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Remote Works w/Tamara Sanderson




Karen Mangia

Today on success from anywhere we'll meet, the designer turned digital nomad, who's on a global quest to up anchor the nine-to-five, grind, and empower teams to set sail toward doing their best work anytime, anywhere. Tamara Sanderson is the co-founder of remote works, and the author of a book by the same name, who's navigated 70 countries, seven continents and sailed to Antarctica.


Tamara Sanderson

Thank you. Thanks for having me, Karen. I appreciate it.


Karen Mangia

Is being in the same location getting boring? I mean, you could be doing this from a sailboat somewhere, I guess.


Tamara Sanderson

Life has a funny way of switching things up on you. So as you mentioned in my introduction, I was a hardcore traveler. It was my primary identity. I studied abroad when I was 20. And I have that kind of cliche story that opened my eyes. And then I saw this whole new world. And I really actively pursued that after I graduated in my mid 30s. After doing a lot of travel, I was an expat for nine years. In different areas of my life, I got a little bit tired, and felt the need to be a bit more grounded. I took a job in Cambridge, Massachusetts, and then the pandemic hit. And so that really kind of stopped me in my tracks. And so I moved into this apartment, I think three weeks before the pandemic, I just started kind of making this my new home. And so it's very playful. As you can see, there's kind of like, I don't know, construction paper, there's a ton of books. I have, like tarot cards behind me. I have a whole art section. But I really just started thinking like, what would it look like? If I created a whole world in my apartment that I could explore versus always feeling like I have to explore things outside of myself. So I do a lot of reading. And I have a hammock outside of a little garden. I've been learning to cook. And so that's really captivated a lot of my interest. People ask me, do you want to fly right now? I actually get a lot of anxiety flying after a couple years of being standstill here.


Karen Mangia

We share that inventive nature because people asked me after so much personal and professional travel through the years if I was struggling during the pandemic lockdown and not being able to travel, and I took up an approach of discovery similar to yours and I imagined where I live as an all inclusive resort. And every week on social media, I would post the adventures I was having in my all inclusive resort unit using only things I own. These could be childhood toys. This could be things other people's children have given me crazy clothes I've inherited from relatives. Some of the more popular ones were a reenactment of the Kentucky Derby horse race, a reenactment of the Indianapolis 500 car race. But I feel like you know you look in the direction of imagination and asking an important question of like, what else could this be? Now in this season of the podcasts, we're talking about nine to five and I'm asking every guest, what was your first paid nine to five job? And for you this might be recent. How did that influence your career trajectory?


