Designing a Healthy Remote Work Culture with Darcy Boles

Darcy Boles is the Director of Culture and Innovation in TaxJar. She is focused on scaling their remote team profitably and effectively through large-scale collaboration, positive psychology, and identifying meaning in the workplace. Darcy inspires people to think about things in a new way and encourages individuals to do their best work where it works for them. She was named Top 50 Remote Thought Leader in 2019.

Follow our guest on their social media:

Remote work leader

the quarter, is going to be really important to how I can look at the next three months and say, “Oh, I could go to Mexico for this month.” Or, “Maybe I feel like I’m going to need to be a little bit more concentrated in my home office this month, because I know what projects are on my plate.” So, that’s first off, right? I want to look at the next quarter or the next six months and say, at the beginning and say, “Okay, how do I want to shape this?” I know things are going to come up, but where am I going to feel like with what I know right now, I’m going to be the most successful? So, that’s number one.

Luis Magalhaes:

Got it.

Darcy Boles:

My days differ. Right now, I’m in Mexico City. In Mexico City, things tend to be, at least the culture here is a little slower in the mornings. I have severe anxiety. So, it’s really hard for me to just pop out of bed and start working. So, the way that I do this, whether either at home or if I’m traveling is I get up early in the morning and I do at least half an hour of breath work and meditation, journaling. And I’m sitting down, getting grounded with myself. If I’m at home, sometimes I’ll go for a surf, if the waves are good. And I tend to do really well when I log to work around 9:30 in the morning, 10:00 AM. I’m a late starter. I do not function well in the mornings. If there’s a meeting on my calendar, of course, I will be there, but I just am not a morning person. I have learned that. I have tried, it does not work for me.

Luis Magalhaes:

I love it, that you considered starting at 9:30. Is not a morning person.

Darcy Boles:

I know you’re from Portugal. You guys, you have such a different work culture. I’m still stuck in this terrible American rat race that I am trying to train myself out of.

Luis Magalhaes:

It’s like, why do you mean? 9:00 AM, is when we start working? What do you mean you’re not a morning person. That’s morning.

Darcy Boles:

So, I think we consider morning person like 6:00 AM.

Luis Magalhaes:

No, we consider that sleep time.

Darcy Boles:

Yeah. Right. And then I think the first thing I do is really check if there are any messages of things I need to get done, emails, pings, or the immediate things I need to respond to. So, I spend about an hour, hour and a half, just making sure I’ve responded to my team. I’ll usually have a couple meetings on the calendar midday. I’ll of course, take those. And in the afternoon, I really hone in on if I’m writing a paper or trying to figure out what experience our remote onboarding is going to have. I will dive in and really sit down and write. And you have that deep work. You’ve heard now, Cal Newport talk about deep work and a lot of thought leaders talk about deep work. And I will actually block that out on my calendar as deep work.

Darcy Boles:

But back to what you were saying before, around having teammates say, this is when they’re online, I usually will have a kind of, “This is how Darcy works. And if you see a block on my calendar, just make sure to ping me, if you’d like to schedule something during that time.” I’m just protecting my time during that time to make sure that I’ve got some time for deep work.

Darcy Boles:

So, I think that that’s important that the flexibility of letting people know why your calendar is blocked or putting it under your calendar, and just saying, “I’d prefer to have this as a deep work. If you need me, I’m online, but I’m going to do better work if nobody schedules time.”

Luis Magalhaes:

Yeah, yeah. You can ping me, but if you do, you’re a terrible person.” Right?

Darcy Boles:

Totally.

Luis Magalhaes:

Just letting you know. No, I get it. I totally get it. I totally get it. That’s a very intelligent way to put it.

Darcy Boles:

And think at the end of the day, a previous CEO of mine really said once, and this has always stuck with me, is if I can with integrity, answer the question at the end of the day of saying, did I give everything I had today to my team and my work? And if the answer is yes, then it’s okay to log off.

Luis Magalhaes:

Yeah, that’s an important point. That’s an important point. In fact, one of the things that I think that’s a little bit of a quiet revolution happened with the latest Apple iOS update, right? For those of you are iPhone and Mac iOS users, that allow you to really set. It’s always, for years, they had the nighttime mode, right? Where there would just be no notifications, et cetera, et cetera. But now you can also customize an after work mode, where you can select which apps give you pings and notifications that could be family related or leisurely related, but then just mute the work ones. And I think that’s very powerful, because phones are part of our life, right? It’s really hard to live a life without a smartphone right now.

