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CREATIVITY & COLLABORATION IN A REMOTE FIRST WORLD W/TAMARA SANDERSON

Matt Hayman
Senior Growth Marketing Manager

Matt is joined by Tamara Sanderson, co-author of the upcoming book "Remote Works
- managing for freedom, flexibility and focus".  The interview is wide ranging
and touches on a number of topics that will be of interest to any remote leader.

In the episode we cover:

[+] The optimal skills, behaviours and mindset required for remote management
and remote work more broadly - what Tamara refers to as 'remote work fluency'

[+] The leadership archetypes that thrive and struggle in a remote first world -
and how to develop your growing edge.

[+] The huge opportunities in creativity and collaboration that remote work
enables.

[+] The role of play in collaboration - and how to ensure it never appears
cheesy or forced

[+] How remote work might evolve over the next five years

And more besides.

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TRANSCRIPT:

Matt Hayman (00:28):

Hi and welcome to leading remotely as always. I'm your host, Matt Hayman. I've
got a great episode for you today. One filled with insights. You'll be able to
put into practice straight away. I'm discussing creativity and collaboration in
a remote first world. With my guest, Tamara Sanderson, Tamara has over 12 years
distributed work experience at an impressive range of companies that include
idea automatic. The company behind wordpress.com and Google.

Her latest project is the book remote works, managing for freedom, flexibility,
and focus co-authored with Ali Green and available in February. Next year, the
interview is wide ranging and full of actionable insights for remote first
leaders, much like tomorrow and Ally's book.

In this episode, we cover the optimal skills, behaviors, and mindset required
for remote work. What tomorrow refers to as remote work fluency, the leadership
archetypes that thrive and struggle in a remote first world and how to develop
your growing edge. The huge opportunities in creativity and collaboration that
remote work enables the role of play in collaboration and how to ensure it never
appears cheesy or forced how remote work might evolve over the next five years
and much more besides huge, thanks to Tamara for being so generous with her time
and expertise. I hope you enjoy the episode as much as I did recording it
without further ado. Let's get straight to the interview. Hi, Tamara. Welcome to
leading remotely. Great to have you on the show.

Tamara Sanderson (02:08):

Hi Matt. Yeah, I'm glad to be here.

Matt Hayman (02:10):

I've been looking forward to this conversation since we first spoke, because
when you talk about alignment between the goals of your book and the goals of
this podcast, I think it's as close as it can possibly get all about inspiring
and supporting remote leaders. So I know in the book that you talk about remote
work fluency, and I think that's a really nice foundational starting point. Can
you just unpack that term? What, what is remote work fluency? What does it mean
to you?

Tamara Sanderson (02:34):

Yeah, so I think we talk about remote work fluency in the book. Cause right now
there's a lot of discussion in 2022, same as like last year as well. Is it gonna
be remote? Is it gonna be hybrid? Is it gonna be traditional? There's kind of a
lot of back and forth on that, but ultimately we think the world is going
towards a digital first way of working and you're gonna need this remote
fluency, regardless if you're a full-time remote worker. If you go into the
office two days a week, or if you go into in the office all the time, but
there's just gonna be more expectancy. If you're sick, you should be working
from home, uh, that people will have a bit more leniency of, you know, working
remotely for two weeks to go somewhere for, you know, you might go on vacation,
you're working for two weeks and you spend a week by the lake or something of
that sort.

Tamara Sanderson (03:15):

I just think there's gonna be more expectation of being with the work remotely
that is gonna become a fluency that you need, regardless of what job you're in,
if you're kind of a laptop worker in any form or fashion. And so we think of it
as, um, cuz our book is called remote work. So obviously like, uh, great for
SEO. Uh, it's also a pun, uh, but you know, we wanted to make sure that people
don't, you know, see our book and are like, oh, well I don't work full time
remotely. Or you know, I still go into the office or, you know, one of those
things, cuz all the principles in our book, regardless of how often you are
working remotely, we think that it is important and it is applicable. And this
remote work fluency will be the same as needing, I don't know, you know, I, I
don't put skills anymore on my resume, but it makes me think of when people are
like, I am proficient in Microsoft word, I think, uh, in the same way.

Tamara Sanderson (04:06):

I know that sounds like everybody should be probably proficient in word if
they're working in a office setting now or a digital office setting, you know,
uh, when I say office setting, I'm just talking about people that have jobs that
are require a laptop for a certain portion of the day. But yeah, you're just
gonna have to have that fluency just like you would any type of like windows
skillset or being proficient at, um, I'm trying to think of other tools, but
yeah, same, same thing. You just need to be proficient in that. If you're
working in a Spanish speaking country, you need to be proficient in Spanish. If
you're working in any type of company where you are using technology as a prime
form of communication, you should be remote fluent.

