Ep. 83 - DuckDuckGo: Ali Greene

Jeff Robbins interviews Ali Greene, who for the past four years has been working as the Director of People Ops at DuckDuckGo, and she’s got a new company called Cohana, which offers consulting services and general remote work advocacy. They talk topics related to culture, vulnerability, and intentionality. They also discuss what it’s like building diversity on a remote team and battling isolation through community support.

Here’s the transcript:

JEFF: Hello everyone. It’s Jeff Robbins back with Episode 83 of the Yonder Podcast, where we talk to company leaders and big thinkers, about how to make remote work. We’re focused on expanding the remote work job market, and helping listeners to create happy, productive, distributed teams. On this episode, we’re talking with Ali Greene, who for the past four years has been working as the Director of People Ops at DuckDuckGo, a privacy focused search engine that hopefully you’ve heard of. DuckDuckGo the company is fully distributed and in fact Ali lives her life as a digital nomad traveling from city to city and country to country every few months. In the past four years Ali has helped DuckDuckGo to grow nearly threefold and she’s got a new company called Cohana, which offers consulting services and general remote work advocacy. Great conversation with Ali. She’s so charming, and we talk about culture and vulnerability. The word intentionality comes up a lot. We talk about building a diversity on a remote team  and battling isolation through community support that remote friendly companies can provide. Stay tuned for the podcast and we’ll [laughing] get into all those things. 

If you’re not already subscribed to the Yonder newsletter, Yonder.io/newsletter is where you can do that. We send out little bits and pieces to let you know about new podcasts, let you know about new articles going up on the Yonder website, and little bits and pieces we find around the internet to keep you updated on the latest remote work thinking. Also, if you’re not subscribed to the podcast that you’re listening to right now, you can do that through Apple podcasts, Google, Stitcher, Spotify, we’re on all the places that you might get podcasts and you should go and subscribe. Maybe while you’re there you can leave a little review. If you’re enjoying the podcast tell other people, recommend it, we always appreciate when that happens.

I also want to tell you about my business coaching and mentorship services practice for the past three years since exiting Lullabot, the company I started back in 2006. I’ve been working with owners and leaders of various types of businesses, both remote and collocated, to act as a virtual business partner. Someone to check in with weekly and to work out the issues that you need to keep your company and yourself, [laughing] healthy, happy, sustainable, and to help you move toward your goals, whether to grow your company or to simply make sure that your company is fitting into your needs and not going to burn you out. You can’t keep running a company if you burn out, and it’s good to have somebody to check in with, and I do a lot of that, and I love it. It’s really great. Super rewarding for everyone involved.

So, jjeff.com is where you can find out more about that. That’s jjeff.com. Alright, let’s get to our conversation with Ali Greene. 

JEFF: Ali Greene. Welcome to the Yonder podcast.

ALI Greene:  Thank you, I’m so excited to be here. 

JEFF: Yeah, I feel like we’ve known each other for years because I feel like the first time that we talked was probably four years, maybe more than that, through email and stuff. I don’t know that we’ve ever actually been [laughing] in the same room together.

ALI: Not yet, but I’m looking forward to seeing you in April.

JEFF: [laughing] You’ve been a part of the Yonder circle group that we’ve been running and so we video chat each month and so, yeah, it’s a testament to virtual connections I suppose.

ALI: Yeah, it’s funny, I think some of my closest new connections in my life have started out very similar to you and I, where we have this email friendship for about a year and talk about really interesting things, and then finally get on video chat. So, you must’ve been in contact with me for pretty much my whole digital nomadic experience so far, and it’ll be really cool to finally be able to see you and the Yonder circle video chats, just really took it to the next level. 

JEFF: Yeah.

ALI: Just a testament for the remote world.

JEFF: So, I oftentimes ask people at the top of the podcast where are you talking to us from today, but I should give a little background to people that this whole digital nomad thing is your thing. It seems like every time I talk to you I want to ask you where you are because your somewhere else in the world.

ALI: Yes.

JEFF: [5:31] And you said, so you’ve been doing this digital nomad for how long now?

ALI: For  a little over four years though I really do think it’s in my blood. When I graduated from university there was a six year stint where every year I would not only change apartments but change cities and move around and was really just trying to find my groove until I realized my groove is constantly changing my environment, and luckily it was at a time where remote work was really taking off, so I was able to bridge my personal needs and my professional needs and now I travel the world, and I’m in a different country anywhere from every two weeks to every two months. So, sometimes it’s really fast paced for me, which is why every time we talk, I’m usually in a different country. [laughing]

JEFF:  [laughing] There’s something different in the background and all that stuff. So, the question today, [6:29] Where are you today?

ALI: Yeah, so I’m calling in from very exciting Detroit, Michigan, where we have had nonstop snow since I’ve arrived about 48 hours ago, and in a few days I’ll be headed to Miami and then a ski trip in the French Alps. So, a little bit of everything.

JEFF: [laughing] I guess so. You know, you want to add a little Detroit into the soup, just to keep things interesting, when you could go to Miami and the Swiss Alps. [laughing]

ALI: [laughing]  Keep things fresh. I visited my family. I have an adorable six year old nephew who doesn’t really understand that when he talks to me it’s daytime for him and nighttime for me, and so I really have to come home and start influencing the world of travel and remote working to him at an early age.

JEFF: [laughing] Don’t get me wrong Detroit is fine, but Detroit in February.

ALI: It’s a little cold.

