Running Remote Teams the Right Way: Systems, Culture & Global Talent w/ Rebekkah Anderson | 🎙 TNC

If I continue to like give grace too long, I end up just biting myself in the back because I'm like trying to be gracious of, okay, well, this seems easier for you, but But in the end, it's not easier for me because I don't even know how to work that theme. And how am I gonna do my own ongoing work on stuff after I've got this project done if like somebody sets me up with the tools that I didn't ask for? And so like being more firm in the beginning and saying that wasn't the scope of work that I, we agreed to. And if you can't do what I asked you to do in this scope of work, then I think we need to part ways.

Welcome everyone to another episode of the Nearshore Cafe podcast. I'm your host, Brian Samson. Before we get into our show, let me thank our sponsor Plug Technologies, plug.tech. Great way to connect talent from all over Latin America with US companies. I'm really excited for our guests today. It's one thing to hire abroad and have a remote team, it's a whole other thing on how to run the right systems, implement it, keep everything straight. So Rebecca Anderson is going to tell us all about that, her experiences, really exciting founder story. Rebecca, so nice to have you on the show.

Thank you for having me.

Well, let me give you a proper introduction. So Rebecca is the president of Wise Elephant Group. Rebecca is also a podcast host. She hosts Business Talk Sister Gawk, which is one of my favorite names for a podcast, and also owner of Diletto Art Gallery. So, I would just love for our audience to get to know you a little bit better. Tell us about the journey. You know, where did you start? How did you get to where you are today?

Yeah. Well, I started my business in 2018, and with that, it was actually before the big move to digital. And I had worked for a company that I was doing a lot of digital software as a service, all that kind of stuff. And I was working with people all over the United States at that time. And then I realized, you know what, like, that's, that's— I can do that myself in my own business. And why not live in the place that I love in a rural area where everyone knows my kids and they're watching out for each other, but also still be able to offer the same level of service on a remote world. And so I started that journey of my own consulting company and it, in that process, you know, you start learning so many things about business and, and being online and all that kind of stuff. So definitely it was a, a slow and steady start to things just in like using all of the different digital marketing techniques I know how to use and whatever else. So that was super fun. Started working with a lot of different businesses that way, doing project management. And like that slowly transitioned into doing work for acquisitions and mergers and helping people negotiate property deals and work with small towns or work in, in general with just grant funding and all that kind of stuff. So that's kind of like my business, helping help other businesses strategize growth or create accountability for long-term success. And in that process, I realized that the other, like, you know, I did workforce development and business development, but the other three-legged stool in that is community work and like community development. How do you really do that? And so that was like my passion of trying to like invest in a town. And so I found a town that I really wanted to start pouring my efforts into using the arts because statistically Communities that have art and public art as enjoyable for everyone see a significant impact in economic development increase. And so that started with me finding a building with no heat, power, or water, and then deciding that I wanted to put an art gallery in and create an art studio. So right now, a couple years in, we have a resident artist with us that's gonna be there for the next 6 months. Who's fantastic, done like movies and all these different things with different industries. And she's, she's just so talented. And then we've had the opportunity to represent quite a few well-known local artists as well. And so yeah, those are kind of all of my, my businesses and the things that I have grown in doing over the years.

Was 2018 your first year as an entrepreneur or did that take place earlier?

2018 was my first, like, I filed my LLC and got everything together. But definitely during COVID I was already doing a lot of stuff remotely, but during that time everyone else in the world was like, oh yeah, we should really invest in digital and start looking at how we can have people work from home or work other places, not necessarily from home, but how are we leveraging cost savings. And I think a lot of larger organizations started to realize we can do this without having to be in person all the time. And don't get me wrong, I think that, that, that is valuable for team building and relationships and having a little bit more downtime to connect with people, to learn about who they are as a person. But for efficiency's sake, in just doing an agenda of a meeting and accomplishing tasks and distributing to-do items, I think digital is a fantastic tool.

Yeah. I know you're in Minnesota, but how far are you from the nearest mid-sized city? Would you say?

Well, it depends on what you mean by mid-sized. We have Duluth, which is about an hour and 15 minutes, but the metro area would be about 3 to 3.5 hours away.

Yeah. Yeah. Do you, so the rural experience you've had more recently. Did you grow up in, in a rural area or like what, what was the, the driver, um, to do that?

