Designing Resilient Remote Teams: IO2020 Replay with Steph Smith, Trends.co / The Hustle / Hubspot

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By Brian Ardinger, Founder of NXXT, Inside Outside Innovation podcast, and The Inside Outside Innovation Summit. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

In honor of our upcoming IO2022 innovation Accelerated Summit, which is happening September 19th and 20th in Lincoln Nebraska. Thought it'd be nice to pull some of the best interviews and sessions from our IO2020 virtual event. So, over the next few weeks, check out some of our amazing speakers and grab a ticket for the upcoming event. We'd love to see you there. Tickets and more information can be found at io2022.com. And now back to the show.

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Interview Transcript with Steph Smith, Trends.co / The Hustle / Hubspot

Brian Ardinger: We are excited to have Steph Smith here with the Hustle and Trends to talk about one of these amazing new trends that we're seeing. It's the whole move to remote work. Steph is the Head of Trends and Product Manager at the Hustle, which is a great newsletter, if you don't subscribe to that. Trends is their exclusive group. And I I've got to say it's, it's one of the best groups out there to talk about new things that are happening out there, new business leaders, things along those lines.

She's got a new book out called Standing Out in 2020. Doing Content Right. And I know she's been doing a series of sessions on that. It's an eBook. You can check it out at stephsmith.io. She's been blogging for a ton of time. And she's also been in this world of remote work. Been a digital nomad for a while. So, with that, I'm going to just turn over to Steph. And we'll talk the trend of remote working.

Steph Smith: Sweet. Thanks so much. That was a great intro, Brian. Today, I'm going to be talking about something that I care a lot about. I saw some other people in the chat mention that they've been working remotely for a long time. Two, I'm going to be talking about thinking past the office and designing what I call resilient, remote teams. And I do this in a little bit of a different way than I think most presentations on this topic are, which give you a lot of super, super concrete, like you must do this.

I like to think of this more so as how do we think about what has changed? What does that mean? And what can we learn from this? So, I use three books and I'll get into that in a second to actually convey some of these points. But just quickly, I don't want to talk about myself very much. Brian gave me a great intro. All you need to know is that I have been working remotely for the last four or five years now.

And I did that originally at a company called Top Tell, which was one of those kind of remote first companies built from the ground up to be remote. Now I work at a company called The Hustle and I've done some remote training for different companies. And in general, have been nomadding around for the last couple years as I work remotely. So that's enough about me. Let's talk about where we are in this world.

As I mentioned before COVID there was a series of companies I'd say only a couple dozen of scale that were built up to be remote. From the ground up, they said, you know what, we're never going to have any offices. Or if we do, we're going to be remote first. Companies like Zapier Basecamp, Web Flow. All these companies were built from the ground up to facilitate positive remote working environment.

Now, as we all know, you saw this kind of trend, the slow trickle of people that were searching for remote work overtime. This is Google trends from 2004 to present. Then as we all know, 2020. crazy year. We see this big spike and we're all remote, whether we want to be or not. And this includes huge companies like Google, Cora, Coinbase. Shopify that at least are either going to be remote for several, several years or in some cases like Shopify have just claimed that they are now remote first from here forward.

The question then becomes with all of these companies with now millions, if not billions of people that are kind of thrown into this new environment, what happens. What happens to these organizations that weren't built from the ground up? Like Zapier, Base Camp, or Buffer.

Some of the questions that I have here, allude to what I'll be talking about in this presentation. So how does remote work or the shift influence how people interact with one another? How does it influence the social fabric or culture of the company? How does this change how potentially leaders should or can operate at these organizations?

And in general, this all brings me back to the title of this presentation. How do we build resilient teams? And resiliency in this case means teams that thrive in the environment that they're put in, right. It doesn't feel like they're kind of pushing against walls. It doesn't feel like there's friction to achieve certain things.

It feels like they're put in an environment where they're put in a place to succeed by nature, by the nature of the environment that they're in. So, as I said, this presentation is really based on three books that I've read and, and I think are excellent. It's Give and Take, Algorithms to Live By and The Four Tendencies.

And I like using books like this to really frame these conversations because these books are actually not based on remote work at all. They're based on human psychology. They're based on how people interact in given situations or environments. And then I just layer on a question. Is this still true with remote work or how does this change as people go from an in-person environment to remote.

