Think Outside The Office w/Ali Greene

EP12 - Think Outside The Office w/Ali Greene

Join host Matt Hayman as he sits down with Ali Greene, co-author of the book "Remote Works" for a thought-provoking discussion on the impact of remote work on the individual, team dynamics and communication. This episode serves as a perfect complement to episode 4, where Matt had interviewed Tamara Anderson, Ali's co-author, and discussed more about creativity and collaboration in remote work.

In this episode, you'll learn:

[+] How self-awareness is a strong foundation for remote work success

[+] The importance of team dynamics and group norms in a remote work environment

[+] Strategies for effective communication in a remote team setting

Don't miss this stimulating and informative conversation with Ali Greene, whose wealth of experience at companies like Oyster and DuckDuckGo provides valuable insights on the challenges and opportunities of remote work.

Click here to listen to the show on your platform of choice:

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Transcript:

Voiceover (00:00:04):

Welcome to Leading Remotely, helping remote first leaders navigate, survive, and thrive in this new world of work. Let's make remote work.

Matt Hayman (00:00:16):

Hi, and welcome to Leading Remotely. I'm your host Matt Hayman. Thanks as always for taking the time to listen to the show today. In this episode, I'm speaking with Ali Greene. Ali Greene is the co-author of the book Remote Works with her colleague Tamara Anderson, who I spoke to in episode number four, where we spoke more about creativity and collaboration.

Now in this episode we're going on a different tack. We're starting by discussing remote works' impact on the individual and how self-awareness is a strong foundation of remote work. We then move on to look at the team, team dynamics and group norms and then lastly the communication between the two. I really enjoyed the episode. Ali has a huge wealth of experience at roles, at Oyster and Duck Duck Go and she brought so much value to the episode. I'm extremely grateful. I found it a very stimulating and interesting conversation. I hope you do too. Let's get to the interview with Ali Greene.

Ali Greene (00:01:12):

Hello. Thanks for having me. Doing pretty well, getting used to cold winter nights, but excited to be here. How are you doing?

Matt Hayman (00:01:18):

I'm very well, thanks. I'm really, really excited to be speaking with you today. We had your co-author on the show back in episode four, Tamara, and it was a really, really interesting episode. Recommend people go back and take a listen to that. We're going to focus on some other areas, but do you want to just introduce yourself and also maybe the relationship with Tamara, how you guys came to know one another?

Ali Greene (00:01:38):

Yeah, definitely. So in true remote work living, Tam and I would not have been able to meet if it wasn't for our two separate remote work jobs at the time. So when I met Tam back in 2017, I was the director of people for Duck Duck Go and I was about to go off on a little bit of a digital nomad adventure in Cape Town. And right before I left one of my coworkers stopped me and was like, wait, you're going to be in Cape Town. My wife who works at Automatic, which is another fully remote company, knows someone who's also going to be in Cape Town. You should meet up and have a coffee and co-work together. And that person happened to be Tam and not only were we both in Cape Town, but we were both doing the same digital nomad travel program together, Hackers Paradise.

And so we landed on the ground, we had a coffee, we had a chat, a friendship started to evolve. And over the years that friendship turned into a business relationship. We planned retreats together in Serbia and Mexico City for people that were curious what it was like to travel and work at the same time. And during the first wave of lockdowns and Covid, I remember us catching up on Zoom and just being so concerned that if people did not get this phenomenon of working from home correctly, that people would not get the same benefits that we had when we first met each other working from Cape Town, working from Serbia, working from Mexico City.

And from that almost fear bred into this passion of why don't we write this book and make this book an asynchronous guide that we can coach people as if we were consulting them on how to make this work at the individual level, the team level and the company level. And I loved that because at that time I had taken a step back from my full-time role in people ops and I was helping companies make the transition from in-office to working remotely, trying to figure out where I wanted my passion for remote work to go next. And it went next into this book and it's been a really awesome journey.

Matt Hayman (00:03:56):

People are probably going to be interested in the book. It's not at the time of recording, at least it's not published yet. Do you want to just update people on where it's at in terms of when the book will be available?

Ali Greene (00:04:05):

Yeah, so people can go and order the book today, just head on over to Amazon or go, you know, to your local bookstore and ask them to make sure that they get it. It will be delivered to people's homes or in that bookstore on February 7th. So we're getting pretty close to the finish line which is really exciting. And if you're more of an audiobook person because you're listening to the podcast, maybe that's a possibility. The audiobook should be available a week early. So if you go ahead and purchase that, you can be one of the first people to listen to all the content.