JEFF:  Probably not the choice of when I would go there. Okay, so let’s get you introduced. I know you probably best as the Ops Director at DuckDuckGo, a wonderful and fascinating company that provides a counterbalance to pretty much that everything Google does [laughing] but you’ve recently left there. [7:56] Why don’t you give a better introduction to yourself?

ALI: Yeah, definitely. So, I was the previous director of People Operations at DuckDuckGo. I was lucky enough to be with them full-time for four years, so as I was starting my location independent life and remote work really building up the DuckDuckGo team as well, and so during my time there I was able to help them almost triple the size of employees we’ve had throughout the world, 16 different companies represented, increasing gender diversity 130% was something I was really proud of working during my time there, and really just seeing how a company could grow from 30 to 90 people without putting limitations on where people live or coming into an office, and things like that. It was just an incredible learning experience for me. I have so much respect for DuckDuckGo’s mission but also how they approach culture and the types of projects I was able to work on. Throughout my time working there another big passion in my life has been forming communities of people that also see this digital nomad life as a more sustainable way of living and what the benefits are for society in terms of learning through travel, and that’s learning about yourself, but also learning about the world and learning about the business. And so, thinking just about what I wanted the next stage of my life to be and how I could future impact the world of remote working, I decided to launch my own remote work consultancy.

Cohana.io is the website and what I will be focused on is really educating and inspiring teams to become more effective and engaged, not just in their professional projects, but also with each other, and supporting the remote work community  as a true community.

JEFF: Yeah. So, let’s talk about DuckDuckGo and your time at DuckDuckGo. Boy, I have all of these stock questions I’ve asked on this podcast over time, but I guess maybe [10:28] I’m just curious, what was it like. So, DuckDuckGo was already a company that had been around for a little while when you started there four years ago. What struck  you about starting work at a remote company like DuckDuckGo is and was?

ALI: So, I think my first introduction to DuckDuckGo is really a good story about what my whole experience was like there. So, I had been living in New York City, commuting from Brooklyn to Madison Avenue for this really “glamorous”, I’m making those air quotes, but you guys can’t see it listening to me, job.

JEFF: [laughing] Everything in New York is glamorous.

ALI:  [laughing] What’s not glamorous is the hour commute on a subway where you’re packed in like a sardine, and people wondering why you’re not…

JEFF: The picture’s glamorous, the smell is not glamorous.

ALI: The smell, the rats, yeah. New York I love to visit. It was not for me. There was a rat race there that really just got me down and so I was really lucky that that is where I started my remote work journey. I was able to negotiate at the job I was there to leave and I backpacked South America and continued on with them as a consultant, and during that time really started to see what consultancy looked like, and what South America looked like, which is amazing, and I still like remote work in digital nomad, it wasn’t a common term. So, I had this amazing experience, I climbed Machu Picchu, went to the Patagonia, and then I was like, “okay, where do I settle down. I need to learn how to put down roots.” But I wanted to do it in a way that’s genuine to Ali. I don’t want to have to be forced to do this hour commute, get into an office at eight a.m. and try to spit out really productive or things before I’d even had a chance to have coffee. Those who know me know that I’m obsessed with coffee, and kind of plan my trips around going to coffee shops, so it’s a really important way for me to start my day. And, I had met Gabriel, the CEO of DuckDuckGo at a Philly startup barbecue and I think I was in Philly only a couple weeks at that point. It was where I decided like, this is going to be my forever place if I have to choose one. So, I moved to Philly, I jumped right into the scene. I went to this barbecue and I met Gabe and we just started to have a conversation around company culture and everything he said made me so excited, and not only was DuckDuckGo trying to really hit the mainstream audience which they’ve now done, I would say, in terms of why privacy is important online, but also why is it important to treat your employees like adults, and if you put trust in them they will do good work, and you don’t necessarily really need to be watching over someone’s shoulder to know that they are really mission driven and want to help you company succeed, and it was one of those experiences where at this barbecue I think I was nodding my head so much, that like my neck was starting to hurt, because we were just agreeing about all of these things. And, he was really, I think, thinking ahead quite well because the company was only about 30 people in that stage. They didn’t yet have a formal People’s Operation team, but he was trying to hire someone to come in and really launch what that team looks like, and focus full-time on how the company could scale, while also scaling culture, and so, I started to work with DuckDuckGo. Back then they had a really long interview process, but what’s still true about the interview process that I had helped refine over the four years was people at that time came in and got to do some test projects and really see what it would be like to work there, and so I did a few test projects, was really excited about them. They were really excited about me, and then it just became a full-time commitment and so that’s how I found out about the job opportunity at DuckDuckGo and then over those four years those conversations that I had, not only with Gabriel, but with the rest of the leadership team, and my peers at DuckDuckGo, were constantly about -- we’re a successful company. How do we make sure that the success isn’t lost because people start to get disengaged or the success isn’t lost because people don’t have the right information because they’re working in all these different time zones? So, really, so much of my time there for the past four years was thinking about how do we make sure that we have the network in place that people don’t feel like there is a loss of communication, collaboration, or make sure that people are not feeling isolated, that they’re feeling fulfilled by this remote work opportunity.  

JEFF: Yeah. Take note dear listeners, [laughing] especially in a remote work environment, these things, culture, trust and mission driven company, or at least one with solid core values are what really attract quality employees to your company and then as you scale, you need to scale those things too, and it’s good to bring in people to help you do that and keep focused on that. [16:00] Talk to me about that end of things. Growing the company. You also talk about building diversity. What was that like. Something that we know how to control, I’m hesitant to use the word control, but when you’re talking about building something that’s hand built, built with loving care,  you want to control it, and we know how to do that in an environment where we can look at each other, collocated company, but how does that work when growing a company like DuckDuckGo, that x number of multiple what? Three times as big you left it as when you came in. How does that work in a remote environment, especially for you?

