Tips to onboard a virtual assistant or remote worker


In this episode we talk to Tiffany Elsner of Northwild Leadership about working in a virtual space and how to onboard a virtual assistant or a remote worker. With the rise of COVID19 cases and more and more cities clamping down on social distancing policies, it is a relevant time to talk about having to work with remote teams.

Now is a good time to lay down the foundations that we talk about so that when the economy revives and you are busy, you'll have had the infrastructure in place.


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Justin Lam 0:05 You want to find your tribe of raving fans. I'm gonna help you do it. This is the Digging Deep podcast with Three Sixty Media, where we help you do better business. Hey, everybody, this is Justin Lam. And this is Episode Seven of digging deep. And we're here with an amazing person, a client of ours, but also a very good friend. She has been the leader of the Year for the Fairmont group in 2015. And she is well she was on her way to work remotely for one full year, all around the world. And that got cut short because well the virus has taken us all over. But so she went to Santiago and then they had to suspend it and she sent it back to Vancouver. So for the time being, I have the luxury of having my good friend Tiffany Elsner here from Northwild Leadership Tiffany How are things? Tiffany Elsner 1:02 Whoo, what a time to be alive, just they are going, I think, wildly. And I think that's, that's a big part of even my brand is is is finding the beauty and the fun and the connection in the wild, right? It's with the with the virus spreading all over the world. A lot of small businesses, including myself are going through a time of turmoil and an opportunity is arising right for us to find out how we can serve and how we can be of value to each other during this time. Justin Lam 1:41 Yeah, for you working remotely was was really interesting. I mean, it comes at a really perfect time because like your whole objective was to be able to help teams and leadership groups to be able to work remotely with teams and help foster a good environment and so It's funny that, like you, you're on this tour, and all of a sudden you get cut off. But But how does that work now? Like, like, what is going to happen? And you know, what are you guys doing as yo your cohort in order to just kind of keep fostering that? Tiffany Elsner 2:17 Yeah, that's a great question. So some context is, there's 25 of us that were traveling the world for one month each for a different country each month. And here we are now sent back to our home countries or going there freely back to our home countries. And now we're all disconnected, but at the same time, very connected. So we're using all sorts of methods like zoom and slack to watch out for each other send videos, send messages of hope, and just help each other. Right. That's one of the biggest things is really being there for each other. Everybody has different talents and skills and it was really an To see some people step up, and you know, oh, I I know I have some experience in trying to get back insurance claims Oh, I have some experience in trying to find flights that are really hard to find. And out of the woodwork came all of these individuals who just had these hidden talents or resources and we're able to share them and that I think, has been the biggest driver of connection is just that giving philosophy Justin Lam 3:26 and so when you're with that, like how does that say go back towards teams that like if you're say, because you train you train leadership teams, right? And you're training them? Do you train them remotely? Or do you train them in person generally, Tiffany Elsner 3:45 I eat the shift I train them in person. Um, but now that I'm virtual and remote team, we create orientation on onboarding and leadership programs all online Justin Lam 3:55 raising and so when you're teaching them to do that was one of the key fundamentals that you have to instill with a leadership team in order for that to be successful. Tiffany Elsner 4:05 The biggest is a mindset. Right. And for some, it comes more naturally. And for others, I think it still can be learned. But it's that mindset of a leader does not always lead from the front, right? The leader sometimes is from the middle, sometimes from the back, right. And actually, leadership is not always taking charge, but sometimes that is supporting others to shine and others to be able to use their talents. The biggest thing is, you know, a leader who tries to be all the things to all people all the time, whereas a true leader understands that other people have the capacity and the talents to shine. And so what that means is sometimes the leader is actually going to say giving their power because power is a more of an abstract thing, but they they give the opportunity or the platform or the space For others to contribute, and it's just amazing what shines, right. And it's the same thing with the dynamic for the group that I was in. We have a program leader who was helping us. But really, she's phenomenal. But a big part of it was her letting other people step in and realize that she doesn't have to do everything all the time that we're all creative and resourceful individuals. And a big part of that was nurturing the environment where we all want to step in and help each other. Justin Lam 5:33 Yeah, and that's, that's really important, like here at the studio. That's something that we really do believe in is it's not really trial by fire, but it's giving the people the ability to think and to critically think for us. I think one of the