Yeah, so, so I did most of my life and I realized, I mean, I, I went to school in the city and, or the Twin Cities here, Minneapolis-St. Paul. And, um, I think that I just realized I was working down there for a little while and I realized like, man, there's so much time I spend in the car trying to get from one place to another, like Everything is like a half hour away or something. And I can get there in 5 minutes if I were not having all this traffic and just all that kind of stuff of like, okay, this is not necessarily my favorite thing to sit in traffic.

Yeah.

But also there's like this feeling of, I don't know if it's the right word, but anonymity, is that the right way to say it? Like you are anonymous and I didn't want that for my kids.

Yeah.

Because I knew what it was like to grow up and be a teenager. Oh. And have people in my own community be able to say, hey, I know you, I know your parents, and like, I know what you're doing and you're not supposed to be doing that. And if you don't stop, I'm gonna go tell your mom. And so for me, I was like, I needed that. Like, there's this aspect of like community values and policing of like helping the community, helping you raise your children that is a bit removed from large metropolitan areas because there's so many people. And to this day, I'm so grateful for that. I can have people call me and say, hey, just wanna let you know, I saw one of your kids, they were doing this and were they supposed to be out of school on lunch or are they supposed to be on campus? And I'm like, thank you so much for letting me know. We're gonna have a conversation about that. So, mm-hmm.

Yeah. I think what I really like about what you're saying, and I can apply it to my own life, is proximity doesn't always mean relationship. Right. And like, you know, I lived in high-rises for a lot of my adult life, Chicago, San Francisco. And I don't think I knew any of my neighbors, even though we were like shared walls, essentially, you know, in these, in these condos and apartments. And then I've lived in Hawaii now for 8 years, much more suburban than rural, but, you know, there's more space between houses that we know our neighbors really intimately. They know our kids, they look out for our kids. You know, the other day I saw a kid on a bike that was probably not being very safe, but I felt it was my job to speak up because we're all part of this community. We're all part of this neighborhood. But it also makes me think about, you know, if proximity doesn't mean relationships, that there's this opportunity for remote companies, remote work, because relationships can, can happen. They don't have to be in a city, right? So tell us about how remote work came into your, your companies? When did you first start doing that?

Yeah. Well, I would say that was pretty immediate for me in just knowing people across the United States to network with and just saying, just to let you know, like, this is what I'm going to be doing now. And so in regards to like developing those relationships and doing, I did a lot of different things at the beginning when I was still trying to figure out what kind of business do I want to have? You You know, that's the beauty of business is you can restart your career so many times if you want to. And so, you know, just, I did copywriting, like content writing, working with like contractors for the Department of Defense, like all, all different kinds of work that I learned how to do just by like people saying, hey, do you know how to do this? I'm like, I'm, I've never done that before, but I definitely would try it. Like building e-commerce websites and launching products. Products across the, the US and what I was like, yeah, I don't, I'll try it. Like, and having people who are excited about doing it with you, you know, and like saying, yeah, this is where I wanna go and be like, okay, well let's, let's try it. And that to me, like was kind of immediate because I would just meet people that I would try things on my own and experiment with them. And then they'd say, hey, like I saw, you know how to do this. Do you think you could help me with what I'm doing? And that just led one thing after another of like, oh, well I know how to use this one software. Software to make sure everybody's on track. And a lot of people really like those tools. And then it was just like, oh, my cousin's looking for somebody, or like, hey, you should talk to this person because they need help too. And so most of the work that I did, um, I don't, I don't think I worked like in my first town with anyone that lived in my town for the first couple years. That's, of course. Yeah.

Like, yeah.

So, which made me like so dependent on my local economy. And I think that that's a huge blessing because a lot of communities are so dependent on one corporation or one manufacturer. And if you can diversify, you're really helping your community stabilize and you don't go through the booms and busts.

Yeah, that's a really interesting economic principle, right? Of what you're, what you're really doing as a small business owner by having a labor market outside of your city or small town is you are diversifying the economy more or less, right? Because labor projects, clients, you know, they're from all over the place. And I think that diversification really mitigates disasters, you know, when one large employer either invests or goes away.

Mm-hmm. Well, 100%. I've seen that happen in many, many towns. And I think that the principle of even like recruiting businesses that have like 10 or less employees, um, and having lots of those in different industries that are across the board is a way better way to manage your just overall, like population risk of, mm-hmm, like a, a town.

Yeah.

Yeah. And I get excited about that because especially with the use of technology, like even in Chisholm, like I'm seeing people buy where I live abandoned properties all over town and it's super exciting to like watch that growth. And there's like a couple guys across the street from me that just bought a building and they're putting in a coffee shop or a chocolate shop.