ALI: Yeah, I think the biggest things there are to start early with creating a framework and knowing that framework can change, and what I mean by framework is having almost like an inventory on what are the core values of the company and what are the rules of engagement, what are the behavioral norms that we want to celebrate, and what are the behaviors that work that will help someone be the most successful here. And, as  a leadership team, thinking about that early, and then not assuming that people will remember that as you grow is incredibly important. So, in an office you might have them plastered on the walls. You might have little tokens with your core values. It’s built into the system because it’s visually there.

For remote work it’s about intentionality, like, how do you take those values and really live by them.

And, then, if you know how to live by them, how do you document that, so that the expectations are really clear. And I think that might sound like a really boring answer to people, like, oh write it down, but it’s true. Write it down and make sure that people know where to find it on the tools that you use across the web. For us, at DuckDuckGo, very tactically speaking what it meant for me is I was spending a lot of my time engaging with various people at the company, figuring out what the best practices were, figuring out what the gaps and understanding were, and then creating a lot of templates that people could take, and then the repetition came, not because values were posted on the walls, but because there was a cadence of communication that looked the same and felt the same regardless of what team you were on. So, the design team would be working on a project and post weekly updates, and those weekly updates felt very similar to what the People Ops team was posting, so anyone in the company could jump in, and the mental overhead to figure out what they’re talking about disappeared, because it felt familiar, and then they could really focus on the content and learn what was going on in the company.  

JEFF:  Yeah, because this whole remote work thing is still new, and while it may be something that many of us had had deep long experience with, still it’s such a small percentage of companies that are doing it, for, I would venture to say the majority of new employees working in a remote work environment, are new to it, at least within a few years, and so, and this is in a great way, there aren’t these tried and true business patterns around what memos look like, or how business meetings happen, and so, it’s nice to be able to rethink those things [laughing] but on the other hand you can’t expect everyone at the company to know unless you start disseminating that, repeating that, creating those cadences. [19:59] When you say you’re creating templates, what does a template look like? Are these literal templates or are they more figurative?

ALI:  So, in this case, they’re literal templates. One of my favorite online tools for collaboration, I’m going to surprise all your listeners because I’m not going to say Slack, is Asana. So, I love Asana and DuckDuckGo, the office was our Asana projects, and so, it became not only a place to get the work done, but a place to communicate with each other and a place to learn, and part of that learning was to have legitimate tactical templates where there were certain, either pieces of information that were always going to be true or clear cut questions that people would take and copy for themselves and then write out the answers to that, to make it really customized to the problems they were working on. And these templates were things anywhere from how to kick off a project and think about what stakeholders you want involved and what the milestones of this project look like, to our hiring process. How do we know what we’re looking for? Who is going to be that A++ candidate? And based off of those answers, how do we go about finding those candidates, and so it really stemmed from, and I think everything in life stems from this, it’s asking the right questions and defining your expectations early. 

JEFF: So, okay, one of the things that people use Slack for a lot is what people often call culture. I’m always hesitant to call anything culture, but these peripheral, kind of like, hey, here’s a picture of my dog. Here’s funny things and you know,  [22:00] does that stuff happen in Asana at DuckDuckGo? Are you using it a little bit more lightly like that or does that stuff happen somewhere else, or does that stuff not happen at all?

ALI: Yes and no. It’s a very like, I think, answer that people give and then you’re like what is this person talking about? [laughing] So, yes, in the sense that the implemented threads in Asana that became part of a behavioral norm each week, to ask people about things going on in their world, so a sort of like an ask me anything, where sometimes it was what’s something that you want to know about a different team and what they’re working on to what movies are you watching lately? But, I do think having a Slack or Slack alternative is great for  more of the answer. I also lately try to stay away from using company culture as a descriptor, I must prefer a company community, and thinking about what culture is and then as you grow remotely people have their own cultures and then the company culture and it kind of gets confusing, but a company community is being on the same page about what are the rules of engagement? What are the norms? What behavior is celebrated? How do we interact with each other? And I think creating that community through fun, through friendly conversations, through banter, is incredibly important, but it doesn’t need to live in the same place that the work is getting done, because they serve two different purposes. So, I love Slack. I actually use Slack more often with my personal communities than with my professional communities. But I love it for talking through what are productivity tips that you need when you’re working remotely. What are great recipes that people are sharing? And this is something I’ve seen happen at DuckDuckGo and other communities that I’m part of, is just, using it as a way for people to get to know each other on a personal level, and using it to substitute passing in the hallway to substitute grabbing that cup of coffee in the kitchen at work, whereas tools like Asana become the desk space. And so, I like to sometimes think about what are the tools I’m using remotely and what would this tool be in the physical world?  

JEFF: I have in my head this giant matrix of communications tools and, things like their a femoral nature versus their archival nature, and how deep and engaging they are, there’s probably three dimensional or four dimensional chart [laughing] but Slack is kind of a femoral. It goes away and there could be important and useful information. Sometimes that important and useful information can be what somebody’s dog looks like [laughing], but one of the nice things about doing things in something more like Asana or, I realize this isn’t exactly a parallel, but like a Wiki or there’s companies that do more internetty kind of internal or Wiki blog kinds of things where it really is archiving things, especially early on in a company could be really good to create a lot of artifacts of, it’s funny because a lot of these companies evolve out of programmer culture and particularly  internet development and development standards there’s a thing called an RFC, which is a Request for Comments, and it doesn’t actually quite work that way, but basically it’s a way of saying, here’s a proposal. Here’s how I think http protocol should work. Hey anybody take a look and comment, and theoretically it’s a way people can collaborate and stuff like that. But, it’s also a way for people to put a stick in the sand and say, this is it. This is our flag. And someone else would come along and go, “Well, what if it looked more like this?” But when  you’re establishing a company, when you’re evolving, I think it’s a nice way to collaborate. 

