch with my company and plan what my next project was going to be in email. And I was like, oh, hey, like this person’s doing everything related to their job anywhere and it doesn’t matter. And so for me, finally, like I did my travels, I moved back to the US. And I was trying to settle down one more time. I’d already tried DC. I tried in New York. So I was like, okay, where’s next? I’ll try Philly. It seemed like a good choice. And it was one of those things that I knew I was going to try to personally settle down, but at that point, flexibility was a non-negotiable for me professionally. And companies were just not getting it. They weren’t getting that I didn’t feel productive going into work certain hours of the day, that I needed time outside with fresh air to recharge my batteries so that I could be energetic and focused and listen to people in meetings. And it was really hard for me. And then finally, I met the CEO of DuckDuckGo and our values just really aligned around adults should just be adults. People should be hired because they care about the mission and they want to do a good job and it doesn’t matter where and to an extent when they get their work done. And that is the basis of remote work. And so years later, I saw this giant argument pop up again in the media, a little pandemic happened worldwide. And it really freaked me out, not for the reasons that most people think, but because I saw people being forced into a giant work from home experiment. And me and Tam, my co-author, had been working remotely and traveling for years. We had met a couple of years before that in Cape Town. And we were catching up personally, and we were just like, what is going on with these companies? I know that they’re new to remote work. I know that people are being forced home and that it’s scary times and this is not real remote work. Why is everyone so bad at it? And I had this pit in my stomach that said, If companies don’t get better at the skill sets required to work remotely, if teams don’t believe that this is possible, nobody will be able to have the personal benefits that I have had. I have traveled the world and worked remotely. I’ve been promoted and excelled in my career while living in different countries. I met my partner, I made friends. Everything that I’ve done in my life, I’ve been enabled to do because of remote work. And I want other people to have the opportunity to shape their life according to their values and their beliefs, not just where they happen to find a job. Um, and so that was really the inspiration behind remote works. It’s a, it’s a very actionable book. There’s lots of exercises and reflection questions and ways to make it personalized, knowing that each company is now approaching this whole thing differently.
Sarah
That’s great. Thank you so much for sharing kind of the whole backstory. And so we all kind of come from the same place. Will you help define those things? Uh, you know, remote work, remote work, fluency, uh, from your perspective.
Ali
I love this question. I love defining things too, because I think so much of communication and this is a core skill in remote work is being on the same page with people. And you can think of a common word and define it really differently. For me, remote work is using tools and technology to enable you to work from anywhere, from wherever you want location flexibility, as well as time flexibility. So working in a way where you’re intentionally designing the sharing of information between stakeholders so that nobody’s held to a critical responsibility of being always on. And then leaning into that time and location flexibility to also have flexibility over how you get the work done, how you prioritize things, and how you work according to what motivates you the most. And so really thinking about it as digital first, using technology to enable you to work, rather than focusing on where you’re located or when you’re getting the work done. And so I think there’s other tool like terminologies that are being used, work from home, for example. I don’t particularly like that because you can work at coffee shops, you can work at coworking spaces, hybrid work. I think, again, like I don’t particularly agree or like that terminology because it’s so focused on office and not office when it’s really should be about even if you are using an office you’re still having remote work fluency. You’re still using the tools and technology to enable flexibility. And so when I speak to the term remote work fluency, what I’m specifically talking about is a combination of a skillset, a mindset, and behaviors that come up in your day-to-day work that allow you to embrace a world where people could have the flexibility that we’re talking about. And so again, it goes back to, you know, what are you doing? What are the activities? How do you do it? What are those behaviors? How do you intentionally think about it? That’s the mindset. And then working out that muscle, like, is it coming naturally to you over time? Are you learning and growing professionally and personally? Do you have the skills? Or are you just copying and pasting what was happening in an office and like trying to do it anywhere. And that’s where I think it’s get messy and they don’t work and people get frustrated and we start to have conversations around, okay, what do we do? Do we go back to the office? And then I’m like, well, it’s because you don’t have remote work fluency.