Matt Hayman (04:46):

So that's on the skills side. What about the, the behaviors or the mindset
that's required to be, to be fluent, I suppose, in, in remote work, what do you
see as some of the key behaviors and mindsets shifts that need to happen to
become more fluent in remote work?

Tamara Sanderson (05:00):

Yeah. So we call this, um, a remote state of mind in our book and we have a
whole chapter and it's all about kind of shifting from this paradigm of how we
used to work to this new paradigm of how we're working today. We use this
journalistic framework and it is called the five Ws and one age. So it's who,
what, when, where, why and how, and essentially you just need to question all of
your assumptions of how you've worked. It's all about just challenging. The
status quo, a remote mindset is you're you're working in this different way and
what we've done. We've done a lot of like copying pasting of how we worked
before, right? So it's like, oh, we used to do meetings. Now we do those on zoom
or Google Hangouts or Microsoft teams. You know, we used to have chats in the
hallway.

Tamara Sanderson (05:43):

Now we have those on slack. It's nice that people were able to easily make those
associations and those analogies, but it actually requires rethinking like why
are we working this way? Uh, what do I actually need to get, get done? What are
the outputs that matter? You know, before a lot of, uh, things that matter were
like proximity and FaceTime and all these things that weren't actually your core
work. We talk a lot about going from like an input culture to an output culture
inputs is when you're seeing things. I don't know. I, I often I'm an American.
So I use the field of dreams analogy. My mom is very into the Chicago Cubs. So
we watched a lot of baseball growing up. I was in umpire when I was in, uh, as
one of my first jobs. Uh, but fields of dreams basically says like if you build
it, they will come.

Tamara Sanderson (06:27):

And I think we've had that mentality a lot within work. If you have an office
and you see people there for about 40 hours a week work will get done, but
you're just kind of assuming it it's, it's not that precise of knowing if people
are getting things done. And so what I like with remote work is that you can
really get to this output oriented state of mind where you're thinking about,
okay, what do we actually need to get done? And when you actually get those
things done, it often takes a lot less time cuz you can, you know, remove a lot
of this like work about work and a lot of the miscommunication and all of those
kinds of things. You get more time back into your life. You're more productive
with your output. And I find that just like a huge win from a, an overall life
perspective.

Matt Hayman (07:08):

If we think about the remote leader, who's listening to this or the remote
manager, how could they do you think start to develop a better awareness of
where their own strengths and weaknesses lie in these areas?

Tamara Sanderson (07:20):

Yeah. So, um, once again, I'll talk a little bit about the book, but we begin at
the very, like the very first section of it talks a lot about knowing yourself.
And I think that is hugely important before you're able to be a remote leader, a
remote manager, cuz we're all gonna have inclinations that are gonna be very
personal to us. So if you're a leader and you have, you know, made way up the
corporate ladder within a very traditional context, you are going to have a
frame of mind that will make you think that that is the way to succeed. And it
doesn't mean that you you're closed minded or that there's anything wrong with
you. That is a hundred percent normal, a hundred percent human. That is your
experience. It is completely valid experience. But I think what leaders need to
require do is like, this is their experience, but it's not everybody else's
experience.

Tamara Sanderson (08:12):

And is this whole idea of separating yourself from other people? There is this,
I, I love roomy. I don't know if anybody else is in into poetry, but there's
this great poem. Um, and it is about like an elephant in the cave and you have
all these people go in. Nobody's ever seen an elephant before. It's dark in this
cave. Everybody touches different parts of the elephant and they describe it.
And so the person that's describing the trunk versus, uh, the tusks have very
different views of what they just saw. So they come out and um, you know, I
guess at the end of the poem, it basically talks about when you collect
everybody's view, you can see the whole elephant, but when you're just seeing
everybody's, you know, individual aspects, it looks very different. And I think
as a leader, it's really important to obviously value your own experience and
what you have learned that is value.

Tamara Sanderson (08:58):

I'm hugely into, um, experiential learning. Obviously I threw myself out there a
lot, uh, within the first, uh, half of my career, I, um, was an expat for nine
years. I went to 70 countries. I really like threw myself out into the world. So
I'm all about experience, but you know, everybody else has their own experience
as well. So with the leader, I would recommend, you know, looking inside
yourself and understanding kind of where your strengths and weaknesses are in
our book. We have this thing it's um, it's like a Madlibs inspired quiz where
you go through and you can, you know, talk about adjectives of, you know, what
was your best manager? What was your least favorite manager? Um, how do you like
to work? What bugs you at work? Uh, all those different questions. And I think,
you know, we all have, I'm very into youngy psychology. We all have different
shadow sides. And I think the more that you can accept those versus trying to
hide those, um, you can be a better leader cuz in your you're more well rounded,
you're you, you're more whole and you can see different perspectives. So that,
that would be kind of my recommendation is just spending some time getting to
know yourself. Uh, if you wanna be a really good remote leader, uh, cuz it
requires like a flexibility outside of how you've worked before.

