How To Lead A Remote Team With Sandra Lewis From Worldwide101

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How To Lead A Successful Remote Team In 6 Steps With Sandra Lewis From Worldwide101 [AMP 105]

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How to Lead a Successful Remote Team in 6 Steps

Do you work remotely? A recent Gallup study shows that more than 40% of the American workforce works remotely, at least some of the time.

Today, we’re talking to Sandra Lewis, founder and CEO of Worldwide101. It’s a premium subscription staffing company with virtual assists, expert marketers, and others across the world. Sandra shares six keys you need when working with a remote team to amplify their abilities and make them successful.

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AMP105: How To Lead A Successful Remote Team In 6 Steps With Sandra Lewis From Worldwide101
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Some of the highlights of the show include:

  • Key 1 – Hire for passion: You want them to be interested, passionate, and obsessive in your service and product
  • Key 2 – Analyze skill sets and strengths: Worldwide101 has two pillars that categorize someone’s strength – structured or creative
  • Key 3 – Amplify those strengths: Amplifying a strength is having someone do what they do best; also look at what can complement a core strength (soft skills)
  • Key 4 – Provide ongoing learning opportunities: Keep people engaged and provide a path and cross training for them to grow their strengths
  • Key 5 – Provide great tools: Try new tools and build a tool stack that helps workers be more efficient and productive
  • Key 6 – Over communicate: Have face-to-face meetings, acknowledge every email, set check-in times to build trust and get to know someone remotely
  • To lead a successful remote team, keep it personal; do little things that make working remotely less isolated; love the people you work with and celebrate them

If you liked today’s show, please subscribe on iTunes to The Actionable Content Marketing Podcast! The podcast is also available on SoundCloud, Stitcher, and Google Play.

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Transcript:

Jordan: Howdy marketers? Interesting stat for you to kick things off. A recent Gallup study found that over 40% of the American workforce works remote some of the time every single year, and up to 70% of the global workforce does sell as well. So if you’re listening to this, chances are pretty good, you work remotely some or all of the time too. And if so, today’s episode will be especially interesting to you because I’m joined by Sandra Lewis.

She is the founder of Worldwide101. A premium subscription staffing company with virtual assistance, expert marketers, and more all across the world. So with a team of about 100 remote workers, Sandra has a wealth of experience about what it takes to make remote teams ultra successful. In today’s episode, she shares six keys to doing just that. My name is Jordan Loftis I’m one of your hosts. Now, let’s jump right into my conversation with Sandra.

Sandra, thank you so much for being on the show today. Well can you just start by telling us what you’re up to these days? I know there have been some changes and pivots at Worldwide101 recently that I’m really interested in, can you tell us more about that?

Sandra: Sure. It’s so great to be here. Thanks so much for having me. Over the last six months, my team and I have been really hard at work, refining the way that we talk about and the way that we explain our brand. So in our case, the new messaging that we’ve been talking about is describing our service as a premium subscription staffing company. So while we haven’t actually changed that much in terms of our core service offering, we’ve decided to make an emphasis on subscription and staffing as a subscription to appeal to a broader audience.

Obviously, everyone is super familiar with subscription these days. In fact, we often joked that most business owners nowadays don’t actually own anything and that we subscribe to everything. So tools, software, office space, obviously including subscribing to a service like CoSchedule to make our lives easier. My company allows for successful business owners and executives to subscribe to staff without having to employ them themselves.

So you get to work with someone highly qualified, someone who is US based, fortune 500 trained, they’re remote, you get to work with them on the flexible and fractional basis. So you can work with them for as little as 10 hours a month without having to recruit, without having to do payroll, without having to do contracts to worry about compliance and you basically pay a simple monthly subscription. We’ve been hard at work at developing this new concept and our new messaging. Obviously redoing our website and giving up to talk about it. So very exciting.