Yeah.

And they sell their chocolate all over the United States and they moved from like Seattle. And so it's kind of exciting to see people who have established presences online and it doesn't matter where you move to, you still have that loyal group of people that appreciate you and the product that you provide. So it doesn't matter where you are as long as they can access what you have to offer.

Love it. Diving more into the labor part, tell us about some of the roles that you've hired for, for your company over the years.

Yeah, so I've done a lot Different, um, a lot of different roles. I've had some, um, I used to have a contract with the state of Minnesota, or I guess I still do. I just don't do contract work for them as much for career counseling for kids with disabilities. So I've had remote employees that travel to the schools and service that. I've had, um, employees that, um, well, I would say subcontractors, I guess, the companies that have helped me through having a virtual assistant. Or social media manager, social media or marketing strategizer. Mm-hmm. So those roles I've had from different parts of the United States and then also I experimented with doing that other parts of the world. And so that's been kind of interesting to dabble in all of the different layers of that.

Yeah. Yeah.

Because, um, and, and exploring it on my own, you know, there's like just a lot of ways you can do it. You know, you can do stuff like Fiverr. I've done that, work with people in like Pakistan to build websites. Or in other parts of the Middle East. And then social media management in like South America. I work with some people from Argentina. My, my family is, or my mom grew up in Brazil, so yeah. Have a lot of appreciation for like South American countries. I feel like a lot of times I'm a hidden immigrant where I live because my personality is very much more loud. So it's, Yeah, I can appreciate like those cultures like way more, I think.

Yeah. Well, a couple threads that I wanted to, to go into separately. So maybe we'll first talk about the digital roles, especially as you've hired for website work, content marketing, you know, things like that, that are, that are pretty digital. What are, what are characteristics or experiences that you look for when you're trying to do a project or add a team member?

I look for people who, um, are able to give me timelines on what they're going to do. Um, because I think, and this is something that I've also learned is like, I have a gap sometimes in the, um, honor-shame cultures. Where I will say, this is what I want. I want this built on this platform with this theme, these plugins, and I will exactly lay out the whole scope of what I'm trying to do. And then where I really realized I need to like nip it in the bud earlier of like exploring that opportunity or whatever is when someone says, yeah, yeah, yeah, I can do that. I'm like, great. And so then we start the process and then I'm starting to see the work back and I'm like, this is not the plugin that I told you I wanted to use and this is not the theme that I wanted. Yeah, yeah, yeah. But I can do the same thing with this because I know how to use this theme. I'm like, okay, but that's not— and, and I think I've learned that I have too much grace in those moments because I'm like, no, I asked you for these things. And if I continue to like give grace too long, I end up just biting myself in the back because I'm like trying to be gracious of, okay, well, this seems easier for you, but in the end it's not easier for me because I don't even know how to work that theme. Like, and how am I gonna do my own ongoing work on stuff after I've got this project done if like somebody sets me up with the tools that I didn't ask for? And so like being more firm in the beginning and saying that wasn't the scope of work that I, we agreed to. And if you can't do what I asked you to do in this scope of work, then I think we need to part ways.

Mm-hmm.

Is something that I think I've been really like, wow, I learned a good lesson in that one to make sure that my time and effort is for what I have asked for.

Yeah. Yeah.

And so just stuff like that. Or when people, I say, okay, this is what I would like, like someone who has an actual business who has been working in this industry for a while. And I will say, this is what I'm hoping to do. What do you think it will take to get there? And having them build out, this is how many weeks it'll take and this is how much of your time I need. And if they can do that well, and then I can hold them accountable to it, Then I know after like a smaller project, okay, this person is legitimately knowing what to do.

Yeah.

Because I've been in situations where I've said, how long will this take? And oh, it's only gonna take this long. I'm like, all right, let's do it. And then we move forward and then it doesn't happen in that time. And then I'm following up and I'm following up and it's like, okay, this, I need to be better at saying, You know what, I appreciate your time, but you didn't follow through on the initial thing that we agreed to in this timeline, and therefore we're not gonna be continuing this relationship. So those are like, I guess my advice of like, as you're interviewing or as you're looking, ask like timeline questions, get your scope really clear and then like double down on when those things are not being delivered on.