ALI: Yeah, and there’s a few interesting things there too. So, one, just in terms of this archival nature, I think it is really important for building community or building culture, because these artifacts become the stories that you tell, and pass down from generation to generation of people that work at the company. We see it in consumer driven industries, the nostalgia factor is real, and building that own nostalgia into your company I think is a really interesting way to create deeper connections for not only employees that have lived through that, but new employees as well, because they have the opportunity to go back into these archives and see how far the company has come in terms of innovation, in terms of decision making, understanding why certain decisions were made and what the company felt like back then. It’s really helping new employees time travel to see the whole history and legacy of the company, which inherently makes them feel like they were part of it and connected even if they are new. So, I think that’s really interesting just in terms of how do you create culture? How do you create community? Having icons, having archives, having stories to tell in various formats is incredibly important. And then, jumping back to the tools, it’s just so interesting because whenever conversations happen, people always want to know what tool should I use? I have the tools I love and use, but I always hate recommending a tool or talking about specific tools, because it’s not about the tool, it’s about how you use the tool, and that’s a very human decision. 

JEFF: Well, to focus on the medium and not the message. The tool and not what you’re creating with the tool. And this is, again, going back even further to culture stuff. I think people confuse the foosball table with culture.  Right? It may be an evidence of your culture [laughing]. It may say something about how lighthearted you are, and you allow people to play games during the day in your office, but a beer fridge is not culture, and likewise Slack is not culture. It’s the way that we think. It’s the set of values. The philosophy, the communication style, the way that we treat each other. It’s the air that we breathe at the company and how that works. 

ALI: And that stems from leadership and from how you celebrate people and how the company actually achieves their goals and then all of the other stuff just represents that.

JEFF: Yeah. [29:24] So, here’s a Segway. One of the things that happens around culture a lot is that companies start searching for other employees that match the culture of the company which can oftentimes lead to a lack of diversity. It could just create these inherent biases of like, “well, we’re all white guys and we talk about white guy stuff, so if we hire other people they should enjoy cigars and going to football  games too,” and it can box in a company in a way that is ultimately dangerous in the long run. As a person that’s thought about diversity, as a person that’s thought about diversity particularly around remote work, which can actually be a little bit even more difficult to find diverse candidates when people are finding you through the web, the evidence of things that you do on the web,  going to your website and looking at the pictures of the people on your site, and pattern matching against that and saying, “Oh, well, I guess I wouldn’t fit in here because I don’t look like the people on this web page.” What have your thoughts been around all that?

ALI: I think it’s a beginning to be really intentional about why you value diversity. It’s 2020 so hopefully I don’t need to go on a soapbox about why diversity is important, but it is important, and the world is full of so many different people and that can be defined in so many different ways, so it’s not just about gender, or what you look like or where you’re from. It’s all of those things, and all of those things means that you have a different life  experience that you’re bringing into the company which will at the end of the day make the product better because you’re going to get lots of people challenging the status quo, and that’s where I think innovation comes from. But you do have to be intentional about it. Diversity wont’ find you, you have to be open about having the conversations, questioning what’s working and not working, and to be honest if you’re just getting started thinking about this as an entrepreneur, as a People Ops leader, the one thing that I think is the most important is, just be honest about your forthcomings so far. Be honest about where the companies at and be clear in your intentions of where you want the company to go and how you plan on getting there. Because nobody wants to feel that they were a token hire, but I do think if you don’t see someone that looks like you on a company hiring page, it is intimidating to be, “Am I going to be the trailblazer that is going to have to always be focused on what women in leadership look like,” for example, which has been my case in my professional journey so far. But then having a conversation about that with a company…

We’re really trying to get better here. We’re open to having conversations about where we’re at right now and what that looks like, however these are the very clear objective standards of how we’re going to make the hire, and so, while we want you because of the skills you’re going to bring to the table but also the new perspective through this aspect of diversity, we’re making the decision based off of the work itself.

So, in terms of just how you communicate that I think really being authentic and genuine with candidates, with people, is really important when it comes to how you make that work in your hiring process, I am a huge component of letting peoples work speak for themselves and if possible whether you’re technology or whether other People Ops team allows you to do those things as blindly as possible and so really looking through, how do people respond to certain case studies? I was always so proud of DuckDuckGo for paying people to do external projects and hiring people based off of the skills shown through those paid work. I think it removes as much as possible because people are human and there is some sort of unconscious bias to fight, but if you have a piece of work and you’re able to evaluate it clearly across the board, it makes a lot of strides there. 

JEFF: [33:50] Are you a proponent of anonymizing, adding layers of buffered anonymity between  hiring people and the people who are being hired? I’ve seen a fair amount of that, and it seems difficult, and ultimately doesn’t help you if you want to be more proactive [laughing] in hiring a more diverse group of people, it doesn’t quite help you. Maybe it does, I don’t know. But you’re kind of rolling the dice with that. I’m curious;  your thoughts. 