Jordan: That’s one of the reasons too that I wanted to interview you and I was excited to have you on the show because our audience is mostly marketers, and mostly people who work on marketing teams and you dig through the studies, you read pretty much any article on Forbes or at the Harvard Business Review, and they’re talking about communication. Communication is paramount for organizational success and ROI and all these different things. When you are working with remote people, that can be a really big challenge and a huge part of the workforce is remote at least part of the time now, I’m really keen on understanding some of your best practices and what you’ve learned over the years on how to work well as a remote team. Can you tell us, what’s your background? How did you start Worldwide101? What’s your personal connection to this problem that you all solved and give us a peek behind the curtain before we dive into how to do this well.

Sandra: Sure so I started Worldwide101 back in 2012. I had been working in New York for 20 years and we just moved our family back to the UK. My husband is British and I’m obviously also not American, I’m French. I’ve been working really long hours in New York for many years as a manager and as a director. I really wanted to take a break from the traditional employment route, you know the 9-5, the office politics.

I also wanted to try to live in the country versus being in a big city but, I wasn’t ready to retire so I wanted to try to find something that would be rewarding and that I could continue to put all my years of work experience at an international level to good use. So at the time, it was the early days of freelancing, 2012 or 2013, there was some platforms like Upwork that got started and that got very popular and I just thought I’m going to try to offer my skills and I did some HR consultancy and some project management work for a few clients. It really started from there. It was completely organic.

You start working with someone and they say, “Can you help my colleague, he also needs help?” and then I realized I can’t do it all, maybe I should assemble a team. This is working, business owners need someone who’s qualified but that they don’t necessarily want to hire full time. They just need someone who can help at ad hocs and for projects. This is really where it all started. We now obviously have more than 100 employees a few years later and we’re a leader in the industry.

Coming back to the problem, my personal connection to the problem that we solve. I come as I said from 20 years of professional experience, I wanted to change the way that I was working but I still wanted to find something that was rewarding and challenging. Our team is basically made up of those people. People who have 15 or 20 years of experience who for whatever reason need a more flexible schedule. they’re either mothers, or fathers, or military spouses, 20% of our team a military spouses which means that obviously they need to be able to travel and they need to be able to travel often and it’s difficult for them to have a steady regular position. They’re only there for six months to 12 months and they have to move on. These people are qualified, they want to offer their services to other businesses, they want to use their skills and it’s a win-win because we connect them with amazing customers who need that support. They get amazing resources and our team gets amazing clients to work with.

Jordan: It’s so cool because it almost sounds like you sort of accidentally started this company and now it has over 100 people who are working with you and with clients all over the world. now since you’ve worked with so many clients in this capacity but also with so many remote workers now, you and I talked about a month ago and you outlined six major themes or points to your philosophy of working with a remote team and amplifying their abilities. You outlined them for me and I thought it was a super helpful framework, can you just give us that 30,000 foot view and then let’s dive into them. What are those six things to look at when working with a remote team and wanting to really amplify their abilities with as little friction as possible?

Sandra: So six steps to hire and then retain that remote team so the first one is hire for passion. The second one is analyze the skill sets you need, the strength that you need in that team member. The third one is amplify those strengths once you know what they are. Number four, provide ongoing learning opportunities. Number five, provide great tools that they’ll work with and the final and very important one, over communicate. That is super important when you’re remote, when you can’t see each other.

Jordan: So let’s look at that first one, passion we hear people talk about being passionate, following your passion, all of those kind of things and it can feel a little bit fuzzy, what do you mean by that? So how do you define passion in this context? Is it enthusiasm, is it just being really interested, or is it being obsessed. What does passion look like here?

Sandra: There’s two different ways of looking at it. When you speak to someone, obviously you want them to be interested in your service and your product. Let’s say you’ve got a dog accessories ecommerce store. You’re going to look for someone who hopefully has dogs, has an Instagram full of dog pictures, knows about the latest amazing dog beds. So you know, somebody who is passionate about obviously what you’re selling. But the other one a bit more subtle is, if you’re looking for an executive assistant let’s say and a lot of the bulk of the work is going to be scheduling.