Matt Hayman (00:04:40):

Brilliant. Love it. So one of the things I want to start this interview with is a quote from the book, which is on the Amazon page, which I thought perfectly sums up where I want to go to with this episode. And it's this, before you dig into what tools to use, how to look better on video chat or which virtual team building activities aren't too lame, you need to build a strong foundation internally. The most significant shift you need to make as a remote leader is self-awareness. If I could take that and that'd be the description of this show or the goal of this episode, I would really love to do that. So let's start there if that's okay with you. Help unpack that a little bit. Like why is self-awareness so important for you in terms of that initial foundational stage?

Ali Greene (00:05:19):

So when I think of remote work, I think of it as a way for people to question everything that they've known about what work can even mean. I look back to jobs that I had and the evolution of my career. And when I went into an office, for the most part, I wasn't just going into a building with four walls, a cubicle, taking the subway, having a messy commute, a lot of the things that people complain about when they think about a return to office program. But I was also being told very explicitly how to act, when to work, how to think and when to be productive. It was expected of me in my early 20s. I was living and working in New York City and it wasn't just 9:00 to 5:00 'cause, you know, New York's a little bit more intense than that. It was expected that I was in my office at 8:00 AM I did the quick round to get my cup of coffee, said hi to people, and I sat down and I started working.

And that didn't take into account things like what if I'm just not productive at 8:00 AM. Tam is historically a night owl and it's really great working with her on different time zones because I'll wake up with all of this fresh and interesting content from her because she's worked late in the night her time. And I joke that I'm solidly an afternoon person. I'm like an old lady trapped in a young lady's body. I hate the cold, I want to go south in the winter. I also don't like to stay up late, but I like to sleep in too. And I get my best work done right in the middle of the afternoon. It's 3:00 PM for me when we're doing this podcast and I love it. This is like my time to like jam to get things done. I think it would take a nap afterwards if I want to do a second round of work.

All of these things that people think is not a good way of being a worker actually can help you be more productive, more creative, more passionate about the work that you're producing. But it starts with getting to know yourself and you're not allowed in traditional jobs, the opportunity to get to know yourself. You have to fit into a mold. And so when I had that quote come up, it was really looking back at the evolution of what my experience was like working remotely. 'Cause first I questioned, okay, why do we need to go into an office? I can get my work done everywhere. I think the whole world is questioning that. But it did take me a long time to unlearn behaviors that I so long forced myself to do because I thought that was what an adult did. I thought that's what it was like to be a professional.

Things like being productive from the hours of 9:00 to 5:00. Things like holding a certain piece of my identity away from my coworkers and not letting them in. And then I experimented with stuff when I first started working remotely and as I started to manage people, I remember doing a one-on-one call with someone I managed and I was so hungry. It's a basic human need to eat and it's something that you think can be really unprofessional sometimes is like, oh, like how do I eat and look nice on video camera? Like what is that about? And I, you know what, I was just like, I'm super hungry, I haven't eaten today. Like do you mind while we're talking on this video call if I just like prepare myself a sandwich And I took my laptop over to the kitchen, I set it on the kitchen counter and I started cooking and we had like this really awesome like vulnerable conversation and got to know each other on a human level.

But it took me so long to do that 'cause I was afraid of how it would look. And then it became this regular thing that many times on our one-on-ones I was in the kitchen doing something and we connected over food and we got to know each other and our relationship got stronger and then our work got better because we understood each other and we trusted each other. And that's what remote work has allowed. It's allowed us to flip the script on what it means to be a worker, to be a coworker, to be a manager, to be professional. And I love that that's what's happening in the world right now. But you have to look inside yourself and know like what are your needs? I had to know I am hungry right now. I'm not going to focus on this conversation, I'm not going to be present unless I take care of my physical need first, which is food so basic, but it's so true. And so that's self-awareness has to come every step of the way

Matt Hayman (00:09:36):

That resonates so well with me because for me I've learned so much about myself and the way that I work since moving to a remote role, it has taught me so much about preferences, discipline, the way I like to work, my energy levels just so much that historically working in an office side by side with people, you would be like exactly as you say, forced into a situation where a lot of those things are left by the wayside as you adhere to the way things are done. So let's dive a little bit deeper. I want to go a little bit deeper on this. So how would you advise people to really start to take the time to really reflect on what they need, how they work rather than a happy accident?