Luis Magalhaes:

The other day, I wanted to go with my wife to the movies, where do I buy my tickets? I buy them on my smartphone. How do I show my tickets? How do I show that I’m vaccinated for COVID? I have to use my smartphone. So, if I have that on my smartphone, I have to take my smartphone out during my leisure times to do all of that. And then I see that email, looking at me with the 20 unreplied emails, then maybe I’m overly sensitive, but that’s psychologically very stressful. So, and now that I have the option of automatically, I can access my movie going up, but actually those notifications, they don’t show up. They’ll only show up for the hours that I define. I find that is a really powerful concept. And I hope that more and more people will take advantage of that.

Darcy Boles:

Absolutely. And I think there needs to be, and I say this as somebody who works in tech, but I wouldn’t say I’m the most tech savvy person in the world. I’m a translator of feelings and I’m a highly sensitive person. And I think that a tool is only as good as you use it. And the more education that we can provide for the flexibility in the tools that are available to us, especially in workplaces of setting your settings and making sure that you don’t want things outside of work stealing your attention when your attention is supposed to be towards your kids or your wife, or whatever it might be that you’re doing. Right? And so, I think that we have to figure out how to control our devices, so they don’t control us.

Luis Magalhaes:

Exactly. Because that’s what they’re made. Right? They are attention grabbing. They are attention grabbing machines. Right? But they’re not smart enough to know what’s okay to grab your attention when you’re out of work. Right? And when you are in work time. So, that’s definitely something to look into that designing aspect. So, speaking of that, what does your, well, both physical, but also virtual office look like? And by virtual office, I mean, let’s say when you open your browser, first thing in the morning or late in the morning, as you like to call it, at 9:30, right? In this podcast, you learn that you are a morning person, Darcy. There you go. This is my gift to you.

Darcy Boles:

Oh, thank you. Thank you.

Luis Magalhaes:

You’re officially a morning person.

Darcy Boles:

In Portugal, I’m a morning person. Perfect.

Luis Magalhaes:

Exactly. Exactly. So, there you go. When you open your browser, first thing in the morning, what does it look like? What are the tabs that are open automatically? What are the apps that make up your virtual office?

Darcy Boles:

Yeah, absolutely. So, right now I’m currently operating within Slack and email. so , really those are the first two things that I’m going to be doing is checking my pings and checking my emails, and making sure that those things get done. We’ll use the G Suite and other things like that to work on projects and whatever it might be. So, I would say it’s actually much more simple than maybe a lot of people think. I think for doing less better, that’s going to be the most important thing, and utilizing the tools we have to the best of the tools ability.

Darcy Boles:

So, I get really overwhelmed if I have 10 tabs open, or 10 things open on my page all the time. I want to just focus on emails, I’m going to do for an hour. Pings, I’m going to do for an hour or whatever the schedule looks like that day. So, I would say it’s much more simple than probably a lot of people think. And it’s really just about that connection points and where am I connecting? So, I’d say that’s my number one thing is the first time I log in is I want to look for connecting with my team and seeing what’s there.

Luis Magalhaes:

Yeah. That’s a really good point. And for the people that get very hung up on tools, I usually say that… I’ve seen people who’ve developed video games, and using as their main chat tool and other video games in game chat. Right? That there’s actually… So, it’s very easy to get hung up on the tools, but in reality, most tools, whatever you have at your disposal is usually good enough, right?

Luis Magalhaes:

Now, of course, as businesses grow and teams grow, some tools can hit certain limitations and then it’s time to change. But usually, if you properly configure your inboxes in your email app and you have a chat program, it could be Slack, it could be even Discord, something else, then you’re pretty much good to go, right? You can pretty much design the way you work around the tools you have, and not always be stressed out, looking out for the next tool, I guess.

Darcy Boles:

Yeah, exactly. And I get hit up all the time on LinkedIn, “Here’s a new tool we’ve created for remote workers. And here’s a new tool. And here’s a new tool.” And I’m like, this is very overwhelming. And I can’t imagine what this is like for people who have not worked in a fully remote operating system, because now they’re trying to decide what is a better tool over the others. When really, I think just like work cultures and coming back to values and everything, we’re going to do best with sticking to what we know and the basics, because people are still learning how to flex this muscle. So, the simpler that we can keep the tool set, the more successful people are going to be.

Luis Magalhaes:

Yeah. And look, every tool has a learning curve. And usually the energy expenditure on switching tools, especially for a team, the learning curve, the energy expenditure, et cetera, is not made up by whatever marginal gains you might have. Right? So, that’s definitely something that I would support. Okay.

Luis Magalhaes:

So, now going into more rapid fire questions, though you don’t need to answer rapidly. I just call them that because I try to make them short. If you could give something to everyone in your team and it couldn’t be money or a cash equivalent, right? It couldn’t be a gift card. You needed to buy in bulk a tool, an app, an experience, something to give to everyone in your team. What would it be?