You don’t necessarily need to have someone who’s going to work with you, who’s going to love your service or the financial industry, or whatever you’re doing. You’re going to look for someone who is a little obsessive about scheduling. Some people believe it or not, some people on our team are obsessive about literally accounting for every minute of their day. So you look for people who live that passion. So you’ve got some people who’ve got a schedule for how they’re going to spend their day. At 8:10 I’m going to be here, and then I’m dropping off my kids and if I’m not back at 8:20, there’s an issue. I’m reminding my husband that he needs to show up for their school at 6:20. People who live and breathe the actual work that they’re going to be doing for you that are literally kind of passionate about that particular task that they’ll end up kind of supporting you with. Passion can be either obsessed with what you’re selling or obsessed with actually the task that that you want me to do and I live it, I do that every single day for myself.

Jordan: So it’s sort of like harnessing something that’s already there?

Sandra: Yes, exactly. An example for us at Worldwide101, we look for people who are passionate about service because obviously, that’s what we do. We serve successful business owners and executives. So we want people who love to serve others. One of the questions that we ask during our interview process is, tell us of a time when you have been successful, and we look for people who don’t speak about themselves. Who don’t say, “Well, when I did this work I was really successful.”

We look for people who see success as a team success who say, “When I’m successful it means that my boss ended up showing up at this podcast because I was able to get him in.” certain questions elicit our ability to see whether someone is going to be a team player and whether someone is going to be passionate about seeing someone else succeed.

Jordan: That’s a really clever way to position it. You know what you want to identify in these candidates before you go into it. I think that’s a really important part. Now, you talked about analyzing strengths and it sounds like there’s a lot of maybe cross pollination between the passion and the strength. So when you come in and you know what you need to be looking for, what are some of the categories? I suppose it’s case-by-case, but talk about analyzing those strengths and how you approach that.

Sandra: We have two different categories. We’ve got someone’s strength is either that they’re very structured or that they’re very creative. We find that those are two pillars in terms of categorizing someone’s strength. It’s super important to be clear what type of person are you looking for. Are you looking for someone who is going to follow instructions to a T and this is really the strength that you need. You know what to delegate, you just need them to implement what you’re telling them to do.

You need them to schedule, you need them to book travel, it’s pretty regimented or do you need someone who is more of a creative thinker. Who thinks out of the box, who you are going to be dialoguing with to try to find solutions, who will research different options for making the work more efficient. Sometimes you can find someone who is good at both but I usually say that it’s better to really play someone’s main strength. Usually someone is either very structured and loves as I said earlier, the scheduling, loves to follow instructions versus someone who is better at being more autonomous, not figuring things out. Those are two different skills and usually different types of work that are given to these kinds of people.

Jordan: I couldn’t agree more and I guarantee you, everybody who’s listening just categorized themselves. Oh yeah I’m that structured person, I’m that creative person, and maybe four people are like, oh yeah I can do both and maybe two of them are right. They are good polls and I do see passion being a huge part of that because you’re looking for someone who is operating in their strengths, and then you talked about amplifying those strengths. What’s your best advice around that? So you’ve identified what category they’re in, now how do you look at amplifying that? Then the second part of that question is, what does that do for retention and engagement?

Sandra: Yes, those are great questions. Obviously, the first thing to do to amplify strength is to make sure you give that person what they’re good at. Just give that person scheduling and amplify their ability to do their job really well, to do what they do really well. The other thing that we think of a lot in our company is amplifying those soft skills. So to that person who loves scheduling and who is an amazing executive assistant. In fact, we have someone like that on our team who loves to see her clients succeed. She’s great at doing the executive assistant tasks. But she is also somebody who is amazing at building relations who truly loves people. What we did to amplify that strength and coming to your point of then retention. To make sure she was really fully happy and fully balanced in her job was to have her develop a buddy system for our company.