Ali Greene (00:10:10):

Yeah, so there's a methodology that's pretty common in user experience design. I'm not a user experience designer at heart, but it's something I've come to love which is a diary study. And so basically if you're doing this for other people, you ask them to write a diary of things that they're doing related to the question at hand. And the first thing I would have any remote worker do is have a diary study of how they're feeling. So in the book, this comes out in a few ways. So we offer prompts to get people going. We have an energy tracker guide that you can actually go on our website and download. And in the book it goes more in depth on how to use it. But it's a way to write down everything that you're doing throughout a day; work, non-work where you're doing it. If it's something you're doing around people are alone the time of day and do you feel more energized before the activity or after the activity.

And over time I suggest you do this for a week, you can start seeing every time I have meetings right after lunch my energy's drained or I love working with people even though I work remotely and they don't even have to be people I know it can be strangers. So I love working in coffee shops and I learned through the energy tracker that if I have too many days in a row where I'm purely working at home, I cannot get motivated to do my work even if I love my work. This is because I noticed that over time I would write, working alone, working at home, working alone, working at home energy 0, 0, 0. And the energy tracker would just have these like red frowny faces and I was like, oh yeah working at a coffee shop and I was like, oh, you're happy.

Like this is great. And so take those prompts and practice and do things differently. And I think if you've never worked remotely before, allow yourself to fail and experiment. I would recommend having a day where you just wake up, forget about work and just say, what do I want to do right now? Am I hungry? Do I want to work? Am I excited about writing? Then go and write. Do you want to go for a walk? Go for a walk. And if you can do all of those things and see when the natural drive to work happens, document that.

And then the second tool we have in the book that helps with after a little bit of experimenting and reflection is something quite similar to those old school madlibs exercises where you fill in the blank about yourself. And so I feel happiest at work when I like getting feedback in this situation. And over time through experimentation I realize that I like getting feedback personally when I can get it asynchronously first and I have time to read it and kind of collect myself and then I can go ask a lot of questions. Whereas I've managed people that hated reading the feedback because they didn't know the tone of voice, they didn't have the emotion. So you have to learn about each other as well. You can do that through these madlibs exercises, sharing your preferences and things of that nature.

Matt Hayman (00:13:19):

Brilliant. Love it. So one of the things that I think remote work has done for all of us is superficially, at least given us the potential for a lot of freedom. The risk of butchering an old cliché, it's with great freedom comes great responsibility. And in a sense I suppose with that freedom, we've now been forced into a position where we have it on the face of it, but in reality it's not always shared by the people that we work with. You mentioned in one of the calls that we had prior to this recording this phrase about everyone is a manager now. And I'd love to really unpack that topic. What do you mean by that? What why is everyone a manager now?

Ali Greene (00:13:55):

I love that quote. I'm a huge Marvel nerd and so that really makes me smile and I think it's true, there is this responsibility now, and this the word I like to use is expectation 'cause I think with remote work everything is about expectation setting and most conflict happens, most distrust happens if expectations are not clear. And so when I say that everybody that works remotely is now a manager, it's because they have to manage themselves in a way where they're making sure that they're holding themselves accountable for knowing what the expectations are of them, setting clear expectations with other people. And if they're in a scenario where the expectations are not clear to go and make those expectations clear and not wait for their manager or a person in a higher position in the company to do it for them. Because there's so many moving pieces at play when it comes to remote work that you could be waiting 24 hours potentially before you get that clarity of expectations with different time zones, with people working at different hours and things like that.

When I talk about what it means to be a manager, I really think the definition of manager needs to change in a remote environment. In our book we talk about four very different types of managers. And before in an office environment we had one person representing all four roles. We had someone who we would go to for our very tactical project feedback. Am I understanding the craft in which you hired me for? Hey, can I get a day off? Is another way that we used to rely on old managers. Autonomy of our schedule was not really our own because we needed permission to be away from the office. A manager back in the office days would be someone who would help us culturally navigate the scenario with onboarding and things like that as well as share the strategy of the company.

Now we don't need people to do that because we have systems that can help us do that. We have the way that we interact with the tools that we're using, we have the expectations of how we engage with other people to do that. So instead of asking for permission to go on a holiday, I can upload my holidays to a PTO calendar or something like that. So the skill that I think is left that's the most important is project management. To be working remotely, everybody has to be a project manager. You need to push your work forward, you need to show your work, you need to be able to be autonomous in getting your work done. You need to communicate it and you need to know what obstacles to overcome and where to get help. And that is the way that everybody now becomes a manager as they work either independently or with different stakeholders in the company.