Sarah
Yeah, I love that term. And like you said in kind of your intro around we all were kind of forced into this experiment, right? That wasn’t the norm, you know, remote work three years ago. And then we all kind of went into it and we couldn’t do things the way we did in office. And I think we’ve noticed and some companies and people are flexing and learning new ways of doing things and I particularly like what you said about both location, but also time. Cause I think often when we think about remote work, people think about location of where someone’s working versus the time flexibility around what works for them and setting up more asynchronous ways of working so people can kind of be brought along and, you know, at the times that work for them.
Ali
Exactly. Yeah.
Sarah
Going a little bit further and to kind of talk more about like, what should companies be doing or organizations or employees kind of, kind of digging deeper into that remote work fluency? What’s critical for those organizations to be having in place?
Ali
Yeah, first and foremost, I think that you need to start to understand a concept of intentionality, in order to work well remotely, you need almost to become an architect, a designer, and someone who is a caretaker of the employee and stakeholder experience. And so that’s something historically in offices have been left up to chance or accidents and people have a nostalgic viewpoint of that the accidental bump in at the water cooler popping by someone’s desk to ask them a question that actually is a really disturbing boundary to just walk over to someone’s desk and ask them a question. You don’t know if they’re in their like heads down focus time. You don’t know if they’re in the right like energetic or emotional state to answer your question. It sounds very simple and casual, but it’s quite invasive in terms of boundaries. And so when I think about remote work, and I think about how you design remote work, everything stems from intentionality. As an organization, how do you want to design things and what are your goals? So do you want people to, you know, we talked in the intro about like we’re both social people, we like being around people. How do you design for that to happen, not just with people in your organization, but in your life in general? What are the types of policies, procedures, ways of interacting with each other that can empower you to seek that out in different ways. And so first and foremost, having that mindset around intentionality comes into play. And then, you know, sometimes leaders don’t really like that answer. It seems very vague to them. They want to know, okay, but what can I actually be doing differently to be really good at remote work? And from there, I think about things like increasing your self-awareness as a manager and for your employees, creating really strong standard operating behavior. So what are the team norms? Can you explicitly write them down and share them and document them on a team? Speaking of documentation, like it’s not glamorous. It’s so important. Make documentation part of your work and then you don’t need to do it later. And so having that that skill set to document things and that mindset of always be documenting is incredibly important, tangible thing. Better writing skills, asynchronous communication is something we talked about to define that for people who might not know. It’s the ability to really talk later, communicate later. So not having everything be instant messenger. I emailed you, why haven’t you emailed me back? It’s been 10 seconds. The slowing down to do work faster is really unusual for people. And giving people that chance to have autonomy over their schedule because of these skillsets and because of these practices, having ownership over your own personal working style increases your performance. And so the more you can get better at documentation, asynchronous communication, self-awareness, the better overall you can be as an organization to move forward.
Sarah
One of the things you said in when you were answering this question was around people wanting to just walk up to your desk. And I hear leaders, you know, touting that as a benefit of, you know, coming back into a hybrid workplace. Right. And so the value of just kind of running into people or, you know, grabbing them and bringing them into something because they’re visible. But how do you kind of help leaders maybe change their mindset around that and, you know, and productivity when you aren’t, you know, seeing people or working at the exact same, you know, hours and times?