Tamara Sanderson

So I had a lot of part time jobs growing up as a kid. A lot of nannying and babysitting. But my first l kind of official nine to five job was when I graduated university and I wouldn't even say it was nine to five because I was a management consultant. I worked 70 hours a week so it wasn't nine to five. It was a lot more than that. But it did really kind of frame my mind of you know, I was making this big transition as a lot of people do from college into the real world. My jobs in the summer in I was in college I was actually a camp counselor for teenagers in a very different realm. No longer was I leaving a chance and kind of bringing people to the lake to jump off of a you know, into go I'm slides and jump into this l blob in the middle of the lake, right. So it was a very different world. But that really kind of made me think a lot about commuting and how we work. So my very first project I started at this consulting firm, I was in our Dallas office, but I was staffed on a project that was in St. George, Utah. And the project was funded by a major airline. And this was one of the regional airlines. So as a part of the project scope, we had to fly that airline which meant that I had to go from Dallas to the airport. And DFW is a huge Metroplex. So that in general took at least an hour and from there, I then had to take two connecting flights at 6am on Monday mornings, where I would then land in Vegas, I was the only person in a business suit. Everybody else is having cocktails and are all having fun. I remember once I was in kind of a Zara suit or something that, you know, your first suit where I'm, okay, cool. I've got to spend some of my money on the soup, but I don't have very much. I remember somebody mistaking me for the stewardess on the airline, because of my suit. I thought okay, this is my life. So anyways, that I would get into Vegas after these, all these flights, we wouldn't get a rental car, we would drive two hours to St. George Utah. I was commuting, probably 20 hours, at least each week, just getting to and from the job on those sides. Then, within the job, we would get up and we would start working at eight and then we would probably work until dinner. And then we would work after dinner. So I was just, I am working all the time. And then I'm on these planes all the time. And I was feeling awful. I have signed up for this. This is not how I imagined my life to be. So I thought about how I could make this more interesting for me. And so I was specializing in aerospace as a kind of discipline practice. And I was wondering how I'm gonna work for an airline somewhere cool. And so the next project I took was in El Salvador, I was working for taka airlines. I'm just gonna take international projects going forward, at least this will make it interesting. I'm just gonna stay there, I'm not gonna commute back and forth every week to Dallas. So I eventually gave up my apartment in Dallas. I lived in hotels for almost two years, a very kind of up in the air, George Clooney kind of experience. But I think from there that really kind of changed my mind on how work could work. Because this was 2006. It was before the iPhone, I had just a Blackberry and an IBM laptop. And I didn't really even use the cloud that much. It was all on some kind of external hard drive. But it made me realize that I could work outside of my home office, I could work internationally, I could work different hours. And so I think because that was my fun. My first experience in the work world, I never really understood the nine to five. And I've been questioning that ever since


Karen Mangia

You were ahead of the curve with your discoveries. You rejected a commute before that was a popular trend. You were working asynchronously and in different time zones. Your comments remind me of one of our guests from the first season, Kate Clifford. She's the Chief HR officer at Accenture in North America. And she talked about this concept of earning a commute. And what she meant by that is what is the reason that you're asking people to get together in person that is so compelling, that the commute is worthwhile. And I'm guessing that you are involved with a lot of organizations right now thinking about how to help them earn a commute from their employees or their customers.


Tamara Sanderson

First of all, I love the idea of earning a commute, because I haven't thought about that. Because there's been some pushback sometimes when I'm talking to people about the idea of, it's a luxury to be able to work from home. What about all those people that actually physically need to be in an office. And I think that is a really valid point. I don't think it's necessarily an apples to apples comparison. But I think it goes back to this point of earning your commute if you're going to require somebody to commute in every day. In a world where that is not the norm, or is becoming less of a norm with, you know, the surge of remote work the last couple of years, do you pay people to commute? Or do you only know how people aren't coming? Because there's a reason why you should come in. I really liked that idea. I actually was working with a client yesterday, and we had this exact conversation. So it's kind of fun. So I'm working with a law firm in Oakland, and they are moving from a traditional way of working to remote. And it's been really fun to work with them because it is kind of a traditional industry. But I think the legal work is actually very applicable to remote work because you're doing a lot of things on your computer. You're doing a lot of things with written words. There's a lot of aspects for asynchronous communication. So it's actually very right for remote work. But it is a field that's been around for a long time and it is somewhat conservative by nature. But when we were talking, they were talking about the commute and, well, people used to commute three hours a day. Now they're not but should they be getting some of the up time back to the verb. And so we were having a philosophical debate about that. But I thought one interesting idea that we came up with as a group was, what if you did a commute once a week, but it's a walking commute. And so if you want people to connect with other people in the organization, or think about belonging, what do you say, Okay, we're gonna pair you up with somebody across this firm, get on your phone, get your dog, and we're going to all do a corporate commute. And you can walk wherever you want, around your neighborhood, you get on the phone, you have kind of a meaningful conversation with somebody at work, maybe you post a photo of where you walk to. And that could be a commute that you all do together. So there's lots of ways to think about that time that you need to decompartmentalize from work to kind of your personal life or what a commute is. But it doesn't need to be, I don't know, being in traffic all the time. I don't drive and I get really carsick. So there's a lot of negative energy that I have towards that. I also used to work at Google, which has lovely buses, they tried to make it as easy as possible. But I was on that highway, from San Francisco to Mountain View too many times, and I would get off that bus and I would be carsick and that's how I started my day. And so I have a lot of feelings towards commuting. And I love the idea that you should earn it. And there should be a reason why you need to work with, be in person, and I am all for being in person, but make it worth that