Matt Hayman (00:16:39):

So this is again, another topic that I'm fascinated by again, as somebody who's been through circumstance, been forced to reevaluate how they deliver on projects and work individually and collectively with other people, what practical advice can you give people around the specifics about managing projects? Particularly ones where they're probably working by themselves, but maybe with occasional contact with other people. What sort of advice would you give to people around that project management piece?

Ali Greene (00:17:02):

Yeah, so I think that the more you can start creating templates for yourself, the easier everything will be. Most projects have basic information that everybody can use regardless of the tool that they have. So it's always important to know why you're embarking on a certain project. Why this now is a really important question. I think everybody should be able to answer for themselves what is the background of this project and what led us there. And through that, I think a really great remote worker and project manager will notice in the context that led me here, who else verbally chimed in on this in the software that my company communicates? Did this project get handed off to me because there were customer complaints? Did this tool get handed off to me because someone in the design team was really passionate about it and they needed an engineer to lead it?

Make a list of all of those people because even if you think you're working on a project independently, you never are truly working in a silo. And so having a list before you start working on a project so you can identify who you could go to for feedback, for support and for help can help make you feel less isolated and less alone as you're navigating how to work on this project. And I think that's a really great piece of advice for people that have never worked on project management before and they're trying to figure out how to do it alone. It's not about how to do it alone, it's about how to do it independently until you need help and where to go get help. And so making that list is incredibly important.

And then figuring out how can I break this down into bite-sized tasks and what do these tasks look like? And then go back to your energy tracker, what type of tasks can I get done when I'm most productive and how can I chunk them up to plan my day? And so then you're not only taking a way of thinking about project management, but you're also thinking about it in a remote work setting. In order to complete this project, for example, let's say you're doing a design study, I am going to have to interview a bunch of people about what's wrong with the current design. I love talking to people, but I only like talking to people in the morning, so how can I batch my interviews so that I have two to three interviews every morning and then I take two or three hours off and I come back and read the synthesis of the interviews. And then you can start really managing your time and having that freedom but also living up to the responsibility of the project management expectations around you.

And finally I would say set clear cadence for communication. So even if you are owning a project totally alone, everybody that is a stakeholder will at some point become interested in your project, whether it's just when it's completed or somewhere along the way. And so set expectations with those people on when you're going to give updates and what those updates look like. As a best practice, everywhere I've ever worked remotely, I've given project updates once a week asynchronously by writing in the project management software that I've used. This is what I got done this week, this is what I didn't get done and why, and this is the top priority for next week. And just crossing those three things off the list helps people go on the journey of the work with you. And it's a really great way to build interest, build trust, and build a sense of teamwork around a project.

Matt Hayman (00:20:34):

That's a really great segue into the next section of the conversation, which is around the team. And I think what you've done as well is you've highlighted just how immature or in the early stages all of this is, this is still not necessarily common practice throughout organizations that are remote first, it really does feel like this whole space is completely in its infancy and I think it's fascinating to watch it evolve, but it also can be quite isolating, quite alienating for people as they try and navigate it. But let's think about the team for a second then. I want to run a little thought experiment with you if I may. Imagine you've got two teams, okay, so one of them, they've worked in person for a period of time, they know one another quite well, but face-to-face and then you have a second who are completely new to working with one another and now in a remote setting. Which of those two groups would you think would struggle to develop norms as a group and why?

Ali Greene (00:21:24):

I think they're equally at risk to struggle. This is a fun question because part of me wants to like be that advocate for the remote team and be like, oh, the team that started remotely will actually be best. And then I think I'll get a lot of naysayers come back and be like that's impossible. What about these people that have built these really great personal relationships in the office? Like of course they're going to do best, but I think they're equally at risk to fail. And that might seem super pessimistic of me, but the reason is a couple of things. It is normal for every team to go through the phases of team development. This is not a concept I developed, it's something I studied all the way back when I was a young university student studying organizational psychology. But it really needs to be revamped for a remote world.

And that's something that we've done in our book is even if you work with a team in person, you might understand the quirks of each of your teammate. You might have a really good rhythm and cadence for working together in person, but as soon as you leave that environment, you're becoming a new team because you have to learn how to interact not just with each other but interact with these systems. And these systems are a part of your team whether you like to think that they are or not. And so new norms and new expectations and a new team culture has to happen in a remote setting in a very explicit way. Or the behaviors that made you successful in person will not translate remotely. And this is the problem we've seen in 2020 and 2021 when really awesome office cultures moved to remote, they had too many meetings, people were super fatigued, people were getting burnt out, they were frustrated that they had to be on Zoom calls to enjoy social time with their colleagues and their work was suffering, their personal lives were suffering. It wasn't good for anybody. And it's because you cannot copy and paste what worked well in the office into a remote environment.