ALI: There’s pros and cons to that, like there’s pros and cons to everything. I think that looking at each stage of the interview process differently, because each stage of the process has different goals and therefore you can reach different diversity goals throughout that interview process is really important. So, if you’re a company that’s large enough to have talent acquisition people or recruiters and then hiring managers that are going to be evaluating work, some tips that I would have is, one, make sure, yes, everybody is on the same page about the importance of diversity and inclusion at the company, what the company has done so far to make improvements there and what are the gaps that still exist, but then the talent acquisition it would be their goal to really make sure the top of the funnel is as equal and fair as possible and so making sure that if they’re getting applications that are all from one group of people, how do they round out the diversity of the top of the funnel, and proactively engage with potential candidates that fit the bill, and that’s totally different than what the hiring manager’s going to see. 

JEFF: And, I think that there’s a certain amount of vulnerability and vision -- I’m a big fan of the alliteration, [laughing]. There’s a difficult hurdle if you have a company, let’s just say for the sake of argument, say it’s all white guys. As the leader of the company you need to admit, we’re all white guys, and I don’t want it to be that way. So, vulnerability is what is inherently potentially if you want to make a change, an embarrassing admission, right, that we haven’t been as diverse as we ought to be up until now.  That’s a vulnerable statement, and then the vision to say, but I want to change, and as you’re able to get out there and talk about it more, you can as you say, change who’s coming into the funnel, right, if you’re out there, speaking at conferences and saying, we need more women, we need more people from different economic backgrounds and go out there and talk about it.

ALI: And the reason why too. So, it’s not enough to just say, “hey, we have this problem right now, we’re very homogenous in terms of who is working for our company,” but to hear in someone’s own words why that’s important and not to fall back on the assumptions that the business world has communicated, I think is really important because that’s when you get an idea of the leaderships vision, to make sure that is going to ultimately, at the end of the day, gel with the behaviors and values that you’re going to see on a day to day basis. Because a company could all look the same, and they could admit that that’s a problem, but not really know why they want different people in the door, and then how is that going to look if you are that different person stepping in? Are they going to be flexible with changing some behaviors that you might feel uncomfortable around? Does the company want feedback and want to make proactive changes to make it feel like more of everybody’s safe space? So, what do those things look like?

JEFF: Absolutely. [38:04] From my perspective running a company, as the CEO, especially as the company started to grow, you start to look at things differently, you start to see the trees as a forest, and it’s like, okay, what kind of forest do I want to build? [laughing] Right? In the past it was sort of thinking about tree, tree, tree, tree, tree, but now it’s like what do I want this to look like as we put it altogether and I want a more diverse team with a wider perspective of views and a wider background in experience that people bring in.   And I think when you start looking at it that way it starts to change things and it becomes a little bit less, as you’re saying, sort of this by rote because we’re supposed to [laughing] kind of thing. 

ALI: And then it’s like, “oh, we have this forest, how do we make sure we have mountains and streams as well? How do we create a whole world of people and their perspectives” and with remote work it’s so much easier in some ways because you really do have the whole world as your team? I think some of the most interesting conversations I have had with colleagues has been people that come from different countries and cultures that’s in those countries that you assume are very similar to yours, especially the English speaking world at times, it’s hard to be like, oh, yeah, we’re kind of the same, we speak the same language, and then you go and spend time in different countries, and as a full-time traveler I’ve experienced this, but even talking to my coworkers that are from different places, it takes a lot of work to recognize the subtle differences and then it takes a lot of work to recognize the ways that you’re all the same, and be able to talk about those two things. One of the most surprising things for me was mental health, and what countries is it okay to be really vulnerable about mental health and where is it not. That was a shocker for me. So, there’s lots of interesting things about getting to know people from around the world. 

JEFF: But I think with all that stuff it’s just a matter of putting it on the table and acknowledging, “hey, we’re going to make mistakes, we’re going to say the things that may be wrong, or you may not fit into your culture, speak up, let us know.” [laughing] I always fall back on being an ignorant American, [laughing] that works for me. See I’m from America, I don’t know these things, please educate me. But it rises up to be able to just speak to people across the world with a variety of different accents and experiences and it’s summer there while it’s winter here and it’s day there while it’s night here, and there’s all these different festivals. It’s the opposite of closed in. I don’t know if I can work at a company down the street these days because it feels so close minded, means not quite the thing I mean it to mean here, but it’s such an expansion of the way that you think and I think it’s really good for a company to think that way, and it leans a company more towards being an international presence anyways when you’ve got people across the world. 

ALI: Yeah, it’s like a fishbowl versus an ocean. You can stay in your fishbowl and be happy but only know so much and then you can go to an ocean and realize there are sharks and whales and jellyfish and that’s really cool. I’ve loved that through working with so many people from different countries. I’ve learned so much about things like how do people in Japan use the internet, was a discussion we did one year at a DuckDuckGo meetup. I actually work on a laptop I bought in Spain and so I have a Spanish keyboard and my Spanish is not good [laughing]. I’m constantly trying to learn. I spend most of my time in Spain and I’m getting there slowly, Buenos Dias, like I can order my coffee, but to type and work on a Spanish laptop, even starts that trigger of problem solving and putting yourself in foreign experiences, hearing about how different employees choose to live their life if you give them the same basic guidelines, is so fascinating to me at a personal, but also professional way. So, thinking about remote work, you can work remotely, you can choose to live anywhere, or in my case, not live anywhere, seeing why people choose rural Scotland, or Saskatchewan or New York City, and what those choices mean for their life, but also what their choices mean for how they structure their workday and when they are productive and when they feel inspired, it’s like you get so much information about the people you’re working with, and I feel more connected to people that I’ve worked with remotely because of those types of conversations with people that I’ve sat across from in an office but never really had a deep conversation with. 