things that I believe in is when you're micromanaging and you're delegating everything, people turn off the critical thinking tasks. And they just become robots and they just do what you want. And then all of a sudden when you need them to critically think they don't they just they don't exercise the muscle. Do you find that that's a thing in your, you know, training in, in your belief system that, you know, it's about empowerment? Tiffany Elsner 6:18 Absolutely. I love that metaphor, Justin is it's a muscle that needs to be exercised. Right. So, you know, it really is interesting, because I've seen it with businesses that don't develop their leaders. And so they micromanage to the point where you have like you said, robots, and then when the time comes for everybody to need to be creative and step in and find their own leadership, that muscle hasn't been exercised. On the flip side, constant empowerment and whatever form that looks like, is really important. creatively, and I'll give you an example even from my own business is that We do things like creative weekly, and we actually allocate time for each of us to do creative pursuits that have nothing to do with the business. And quite a number of tech companies do something similar, more so with their, with their trying to find more development opportunities, but for this is I allocate time on the payroll for us to just be creative. And so that way, they're not always thinking about task check, task check, task check. But now that mindset is when I have the opportunity to create what other things are coming out of the woodwork and then we talk about that. Right. So whether it's, I decided to do a painting class or he decided to do like a cooking, you know, fun exercise. What did we learn from it, and how can that be applied to the business as always the cool bridge? Justin Lam 7:54 That's interesting. I think that's a really, really interesting way to integrate creativity. And I mean, would you say that in the real in the real world that's sort of like team building exercises? Or, you know, are you would you would you liken it to like, people doing their own thing outside of, of the team environment? You know, and then coming back with with that experience and in that refreshed brain, or do you feel like it's, you can foster the same in person when you're when you're having a group and like, you go out to do some sort of team building exercise where, you know, it's not necessarily mindless, like you're not bowling or something, but something that that constructively requires them to, to critically think and work cohesively as a team. Is that similar? Tiffany Elsner 8:45 I would say it's more of the latter. So it is more of an individual exercise. I have nothing against team building exercises, but I do think somehow, sometimes when they're executed, it actually serves against the purpose. When people feel like they're forced to do something, especially with the people that they are working with all the time, the reason that I chose this particular exercise of allowing time on the payroll to go and do something creative, whatever they choose, is that idea is everybody has that creativity inside of them, you know, there's tons of people who'll be like, Oh, I'm not creative. give them space and time. And you'd be astounded by what happens. And really, it's it's fascinating what they choose and how much you learn about them. That actually strengthens the relationship in the business. For example, I have a teammate who's learning another language and so every, you know, they do it more than just the time that I allocate. But that was that kind of lead in to start learning a language because, okay, we'll have time to do something interesting. And then we talk about what did you learn like what are we learning as you Learn that language. What does that have to do with business? What does it have to do with marketing? What does that have to do with growth? And there's a lot of lessons that, that bridge over. The key for me and as I do my Master's in transformational learning, is, quite often learning happens when we're not focused strictly on the learning. That's why we do this exercise of creativity. Quite often, when it's too forced, like I'm sitting you down in a classroom, and you're gonna learn, the majority of the learning happens, actually, when it's applied and experienced. And so without explicitly saying it, this exercise of creativity is their learning. They just don't realize that they're learning until we talk about it. Justin Lam 10:46 Yeah. And you know what, it's funny because children are the same. And, and I liken it to that everybody feels like especially now this is really relevant for anybody who has children at home, but when your children are at home Parents have this innate need that they feel like they have to keep the kids occupied at all times. And whether that means that they put them in front of the boob tube, like the television, or they're trying to do an activity or make them, you know, do do stimulating things. What they forget is that letting children be bored, prompts them to be creative, like so. So here's a case in point like we have Val here, because now the daycares are closed. And, of course, we didn't really want to put her out there. Now that it's getting really widespread, so, you know, she's there, and we structured a part of her day where, you know, we do have some exercises and stuff like that, that, you know, relate to learning, but then we give her time to be bored. And of course, the first five or six minutes of that boredom type is she's clinging on to us. She's wanting us to engage in her she wants us to