Ali
Yeah. So the first thing is I think there needs to be a reset around the definition of productivity, going back to definitions. People often conflate productivity and time management when they’re quite different concepts in actuality. Productivity is more about pushing things forward and creating value. So let’s say you are redesigning a website. It’s not about in 24 hours of the day, did you redesign the website? It’s about Did you first, you know, do a user diary study to figure out what’s wrong with the website and why people are clicking on the wrong buttons or why they’re not spending time on your website? Are you doing wireframes? Are you getting the mockups, you know, sent over to your design team? There’s breaking the project down into stages and moving things forward, that’s productivity. It’s not how many things you scratch off your to-do list, even though it feels really good, like I’m a scratcher offer. It’s great, it gives you that burst of like endorphins, maybe adrenaline, I don’t know what it is, but that’s not productivity. That’s just getting stuff crossed off a list. And if you’re putting the wrong things down on the list, then you’re just making yourself busy and you’re taking up your own time without needing to. And so the first thing that I like love around the conversation about productivity and remote work, that’s a mindset shift for leaders is don’t talk about time management, talk about energy management. And for me, that’s about, Do you know as a worker and do you know this about your team, what increases people’s energy so they feel more motivated at work and they’re happy to get their work done? There’s been studies that show that if you’re working in your peak performance hours, that you’re five times more productive than if you’re working when you’re not, you know? And that seems like a really strange concept to understand. I think about it like what’s something that you hate to do in your job and imagine forcing yourself to try to do it. It feels like it takes forever to get done. Versus if you’re doing something in an environment you love, you’re doing a task that you love, it’s like time flies when you’re having fun. And that’s what energy management is all about. So learning about your team, what are the times of days that they have the most energy? Do they get energy working alone in a quiet environment? Do they get energy working with people and in a loud chaotic environment? Do they get energy after they’ve spent time in nature or after they’ve had time to work out? Based off the different time zones where everybody’s living, we’re going to have our team meetings on this day at this hour. For some people it’s lunchtime. We know that’s an energy booster for you. So what’s something fun that we could do to increase that energy in the meeting? And it could be as simple as using built-in time in the meeting for social connection or for, you know, shaking your hands and do something silly together as a team and having that like vulnerability through like silly movement behind a Zoom camera. These are the things that I think people get hung up on because they try to create these things out of nowhere without intention. They’re like, oh, Zoom happy hour, let’s do it. Without thinking about, that’s just another meeting on a calendar. Maybe that’s an energy drainer. Instead, what’s a ritual that can give social connection, that can give that cross-pollination of ideas? That’s what people miss in the office. They don’t miss people interrupting you. They miss cross-pollination of ideas. So how can you do that in formats that already exist and build on those rituals. And so another example is in all hands, I think the worst all hand meetings for remote companies is watching someone present something to you on Zoom. Like just send me a video and send me a written recap and I’ll write questions down of what I have. Instead, what if you use that all hands to do breakout rooms and you do breakout rooms once based off of personal interests. You do breakout rooms once based off of a value in the company that you wanna talk about how you could have that come out more in company rituals. Do breakout rooms based off of what company objective do you know nothing about because it’s not in your sphere of work. And then you can have really engaging people with social interactions, impromptu sparks of, oh, you’re working on that project, this relates to my project, but it’s already in sacred time. So you’re not asking more of your employees. I feel like I’m now just like getting on this soapbox of lots of different ways that you can integrate these two concepts together. But I think this is again, where that designer mindset comes into play of how do you intentionally think about what you’re doing instead of just throwing something on a calendar because you see other remote companies doing it as a best practice.
Sarah
Yeah, I love that. And I think one example that we did actually is with our all hands. We were missing those moments of connection. And instead of adding, you know, yet another, um, meeting to the calendar, because, you know, we have a lot of meetings as a consulting firm with internal, with clients, with consultants, that doing that’s kind of draining. Like you said, we just added like set aside time to ask a question, like allow people to share. And it wasn’t work or, you know, it wasn’t always work related. It was, you know, just learning more about people. Um, So we could build those stronger connections. So I love that you pointed out, you know, that example, um, around all hands and like changing it up and, um, Kind of getting away from the presentation. I’ve also thought about that too. A lot. It’s like, if this is something that could be recorded and sent via, you know, a video to the group. Like let’s do that and let’s save the time that we have in person for more of that, you know, collaboration and time spent sharing ideas and, and moving things forward that way. Yeah.