Karen Mangia

Commutes community connection, I mean, the common denominator there is challenging, long standing beliefs about our relationship with work, you know, the hours that it needs to happen, and to what degree an employer should be dictating that. And what I love about the example you just shared is a law firm, a traditional business that has been based on commuting, and that that connection is equated with busy work and overwork and being fully consumed. And you're helping them back to the same example in question we use with your apartment, ask, what else could this be? And I'm sure they're bumping into some limiting or long standing beliefs. What are some of the biggest beliefs that employers and employees need to challenge to even make progress on disrupting this nine to five workday or traditional workplace,


Tamara Sanderson

There is a concept we talk about in our book called The Remote State of mind. And that is all about challenging the status quo. Because the technology for remote work has been around for a while, when I was talking to my dad about this book, as I kind of opened his eyes to what remote work was, all of a sudden, he started claiming it. He's a remote worker in the 80s. But he's never claimed that before in his entire life. When I moved with Honeywell down to Texas for a year, I was working from the house on my phone. So we've had the ability to work remotely before. As long as you have some type of way to connect, you can do that. The thing is, is I think there has been a lot of lag, and it's been on the behavior side. And so changing human behaviors, and what are norms. And I think there's a couple of things that stand in the way. So first of all, if you are a leader in an organization, however, you made it up that ladder, you're going to assume rightfully so this is very human. But that's the kind of the right way to do it that you succeeded in. This is your worldview of how successes and how this organization works. And for the most part, people leading organizations have only worked in a very traditional form, even Google, which was considered a kind of alternative at the time, because it had a college campus and feel. And it had bikes, and free meals. It was very collegiate. So they were surprised that people could wear T-shirts. And that they can juggle at lunch breaks, it felt very different. But still, there were a lot of aspects of traditional culture there, you are in person, you are at work, you have a clear hierarchy, you have a clear promotion. cycle. And so I do think a lot of people are having a hard time. Getting rid of the mentality of this is the way things should be. And that is very hard. What you're describing


Karen Mangia

It’s a foundation of relaxation, and release, you know, just for a moment. And don't feel the need to run your success playbook from the 80s or your last promotion or whatever that looks like, relax and release into what's showing up right now. Right and get curious about this tension. And you referenced the remote mindset a moment ago. Could you tell us what that is? And how do we get it? How do we get this remote line?


Tamara Sanderson

So one of the ways I think it is in general, challenging the status quo, but we go through some differences. stops to enable people to do this. There's a framework from journalism that I really like because it allows you to really investigate and dig holes into your current premise. And so it is called the five W's and one H. And so that is the who, what, when, where, why, and how. And so what we recommend, before you even start thinking about using Zoom or Microsoft Teams, or like is slack cool or not cool? Or what is this asynchronous communication? Should I have a cool zoom background? All of those I think are superfluous in certain ways to actually the core thing of why am I working this way? What am I trying to accomplish at work? How can I do this better? It’s asking those fundamental questions, I think actually will start opening people's minds and starting, you know, asking questions, because essentially, we have this really unique opportunity right now. I think historically, we've kind of created our lives around our work. A very clear example of that is that I am from a suburb of Dallas, but through different jobs that I've had did require me to move to different places. So if I wanted to be in tech, I moved to San Francisco. I wanted to work in Asia, and Singapore, these were all things I really wanted to do. But it didn't make me have to change my entire life and where I live, and what I do. And so I think there's something really interesting about remote work. Now I can change my life, to the point where work goes around my life, and where do I want to live. And I think I made that change a lot. When I moved from Google to automatic. I liked a lot of places I've lived before. But when I joined automatic, which was an all remote company, before the pandemic, and one of the largest ones that it owns, wordpress.com, Tumblr WooCommerce. But I actually sold everything I owned. And I lived out of one carry-on bag for almost three years traveling the world. And so during that time, I was working from Cape Town and the country of Georgia and Mexico City. And it was something I had really wanted to do. And it was like the first time that I was able to truly organize my work around what I wanted to do with my life. And before there were always a lot of stipulations. And so I love that for somebody that felt no matter what I did, I always felt a little bit hindered by work and I was always trying to balance wanting to be a professional with this need to explore and allowed me to actually completely marry those two for a couple years.