You can copy and paste those emotions, those feelings of trust and camaraderie and that you really care about somebody. But there will be conflict as you figure out what project management tool are we going to use and why and how are really important questions. In our team working together, what is the cadence of communication and what do we do if someone doesn't communicate back to us? So it's not like in an office where when I was really young, a best practice I got was if somebody does not respond to you, walk over to their desk and tap them on the shoulder. That does not work in remote setting and also that shouldn't have worked in person. I think it's frankly kind of like rude and ridiculous.

So what are the norms? Is it that you expect people to get back to you by the close of business day every day? Well, what is the close of business day if people prefer working at 10:11 PM. So you have to be so, so explicit in what a communication cadence looks like. What are your team norms going to be and why. A team that starts off remotely, they don't know each other and they don't know how people work in the office. So I would say there's pros and cons to that. The pros are they get to start from a clean slate designing very intentionally how they want to engage with each other in this virtual space. The cons are in that way of working, they also need to take on the hard work and effort to build a sense of vulnerability based trust and rally themselves around a mission where they might not have had that opportunity to rally around that mission before going off and being remote. But the challenges are for me, apples to apples.

Matt Hayman (00:25:12):

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So one of the things that leads on from that is where I see a potential point of friction between someone in a leadership role and somebody who is not where the person in the leadership role has a certain set of expectations, a certain set of requirements, but that might not be shared by somebody in a more junior role. What advice do you give to somebody in a leadership position who in a sense wants to lead and wants to set those expectations, but at the same time knowing that they're working with a workforce now who are undoubtedly over the years have become much more focused on what matters to them and what matters about, you know, what drives them? How do you try and sort of bridge that gap for a leader in particular?

Ali Greene (00:26:33):

Yeah, I think leaders historically are really bad at understanding and defining culture. It's just true, like throughout my career in people apps, I used to hear things like, oh, in order to have a really effective team, we need to make sure that we're hiring people like us or we need to make sure that we have a good value fit. And not only is this just like super bad for de and our efforts, but it's assuming, and this is again the same assumption that was made when I was working in an office, that people are the same or similar in how they work and how they get things done and that it is going to make it easier to work with each other if that's true. That's just false. And so I don't think leaders should try to dictate down what those expectations are. Instead they should think of themselves as creators or problem solvers or someone that's trying to, if you really like puzzles, put together that thousand piece puzzle together.

That's the new job of a leader in a remote setting. Their job is to understand what are the preferences of everybody on the team and how do those preferences work together to create a set of team norms? Where are there similarities between everybody in how they like to get work done and where is potential conflict going to arise and how can we lean into that conflict and navigate it and use it as a force of good? And so a really easy example is time zone preferences. And when people like to work and when they like to have meetings, I think that there's a false assumption that you should fit meetings into when it's going to be the most convenient between the hours of nine to five for the most people and maybe one or two people will be super inconvenienced. So there was a time when I was living in working in Vietnam and Thailand and in places in Asia and the bulk of my team was in the United States. We had one person in Europe. So that made it extra complicated and it was assumed that because I was the one choosing to travel that I was the one that should be inconvenienced. And because there were four people in the US that they should be convenienced and a leader could easily come down and say, this is what's better for the majority of the team.

What that leader might not know is that some people in the United States are really early birds and so having like a 6:30 AM or a 7:00 AM meeting if it's only once a month actually doesn't really matter to them. And that would mean it would only be 6:30 or 7:00 PM for me, which also doesn't really matter for me. They might not know who the most influential person on the call is, who has the most information or who has the most opinions on the call, that that person needs to be very mentally sharp so that they can brainstorm and add the most ROI for the call. An easy way to figure that out is doing an asynchronous pre-call and get everyone to share their thoughts. And you can easily see like, oh wait, Ali has a lot to say on this subject. Maybe she should facilitate the call and then she should find the time that works best for her. Or Ali, like actually she's fine with any outcome, so maybe she doesn't even need to attend the call and the four people in the US can just attend without her. So there's all these creative scenarios that you can think out of the box if as a leader you're just kind of finding solutions instead of dictating norms.