Matt Hayman (10:10):

So clearly the pandemic has thrust a very diverse range of leaders into becoming
remote first leaders. In many cases, I opposed with minimal choice in the matter
when you look at leadership archetypes, which archetypes do you think thrive and
which are the ones that struggle most in remote settings?

Tamara Sanderson (10:28):

Yeah. So, um, in our book we got really into this music analogy and we were
thinking about all the different, you know, leaders we've seen, we wanted to
make our own IP and our own thoughts on this. So we didn't wanna just copy and
paste something from another book that would've had this perspective actually
from a very traditional workspace. Um, but within these, we came up with like a
couple different types. And so, uh, we have like a composer, the band leader of
the agent and the promoter. And I would say the tight that I think has the most
difficulty within remote work cuz remote work requires a lot of like trust
everybody within the company needs to be a project manager, regardless of cuz
you're managing your own workflow more. Um, you're not gonna have as much, you
know, oversight for the most part.

Tamara Sanderson (11:13):

You are gonna have more flexibility on when you work. All these things can be
very difficult for a manager that has liked to have a lot of control and wanting
control is a natural part of being human. You read anything from like Buddhist
philosophy, it's all about how control and attachment or something. That's very
human, but it leads to a lot of suffering. Um, and so I think, you know, if you
are a manager that has needed a lot of control and needed to do a lot of hands
on, I think you're gonna probably have the most difficulty. Uh, when our book we
call that kind of the agent mentality we talk through. Um, I used to live in
Singapore for four years. Uh, I really love K-pop. And so we use girls
generation as an example, they're incredibly talented, but there is a lot of
control over, you know, how they perform, how you find the next person for
girls' generation. And so we use that as example, cause that is a manager that
needs a lot of hands on control and they also are kind of very like organization
focused. Like they need to make sure that they look good for everybody else. And
I think that can be valuable at times in remote work, there is value of all
these archetypes. You have to use them at different points, but I think leaning
a little bit away from control and towards trust is gonna help most remote
leaders out there.

Matt Hayman (12:36):

Do you lead a remote team, but struggle with spontaneous communication and
collaboration? If so, I'd like to invite you to check out our platform,
wonder.me a virtual workspace where teams connect, collaborate and grow working
side by side from anywhere for a limited time only podcast listeners can use the
discount code L R P 30 to get 30% off your first three month subscription or
annual plan head on over to wonder.me, start your free trial today and use
discount code L R P 30. Now back to the interview for the archetype, the person
who maybe reluctantly realizes that that control is quite a big part of, of how
they, they manage, what are some of the steps they can do to start to relinquish
that. And cuz that's not an easy thing to do, but what, what are some of the
things they can do to try and take some small steps in that direction?

Tamara Sanderson (13:26):

So I would say, I think everybody's gonna struggle with this again, it's human.
So I guess you think about parenting, you can, you know, there's the helicopter
parent, which might be one that needs a ton of control. You have the free range
parent, but ultimately everybody needs some type of control over their kids. And
I think in some ways there is a parallel to work that you need some type of
ability to oversee the team that you are managing, cuz it is called management,
right? And so not all companies have management, but for the most part, a lot of
them do. I had a great coach at automatic. He is also interviewed in our book
and he used to always kind of recite this quote from Victor Frankel to me. And
it says between stimulus and response, there is space in that space is our power
to choose our response and our response lies our growth and our freedom.

Tamara Sanderson (14:15):

And so I would notice I would start getting triggered by something at work. So a
heated conversation, not knowing if something would work out wondering like how
people were, you know, feeling about different things. Uh, I was managing a lot
of large partnerships with major tech companies there. And so there was
negotiations and I remember being like very easily triggered and then kind of
spiraling of like worry and what's gonna happen and feeling, and that, that was
because there's a lot of things that were outside of my control because if you
were in partnerships or you're in corporate development, both of those are
outside of your control because there is somebody else that is very much, uh,
has the, you know, decision making power and I'm just trying to influence it
ultimately. And, and so, you know, I would be spiraling and you know, uh,
actually would help me just come up with, okay, there's nothing you can do
within this, this time you've made your response and maybe that's an email or a
decision or, you know, I'm just gonna wait for a week.

Tamara Sanderson (15:14):

So whatever it is, whatever my response is, is just saying, this is gonna be my
response to this thing, this stimulus that is bothering me and then just trying
to stay with that response as long as possible. Um, because that in between of
continuing to react and react and react to a stimulus, I think that is where you
feel a lot of that anxiety. And so I would re recommend for remote leaders.
You're gonna have those stimulus of like, I have no idea what my team is doing
or are they gonna actually come through on that deliverable? Or I am getting a
lot of heat from somebody above me and I can't see what people are doing. And I
used to be able to see it. And I used to be able to go over to their desk and
see what they were doing. You are going to have those feelings. I think it's
completely natural, but it doesn't mean you have to act on those and you can
come up with your response in different ways that you can get those needs met.
There are ways within remote work that you can get more visibility and more
transparency. Uh, you just have to be a little bit more intentional about it.