Yeah, I think that's really important. Um, I love the timeline aspect to it because then you have an immediate feedback point, right? Are they going to follow it or not? The other piece I think is really interesting is, and a mistake I see a lot of first-time DIY outsourcing, the scope is too vague. And, you know, later on, at least in my experience, you know, as you hire people, you can give more ambiguity and you rely on them to give you recommendations or even make choices. But I think the very first project or two, the more that you just, you're just really tight on exacting, you know, what you want, then there's, there's really no ambiguity, you know, it's either, it's a black and white deliverable.

Yeah. Well, and I think, I think that's definitely where people are like, well, this person knows a lot, so I'm just, and they're not that expensive, so like, I'll just have them tell me. And it's like, but if, if really they knew exactly what you should be doing and the way to get there instead of like giving like in charging the price they are, they wouldn't be charging the price they are, you know? Like, I feel like that that's the, the catch-22 with that is like knowing where people are at with their actual skill levels. Yeah.

Um, tell us more about Argentina. So you've hired a few people from there. What kind of projects and what was your experience?

So I did a lot of graphic design, like brand manual stuff, as well as, um, just social media support and, uh, I guess my experiences would be that the people that I was working with, they were really good at the visual stuff. Like, I mean, to this day I still use that brand manual, like knocked it outta the park. And so like stuff like that where it's like I was able to put scopes together of, I'm looking for a brand manual, here's some examples, this is what I want. I want you to only choose fonts that are available for free to do the, the complimentary and the web like web stuff and whatever else, because working with some people that they don't have the huge budget and they wanna be able to use stuff. And so like just getting it all together really well and saying like, here are examples. I think examples are so fantastic because you can write as much as you want about something, but if you can actually say, here's like the visual of what I'm looking for, an example of something else I've liked, I just think that, that Speaks way better to, um, what I'm trying to go after than just trying to type it all up and then have them translate it into Spanish and whatever else. So I think—

I like where you just went there with, you know, it's one thing to be super specific with every single thing you want maybe in the very first project you have someone do, but I like how you, how you describe that, you know, find a font that's free, which is different from use this exact font, you know, find a font that's free, build this according to these guidelines, you know, these guardrails. And I think that's been my experience with Latin America is you can do more guardrails, guidelines, and the quality of work ends up being really high. And I think they make Generally good decisions.

Yeah. The critical thinking skills, if you find the right people are great because then they can really play with it. And, and, you know, I think that the team members that I've had in the past have been really good at coming up with new ideas too, even though it's not part of the scope. And they're like, what do you think about this? And I'm like, oh, that's really cool. I don't know if I would do that just because it's not on brand for me, but like, that's a really interesting concept or. Like, show me where you're seeing that being done other places, just so I kind of have it in the back of my mind if I ever want to transition to that, you know?

Yeah.

So I think that just finding the right people that are, are willing to like explore with you and experiment along the way, I think is really fun.

Yeah. And then I want to go back to your mom. So your mom's Brazilian. When did she come to the States?

Well, she actually was here in the United States, but my grandparents were missionaries to Brazil for 40 years and my grandpa was a pastor there. Okay. And so my mom grew up in Brazil and so it's kind of interesting that way. And that's why I say hidden immigrant because yeah, we look very Nordic but have the voices and personality of a Brazilian family. So yeah, so she was, uh, there all of her upbringing and then came back to the United States to go to college. Yeah. So, which was a pretty big culture shock. Yeah. And at that point, you know, because of like living there so long, she actually became an English as a second language learner. Wow. To make sure she could like get back into understanding English.

Yeah.

Which, which actually was to my benefit because, um, I was homeschooled. So my mom, like she said, we are gonna learn English the right way. Yeah. And I attribute a lot of my ability to craft an email to my mom. So she knew what she was doing.

Sure. For sure. So for those that are listening, that, and Brazil is an incredible market for talent. For those that are listening, what advice would you have for people in the States that are looking to hire talent from Brazil? How can they get the most out of them and any other advice or tips?

Hmm. That's a good question. I think that It's important to always look at the quality of work. I think it's always good to say, show me your portfolio.

Hmm.

And ask questions about what they did and what their role was in that process. I think that people in different places of the world can be very good at like agreeing with you or like, oh yeah, no problem. I can do that cuz they wanna make you happy, but At the same time, if you don't understand their role in things, they could be telling you something that's not the full picture. And I don't mean that to be a bad thing, but it's more just like they were, they were involved in that project, but like what was their actual role and what did they contribute? And so understanding those things can really help you dig into someone's portfolio. But it would be the same thing with any kind of web developer or whatever you're saying. Okay, what did you actually work on in this application? And show me some of the struggles that you had in that. And just really getting into like what their thought process was through their job and all of that. You're really gonna start seeing a whole lot more about them as a person and their knowledge capacity than just a surface level like resume of, yeah, I, I designed these things and they're so cool.