So what I think leaders should do instead is help teams go through the stages of team development and get to that norming stage and that is helping teams find what their standard operating behaviors are, actions that can be rewarded and accepted by everyone on the team, even if it's not perfect for everyone on the team. And some examples of that can be we're going to have our daily standup using Slack instead of having meetings once a week and that has to be done by 5:00 PM eastern time on Tuesday. So people have a window in which to operate and a norm of when it needs to get done by. Or at the close of every project, the project manager's responsible for putting documentation in this folder in this project management tool and everybody else on the team has 48 hours to leave one piece question or one piece of feedback to make sure that we're improving for the next project.

So those are ways you can create norms within how to act on teams and that helps build culture more than other ways we've thought about culture in the past such as the colors of the office or what signage you see. It's really are people operating under a shared set of expectations without giving it much thought when they've had time to practice?

Matt Hayman (00:31:15):

The two things that stand out to me from what you've said there is the importance of behavioral flexibility amongst the leadership that there needs to be an inherent flexibility and not just a replication of what's been done in the past. I think that's a really key skill that's come up a couple of times in the podcast and previous episodes, but also this focus in terms of a skillset of leadership about creativity, about thinking creatively about how you solve the problems of having a team evolve and develop in person. What are some of the things that a leader can do to maybe bolster that behavioral flexibility? What are some of the things that they can do to really improve that skill?

Ali Greene (00:31:52):

So I think first and foremost, they should go back to the original two tips at the beginning of the podcast and for themselves question assumptions. Do an energy tracker and do the madlibs working style preferences exercise and see as a leader even that you get more benefits being flexible and creative in your own work life than you do if you just follow the same regime that you've become used to and share these prizes with your team. I think it's really interesting for people to know what new things you learn about yourself when working remotely and as a leader, that you've questioned things and you've learned new things about yourself and you've been able to change your behaviors as well. And so first and foremost, a leader, just like any other person needs to find these new things. The second thing that I think a leader can do is really learn how to be almost like a surveyor of culture.

There's all these new skillsets and we used to call them soft skills that leaders need to know when they engage with the team. So instead of having a lot of importance be on things like having a lot of influence over a team or having a lot of like negotiation skills to get their point of view, be the point of view that everyone buys into, this kind of persuasion on a team, I think the new skillset that we're going to see is how can they compile information and really pull out the themes that resonate that will help the team be successful. And so instead of having a mindset and having that mindset be how can I convince others to have my same mindset, it's about what are all of the mindsets and what are the interesting themes and strategies that are coming out of this? And now that I know what's important problem solving, what are the tactics that we can implement and experiment with and decide if they're successful or unsuccessful in order to have these themes be true? And this sounds really complicated and I'm not trying to make it complicated. I think a really easy way to do this for a team is as a leader get really skilled at having surveys. So I love doing a survey called the team charter where you can talk to your team about what do you think our team goals are? How do we want to do meetings? Do we want our meetings to be one hour once a week? Do we want our meetings to be 1:20? I did this for, for my team back in the day, we had one 20 minute meeting once a month and one 90 minute meeting once a month with two different purposes. And that was because we pulled out themes of what people wanted and why they wanted them.

What do you want to collaborate on live synchronously and what do you want to collaborate on asynchronously? And then as a manager, highlight everything that people agree on. This is easy, this is the stuff to celebrate. This is where also your management skills of recognizing and cheering people on come into play. And then focus on the areas where people don't disagree and turn on that problem solving brain. Okay, if half your team wants in-person time together and they want to do like retreats quite regularly and the other team does not want to travel at all ever, like they hate planes and they will not get on one, how do you solve that problem for your team? What are the different ideas that you can have? Do you want to do optional retreats? Do you want to only go to the country where the person who doesn't want to travel is how are you going to hire people for this type of team in the future? So turn on that problem solving that creativity, that brainstorming brain and get feedback from your team about what works and what feels good.

Matt Hayman (00:35:34):

So Ali, it's funny you mentioned asynchronous there a couple, couple of times. I've spoken to multiple people now for the podcast, super interesting people and every single person who comes on the show talks about asynchronous communication quite rightly. But I have this fear and the fear is that in the next year or two where we go with asynchronous communication is it becomes an aspiration, it becomes what we know we should do, but in reality we never do. What are your thoughts? Are you optimistic or are you pessimistic about the future of asynchronous when it comes to remote work?