And so, we'll talk specifically about how giving and taking behavior may change with remote work. We'll talk about how we can design systems. So, using something From Algorithms to Live By, Game Theory. How do we incentivize people to actually act in their best interest? Because they don't always do that on their own.

And how do we in general make remote work sustainable. And then I'll talk about the potential archetype of remote worker using this four tendencies framework. To preface the three books and the three things that we'll talk about, I want to jump back to summarize where we are.

So, we as a society had a majority of people working in offices. And now we have a majority of people working remotely. And I like to kind of facetiously say that when you work in an office, you work in a box. And that box is predefined for you. And even though it's a little facetious in terms of the analogy, a lot of that is true in the sense that you have a lot of things, whether it's, you know, where you're physically working, how you're working exactly, when you're working.

A lot of that is super predefined for you. And for some people that's actually better. Some people that's worse. I'm not trying to ascertain whether one is better or worse, but the idea is that before you had a lot of things mapped out for you, right? And now when you're working remotely, the way, the analogy that I like to give is that box is kind of like stripped clean.

So, you get rid of the walls, you get rid of exactly when, how you work. And now a lot of people are left to figure out how to build their own box. And what I see a lot of people doing, whether it's individuals or companies is they basically do this Control C Control V where they basically say, you know, we had all these things, these processes, these systems, these frameworks that worked in our office. So, let's just take all those and let's paste them into our new environment.

And that can work. But what I think we have a unique opportunity to do is in fact, rethink the box. So, build our new box from the ground up. So instead of just copying everything and saying, oh, this worked there. It should work here. Let's just rethink what are the things that we should operate by in this new environment? How do we rebuild our box?

And something more important than that is instead of giving our employees a new box saying, hey, this is your box. Please take it. And again, abide by these rules or operations or logistics. Let's actually just give them the tools to build their own box.

And this kind of summarizes part of what I'm, I'm getting to at least to preface three examples is, is a quote from Amir. Who's a CEO of Doist one of those kind of remote first and companies. And he says, basically, remote. Isn't just a different way to work. It's a different way to live. We have to acknowledge that we're kind of blurring these lines and people, you know, experience isolation, anxiety, depression. And in general, we need to figure out ways in systems to resolve this new, almost more complex issue where you have people, people's work and their lives just meshing into this continuous system.

All right. So, what are the cornerstones of remote work? I mentioned this because this bleeds into some of the examples. So remote work overall, at least prior to COVID, when people weren't forced into it, really prioritized three things over three other things. Meaning output trumped input, which meant that didn't matter exactly how many hours you were working or exactly what you did to get to the impact that you're driving for a company.

What mattered was the impact, the output. Similarly, remote work tended to favor autonomy over administration. Again, this idea that didn't matter exactly how you got from Point A to Point B. You had the autonomy to figure that out. And similarly, flexibility over rigidity. So, let's keep these cornerstones in mind throughout the presentation. And consider that even those cornerstones sound kind of resoundingly positive, all of us at face value are like, yes, I love being graded on my output. I love being graded or given the autonomy to figure out how I deliver that output. And I love being given flexibility.

But let's just keep those in mind and consider that they're not always strictly positive. All right, so let's dive into the first example in the book, Give and Take. Obviously, these books are very in depth and I only covered one small sliver of them in this presentation. But the key takeaway from Give and Take is that Adam Grant, he's a professor at Wharton, amazing writer as well. He talks about three different types of individuals. So, Givers, Takers, and Matchers.

All you need to know about them for the purpose of this presentation is that givers basically believe in this world as a positive sum game. Meaning they believe in mutually beneficial situations. They're willing to give without expecting anything in return.

Takers are kind of the opposite of that. They think zero sum game. I'm sure you can imagine or conceptualize people in your life that you've encountered that really are trying to get ahead at the expense of other people.

Now matchers fall somewhere in the middle. They basically believe, or kind of function off of this idea of reciprocity and fairness. All right. So with that in mind, the question or sorry, before I even get to the question, something I want to mention is that the whole premise of Adam Grant's book is a little surprising in that most people would expect that given Takers and Matchers and Takers in particular, their approach to life in terms of kind of utilizing other people to get ahead or prioritizing their own growth over other people, you would expect those people to be the most successful.

Now, interestingly enough, he found that Givers were both at the very top of the spectrum of success, and the very bottom. You can notice two different types of Givers here. One is selfless. One is, is otherish. All you need to know here is that Otherish Givers are Givers but have found a way to prioritize their own needs.