It gave her the opportunity to speak to people in our team and to develop something where it was at the core of her love and of her strength, getting people to talk to each other and being social, and connecting people that had similar hobbies and things like that. Amplifying a strength can be obviously having someone do what they do best, and then also looking at what else can complement their core strengths and in our case it was a soft skills and amplifying that by giving them projects that they will really take that other box and make them happy.

Jordan: Hey, are you enjoying the actionable marketing podcast? Do you like guests like Sandra Lewis who is sharing her expertise in such an important field? If you do, you have a chance not only to help our show out but also to win some swag for yourself. If you head to iTunes and you leave a review of our show, the Actionable Marketing Podcast, all you have to do is take a quick screenshot of that review and then email it to podcast@coschedule.com along with your mailing address and we will send you a care package to say thank you for the review no matter what you say, it’s going to be on its way to your doorstep. So please head over to iTunes, leave a review for our podcast and make sure to send it along to podcast@coschedule.com and we will have a swag bag winging its way to your doorstep in no time. All right let’s get back to the interview.

They sound like they’re important just in general for managing any kind of team. Whether you’re managing a marketing team or even anyone who’s on site. Why are these so particularly important for remote work?

Sandra: Well, perhaps it comes to the communication point as well a little bit. It’s like when you can’t see people, it’s really important to tune-in to what they’re good at and to amplify what they’re good at. Because, when you are all in an office, you see people, you chat at the water cooler, you get a read on people’s mood and you get a read on whether someone is on the verge of quitting. Hopefully it doesn’t get to that point but you know what I mean.

Jordan: Point taken.

Sandra: So when it’s remote, you can’t see them. So you have to really be attuned to over communicating. And then by over communicating, really finding out, “Okay, you’ve been doing scheduling now for a year. I know you love scheduling, I know that because that’s what we hired you for. What else can we do to really give you an even better rounded experience and develop yourselves in other ways as well. What else can we amplify about you? Maybe some of your other strengths that we don’t know about.

Jordan: That makes a ton of sense. To this tune of keeping people engaged, I guess it’s almost like just providing a path for them to grow in their strengths and what makes them passionate and just make sure that this is a vehicle for growth and that you talk about ongoing learning and what does this typically look like for you? How are you intentional about this and not just sort of giving lip service to it?

Sandra: Yeah, one of the things that we do on our team and it takes a number of boxes, the ongoing learning is a big one, it’s cross training. We’ve got professionals, we’ve got 10, 15, 20 years of experience who hopefully stay with us for years and who work with our clients for years and what we do is we provide backup. So you know, one of them is on vacation, one is sick, when things happen, there’s someone else that can step in. it provides great learning opportunities. Our team really loved it.

It’s part of one of the almost like a perk of being on our team is that I’m not just going to be linear working with my two clients for a couple years, I’m also going to get a chance to learn about that email marketing campaign with constant contact because so far I’ve just been doing matching. But my colleague here is doing constant contact with his client. Great, I’m going to provide backup for you and I’m going to get to learn this.

We try to do this as often as we can so that there’s cross training. So it’s great for our clients because they never go without help and it’s great for team because it motivates them and everyone wants to keep learning, it’s part of staying motivated in what you do.

Jordan: It’s sort of like project based then. It’s not just like, “Okay, go do this training that maybe in the future will have something to do with your job.” it’s really like, “Hey, there’s an actual need and you’re going to be doing something and producing work but in this cross training way.” but it’s still like definitely business focused and they’re producing a result.

Sandra: Absolutely. Yeah, it’s hands-on learning.

Jordan: All the teams I’ve worked with like our marketing automation lead here and that is an interesting bear to try to hug. It’s a lot of technical stuff. So as we onboard people onto the team, the best thing that we found instead of like, “Hey, go through this training for three days in this checklist.” It’s like, “Well, we’re shipping this this week. So we’re all getting our hands dirty and we’re working on it together.” you learn on the project. I think for tools, that’s really important too. You mentioned that tools is one of the six things that you’ve identified as a paramount for remote teams using great ones. Talk about your approach to building out a tool stack.