Darcy Boles:

Permission.

Luis Magalhaes:

Okay.

Darcy Boles:

Yeah, absolutely. I’d give them permission around the work that we have, permission to set up their lives in the way that supports their work.

Luis Magalhaes:

All right. Because I think there’s an app called Permission, that’s why I –

Darcy Boles:

Oh, no. I just meant the value of permission, like the psychological value, not an app. I wouldn’t give them an app. They have too many apps.

Luis Magalhaes:

Exactly. So, you were describing the very nice story, by the way. Thank you for telling me the story about the person that really made a difference in their work life by getting a musical instrument. Right. So, I actually have a question about that. So, for you, for yourself in the last, let’s say one year to six months, what purchase has most impacted your work life?

Darcy Boles:

Honestly, one thing, I was a big resistor of EarPods like AirPods, the wireless headphones. When I go on long walks, I take my dog on really long walks, a lot of the time I do them tech free, but sometimes there’s an audio book. I learn really well auditorily. And I just bought some AirPods through an office reimbursement program. And it has completely changed my walks. I am listening to educational remote books. I’m listening to leadership books. And it’s something that I didn’t realize how freeing my hands would feel. And I actually really enjoy my walks a lot more now that I have these AirPods that I just thought I don’t do well with Bluetooth, because I forget to charge things all the time. But now I’m realizing how helpful they are and just me learning about things that I want to learn about.

Luis Magalhaes:

Right. So, I actually have a pair, but they’re just a weird brand, Bluetooth ear plugs. Are you talking about those in general or were it specifically the fact that they’re AirPods?

Darcy Boles:

Oh, I think just in general, wireless. Yeah. Wireless, really light auditory mechanism that will help me listen to an audio book that I’m learning from on a walk.

Luis Magalhaes:

Got it.

Darcy Boles:

I guess, I just didn’t realize how magical it would be. I’d always just saw people with these things in their ears. I was like, “I don’t want to do it. I don’t do it.”

Luis Magalhaes:

That’s a bit weird when you see other people-

Darcy Boles:

It’s a little weird, you look like a robot. And then I just caved in, “This is actually pretty cool.”

Luis Magalhaes:

Yeah. And I always, how are they holding these things in their ears? I’m sure that I’m going to lose them. I’m going to drop them in the first day.

Darcy Boles:

Totally.

Luis Magalhaes:

But yeah, maybe I’ll need to give it a try. Okay. So, let’s talk a bit about books. Are you a book gifting person? Do you enjoy gifting books?

Darcy Boles:

Absolutely.

Luis Magalhaes:

What are your most gifted books?

Darcy Boles:

My most gifted books, there is a book called, this isn’t necessarily work related, but there’s a book called The Body Keeps the Score, that I’ve given to many people, that I absolutely love. It’s just about how our past trauma show up in our bodies.

Darcy Boles:

Powerful is a leadership book that I have given many people. It is by Patty McCord. She was the VP of people and culture at Netflix for 14 years. I find her book to be incredibly fascinating.

Darcy Boles:

Iwo Szapar of Remote-How also just wrote an incredible book called Remote Work is the Way, that I think everybody, everybody should read if you’re trying to lead a remote team. So, that would be the third one. And I’m trying to think. And the other one is really, I think a lot of people have this book, have read this book, but it is The Little Prince. And that is a French.

Luis Magalhaes:

That is a favorite.

Darcy Boles:

It’s a French children’s book that I actually fundamentally believe that every adult should read every year in their life. I have the snake who swallowed the elephant tattooed on my right ankle. And I think it has lessons for us to not forget our childish wonder and just know that magic is everywhere, but it’s really inside of us.

Luis Magalhaes:

Yeah. That’s a good point. And there’s always some amount of pushback when a guest recommends a non-business book on the show. But I actually like to tell my audience that I find that some of the biggest lessons, business or otherwise, but very often business related as well, can come from fiction. We learn very well from just as a species. We’ve been telling stories for thousands of years. We’re primed to learn very well from fiction.

Darcy Boles:

Absolutely. And I think it’s important to realize too, that businesses are made up of human beings. And human beings are complex interesting humans who have breadths of trauma, and scary and wonderful, and interesting experiences. And everyone shows up based on their past experiences. And the more we can understand about how to work with people and really flex that EQ muscle, the better businesses we’re going to run and the better leaders we’re going to be.

Luis Magalhaes:

Yeah. Yeah. For sure. Absolutely. All right. So, my final question is a bit longer set up, so please bear with me. But let’s say, I don’t know what’s the situation in your home base. Is it San Diego, right?

Darcy Boles:

San Diego, yes, California.