Ali Greene (00:36:04):

So I have to be optimistic because I believe so much that asynchronous communication is the key that unlocks so many of the benefits of remote work. Such as having flexibility, freedom not just in the location of where you work, but also the time of when you're working. It also is proven to help with things like being able to just get your work done and be able to focus without these constant pings or calls. Helps with better planning, gives you time to reflect, can really help someone focus on developing new skills such as critical reasoning. However, change is hard and so I think it needs to be not just a button that we switch overnight and expect people to do perfectly. And so thinking back to creating team norms, if your team truly is not ready to make the leap to asynchronous communication and you do that analysis and you see these thematic results that everybody has different reasons but reasons why they're still hanging on to synchronous calls and time together, I think it's the job as a leader to figure out how to balance and respect those needs for the current team. How to push them forward and help develop the asynchronous skillset to be able to use that method of communication moving forward. Maybe it's a emotional fear, maybe it's that they don't have the ability to be successful in communicating that way. Maybe they don't like writing. And so you need to think about asynchronous communication as it's not just writing boring long documentation for people to read. It can also be uploading quick videos or I used to be notorious for drawing pictures and taking photos of them and uploading them into Asana and saying, this is what's in my brain, do you understand it? And my team would be like, yeah, but you're so funny that that's how you are still communicating nowadays. Like don't you want to do that on like a mural or something like that? I was like, no, but my pen, my paper.

That's besides the point. And I think that's really important to know where you are and where you want to get to. It's important for your current team. It's also incredibly important for hiring. And so for a remote team to be able to say, this is where we're at, these are our expectations of you and intentionally this is what we want and what we're happy with and maybe you won't fit in on the team, I think is really impressive for companies to be able to do because you don't want to join a remote company that you think is fully remote and you have an assumption of what that means and you get there and you realize these team norms are different. And I think asynchronous communication and your ability to be or not be on meetings at certain times is a big part of why someone would want to take a job or not take a job. And so I think there's a lot of things that go into the importance of asynchronous communication, where you are, where you want to get to, how you're going to get there and why you're growing on that path. So optimistic to answer your question, but I think it's going to be a lot slower and a lot more of an intentional learning curve then people really are willing to give it and it's going to take a lot of hard work and effort to get people prepared to do it correctly and successfully.

Matt Hayman (00:39:23):

So I've been going down a bit of a rabbit hole recently when it comes to async. So async for me is synonymous with video, video updates and I'm very, you know, you can see you've got the DSLR camera here and video I realize the importance of video and I've been going down this rabbit hole of eye contact around video and having eye contact, maintaining eye contact on video. So for this last question, I want to go super specific and super nerdy on this 'cause it really, I think it matters to me, and I'm guessing eventually it all matters to other people as well. I feel like we're in this twilight zone right now where we're so accustomed to not actually having eye contact with people for such a long period of time. I think it's going to have an unintended consequence just in terms of what our expectations are when we do meet people face to face. What are your thoughts about that in terms of coming across well on Zoom or being on video calls? Is eye contact important and if so, what can we do to try and improve it?

Ali Greene (00:40:13):

So this is something where my opinion has drastically changed since 2015 when I first started working remotely. And I think it's changed because of the sheer number of meetings that people now have and are expected to do when working remotely. I think that when you're on less meetings throughout a given week, then there is this really great ability to connect with someone and build relationships with cameras on. There's a psychological saying of the mirror exposure effect that simply by just seeing someone, you're going to be able to trust them more. But there's a lot of implications that go into that that again need to be baked into your team culture such as what is acceptable or not acceptable to have in your background. There's like jokes going on right now on the internet and like news articles around having a bed in your background and is that professional and people aren't considering what it means for people of different socioeconomic means and not being able to have separate offices in their households or the ability to simply work outside of their bed or not.

I think the idea of having a blurred background or, oh, I have a white background because I'm in an Airbnb and this is the background of where I'm at. It's not necessarily my personal decor style. It can be like a way to either connect or not connect with people. So I might seem like super serious right now, but I'm not giving you any of my personality, you're not really being invited into my home. And there's different things besides just eye contact. I will answer that question in a second that that can be important when considering with video calls. So it can be as tactical as what am I showing behind me? If my goal of the call is to build a relationship and I have really cool movie posters behind me, then I can build the relationship because I get to have a talking point with someone who might otherwise have nothing to go off of and the conversation might feel awkward or stilted.