JEFF: [43:39] Yeah, we get so used to protecting ourselves in a physical environment with people that you’re kind of, respecting their space, respecting their privacy. But, when you’re talking on Skype or even on Slack, you choose how much of yourself to share and I think it creates new and different boundaries and barriers around how people are communicating. Also, the other thing is that you try to hire people who are good communicators to work at a remote company anyways.

ALI: Yeah, communication in not remote companies is key too. They have easier ways to not be as intentional about it but it’s always an important skill. What’s most interesting to me, and this is the word of the day I feel is, vulnerability, because there is a sense remote work is blurring the lines between your personal life and your professional life and it’s all just becoming your life. You’re working a lot of times in the same space that you’re living, but your hobbies exist and so that vulnerability shows as a video chat is a window into someone else’s life experience. I know when we talk on video and I see some of your music and audio things in the background, and I got to learn a little bit more about your hobbies, whenever I’m on video and  you see a different background all of the time it’s interesting on why and how I choose different places to live and those are questions that are triggers because of the scenery that we’re getting behind the computer screen. 

JEFF:  [45:34] Talk to me about isolation, but also about community. I don’t know if they’re necessarily different ends of the same thing. Feeling connected to people versus not feeling  connected. As we’ve got people spread out all over the world, especially in different time zones, communication can happen a little bit less synchronously, a little bit less connected, a little bit less real-time if somebody’s sleeping while your awake. What are thoughts about this? I know you’ve got a lot of thoughts [laughing] because you got a new company that’s thinking about this. But let’s maybe start with isolation particularly, and what you learned at DuckDuckGo about that, and then we can expand into the stuff you’re thinking about now. 

ALI: Definitely. So, there’s a really interesting study that recently was posted on, I think it was Buffer and Angelis collaborating, and I was surprised the number was as low as it was, it was 20% said loneliness was a struggle for them in remote companies, 20% is a really decent amount. I definitely felt isolated and lonely in my work experiences in the past and what I think that I’ve learned about isolation is that it is a area of remote work that really will impact all of the aspects of your life, and in order to combat it, again, the word of the day, vulnerability, is huge, and so I think a companies responsibility to make sure that their employees are not feeling isolated, it is about building a safe space for them to be able to be vulnerable with their struggles they have around it, and really think through what is the most respectful way to include the right stakeholders at the right time.

That answer for every company will be differently. I’ve had plenty of experiences working in Asia when the majority of my teammates were in California or Philadelphia or Poland, and not really sleeping that well, feeling isolated in some ways because I would see friends that were there that were out hanging on the beach and then going out to dinner, when I was just starting my workday. Yes, it was my personal choice to be there but that doesn’t mean it was any less difficult, and so just having that understanding through a company to say, “Well, while you’re here maybe some of these meetings since you’re a key stakeholder won’t be at four a.m.” It’s not only going to make the person tired, but it’s going to make the meeting less successful. Do you really want someone who’s half asleep showing up to your meeting and making really important decisions, or brainstorming and talking nonsense cause they’re sleep deprived? Probably  it’s bad for business and it’s bad for the person. Instead, what is the most respectful meeting time, not what is a meeting time that’s optimal based off of business hours in any time zone.

If you think about that, the window opens up for times you can communicate because for someone in North America talking to someone in Asia, it gives you six hours a day if you’re thinking like 7:30 and 9:30 a.m. and p.m. are not that terrible hours to work if you get the rest of your day to own and control. So, I think, shifting the perspective of not what’s normal, but what’s most respectful, is it most respectful to wait for this asynchronous conversation to happen and make a decision over the span of two days. Like, what’s going to be the business impact of waiting and what’s going to be the cultural impact of waiting, versus making a decision without someone that you know is really passionate about this project.

So, I think having leaders ask those questions at work is really important in terms of what the community looks like. I also think that progressive companies will start to realize that this feeling of fellowship you can have with other people does not have to be with your coworkers. It’s amazing if it is. There’s an awesome gallop article talking about how friends at work really do matter, but friends in life, in your professional area of expertise, don’t have to be part of your company to still be productive allies for you inside and outside of work, and so, one thing that I think is a really great benefit that companies are offering, DuckDuckGo did this, is coworking benefits, and it’s not just being productive and having fast Wi-Fi, that’s really great, but it’s about if you’re in a community and there’s other remote workers in that community, how does going to a coworking space and those kinds of spontaneous conversations around different design tools or if you’re really frustrated by a bug and you can’t figure out what to do and you go and blow off steam and have a conversation about whatever cool TV show people are watching these days in the kitchen at the coworking space, that can reduce stress enough for you to go back to you problem and work on it on your own. So, I think really progressive companies moving forward will think about:

How do I shape internal company community, but how do I provide the benefits or support to employees to create a network outside of work where they can learn from, be more happy and engaged in their life, and bring that engagement back to work.

JEFF: Yeah, it’s a thing that doesn’t get talked a lot about in business in general but certainly around remote work. There’s a high percentage of people that get a job at a company or a place, a restaurant, because they want to meet those people [laughing] and hang out with them, right? It’s a whole social aspect and oftentimes people have met their spouses through work and all this stuff, and how do you handle that if there is no workplace for people to meet? I wouldn’t advise that you create a dating event at your company retreat, that’s probably not where you want to go, but I like this idea of supporting people having social connections outside of work, that a workplace might otherwise offer if it weren’t distributed. 