So really interesting that Givers not only elevate other people, but they are actually the most successful on their own. So, this is kind of a summary or a quote from Adams, which basically says they succeed in a way that creates a ripple effect, enhancing the success of others around them. You'll see that the difference lies in how Giver success creates value instead of just claiming it.

So, in general, I think the obvious takeaway here is that we want more Givers at our organizations. Now the question becomes, and this will be a repetitive question throughout, is this the same with remote work. Or how does this change with remote work? Some of the sections here are based on actual data sources.

This one, not so much. This is me more hypothesizing. And what I've come to in terms of my many years leading teams, interacting with teams, being individual contributors on teams is that because if we remember the cornerstones of remote work, we prioritize output. We prioritize impact. That which in remote, all that matters is that impact, right?

Are you delivering value? Are you worth your salary? Are you hitting your KPIs. In person when you're in an office? All that stuff matters. But it's also weighed against certain unspoken things, unspoken rules, like the amount of time you're spending in the office. Whether you're on time for things, whether you stay late to help another employee in general, everyone knows who the team players are in an office.

That's not always true when you work remotely. I think if you've worked remotely over the last couple months, especially if you were in an office before, you can probably resonate with this idea. In remote, there's a couple thing, other things that I want to know. This idea of staying on longer to, you know, as a Giver, let's say you're helping other people.

That's super difficult to quantify because when you're working remotely again, our work life and our lifeline blend together. So, it's actually hard, if I were to ask anyone on this call, how many hours did you spend this week working remotely? I think a lot of people would struggle to actually quantify that.

So then layering on, am I working extra? Am I not working enough? It's really hard to kind of parse that out. Additionally, if you support someone. Let's say I have a friend and her name is Sally at work. And she says, Hey Steph, can you help me with this project? And it actually takes like, you know, five hours out of my day.

I end up helping her. All of that work for better or for worse is hidden online. Sally knows about it. But everyone else at work, didn't see me stay late to help Sally. They didn't see the output of that work. They didn't see the Giving behavior. And so, in addition to this, KPIs in general, when you work remotely by nature of trying to ascertain that output of people, tends to be more individual. You even hear people use terms like manager of one when they're working remotely.

And in general, the idea that I'm trying to get across here is that by nature, when you're working remotely, because there are so much emphasis on output and impact, which has many positives, basically takes away the recognition that you typically get in an in-person environment of these Givers, and what happens is these Givers end up burning out, they become more of those selfless givers that you saw at the tail end.

Instead of the Otherish givers that were the most successful individual. And something I want to call out here is that regardless of intentions, morals, or values, and what I'm saying here is it doesn't matter if someone's a good person or bad person. That's not what I'm trying to ascertain. Bad incentive structures result in bad behavior, no matter how good of a person you think you are.

So, what's the takeaway here? Again, I'm trying to go through this quickly, so I won't go through everything. But the idea here is that you still won't have a water cooler. In the office, which almost acted like, you know, animals in the wild. There's like a certain hierarchy and there's a kingdom and, and it kind of regulates things, right. You just subtly, but it does. You don't have that anymore with remote, or at least it's not created without intentionality.

And so, there are a couple quick things that you can do. The first thing is just ask your team very simply who helped you this week? Who did you work with? Where did you put in extra hours? Where did someone else put in extra hours for you? You must ask this because it will not be surfaced as naturally as in the office.

The second thing is build KPIs to incentivize teamwork. This is a little harder to do because again, when you work remotely, you're trying to ascertain output. But think about how you can do this to incentivize teamwork. So, you're not kind of encouraging people to act more as Takers versus Givers. And then finally create an environment where you're not just recognizing good behavior or giving behavior, but you're actually rewarding it.

So, some companies like GitLab have actually started things like micro bonuses, where in addition to the bonus structures or the compensation structures that you get from your boss, other people around you can actually reward you based on your giving behavior. Because that's really important. You're not just recognizing it in like kind of shout outs or things like that, but you're actually rewarding this behavior. So, you're incentivizing people to continue doing it.

The final thing I want to call out is that you can do as much as you can once you have people at an organization to incentivize giving behavior. But you can also kind of integrate this into your hiring process. Which means bringing in people who are more naturally Givers.