Well, yeah.

How much of that did you actually do and how big was your team and all that kind of stuff? Yeah. I think that's really helpful to get into.

Yeah, let me ask one more follow-up on that. Culturally, is there any advice on hiring someone from Brazil that someone watching this or listening can take away and give them a better understanding of Brazilian culture as they go through the hiring process?

I think that it's important to understand that people are still people and like, it's not like you're asking AI to do something for you. Yeah, people are still people. And they're gonna have good days and they're gonna have bad days, too. So I think that for somebody who may have a frustrating day and they're telling you about it, and all of a sudden it's just like they're talking super fast and they're like this and this and this and this. And I don't think that that's a bad thing. I think people. For people to have the ability to share what's going on and know that that also, like, can reflect a little bit of their culture in how they're responding in a situation. Yeah. Because I think a lot of times in other cultures, like I see this with my kids, like people are, my kids are like, you're yelling at me. I'm not yelling at you at all. I was just like telling you exactly what's going on because I'm like, this is very serious. And like, you know, like just, I think of specifically like one of my kids wanted to quit the violin and I'm like, you told me you wanted to do the violin. Like, why would you tell me to go get this whole contract for renting playing a violin and all this stuff. And he's like, stop yelling. I'm like, I'm not, I'm not yelling. Wait, like, I was just telling you very specifically the accountability piece of what you asked of me, and that's what I did. And I was like, okay, this is my, this is like my upbringing coming out, and my kids are not used to that because we're not surrounded by that culture. And I think that sometimes, like, when you work with people from other cultures, you can be like, whoa, this person's being unreasonable right now. And it's No, actually, like, that's normally how people express themselves and it's not bad. And, but being able to like understand the cultural differences there and be like, okay, like you're just, you're just telling me like the honest truth. And so how do I receive that in a way where I'm not like upset, you know, or whatever I think is, like the give and take of grace of having, working with people on a multicultural team.

Yeah, I think that's great. That's great. Back to the tools for a second. Uh, if you could give, uh, advice on like maybe the top 3 or 4 softwares or tools that you use as you're running remote teams.

Okay. I really like Asana. It's a project management tool. Like there's a lot of them, like Notion. I personally like Asana just because it's super versatile for even if you're a small team, you can share a project with up to like 10 people for free. If you're like a one, one person show, but it grows with you, so that's super nice. And I think that I really also like stuff like Toggl, which is like a time tracking tool. But there's other ones like Harvest that integrate with Asana. I mean, I really like the ability to have those like API tokens that connect things together so you can actually see the amount of time people are spending on tasks and what they accomplished in that. Um, just for the accountability's sake and seeing reports regularly on where people are spending their time and what tasks were the most difficult for them. Because then it can kind of show you where maybe you need to adjust somebody working on something to a skillset that's like, they're really knocking it out of the park in this category, but maybe not this. And so I think, I think those are helpful tools. I use Zoom a lot.

Yeah. I think that's a good list. Yeah. I think that's, that's really helpful.

Okay.

Yeah, yeah. Thank you. Thank you for that. Then as we start to wind down, for our audiences to know, Rebecca and I have something in common. We're both foster parents and I just wanted to recognize you for that. And, you know, the country needs more foster parents. There's, you know, over 400,000 foster kids. If you could share any But just any thoughts on the subject that, um, you know, as your, your last words on the show.

Oh yeah. So my husband and I actually, we are adoptive parents. We adopted out of foster care. So right now we don't have any new foster kids running around.

Okay.

But that's the nature of it. Um, if you are a foster parent and you have kids in your life that you, um, realize, man, this person needs a home. That's how a lot of foster parents get out of the game because they end up adopting and they have so many kids and then all of a sudden they're like, our home is bursting. So there, there is a huge need for more foster parents to, to take on the torch because there are so many kids that are really in circumstances where they need somebody that's just a solid, stable person in their life to support them and see them be successful.

Yeah, I love it. Thank you. Thank you for sharing that.

Yeah, absolutely.

That is, yeah. Well, that is all the time we have on the Nearshore Cafe podcast. We're so thankful to Rebecca for making time to join us. And again, thank you to our sponsor Plug Technologies, plugg.tech. You're listening to the Nearshore Cafe podcast. We'll see you next time.