Sandra: Yeah, it’s super important particularly when you’re remote. I guess in an office too but tools for us is really the way that we communicate, the way that we can see everything online and seamlessly and everything. one of the things that I always say is I think a lot of business owners and I’ve been there, I’ve been tempted with, “Oh my gosh, this is a new tool, oh great. let’s try it.” just trying and trying tools and I really would recommend that before you get excited about the new kind of toy that’s out there, that you ask the people who do the work what they need to do their work better, and what they need to be more productive and more efficient.

What I have found is that when building your tool stack, you can actually really slow down the work and the processes because if you get started with a tool, it takes a lot of commitment for your team to learn it, to get their head around it, to try it. So if people or not really behind it and thinking, this really looks like it’s going to help us then you waste a lot of time. So I would say first start by asking your team, “What it is that you need to succeed?” particularly again you’re remote, you might not see them at their desks. You might not kind of realize some of the pain points that they’re experiencing day-to-day. Obviously, we all want to be more efficient. So what do you need to be more efficient and more productive and then kind of building from there.

Jordan: And really avoiding that shiny object syndrome. I completely agree. One of the things at CoSchedule that we found, we just had a couple of big conferences. You talk to hundreds and hundreds of people and it came up again and again where people are like, “Well, what tools are you using?” because obviously we’re a software company and they’re like, “Well, we’re using this tool for this, this tool for this, this tool for this.” You actually draw it out on a piece of paper and people are like, “Whoa.” we’re using nine tools.

A bunch of them kind of do the same thing but not super great and it’s like when you really do that analysis, you find out there’s a lot of friction and then you sort of like, you can’t even buy yourself out of the problem because you can’t just add a new tool because that sort of makes everything worse. It just becomes this yarn ball, this barrier when your tools are supposed to enhance what you do and that makes a ton of sense remotely. Especially as we teed up on probably the most important point, the communication. So obviously, your tools have a lot to do with your communication channels and notifications, people being able to see one another. Let’s really sit on this idea of over communicating. Can you talk us through that?

Sandra: Yeah, this is about making sure that you are clearly understood. So when you’re in an office you can see each other, you can see body language and you can also get to know each other. When you are remote, it takes longer to build that trust and to really get to know someone. So we always say, be sure to have face-to-face meetings. I mean even if it’s literally 10 minutes every morning, or 15 minutes every other day, or 20 minutes every few days. Just have some face-to-face where you get to know each other, where you understand how you communicate, how the other person communicates so that when you get to work and when you have to send quick messages or quick emails, the person does not get offended. They know who you are, “Okay, well he’s in a rush. I get it.” you don’t have to kind of go good morning every time and wish you the best.

Jordan: Yeah, you don’t have to write them a Christmas letter update like, “This is what our family did this year. How are you? That makes a lot of sense.

Sandra: Yes, over communicate so that you can build trust and so that people get to know you for the person that you are and so that in the end, the work is more productive in that way.

Jordan: So how do you set expectations around communication? I ask this question for a couple of reasons. One, I’m interested in this for maybe an agency, someone who is in marketing in an agency who might be working with lots of clients because you’re dealing with communication on two levels. This is how we communicate with our clients as Worldwide101 but then also, this is how we communicate internally. So how do you set those expectations and those systems up?

Sandra: Two things and absolutely we have two different prongs. Internally, which is also with our clients but internally, we’ve got this thing where you need to acknowledge every single email that you get within a couple of hours with, “Got it. Will get to it by 3:00 PM, 4:00 PM tomorrow or whatever.” or obviously you can also do a full answer. But if you don’t have the time to do a full answer, then at least you acknowledge that you’ve got it. That’s super important because again, I can’t see you, where are you, what’s going on, have you gone for the day.