So, Adam Grant mentions in his book. This is directly from Give and Take where he, during the hiring process asks this question, can you give me the names of four people whose careers you have fundamentally improved? And the idea here is that people who are Givers tend to mention either people at the same level as them or below them in terms of the people that they've helped.

And it's a natural response. Of course, this is again, not quite scientific versus Takers, tend to mention people that are above them. That they've helped, because again, there's this nature of people who are Takers, trying to get ahead and using things like status to get ahead. So, something to keep in mind as well as you're hiring.

So, the second example that I want to go through is from Algorithms to Live By. Again, excellent book. This is a book where basically they take principles from software development or software engineering and use it to help us think through problems that are outside of that scope. So, things like Cashing Theory or Kneeling or making intractable problems tractable.

The one that I want to talk about today is Game Theory. So, in Game Theory, I'm not going to go into depth, but it's this idea that within a game, there are certain rules. And within those rules, they incentivize people to act a certain way. And once a game is predefined, you tend to get to this equilibrium where all the players individually are acting their own best interest.

But sometimes the kind of aggregate of those actions actually may result in outcomes that are worse for everyone. Again, depending on the rules that were set for that game. And this equilibrium that I'm specifically talking about is called the Nash Equilibrium. And it's this idea again, there's this kind of long definition and talks about a stable state.

The idea here is the Nash Equilibrium is within an environment within a game. It's the outcome or the optimal state, where there's no incentive for any individual to deviate. Now, this may not sound super actionable. So let me give you a precise example of what I'm talking about. So, with remote work, a lot of remote first companies tend to go with unlimited vacation.

And I think this is something that probably more companies will end up moving towards as well. But something you keep in mind here is the Nash Equilibrium of unlimited vacation approaches, zero days. And the reason for this it's a little counterintuitive because you think unlimited vacation sounds amazing. Sounds like a great perk.

Well, what happens with unlimited vacation is that people look to be perceived as more loyal, more committed, more dedicated than their peers. And therefore, they look to take just slightly less vacation than their peers. And what happens is a cascading effect, which approaches zero.

This is actual data from Buffer's Data Remote Report from 2019, where you can see in blue, the amount of vacation offered, and then in orange, the amount of vacation that was actually taken. So, you can see around 30, 35% of people had unlimited vacation. And if you look at how that's actually distributed, most of the people who had unlimited vacation took anywhere from no vacation to two weeks’ vacation. Versus the people who had, you know, six weeks, five weeks, four weeks were likely to actually take that amount of vacation.

So, what is my point here? Well, in Game Theory is this idea where basically you have a game and then those rules are set for the game. And then you just see what behaviors actually emerge from those given set of rules. Well, I think with remote work, we have to be a lot more intentional about not just kind of throwing rules out there, again, kind of redefining our box and, and not just taking a box that already exists.

And you can do that through Mechanism Design, which is kind of flipping that script and saying, what are the behaviors that we actually want and what rules do we need to establish to actually generate those behaviors? So kind of again, reversing the question and figuring out what behaviors you want to incentivize. And then figuring out what rules need to be in place to actually achieve that.

As I mentioned, the box has changed, the game has changed. So, here's a couple examples of things that people struggle with from the same report, when they're working remotely. It's things like unplugging, loneliness, distractions, culture, and communication. If you were to ask the same question to people who are working in an, in an office, these would not be the case, which shows us the game has changed. The problems have changed. The things that we're solving for have changed and therefore you must come up with rules or incentives so that people act in their own best interest.

So again, you're thinking backwards. You're asking the question, what are the KPIs that you need to actively design to encourage people to, for example, have a work life balance outside of just the freedom to define their own. And this is really important because it sounds counterintuitive to say a I'm actually going to define more rules. Because flexibility sounds like a great perk or sounds like a great thing to have. But actually, you can help your employees in certain situations to actually help them again, this idea of building their own box.

Something I want to call out here is again, is Wall Street, which is again, the most like capitalist type environment there is, has mandatory off hours. So that brokers don't push themselves to their Nash Equilibrium, which would be the sleepless equilibrium, where they're constantly trading. So, you have to think backwards and figure out how to design an environment that people succeed in.

Quick couple examples before we move on to the third example. The third book are things like a minimum vacation policy, mandatory days that they must take off, allowing people to take back their calendars and actually block off significant parts so that they're not encountering what people call Calendar Tetris. I like this example from Keith, I don't know Keith personally, and this was pre COVID.