Karen Mangia

We jumped to changing the Zoom background or designing the next fun after hours activity for connection typically because it moves quicker. And it feels easier. Right? Which zoom background to use or what our company colors are, yes, there might be some debate or personal preference involved. We're not getting to the underlying questions, to your point when we're solving those quick check the box items and not asking the core question of what's the work that needs to be done now. Right? What are the greatest aspirations of our workforce? What are we hearing? Right? So it's using what you just described as that explore mindset to dive in deeper. And in your book, you talk about the five levels of remote autonomy. What are they and how could the folks who are listening, assess where they are in your five levels of remote autonomy framework?


Tamara Sanderson

Yeah, so the five levels of autonomy actually came from Matt Mullenweg. And he wrote the foreword for a book. He is the founder, co-founder of WordPress, the kind of open source community which actually powers 43% of the internet. People don't realize that WordPress is not just blogs, but most corporate sites are on WordPress, and a lot of newspapers are on WordPress. It runs so much of the internet as a content management system. But the levels of autonomy come from Matt and I worked at an automatic and that really shaped a lot of my thinking about remote work. Although I was practicing lots of aspects of it beforehand. This was the first time I'd been at a company that had been built round up remote first. WordPress as an organization started in 2005 by two developers that lived in different countries and it was an open source community. So all of its roots were distributed From the very beginning. And so this was kind of a framework that Matt put out in the world around the beginning of the pandemic of these levels of autonomy. Autonomy is so important for remote work, because essentially, you're wanting to move towards more autonomy. And what autonomy means is that you're owning a lot more of your workflow, and owning your process. And the more you can own your workflow in your own process, the more you can get out of that nine to five, because it doesn't have to overlap with everybody all of the time, right? And so at the very bottom, I think of this pyramid as being kind of like, no ability to be autonomous. And so you know, an example of this might be if you are a nanny, you cannot be autonomous, but the baby, right, you have to be watching the child, you have to be in the you have to be in the house, maybe there's a little less autonomy, if the kid goes to sleep, maybe you can, do a couple other things. But for the most part, you cannot work separately, because of the fact that you need to be always on it could be the same as somebody, that's a plumber, you need to be in the house with the pipes, jobs, those sorts. So that's a level where there's not that much autonomy. But as you go up into these different stages, it's allowing yourself to work at your own pace. And so you can co work with other people, but not necessarily on their time, it does not have to be synchronous. And so as you're moving up these you may notice, I think a lot of people move from a kind of stage zero at a company to maybe a stage one, during the pandemic or even before the pandemic. So if you were working, if you were often traveling for work as a salesperson, if you were going to conferences, if you could work from home, when you were sick, all of those you are practicing some level of autonomy that is equal all the way up. And I think the very big top is kind of Nirvana, that actually means that everybody can be distributed. And you can actually be working better than a traditional company, even though you are all working at your own time, at your own pace, and making all those decisions for yourself. So that's kind of the level of your autonomy there. It is a way to kind of stretch your thinking about what is autonomous. And so we give a lot of my co-writers and I give a lot of presentations on communication, the recent autonomy. So I think autonomy, we think about, I don't know, autonomous robots and autonomy and industrialization. But really, autonomy needs to be that you can actually do your work without having to be online with somebody else at the exact same time. That's how I think about it. And that usually requires a lot more written communication, a lot more documentation, a lot being a lot clearer on the kind of deliverables and outputs. And sometimes that can sound, Oh, do you just care only about work? Don't miss all the personal aspects, we can go into that thing later. But I think what's really valuable is all of a sudden, you don't have to be at the will of somebody else for 50 hours every day. And you can all of a sudden, do your best work when you want to. And even when scheduling meetings, even if you're doing synchronous work, I often work in pairs. I co wrote a book, I have synchronous meetings a lot with Ali. But there's something really nice about the fact that we get to set up our meetings when we want to. And so she lives in France, I live here, our hours are different. Actually, I'm a night person, and she's a kind of afternoon person. And so we could actually define our own schedule. So even if you're working with another person, I would say we have a lot of autonomy because we get to make those decisions on our own.