Matt Hayman (16:09):

So as you know, at wonder, we are all about creativity, collaboration, creating
a workspace where, where people can engage in those activities in a remote
environment. What do you see as some of the main challenges and opportunities
specifically around creative work and collaborative work?

Tamara Sanderson (16:23):

Yeah. So first I'll start off. One thing I really love about wonder and what it
does is that you actually add visibility and like visual cues to where people
are working. Cuz what we've noticed is, you know, you in the fiscal world,
obviously, first of all, you know, we're human. So, you know, we have all of our
ancestors have been queued on how to deal in this fiscal world, but you go into
an office and there's a lot of cues on what to do in different places. You go
into a meeting room and you know, okay, if it's a two person meeting room, maybe
it's kind of for a one-on-one. If it's a large meeting conference, it's gonna be
something more formal, even the type of meeting room that it's set up for the
type of conversation you're gonna have there. Some might have whiteboards, some
might have a projector.

Tamara Sanderson (17:05):

All of those are giving you cues on how you're gonna act in that meeting. You go
to your desk. Usually that's where your laptop is. It's a bit quieter,
especially if there's cubicles, you know, you, you know that you're gonna do
heads down work. Maybe it's an open platform or open stage workplace and you may
have some casual conversations, but they're around people that sit next to you,
which might work with you or work in the same domain. Then you go, you know, to
the water cooler, people will talk about the people layment the water cooler so
much in remote work. It's interesting cuz I was like, I don't remember anybody
talking about the water cooler when I was there in the office. Uh, but like
everybody wants to like cry about the water cooler now, which I'm like, okay,
cool. Nostalgia is a thing.

Tamara Sanderson (17:47):

Um, but let's say you're getting, getting a cup of coffee with like a coworker
or something of that sort. You, you run into them somewhere in the hall and you
have kind of a more casual conversation. Maybe there's a little bit of office
gossips and like politics that are going on, but you knew what you were doing in
all these different spaces. And it would be inappropriate if you were in a
meeting to do all your heads down, work there for the most part, unless that was
like a norm within the company, which sometimes in like organizations that have
meeting after meeting, after meeting, you actually find a lot of people on their
laptop during the meeting. Um, but that's not really its intention. That's
usually because of an overload of calendar. Um, but what I really like about
wonder is you're adding that kind of visibility and that kind of spacial dynamic
to remote work, cuz that can be very difficult when people are like going
between different tabs.

Tamara Sanderson (18:30):

And they're like where, what happens? Where? And by seeing like, oh, okay, this
is the notion. And this is the notion that is associated with where we do
engineering work or you know, this is the CRM, this is the sales force that we
use for partnerships. And then maybe you go over to a different, you know, area
of wonder and it's like the CRM that you use for sales, this could actually be
very different within, you know, the same platform. But I love how you visualize
that. And we, in our book, we call that your digital house, um, because we were
also trying to get towards this thing of needing to visualize how all of that
works. Um, so that's the first thing. I think there's something really beautiful
about what you've done of translating that. Uh, cuz I think that works really
well with spatial memory.

Tamara Sanderson (19:12):

There's a, uh, this is a popular example. Um, and I know that you're British,
uh, but I think they've done studies on London cab drivers, at least before Uber
and you know, maps and all of those existed. But their brains were actually like
quite different from all of their S spatial memory of learning, how to navigate
all the streets of London. And I think there's something really interesting
there, cuz it does show that our brains are wired for, uh, location and
understanding where those are. And I think your other part of this question was
on creativity and collaboration. And so, um, I used to work at IDEO for a while.
So that is uh, known for design thinking. It's all about creativity. I learned a
lot there, but I also in general read a lot about creativity. I have an art
practice, I just wrote a book.

Tamara Sanderson (19:59):

So there's a lot of things that I like to do from a creative perspective. And I
know that people mention a lot that, you know, there are really struggling with
collaboration or having new ideas. I do think that within your Workday, not
everything needs to be collaborative and not everything needs to be creative in
a lot of jobs. You don't want an accountant that is incredibly creative all the
time. Cuz usually that would get people into jail. <laugh>, you know, you
actually don't want a salesperson to be incredibly creative cuz that might
actually lead into bribery. So I do think within, you know, different realms,
uh, even somebody that is a creative. So when I was at idea, we would be on
creative projects. There is a portion of the design thinking process up front
that is very creative and ideation oriented and you're getting all this
inspiration, but at some point in the project you're gonna have to deliver.