Ali
And also I think like this is something I think about a lot, depending on the company size and what kind of company it is, like in your case, what are shared learnings from different projects that come out and like, how do you actually just like instill that knowledge for everybody or for certain companies like FaceTime with leadership can be incredibly important, especially for junior employees that like want to really know how to navigate their career in a certain way. And they see these like potential end goals if they’re particularly driven towards having more ownership or leadership in certain strategic areas of the company or people leadership. And instead of having that leader present something that can be delivered asynchronously, having that leader spend time with people, just chatting, like just let people getting to know you and giving them access to you, because that’s something that otherwise can be quite hard remotely. And even in an office, there tends to be this separation between top level executives and junior level staff. And I think remote work can even the playing field in terms of, okay, we’re all one square on Zoom. And how do we pass knowledge back and forth to each other. I’ve been saying on a few podcasts now, I don’t know anyone of the next generation of workers and I really want to get to know Jen Zee more, it makes me feel old. But I would love to know how they’re approaching work and what challenges they’re having. And I’m sure I can share like a lot of information around mistakes I’ve made in my early days like trying to, you know, get promoted and do different things in my career. And so knowledge transfer does go both ways. And I think that that’s really important to remember in remote work as well. It’s not always knowledge transfer about projects.
Sarah
Yeah, thank you for pointing that out. And then one of the things we touched on again, back to us being, you know, social creatures and loving to kind of get together in person. You know, this is something we’ve tried to figure out because a lot of the team, you know, really appreciates the remote work and the flexibility and they work their best in kind of their, um, the environment they have set up for themselves. But, you know, there are times that it’s good to bring maybe the team together in real life. If you are, what are the most important things to consider as to why, and then how can you maybe sustain those benefits of getting together in person after you do so?
Ali
Yeah, I love this topic. So in-person retreats might be one of my absolute favorite things. It’s something Tam and I have organized for Digital Nomads before we wrote the book together. So personally and professionally, this is something that has been intertwined in my life for many years now. I dislike that because of the past couple years people forgot that remote work, like it doesn’t mean that you’re always working like remotely and distantly from the people you’re working with. Creating relationships and building and deepening those relationships through shared experience is so important. And I think that remote work is one of those things where of course you’re opening up the talent pool And so there’s different considerations in terms of people’s comfort level with travel, their comfort level with spending extended time away from their families or with coworkers. But as long as you’re approaching things in an inclusive way, I love doing this by design again, like creating surveys to really figure out what people’s boundaries, desires, hopes and dreams are for retreats before you even start locking in dates and logistical things. And then setting expectations around, you know, what is the intent of this trip? You asked about different ways people can come together. I think people tend to default to twice a year meetups, once as a whole company and once as a team. I think that is like kind of a bare minimum approach. I like to think about it as a use case meetup. And so scenarios where I think it’s important to get people to come together that usually are remote in person is if there’s been a major shift or change on the team, all of a sudden you hire a lot of people or people have shifted roles to different levels of leadership or people have left the company and you need to redefine what that loss looks like on your team. That’s a great time to come together and talk about team norms. I think if you’re kicking off an incredibly strategic, incredibly complex, cross-functional project that has a big financial impact on the company. Getting together at some point in that project to ensure that stakeholders are on the same page, milestones are being met, any tension in working styles is figured out, is incredibly important. Bringing people together based off of just their shared interests so you can create a network effect in your remote company. Of course, you’re going to get to know your co-workers. You work with them quite regularly. But do you get together with people who really love hiking? Like, did you even know there’s other people that really love hiking in your company? And so I love the idea of having stipends for co-locations and that’s something DuckDuckGo did really well. I helped play on the first ever trip. We took a group of five cross-functional people, no one overseeing anybody else to Japan because we had an employee who at the time that was like the most ostracized time zone. And we were like, hey, why don’t we go experience what working here is like