Karen Mangia

Some who are listening might be critics of your concept, because they'll say, Well, that's great. If you're an entrepreneur or if you're young, these kinds of sounds great. I mean, autonomy is fantastic for somebody else's business, and it won't work here. What would you say to the naysayers of these organizations?


Tamara Sanderson

To a naysayer? I would say, just try one simple experiment. Just I mean, what would it look like just to have a little bit more autonomy throughout your day? What would it look like if on Fridays, you had a no meeting day? What would it look like? If you created bands for your week, people should be synchronous and online for these four hours, but you give people flexibility? What if you move one meeting that you're always having and see experimenting with what it could be if it was written? My recommendation is it doesn't have to be a binary decision. You don't go from stage zero of autonomy to the most autonomous company in the entire world where everybody is magically seamlessly working independently. That doesn't happen, all it is, is it's a spectrum and well how can you give people just a little bit more autonomy because even just a little bit more autonomy can be very meaningful.


Karen Mangia

At the core of agency and autonomy is employee experience. The reason organizations and employers are exploring autonomy more is because to some of the examples you provided, employees aren't demanding it. You know, employee expectations are shifting in a variety of ways. And one of the inflection points you talk about in your book is employee expectations shifting from having a manager as a supervisor, to a manager as a coach and connector. How do we reskill managers to make this shift,


Tamara Sanderson

There's this movie about Field of Dreams. And the whole concept of it is, if you build up people, people will show up, things will happen, right. And I think that's how we've addressed work for the last 100 years. If you have this office, you have butts in the seat, something's gonna happen, they're there for 40 hours a week. But we were actually measuring the success of our company based on things like proximity, and FaceTime, and just visibility, all those aspects. But I don't think those were super precise for what you were actually trying to measure. And so in this remote work place that we're in right now, I think we can actually get closer to measuring outputs. And so if you are a manager today, I think rather than making sure that Pete, there's butts in the seats, and people are there, and you're going around and checking to make sure that when people have left, if they're going out of the office for lunch, listening in on conversations, tapping them on their back, anything that reminds you of office space, you know, that whole kind of thing, you can move to an output oriented world, where instead as a manager, what you should be thinking about is both short term outputs and long term outputs. So a short term output would be, what's the deliverable that we need to have for the end of the month?


Karen Mangia

If you were to support the middle manager shift, you created a series of manager mantras? What are they?


Tamara Sanderson

With these measurements, we have mantras in our book that are specific to how I can make sure I'm showing up in supporting that security for my employees. How can you make sure that you are not only helping people feel connected to one another on a team and connected to you as a manager, but also connected to the mission statement that needs to be something that people feel like they're getting up for in the day, and that there's value to what they're doing. And so that's how we ended up using a lot of these mantras. Are these kinds of simple statements to ensure that you are thinking about the motivation of your employees?


Karen Mangia

Well, speaking of social support, and connection and the water cooler, we have a segment on the show that is our virtual water cooler. So imagine you and I meeting at this virtual water cooler and having a spontaneous conversation. These are five quick questions to help our listeners get to know you a little bit better. So just say the first thing that comes to mind, are you ready?