Tamara Sanderson (20:45):

And once you start having to deliver, you get into this heads down mode of,
okay, we have like the graphic designer coming in and doing this. We have
somebody writing the business plan, uh, you know, this is how we're gonna do our
presentation. Somebody is coming up with a storyline. All of that is very
execution focused. So I think within your organization, it's important to think
when is a time that we need that ideation and that creative energy and when are
we gonna be in that, uh, execution mode. And so I think distinguishing those is
important. Um, because once you're in that execution mode, I don't think you
necessarily need to be in that creative space. They're different mindsets and
they're both incredibly valuable, but it's very hard to do both at the exact
same time is what I've noticed. Um, cuz they actually like if you are being too
execution minded in your ideation stage, you're gonna like take away that like
free forming, beautiful brainstormy lens.

Tamara Sanderson (21:38):

Um, and if you're being too creative in the execution mode, you're kind of, you
know, going back on everything you decided during that brainstorming portion. So
I do think there's important. There's importance in thinking about the phases. I
think there's a lot of ways for remote work. You can be very creative in a
different way. And so maybe I'll talk a little bit about that. So, uh, within
design thinking at the very beginning of the stages, there's often, um, a
concept of getting analogous inspiration. And so if you're trying to brainstorm
a new way of doing things, you know, I, I think like a popular example we had at
IDEO was we were doing a project for a hospital and it was talking about like a
surgeon team. And so they had everybody go out to jet blue and watch how they
got an airplane ready.

Tamara Sanderson (22:22):

And so there was some like analogous examples of, you know, how do you get like
an, like a pit crew and all the things that they're doing and doing that really
fast and getting ready to fix a plane. And it's, you know, it's high stakes. You
really don't want a plane to crash. It's same with surgeons. You know, it's high
stakes. You don't, you want your patient to live through the operation. And so I
thought that was a really interesting analogous example, but there's tons of
those. And I think within remote work, when we have this freedom of where we're
based, you can have those analogous experiences more easily. So if I were a
leader in an organization, it depends on what your problem statement is. But if
you were, I don't know, you can have, you can send people out to a museum for
the day and take, you know, let's imagine that you are on a design team, you're
doing a rebrand.

Tamara Sanderson (23:09):

And so you're thinking about different colors, right? And you could have people
go and do a whole day of research on their own in all different types of
locations. You could have somebody go to a museum and take pictures of color
combinations. They really like, you might have somebody actually go to target
and just see what are the color combinations that are popular in this store
right now. And then you might have somebody go to a botanical garden. What kind
of colors are really popular in nature? Everybody can then come back on some
type of visual board. So, you know, there's a lot of different tools that are
out there. Um, and you can like display all of that. And then people are coming
in with all this different, you know, really rich ideas that are gonna add to
it. Versus if you were in an office, you would be on a Blackboard or like a
whiteboard, sorry, Blackboard is more like school from the fifties, but, um, you
would be on a whiteboard and you would be talking about colors and usually
there's this term called hippo, but it's basically like the highest paid person
ends up being the one that makes the decision.

Tamara Sanderson (24:04):

So you have everybody kind of catering to the person that's the most senior in
the room and you're not really getting any kind of new ideas or inspiration. And
so as a leader, I would really try to be intentional about what is the value you
can get from people being remote. Um, I interviewed a ton of people for our book
of different kind of remote experts. And what example I thought was really cool
was, you know, you have people all around the, all, all over dispersed and they
said that they were making a design product. And so they said, if you know
anybody in your town that in any form or fashion says that they're a designer,
you can take 'em out, you can expense the meal and ask them some questions on
the tools they use, unlike how they do, how they do their design tools.

Tamara Sanderson (24:43):

And so, you know, come back, give us like a writeup, but that's really easy way
to do user research. You're getting into the local environment, you're getting
people more connected to the product. And I think that is hugely important cuz I
remember Google has lots of incredible things about it. So I'm not, I think this
is an example that I have lived through that I think is very common to most
corporations. Um, but Google is often in like certain locations, you have a big
office in New York, you have a big office in Singapore, you have a big office in
San Francisco. Um, but users are spread all over the world, right. And there's
users all over the us. And so how can you get the, you know, uh, my parents live
in McKinney, Texas. How do you get the, the life experience of somebody that is
74 in McKinney, Texas, if everybody is in the office every day in San Francisco
and in mountain view. And I love the idea that with remote work, uh, it gives me
more freedom. Let's imagine that I was trying to come up with a marketing
campaign to reach people that are boomers that live, uh, in the Midwest. I could
interview my parents and that would be really important and new feedback than if
I were to be in an office and like assuming what people might want if they were
a boomer in Texas.

Matt Hayman (25:54):

So what role does play have in creativity and collaboration and how can a leader
foster that among the team in a, in a natural or, um, unforced way?