When I first started managing somebody who I had never met in person, they had little action figures on their bookshelf behind them and we were able to bond over that. And I was a bit about to talk about like Marvel movies that I liked in different cartoons and they were able to talk about why they love design and things like that. And it really helps, you know, bridge this weird, like what do we talk about? It's our first meeting. On the flip side to that, not having camera on can be a really great choice because as we said, people are not yet experts at asynchronous communication. They're on meetings all day, people are tired, people are looking at themselves too much, which is like a whole nother thing. And being able to relearn communication styles and navigating things like when are you waiting for a pause so it's appropriate to jump in a conversation. What does empathy sound like when you can't see someone when you're just listening to their tone of voice can really help build on like human intuition that I think is an important skill that will be important in the years to come in something that we shouldn't lose. And when it comes to eye contact directly, I do think that this is incredibly important if you're in a meeting where the eye contact is going to mean something to somebody. And so if you're giving a workshop or a lecture or you're having a learning opportunity over Zoom, you don't necessarily want someone like staring down like this talking to you because you feel intimidated. You don't necessarily feel invited to share information. And so it sounds so silly, so tactical that that, that we need to educate people and talk to people about this.

Matt Hayman (00:43:45):

But we do.

Ali Greene (00:43:45):

But we do. And where your camera is can mean something to somebody. And so if you were looking down at a camera, it feels like you're looking down at a person. It's not building trust and you're not maintaining that friendly atmosphere, which is what you want. If I'm talking to you like this, like it's pretty obvious that I'm not invested in the conversation. So it's like fine, if we already have a level of trust in banter, like the scenario where I used to manage someone and I used to prepare my sandwich during the one-on-one, I had met that person in person a bunch of times. Like I showed my sandwich afterwards, like it was moments of being distracted but if  had my whole entire like hour that we were talking on the podcast doing this, like it’s clear that I’m not invested in you and you can see that and you can feel that and that's not okay. Eye contact matters. Choosing to have the video on or off, how it relates to your culture, it matters. Every decision matters and that is what we mean when we say you need to be very intentional when it comes to remote work.

Matt Hayman (00:44:48):

Yeah. Intentionality is the key without a doubt. So, although I said that was the last question, I've got one more for you. I ask this of all the guests that come on the show, and I'm keen to get your thoughts on this. What are the three tools that you would use or three tools that you have that you would be completely helpless without when it comes to remote work? They could be software, they could be items, they could be anything you choose, but I'm interested in three things you couldn't do without when it comes to remote.

Ali Greene (00:45:12):

Yeah, I love that question. My phone, I think I use my phone sometimes more than even my laptop, as my way of just being able to navigate and be fully remote and flexible with where I go. Whether it be tethering to my data plan to be able to work in exotic locations or writing emails, like everything I need. I can be a remote worker with just that, which is awesome. I think old school pen and paper, I need a creative outlet to feel connected and grounded to my work. And I draw things a lot. That's important for me. I think what your audience probably like really wants is like a real tool request. But for me, like you can get everything done if you meet somebody where they're at. Like I've used WhatsApp before purely to work like I've used Asana in a highly customized way. It doesn't matter for me. But I will say one tool that I like geek out on hard and I love and I wish people use more often is Loom. I really like doing quick videos of this is what I'm doing, this is what I struggle with, and that people can comment on the exact second in the video and leave their feedback, I think is a really fun and engaging way of getting things done. So for the one recommendation that maybe people aren't using, that would be mine.

Matt Hayman (00:46:31):

Yeah, I'd plus one that as well. I used Loom for the first time about three years ago, very, very early days and it immediately you could see the potential that it had in terms of that ability to annotate that ability to comment on asynchronous video. Brilliant. Love it. And also being able to search the transcript as well more recently, which I think is super, super helpful. Ali, thank you so much for your time. I've really, really enjoyed this conversation. It's been fairly wide ranging. Some high levels, some super specific tactics as well. So a nice mix. Before we go, how can people find out more about you and your work with Tamara and the book?

Ali Greene (00:47:02):

Yes, of course. So I love to hear people and just continue to debate, chat, share ideas around remote work. So feel free to find me on LinkedIn, Ali Greene with an E on the end. Or you can check out our website, remoteworksbook.com and we send out monthly newsletters with reflection questions and interesting thoughts as well as very tactical tips on how to bring your management into a remote world state of mind.

Matt Hayman (00:47:32):

Brilliant. Thanks so much for your time, Ali. Really appreciate it. All the very best.

Ali Greene (00:47:35):

Thanks so much. Talk to you soon.

Think Outside The Office w/Ali Greene