Acknowledging communications within a couple of hours is super important. The second thing we do with our clients is we set times during the day where they can expect than we do their work for them, that we’re going to be communicating with them. As I said earlier, some of our clients are subscribing to 20 hours a month. So that’s only one hour a day when you break it down. But even for that one hour a day we’ll say, at the beginning of the partnership with that client their team member is going to say, “Listen, would it work for you if I check in my inbox for you for that one hour a day maybe at 10:00 AM and 3:00 PM so you always know that you’re going to hear from me at those two times during the day.”

Obviously, that depends on where the person is, time zones and everything but we always make sure that the expectations on when we’re going to communicate and when they can hear back from us are super clear and that has been amazing and really yield a great rate of successes and results and everything because the person doesn’t panic. “Okay, 4 o’clock I’ll hear from her, if I don’t hear from her at four, then I can panic.”

Jordan: I think that is so simple but that’s such a great solution even for people who are in the office. At CoSchedule, we have two offices. We’re in two different cities. I think even that I’m already thinking about, “Man, I should really be doing that for my team,” because two of the other people who are on my team there are in the other office. It’s like you just acknowledge and then you say, “I’ll get to this by this time.” So then you’re committing to it as well but that sort of does just alleviate any tension. There’s less anxiety and I found too when you’re worried about something, you’re just not as productive either.

Sandra: Yeah, exactly. In way, you can just focus on the work and not worry about whether someone has got a new email and when they’ll answer it

Jordan: Yeah, or even being able to communicate back to a client and like, “Okay, if this is contingent upon hearing from this other person, we’ll have that to you by tomorrow,” or whatever. But that’s so simple. I love that.

Well, one question I always like to ask is, if we got to sit down for coffee for one minute and you only got to tell me one big piece of advice for leading a successful remote team, what would it be?

Sandra: I think it would be keep it personal. Do the little things that will make remote less isolated. We celebrate virtual birthdays for example. We send handwritten cards to feel connected. We obviously have a Slack channel for water coolers. All the little things that you assume are normal in an office, we really try to make a big deal of them remotely. So keep it personal, love the people that you work with and celebrate them in a remote environment.

Jordan: Sandra, thank you so much for sharing with us and being on today. I learned a ton and I guarantee you, anybody else who was listening did as well. Whether we’re in person or whether we’re remote, these are fantastic pillars to stand on.

Sandra: Thanks so much Jordan.

Jordan: So if you are working on a remote team of any kind, especially if you are in managing a remote team, think these six pillars that Sandra shared with us are incredibly helpful. I’m going to recap them real quick. Write these down if it is something that’s part of your daily or weekly work. One, look for passion. Hire passion about your product and service. Look for that enthusiasm, that keen interest, even that obsession with doing the things that your product or service does. Parlay that into number two and number three, it’s analyzing strengths and then amplifying those strengths.

The fourth thing she shared I think is a way to do both of those which is, offering opportunities for ongoing learning. This helps keep everybody engaged. This offers new challenges and really a path to growth because unless you’re learning and acquiring new skills, you are moving backwards. Especially in an industry like marketing that changes so stinking fast. Number five, I thought this was a really good one not just because I work at a SaaS company but using great tools is absolutely paramount.

If you think about it, if you go into an office every single day but the water doesn’t work, and the ceiling is moldy, and the carpet is torn, and the floors are falling apart. If the building isn’t conducive to actually getting work done, then your productivity is going to suffer. Well the same thing happens if you use crappy tools. If your tools add more friction than they remove, or if they don’t play nice together, get rid of them. So when you look at your tool stack especially when it comes to a remote team, make sure that you have great tools that enable communication instead of preventing it.

Number six tee it up the most important one, this is the summit of remote work. It is communication. Over communicate, make sure that expectations are clearly outlined and I love how she put it. Especially for you agency folks and consultant folks, communicate expectations both to your team and also to your clients. When are you going to be available? How fast should they expect a response? How can they rely on you if you’re not in the same room to get them the information or the data that they need when they need it.

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