Tamara Sanderson (26:06):

Yeah. Ooh, I love this question. So actually, so my co-writer Allie green, we
met in 2017 in Cape town and we actually, it was kind of like a cute, like, uh,
meet, cute story because, uh, she was at duck dot go. I met automatic, very
prominent, all remote companies before the pandemic. And we had coworkers that
both knew that we were gonna go to Cape town and they were a couple and one was
an engineer at automatic and one was an engineer at duck dot go and they lived
in Uruguay. And so I feel like that's like a great story of like, Hey, there's
these two people like that we have met, uh, through our remote companies, you
should meet in Cape town. And so that's actually actually how I was introduced
ally. Um, before we started, you know, writing a book, but we used to host
salons for remote workers.

Tamara Sanderson (26:50):

So we did that in Belgrade and we also did that in Mexico city and ally led a
great salon on the aspect of play and I read a lot on play as well. And so
again, I think this goes back a little to what mode you're in and how a leader
can set up those modes. If you are trying to get work done towards a deadline,
it's not the best moment to like add a little play into it. I don't think, um,
cuz I think that can be actually a weird juxtaposition. Um, but I think there's
a lot of value of adding a bit of play into anything that is already routine
within your schedule. So a lot of teams will have a weekly meeting. How do you
start the first 10 minutes with something that is fun and that is playful. And
how do you actually like, I, I don't think the leader needs to be the one that
is the playful one.

Tamara Sanderson (27:36):

I think they just need to make space and approval for that. An acceptance of
that play. Cuz there are so many people with an organization that are creative
that are waiting to have this moment to like share something fun. And so I think
within that, the leader's responsibility is to give space and make it okay. And
so that is what I would recommend. But I think a lot of people I know, um,
within remote work they just say, Hey, the first 15 minutes of our, you know,
weekly meeting, it's gonna be fun. So maybe it's a, maybe it's a game to have
people play. Maybe it's a quiz. Um, maybe it's a sh like a show and tell maybe
it's just like a casual chat. Maybe you start off with a question like there's a
lot of those card game questions from school life or things like that.

Tamara Sanderson (28:19):

So there's a lot of ways just to integrate something that is a little playful
there. I also think if you are doing that meeting on zoom and you're in a
different location, part of your play can just be like, what is behind you? Like
I, I have <laugh> I made my own little, uh, I don't know if you can see, I have
like construction paper behind me of like those little, like, I don't know, um,
decorations they make during Christmas. And I, I made those with my nieces and
nephews when I was home in Dallas and I kind of missed them when I came back.
And so I made the same thing. And so that there's stories behind you. There's
stories of books behind you. Often people have like a cat come in or their kids.
Those are like great ways to add an element play into work.

Tamara Sanderson (28:59):

Uh, I also think with play, you need some like space to be able to play. And so
how do you create those spaces? Um, most remote companies, I know bring people
still in person during occasions throughout the year. And so I'll use an example
of automatic, but obviously automatic was, um, had a lot of resources at its
hand. So I don't, this isn't gonna be possible for every single corporation, but
they would bring everybody for a grand meetup once a year, all in person for
seven days. And during that time it was actually like only really focused on
kind of fun aspects in play. Uh, very little was focused on work. And I think
that was really important cuz basically what they thought was okay, this is our
moment in time. We're bringing everybody here. We're putting a lot of expenses
here. This is to build trust.

Tamara Sanderson (29:45):

This is for people to get to know their coworkers. This is for people to have a
really like lightened mood to celebrate. Those were the aspects of the in person
meet up. And so some things that would happen is, uh, every single new
automation had to give like a five minute talk about anything they wanted in
front of the, the organization. And so I gave mine on what was in my carryon
bag. And so I gave a whole thing on that. Uh, one of the guys that was on my
team that had just joined, he was, uh, potty trading his toddler and there was
some book about like poop, um, and animals. And so he gave his whole thing on
like potty training in a very funny way. Um, but you could choose like, I, I did
that because like the, the shows that you could really choose anything you
wanted, there was a lot of office that came and spoke.

Tamara Sanderson (30:26):

Cheryl stray was there one year we went, uh, to Harry Potter world. And so there
was just so many aspects there that was all very playful and fun. And uh, it was
to get people to socialize and get to know each other. And I think having that
intention and creating the environment is important, but it's all about creating
the environment, but you can't be like, Hey, now it's time to play cuz then
that's not play. Right. Um, and I also think if you're like trying to get
inspiration for play, just go to the playground and see kids like, um, this
summer, uh, the, actually the last two summers beauty of remote work is I run a
<laugh> I run camp Sanderson. Uh, I'm a counselor TA, which is my nickname from
my four nieces and nephews. And so I had like a whole crack corner. We went to a
petting zoo, we went to the water park.