Luis Magalhaes:

I don’t know what’s the situation in your home base right now, but let’s assume that it’s perfectly fine for people to mass in large amounts and have dinner together. Right?

Darcy Boles:

Okay.

Luis Magalhaes:

So, let’s say that you’re hosting a dinner and you’re inviting people from the decision makers, from tech companies from all around the world to that dinner. There’s going to be a round table on the remote work. That’s what the conversation is going to be, right? Remote work and the future of work. So, the twist is that this dinner is happening in a Chinese restaurant. So you, as the host, get to choose the message that comes inside the fortune cookie. So, what are these guests going to read when they crack open their fortune cookies?

Darcy Boles:

That’s a layered question? The future is anything you want it to be, you have a choice of how to shape it.

Luis Magalhaes:

That’s a good fortune cookie. That’s a good fortune cookie. Congratulations, you passed the fortune cookie test.

Darcy Boles:

Thank you.

Luis Magalhaes:

All right.

Darcy Boles:

Should I switch careers and write fortune cookies now?

Luis Magalhaes:

Well, if you can-

Darcy Boles:

I always have a choice.

Luis Magalhaes:

… make that workout for you, right? Sure. I’m sure you would make many lives better. Right? We were just talking about how fiction can change people’s lives, so fortune cookie can change people’s lives as well.

Darcy Boles:

It can.

Luis Magalhaes:

For sure.

Darcy Boles:

Moments, the power of moments.

Luis Magalhaes:

Yeah. So look, it was an absolute pleasure having you here, Darcy. Now, when people want to continue the conversation with you, how can they reach out to you? How can they get in contact to continue the conversation? And how can they learn more about what TaxJar can offer them, what you’re up to, et cetera?

Darcy Boles:

Yeah, absolutely. So, to connect with me personally, it would be best to connect with me on LinkedIn. It’s where I’m most active. And it’s where I post articles and podcasts that I’ve been on and resources for remote work. So, TaxJar is now part of Stripe payments. And we are hiring. So, be sure to go to Stripe’s website and check out our culture, check out our job openings. And that would be the best way to get in contact with learning a little bit more about what Stripe and TaxJar does.

Luis Magalhaes:

All right. So, thank you so much. It was an absolute pleasure. Thank you for being a guest.

Darcy Boles:

Thank you so much.

Luis Magalhaes:

Ladies and gentlemen, this was Darcy Boles, the director of culture and innovation at TaxJar. And I was as usually your host, Luis Magalhaes at DistantJob on the DistantJob Podcast, your podcast about leading and building awesome remote teams. See you next week.

Luis Magalhaes:

And so, we close another episode of the DistantJob podcast. And if you enjoyed the episode, please, you can help us out by sharing it on social media. That would be great. It’s how we reach more listeners. And the more listeners we have, the more awesome guests I can get in touch and convince to participate in these conversations that are a joy to have for me. And I hope they’re a joy for you to listen to as well.

Luis Magalhaes:

You can also help a lot leaving reviews on iTunes or your podcast syndication service of choice. Reviews are surprisingly helpful in helping the podcast get to more listeners.

Luis Magalhaes:

Now, another thing that you might want to do is go to distantjob.com/blog/podcast. Click on your favorite episode or any episode, really, and subscribe. By subscribing, you will get a notification whenever a new episode is up and whenever we get the transcripts of the episode up, so you can actually peruse the conversations in text form.

Luis Magalhaes:

And of course, if you need to find a great employee for your team, a great remote employee, you should take the whole world into consideration and not just look to hire locally, not just look to hire in your country. Look around the whole world because that’s the talent pool that contains the best talent. And to help you with that again, distantjob.com is the perfect place to start. You will tell us who you need, and we will make sure that you get the best possible candidate, 40% faster than the industry standard. And with that, I bid you adieu. See you next week on the next episode of the DistantJob Podcast.

 

More ways to listen:

While company culture has become a buzzword nowadays with thousands of definitions, one thing is for sure: culture is a core aspect in businesses. Whether you define culture as the values of your company or as the essence of it, learning how to build it remotely is challenging.

In this podcast episode, Darcy Boles shares her experience designing and building a healthy remote work culture that makes employees thrive. She shares interesting insights about why remote work has become fundamental for companies these days.

Highlights:

  • How to create a work-life harmony
  • The challenges of building a healthy work-life structure
  • Tips to avoid burnout while working from home
  • How to manage your energy and productivity as a remote worker
  • Tips to successfully manage your remote team
  • How to improve the remote employee experience
  • The 3 pillars all leaders should focus on their employee experience

 

Book Recommendations:

 

Don’t forget to SUBSCRIBE so you won’t miss all of the other interesting episodes that we have coming up every Monday!