Tamara Sanderson

I'm ready.

Karen Mangia

What time of day do you do your best work?


Tamara Sanderson

Oh, well, first of all, I love this question, because I think that breaking the nine to five is all about working around your own energies. Well, this is this is part of why I like remote work because I am a night owl. Without a doubt. There's actually three different Chronotypes. We interviewed a professor at Berkeley, Sahar Yosef, and she's excellent. She's a neuroscientist, but 20% of people are night owls. 25% of people are mourning birds and the rest, the majority of people about 50% Are biphasic. But as a night owl, it means my first energy peak is five to 7pm. It's actually after traditional working hours. And actually, my second energy peak is from 11pm to one. And so as mentioned, I do have a lot of autonomy now. So this is a shift from what I used to do. But I have been going to bed much later and doing a lot of my work at night. And I've been shifting and waking up later and then doing things during the day. And that's actually how I'm the most productive.


Karen Mangia

If there were no dress code, how would you dress for work?


Tamara Sanderson

Well, I guess when I'm online, and doing remote work, my favorite thing is kind of business on the top, comfortable on the bottom. So right now actually, I just took a Thai massage class and I learned how to do it. I'm certified in basic Thai massage, I can give a 90 minute Thai massage, I have these massage pants on. That's what I'm wearing right now. But I have kind of a business top. So that's kind of my favorite, remote work thing. But I just like being comfortable.


Karen Mangia

What is part of your daily routine that you look forward to every single day?


Tamara Sanderson

I try to take a picture or find a quote or something in my life that feels special and sacred in some way to me. So yesterday I went on a walk last night and I took some pictures of some different flowers that I saw, and a quote that I read in a book. So I would say that is kind of my daily practice of something I really look forward to and then I am a huge, huge, huge reader. Hence writing as well. Those are very, directly linked. And so every day I read and I read a couple books a week.


Karen Mangia

If you could have any job in the world, what would it be?


Tamara Sanderson

Probably what I'm doing now.


Karen Mangia

Imagine you now have 25 hours in every day instead of just 24. How would you invest your extra hour?


Tamara Sanderson

Ooh, that's good. So right now I already invest quite a bit in sleep. I'm a big advocate of that. And so I take naps in the middle of the day between work. Because I'm all about doing work in sprints, I actually think it's a lot more effective than trying to work in the marathon type format. I had an extra hour and I was very awake during it. And very energized. I would I'm writing a kid's book right now. And so do more of that. So really focusing on more creative work.


Karen Mangia

Before we close, where can listeners connect with you and find your book?


I am on LinkedIn, Tamara Sanderson, you can find me if you also add in remote works there. So I try to post pretty regularly on that forum. Our website is remotework book.com.


Karen Mangia

Well, one last question before we close today, what is the only synchronous lesson you will ever need?


Tamara Sanderson

The only async lesson you've ever really needed to know is we go into me, you basically need to address and set expectations. And we have kind of a cute formula for that in the book. But it's all about expectation setting. And you want to make sure that people know when things need to be delivered, what needs to be delivered, who needs to be involved in a conversation. And then we use the term Wawa I don't like in that sound? It's in the Urban Dictionary. But essentially what wha means what happens if nobody responds, because I think that is often the holdup in remote work. Well, I sent this email, I said we're gonna do this. Here's the timeline. Nobody's responded. And so I'm still hurting these cats around the office or the virtual office, right? And so that won't wha is usually said if I don't hear back from anybody, or if you do not respond by this time, I'm going to still move forward in this way. And so I think that can be incredibly important so that you're not left hanging.


Karen Mangia

Thank you, Tamara Sanderson, co-founder of remote works, and co author of remote works, managing for freedom, flexibility and focus for revealing how to work remotely without becoming distant today on success from anywhere because success is not a destination. Success is not a location. Success is available to anyone, anytime, anywhere.



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