Tamara Sanderson (31:16):

Um, but my brother went to The Bahamas and I watched his kids with, um, at my
parents' house. And so, uh, we had camp shirts and I actually like, I paint face
painted their faces every day we would go out in public people like what camp
are you at? They're like camp Sanderson <laugh>. And so, but I thought it was
just like a, that's a fun way to play. Like I, I, I, I think play is so innate
in humans that you just need to get people out there, like with being permitted.
And then I think some ways that are easier to play at work is through games. Um,
at automatic, when we would have these meetups, there would often be a game
room. And so people would be playing different types of video games. It was
definitely an engineering culture, but I think by having some of those aspects,
it, it gets people naturally involved.

Tamara Sanderson (32:04):

So whether it's board games, a sporting event, you could be playing, um, I don't
know, what's that, uh, there's this game corn hole in the us that people play
where you like throw bean bags into, I don't know it, you could do Bo Boche
ball. You can do bowling. Uh, I organized an event once for my team at Google
where we all went to, uh, the trampoline park and we all just jumped around on
trampolines for a while. So there's just like lots of things you can do. And it
just gives people, you know, a break. We also, when I was at Google, something
that I had our team bring in was, uh, a dunking booth. And, uh, we would like
throw like baseballs and then we would dunk the director. And so all we had a
pinata ones, we would just like bring things in that were kind of silly.

Tamara Sanderson (32:47):

And the reason that we were doing it is cuz we were 26 years old <laugh> we were
like, and we had all come from management consulting or private equity. And we
were like, this is a lot more fun than what we were doing before. And um, yeah,
but it was playful. So I would recommend leaders take the energy of people that
are younger at your organization, cuz I think not to be ageist, but a 26 year
old is gonna have some things that, you know, are gonna be really fun and it
might be nice to like bring in that energy and you know, I'm now almost 40. I
would love for somebody to play on something that's 25 for me. Like I bet it
would be really fun. And so I think give, give people the budget and the energy
to be playful and plan something and kind of show their skills.

Matt Hayman (33:29):

So if we think about directional trends five years ago, remote work looked very
different to how it does today. I'm gonna get you to try if you can and predict
the next five years, what does remote work look like five years from now?

Tamara Sanderson (33:42):

I do think you're gonna see as we continue to question the status quo, you're
gonna see more norms break. And so I think the next one is probably to fall and
I think it's already falling as the nine to five. I don't know if this is
completely true or if this is part meth, but in the us, the nine to five kind of
started with Henry Ford and the building of kind of Ford cars. But anyways,
there's like different myths of how we got into this nine to five to begin with.
And I think it made sense if you are going to be commuting and you're going into
a location, you don't wanna be there all seven days. You also need to be there
for a chunk of time cause you're not gonna be commuting back and forth. And so
it made sense to do this nine to five, but I think that is gonna start falling
as we add in more asynchronous communication.

Tamara Sanderson (34:26):

So asynchronous communication, it's a long word. It sounds fancy, but really
it's all about, do you have to communicate now or can you communicate later? And
so now communication is synchronous communication. So if you're on a call with
somebody, if you're going back and forth rapidly on slack or in emails, that is
all now communication cause you are answering at that moment. Asynchronous
communication is when we can answer on your own time. So that might be a ping in
a Google doc of some comments and you need to like review a proposal, but you
can do that within the next three days. That could be, if you have a really good
policy where people aren't asking you to respond all the time to emails or slack
messages, if you can answer a slack message or an email on your own time, that
can be asynchronous communication.

Tamara Sanderson (35:10):

If you're watching a video replay of an all hands that's asynchronous
communication, but the more you move to that asynchronous communication, the
more you can work on your time. And when you can work on your time, you can work
according to your rhythms and your energy and your schedule. And so I think that
is when remote work looks really beautiful. So I'll give an example. I am very
much a night owl and um, very early signs of this growing up. I was like the
last kid to go to sleep at any like sleepover. I like would exercise at like the
very last slot at the college gym from like 11:00 PM to 12. I could stay up all
night, very easily. And then I got into the working world and nobody wants to do
that. It was fine in college where I could write, you know, a, a paper late into
the night or I could study at IHOP and that was all good and fine.

Tamara Sanderson (36:02):

But once I started working, I needed to be up at like 6:00 AM, 7:00 AM. And I
remember it was actually like a real struggle, cuz that is not when my brain is
like ready to go. And you know, I thought this was just, I don't know. I, I
didn't really believe it. I was like, oh, we talk about people being night owls
or like early birds, whatever. Um, but within our book we interviewed a
neuroscientist who is a professor at Berkeley and she was just talking to us a
lot about chronotypes and it is scientific. We actually, you know, 25% of people
are, uh, morning people, you have 20% of people that are night owls and most
people kind of fall in the middle of this, like biphasic rhythm where they have
two peaks throughout the day. But when you do remote work and you can work at
your own schedule, you start being able to like curate your time around that.