through that person’s eyes and also just like be able to enjoy the culture of this place and get our work done. And so I go back to what is the unique value of being in person get you that you cannot replicate remotely. And if you lead with that, then you can find great ways to do in real life, right? Again, I think there’s, do like a whole conversation about this, really like nuanced details around how much time you’re taking to be intentionally planned, versus how much kind of informal time you’re providing people. I like to say that 80% of the time should be intentionally thought out, but that doesn’t mean that it’s scheduled time. It can be intentional but informal. So intentionally giving people breaks is really important. Intentionally giving people time to take care of their fitness regime, if they’re really into that, is really important. And I think that often gets overlooked on retreats. It’s not that you now own that person’s time and you can jam it packed with things. Some people are really quite social, but also introverts. I fall in that category. Like I love being around people in real life. I also really need some time in the morning and evening by myself. And so taking care of all those nuances is incredibly important when you’re designing the retreat. I also think companies need, need to get better at supporting and encouraging and enabling employees to have in-person time with people outside of their organization. And so time to co-work with people that just boost their energy, again going back to productivity. Yesterday, I planned a co-working at a local cafe with four other people. None of us have anything to do with anything work-wise. It was sort of, we’re parallel playing, but just sitting together, doing our own work, taking five minute breaks to chat. And it was really rewarding. Meeting with people in their industry they might not always have access to. Like as a PeopleOps professional, sometimes I’m the only one in the organization. And so it is also important to spend time with other PeopleOps people. If you’re a designer, other designers, what are the trends? What’s your company doing with design? How do I bring that back to my company? Going on field trips in your local community and just talking to folks and getting inspired and bringing that back to your company. So there’s lots of ways to think of in-person time besides just retreats, even though the retreats is just so important to elevate the company to the next level.
Sarah
Thank you so much for sharing that. And I got lots of good tips from that. And I think I need to go just find some people to co-work with. We do co-working as a team with some local people, but there are other people that bring me energy that are also, you know, working remotely from different companies. And if we just got together and spent some time, I think that would be, you know, really great way to have my work day.
Ali
Even if it’s just once a month and even if it’s just a couple of hours of work and then you’re having lunch with them, for example, it’s just something to kind of shake up your routine and have that human connection, reminding people that we no longer have to work from home. Like it, it can expand beyond that level.
Sarah
Yes. We talked about a lot of things today and a lot of things to consider. if you could leave leaders with one thing to focus on, um, as it relates to remote work, remote work fluency, what would that be?
Ali
The number one thing I would say for leaders, um, it’s sort of like an anti-tip is to start unlearning everything that has been ingrained in your mind from the traditional way of working thus far. Um, I think that can be really scary for people. They’ve been successful in their career by doing things a certain way up till now and then all of a sudden you’re asking people to change it. But until you are able to forget that maybe you do not do your best work sitting from home, sitting in an office, maybe you do not do your best work from nine to five, maybe you do not do your best work when you have multiple meetings a day, until you’re able to question those things, you actually will never know about yourself how you do do your best work, and then you won’t be able to mentor and coach other people on it. And so I recommend if it sounds too overwhelming to try to forget everything at once, like we don’t have a reset button in our brain to pick one day a week where you do one experiment that’s new and see how it goes for you and get out of your comfort zone. And if you want even more support on our website and in the book, we talk about energy tracking and we talked a little bit about that with productivity. We have a free energy tracker on our website and we talk about it in our book and it’s a great way to take notes and start to learn about yourself as you unlearn what society has taught you in the past.
Sarah
That’s wonderful. We’ll include a link to that in the show notes so everyone can go grab that. Um, well thank you so much for your time today. I so appreciate it. And I know I took away some things as a leader running in a remote workforce as well. And so thank you so much.
Ali
Thank you so much. It went by so fast.
Sarah
Thank you for listening to this episode of Humans Beyond Resources. Visit ReverbPeople.com to find free resources, subscribe to our newsletter, and connect with our team. If you haven’t already, subscribe to stay up to date on all of our upcoming episodes. We look forward to having you as part of our community.