But basically, he decided to close his office on Friday. Simple things like this, where he basically said it's a mandatory weekend. You are not allowed to work, even though it seems strange in a digital environment. And I'm giving you 50 bucks to go eat at your favorite restaurant. So, think about how you are intentionally designing systems for your employees.

Finally, third example that I'll breeze through is the Four Tendencies. And I'll caveat this example with this quote directly from Gretchen Rubin, the author that says the happiest, healthiest, most productive people aren't those from a particular tendency, but rather the people who have figured out how to harness the strengths of their tendency, counteract the weaknesses, and build lives that work for them.

So, what is the Four Tendencies? It's this idea that there as it sounds like four tendencies. Upholder, Obliger, Questioner, and Rebel. Now these two highlighted in green are not highlighted, because they're the best. As Gretchen said in that quote, it's just that they're they are the most common. Now the Four Tendencies is basically a two-by-two framework, which identifies how people respond to expectations or accountability.

So, do they readily meet outer expectations? Do they readily meet inner expectations? Do they resist both of them or do they kind of fluctuate towards or air towards one or the other? So, I personally am a Questioner. I resist outer expectations and I meet inner expectations. To give a quick example, if I wanted to get fit, having a gym buddy as an outer expectation expecting me to show up that actually wouldn't help me. And that actually is something that I've tried to do throughout my life. Hasn't worked.

Meanwhile, something like actually understanding the science behind why I should be fit or kind of convincing myself that my identity, or I want to be the type of person who, you know, respects their health. That works for me. So as a Questioner, I meet inner expectations. I resist outer expectations.

Now I did a poll on Twitter a while ago, got around 400 votes from people who had been working remotely again, pre COVID. And it was interesting to see that the most popular tendencies among this again, non-scientific poll were Questioners and Rebels, and I thought, huh, that's interesting.

If you remember questioners and obligers for the most common in the overall population with remote workers, or at least those who sought out remote work. Where questioners and rebels with the, the familiarity or the common thread here is that they both resist outer expectations. I thought that was really interesting.

And I think that relates to this idea that there's a level of self-selection or misalignment with outer expectations of society, of people trying to at least identify their own work norms, identify their own vision or how they can actually build something, build their own box. And this isn't again, mean that they're more successful or less successful.

It's just perhaps that they actively sought out this type of environment. Now, what's the takeaway here. This is a brief section compared to the other two, but it's the idea that people actually respond differently to inner and outer accountability. We used to have everyone in an office and that didn't necessarily work with everyone.

Now we have everyone remote that doesn't necessarily work for everyone. So, I think the idea here is that leaders need to actually learn past, just the high level this person is good at these skills. This person is good at these skills. This is my top player. This is my, you know, less valuable player. And more so think about how to tailor their leadership stylers to figure out how to motivate their employees. Whether they're in a remote environment or not. But especially if you're in a remote environment, how do you incentivize, if we just quickly go back, how do you incentivize Upholders and Obligers when Questioners and Rebels tend to naturally seek out this environment?

And on the flip side, if you're in an office, how do you naturally incentivize Questioners and Rebels so that they're motivated when Upholders and Obligers may more naturally fit into those traditional environments. So just something to consider. Right.

This is the final slide I have, and I know we're running out of times, but the idea here is just, again, there are certain things or certain ways that humans tend to interact in, in an person environment.

And they don't necessarily act the same ways in a remote environment. And in particular, they may not even act in ways that benefit themselves all the time. So, we must as leaders, if you're leading a team, if you're leading a company, It's good to consider some of these things and figure out A: How do I encourage Giving through discovering, hiring, promoting, and acknowledging and rewarding as I said before Givers.

How do I select incentives or develop the right systems so that we're using Mechanism Design and not just throwing people into a game and hoping that they choose the best outcomes that are best for them or best for everyone?

And then finally, how do we actually learn about our people past the face value in terms of their skills and figure out how to harness their unique strengths, whether they're in an in-person environment or a remote environment.

If you want to find me, or if you have questions, happy to answer them now, but you're also welcome to email me or DM me on Twitter and that is it.

Brian Ardinger: That's it for another episode of Inside Outside Innovation. If you want to learn more about our team, our content, our services, check out InsideOutside.io or follow us on Twitter @theIOpodcast or @Ardinger. Until next time, go out and innovate.

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