ALI: Yeah, and I think I can most eloquently speak about that in a digital nomad community because that community is just growing and as interconnected as anywhere. I was recently in Buenos Aires for three weeks working, and even before my flight landed I realized I knew 15 other people there that were my friends,  but also remote workers, which meant from the day that I landed I had 15 people to help me be motivated if it was a really sunny day and I didn’t want to work, but we all went to a café together and helped each other get excited about the projects we were working on, because we got to brag about the cool stuff our companies were doing. I had 15 people socially to go out to dinner with, so I was taking the necessary time away from my laptop and away from work, to recharge and not get burnt out and have a little bit of fun so that the next day I could get right back into the grind of work. Because I do think that sometimes [laughing] and I’ve been really guilty of this as a digital nomad if I choose the wrong location and there’s nothing to do, my fallback is work, but then I’m not having inspiring ideas because I’m not fulfilling myself socially.

JEFF: Yeah, burn you out, yeah.

ALI: And so, I think it’s really cool. Yeah, like burnout as a nomad is real, and I’m so guilty of this. My Instagram you see me hanging out at a café working with an ice cream Sunday or you see the fact I was able to go on a lunchtime hike to a private beach in Brazil. Yes, I’ve done all of those things, but I’m not showing you the days where I haven’t changed out of my sweatpants and I’m in Poland alone and it’s getting dark at two p.m. and so, I just work all day and all night because I’m bored, [laughing] and don’t know what to do.

JEFF: Well, it goes back to that vulnerability thing. That needs to be acknowledged that that happens to people, that that’s okay, and that there’s a means to be able to talk about that in some work channels of some kind. Because it really holistically we’re talking about morale. That’s a word that gets thrown around. I almost feel like it’s a cynical word because you don’t use morale to refer to happiness otherwise, right? [laughing] You know, “how’s employee morale? Are they gonna stick around? Can we keep exploiting them or are they going to leave?” But, yeah, happiness, but if people can’t express what’s going on with them, they start to feel shame about it, they start to hide it away, and they start to feel isolated. So, this relationship between isolation and company culture that allows a certain amount of vulnerability, allows an acknowledgement of the difficulties of work and life and allows communication around that, is really important. 

ALI:  Yeah, and I think there’s certain triggers and tools and clues that leaders in remote companies can look for. I think that the problem with isolation is that it’s in some ways a self-fulfilling prophecy or it’s this terminal circle that keeps going around and around and around because if you’re going through something difficult and you work in an office, you show up to that office, you’re probably not looking at your healthiest state emotionally, and whether people ask you about it or not, it’s more telling that you’re going through something. In a remote company, and I’ve been there and done that, I have gone on to a Zoom video call, like fake it till I make it, kicked butt on a really cool training session, closed my laptop and cried because I was going through some personal shit that I didn’t know how to bring it up with my coworkers. It took me a long time and I work in People Operations and I know how deep this goes. It took me a long time to be like, it is not only okay to ask for help but it is celebrated, and in the long run it’ll make you closer to these people that do care about you and want to help you, and then it’s better for everybody to, in a healthy way that’s respecting people’s boundaries bring this up because it is better for you as an individual to have support to be able to maybe not do a certain piece of work that can give you more time to focus on the stuff that you need to mentally process things. It gives somebody else an opportunity to get to know the stuff that you’re working on, to feel connected to you as a person, and help you, and it helps the business because nothing is being slowed down. So, as a leader, I would recommend that people really pay attention to what do people look like normally in conference calls and not just in terms of what they physically look like, but are they really engaged, do they have their video camera on? Are they looking into the camera or not? Or do they have their videos turned off more often than not? Are they coming to the meetings and not engaging with people, not speaking when they normally speak? Those are the clues that you get in an office space that you can take time to look at in a remote company, and paying attention to those things, and building the trust and asking from the get go even though it’s uncomfortable to get to know this, but it goes back to our conversation around paying attention to the physical cues of what’s behind someone’s computer screen and starting to have those ice breakers early so you get to know their hobbies because that’s a way for you to then start asking them, “Oh, you know, Jeff when’s the last time you played that guitar that’s hanging behind you?” If you say, “Oh, I haven’t played in weeks because I’m so overwhelmed and busy,” like hey, you might be at risk of burnout and as a leader in an organization let’s have a conversation about it.  

JEFF: [58:48] Obviously you can’t force people to talk and you don’t want to even coax them necessarily if they’re not wiling to talk about something, and the fact that you can fake it through a Zoom call and then close your computer, there’s some beauty in that. If you’re not ready to share something you don’t have to. And there are ways even that you don’t need to necessarily, you know, you see people using the phrase ”make it through the workday,” right. You don’t need to make it through the workday, you just need to make it through the Zoom call, or whatever. And so that’s kind of nice, but again it goes back to that word intentionality, like, creating an environment where you can say, and there’s also, it’s a whole other topic to get into, [laughing] but the book Nonviolent Communication, that whole realm of thinking is really interesting, and in that way of communicating to say, ”Hey, here’s what I’m seeing. It looks like you’re disconnected,” and be honest about that, and, “if you ever want to talk I’m here to talk and it’s okay”, but not demanding, “AND YOU HAVE TO TELL ME WHAT’S GOING ON OR YOU’RE GOING TO BE FIRED.” That’s obviously outside the realm of even probably what’s legal. 