Tamara Sanderson (36:48):

So I remember it was a huge unlock for me when I'm, you know, started automatic.
I, my first spot that I was at was in Lisbon and all of a sudden, I like I did
have some partnership calls. Most people with an automatic actually don't have
very many calls, but I was working externally. So I would be talking to people
in the west coast and east coast of the us quite a bit. And what was lovely is I
could actually take those calls and like later in the day or at night, and
that's when I was having the most energy to do that. So I completely changed my
schedule. I would do a little bit of work at 10 in the morning. I would answer
some, I would write some blog posts. I would do some thinking. I would have like
a nice like cup of coffee and like a cool cafe in Lisbon.

Tamara Sanderson (37:28):

Then I would, you know, do a couple hours of work. Then I would walk around, am
I go to a museum I'm experiencing the best hours of the day. It's sunlight. I'm
by the water. I'm like, oh, this is so great. I'm like living this different
life. Uh, I might have like a late dinner and then I would go back and I'd do
more hours of work at night. And that actually worked really well for me because
I was still, you know, putting in the same amount of time, the same amount of
effort that I would in a normal job. But I felt like I was able to really live
my life and also really able to enjoy the daylight hours, which I know we like,
that seems very silly, but it's, it's free. Like you can do a lot of things
during the day that are free and a lot of things at night cost a lot of money.

Tamara Sanderson (38:07):

And so, um, I think just from a, a lifestyle perspective, you can take a walk,
you can go to a park, you can go to botanical gardens, you can do all these
public activities where at night, if you're trying to socialize, it's usually at
a restaurant or at a bar which requires money for entry, or you might be, you
know, at home watching Netflix, but that's not kind of the same type of
recreation. So long story short, but I think the nine to five is gonna be the
next thing to fall. Uh, cuz I, I don't, I don't think when you are working at
home, those hours make as much sense when you don't have that commute. And I
think people are gonna be able to better bash their schedules based on their
lives. So, you know, I mentioned something of somebody that was a traveler, but
let's say my brother, for example, he has four kids between the ages of two and
eight.

Tamara Sanderson (38:54):

He doesn't wanna, he does not wanna arrange his schedule so that he's taking
calls late in the night. Like his kids are gonna be up at like five in the
morning, the next day. So if he were to do his remote schedule, it might look
very different where actually he has a very early start. So he might be doing
work, you know, right after the kids go to school. And that's when his best
times are. And he may, um, you know, schedule things for later in the day. I
don't know whatever he does, it would look very different than my schedule. And
what I think is beautiful about remote work is it allows everybody to curate
their schedule around their lives. It's not just one way. Um, and I, I think
that'll be a really cool world, hopefully in 2027 that we live in where we have
that freedom and that flexibility. So that's, I'm an idealist. So I know that
there's always like ways that, you know, remote work could, I don't know,
negatively impact, you know, when people are kind of like worrying about
automation and all those kinds of things. But I think from, uh, an idealistic
standpoint, I imagine a lot more freedom and flexibility and people to orient
their work around their lives versus orienting their lives around work, which I
think is a significant change in dynamics.

Matt Hayman (40:02):

So Tamara, thank you so much for the interview today. I found it extremely
interesting and insightful and I really appreciate you taking the time to, uh,
to take part in the podcast. So thank you so much for that before you go, let's
just discuss the book briefly. When's it out? Where can people get it? What's
the book about

Tamara Sanderson (40:20):

It's called remote works, managing for freedom, flexibility and focus. It comes
out February 7th, 2023. So also also a futuristic date. Um, but we have written
it already. We just got our like final proofs back from our editor. Um, so we
it's published by bar Kohler. It'll be distributed through penguin, random house
internationally. We are really excited about it. We're planning some really cool
coworking popup events around the launch. We'll be doing a lot of different
webinars and activities, but we're really excited about putting a lot of those
thoughts out into the world. The book is incredibly interactive and reflective.
I know we talked about play, but, um, as far as a business book can go, we do
think it is pretty playful. There are like quizzes and exercises and activities.
You can do reflections. Um, but we really hope we don't think there's one way to
do remote work, right?

Tamara Sanderson (41:10):

There's millions of ways to make remote work work for you. And the book is
giving you fodder to think and reflect on how to make it a lot better for your
life, your team's life and your organization. And so we're really excited to put
those ideas out there. We interviewed lots of great experts from all different
types of organizations. So it's not just our two thoughts. It's a lot of other
people's thoughts as well in the book and the forwards written by Matt
Mullenweg. He is the founder of WordPress and automatic and he is an OG, uh,
legend within remote work. And so I was really excited to have him write our
forward because I know, um, my job at automatic really influenced how great I
think remote work can be when it's done well.

Matt Hayman (41:52):

Well, I hope the book. I'm sure the book will be a huge success. Thanks once
again for coming on the show tomorrow and uh, yeah. Thank you again for sharing
all of your insights with us today.

Tamara Sanderson (42:00):

Awesome. Thanks Matt.

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