ALI:  Yeah. I think it goes to creating that safe space, creating the opportunities for vulnerability and it’s up to the individual to take it, and then also when we talked about this earlier, if they choose not to take it with the company or if they choose not to take that safe space and vulnerability with the people they’re directly working with in terms of the projects they’re working on, who are they physically around that they’re working with and how can you create a safe space for them to get  support in those environments, and so for me, in my example of there are times when I was feeling isolated or lonely, and I would have those experiences of faking it through the Zoom call and then being lonely and alone in a random Airbnb somewhere, then thinking about “oh, but I actually have this coworking benefit so I can go to a city with people that I know I’m friends with and reconnect with my friends and that’ll solve my problems of loneliness which will help me solve my problems of being able to focus at work,” and so it’s like companies can offer support by creating the environment for people to get support whether it’s directly through the company or through other means, and I think that’s really cool. It’s like it doesn’t just have to be what you talk about at work, but it’s making sure that as an individual you know how to have ownership over your day and over the resources available to you, whereas in an office you might have to be there 9 to 5 and remote work if you’re feeling really crappy one day and you need three hours to do something that will make you happy or lay low and you’ll get your inspiration later that night, that’s okay too. I think that’s really good if people just know more about themselves and they know, here is signs when I’m hitting a wall. Here are signs, now I know how to deal with that effectively, and it’s not going to impact my work because it’s really stressful to be feeling burn out, to be feeling isolated, and trying to figure out how to deal with those things, and not have it ruin the quality of what you’re offering a company, and your reputation and your professionalism, and so reducing that anxiety is really beneficial.

JEFF: Well, and you feel like you don’t have options to know that you’re working at a company where you could talk about the problem you’re having. You could go to coworking. There are any number of these things that you could do, just keeps you from feeling so trapped and this existential stuckness. And I know there are companies out there, “we offer a coworking benefit but nobody seems to take us up on it so we may discontinue it.” Don’t discontinue [laughing] it, right? It’s working perfectly, if people know that they can if they need to, and I think there are a lot of things that fall under that heading. Like, not necessarily that people need to be communicating every thought in their head and their deepest existential angst, [laughing] but to know that they’re not trapped and don’t need to necessarily feel too much shame around that, at least from the work culture.

ALI: Exactly. It’s like having the toolkit and you don’t always have to touch the toolkit but when you open it up knowing that the tools will help you, that’s perfect for a company to offer, I would say.

JEFF: [1:03:49) Okay, let’s talk about Cohana. You’re doing your own stuff now. Talk to me about the mission of Cohana and now that you’re out on your own, what are the horns that you want to trumpet? [laughing] Ah, that metaphor didn’t work. [laughing]

ALI:  Yeah, so for me, [laughing] the bells I want to ring, I don’t know what the metaphor is, the drums I want to beat [laughing], so for me it was really about thinking through what are the aspects of my life that I’m most passionate about and also feel that there is a gap between what currently exists and what the future could hold, and that is what the inspiration behind Cohana was. It was, I’m a remote worker and a very specific type of remote worker, and I think there’s so many amazing conversations going on between why remote work is good for companies. Why remote work is good for individuals. There is less conversations around two things. The first one is, okay we know it’s good for companies, but we don’t know how to successfully implement it. What do we actually do next once we’ve decided that we want remote work? How do we make sure people don’t feel isolated? How do we make sure we’re talking about boundaries and definitions and expectations that work? And so, one of Cohana’s goals is to help companies get to the point where they can successfully offer these toolkits to their employees so that more people have an opportunity to explore remote work and how they can make remote work for them. So that brings it to the second goal and mission, is really around, okay, now we’ve made it easier for people to work remotely, the companies are more successful at offering remote work, what is the bigger societal impact of that and what’s the next phase of remote work, what are the projects there. So, some of the things I’m really passionate about exploring through this new venture are things like, rural areas and there’s a psychological benefit to being out in nature. It’s proven to reduce stress. People  don’t have to live in cities anymore because they have remote work. How do you take those two things and revitalize a rural community with new energy, new money, new young people, and what does that impact on the towns community as well? So, if you’re bringing all these remote workers and attracting them, well non-remote jobs could potentially be increased as well, and so this idea of forming communities online and in real life to challenge the status quo of remote work and open up the conversation to be around things like urban planning, rural development, the gap between remote work and physical and mental disabilities and what could be solved there, families that want to travel and how can the educational system be changed with remote work. That’s like, all of the things that consume my brain at any given time that I’m excited to explore and play around with in the future. So, that’s like probably Cohana like 5.0 in the meantime I’m doing consulting and helping companies really get off their feet with the tactical endeavors of creating internal processes. I’m hoping to release soon some worksheets and interactive guidelines so companies can do for themselves some of the things that they should be thinking about or having the right conversations internally. But then hopefully in the future I’ll be playing around with planning some of these interesting retreats and challenging societal norms through remote work.

JEFF: I love it. You’re speaking my language. It’s great stuff. Cohana.io, that’s where you can find out more about that. Ali, if anybody wanted to follow-up and maybe their brains were stimulated by some of the exciting things we were saying today, and they wanted to follow-up to tell you how great you are or ask questions [laughing] where should they get in touch with you?

ALI: [laughing] Well definitely visiting my website Cohana.io is a great place to get in touch with me. I’m also huge on Instagram and love sharing more about my digital nomad life there. The beautiful scenery in my pictures and the flubs and challenges in my stories. [laughing] So, if people want the inside look at Ali as a nomad they can go to seeinGreene on Instagram (that’s one ‘g’), and I’m always doing weird things on there. [laughing]