play and, you know, we've now made it up. Where we tried to ignore it and force her to go on her own to do things. And it is really amazing because that creativity all of a sudden exists, she will tell you that she's bored. And I imagine that that's the same as a person saying, I'm not creative. But at the same token, you leave it for a little bit, and their mind goes, Well, they're not going to engage, I might as well do something and they go, and, you know, she'll go draw, or she'll make an arts and crafts or should go play and use toys or whatever it might be. But I think that creativity sparks out of when your brain gets a moment to breathe and isn't constantly stimulated. Would you agree? Tiffany Elsner 12:40 Absolutely. Because think about it. And I even think about my own life, you know, as an entrepreneur and a traveler and a girlfriend and a daughter and like all of these roles that you're like, filling all the time. Wouldn't you actually sit like, even when we're in the grocery stores, we're on our phones. When we're in the doctor's office. We're on our phones and My phone died like a few weeks ago. You know, just because I didn't charge it. But just standing there looking up being like, Justin Lam 13:11 SKY! Tiffany Elsner 13:13 And it's amazing how much comes when your mind isn't occupied about a specific thing, right to let our minds wander and explore. And I mean, a lot of people do that with meditation or yoga practices. But the reality is that's not accessible at all levels right away. It takes a lot of work sometimes to access this. But there's simple ways, like I said, you know, tapping into something that somebody's like, Ooh, this is a creative, fun exercise that does the same thing without having to sit there trying to be like, I'm focusing and focusing and focusing. It's, you know, it's it's different ways to achieve a very similar result of tapping into you know, what, what's going on in your mind on a bigger level. Justin Lam 13:59 Hmm Okay that's really interesting, I think, I think people who are listening to this will find that quite a useful, useful piece. So why don't we turn our attention to working remotely. So this is an interesting thing. And this is something you've been been working on for quite some time to get your business to be able to, to weather, things like this, where you are not able to be in person. So, you know, what are the things that you put into place for your business in order for you to be able to do that and function and make sure that the clients that you serve are supported? Tiffany Elsner 14:33 Yeah, I mean, it was a very interesting road to actually transition. A big part of that was even while I was serving local clients was to start using all of the tools. So as you're familiar, zoom is a great one. slack is great, you know, some companies use things like Basecamp. But the important thing is even before your remote is to start using those tools. Already. You People who work in offices who already use these types of communication structures, because I've been experiencing it like as I see universities, all of a sudden flailing because they do not know how to teach online. I've been talking to, I met some university students who were studying abroad in Chile. And as that transition happened like this, they were appalled at how people, you know, their professors or the administration had no idea how to structure things virtually, which is kind of surprising, considering that this technology has been available and a lot of it free. So the fact that there hasn't been kind of that progression into at least learning about it, even if they're not teaching virtually. So this is been a very fascinating way to see which businesses have prepared for the fact that virtual work and virtual learning is becoming a thing versus those who perhaps were resistant to it have learned very quickly through, I guess trial and error, what it means to set that up. But Justin Lam 16:11 So just a quick thing, because I've got a thought in my head. But when I say a person from a university does maybe see this podcast, is Northwild Leadership geared to help a university trained and get their things online, like, are you able to help implement some structure and or infrastructure for them to then take their courses online? Or is that out of scope for you? Tiffany Elsner 16:39 Absolutely, um, this is an opportunity that we haven't seen before, right? There's a lot of online learning forums and platforms. I've even been the student of several online. And what I've learned from both aspects is what works and what doesn't, in terms of learning retention, and I'll circle back to what matters masters is, is my master's program is entirely virtual. And the beauty of that is really understanding how do we create experience when you're not together? And so we focus on both for businesses and educational institutes is how does that learning happen? Obviously, it's slightly different for the corporate world. But the more that I dive into the work with my professors, I'm able to use those same principles and apply them to, you know, education, that that rapidly needs it right now. Right. It's how do we create that infrastructure? And the funny thing is, it's it's not as difficult as it needs to be. And that's the that's the interesting thing is sometimes this just keep it simple. Right? Justin Lam 17:48 Yeah, I think a lot of people try to overcomplicate things. And even I think, as more and more business owners are starting to move to zoom, as a platform just to kind of engage in people. I I see that there's such a steep learning curve. And there's such a resistance like, because it's new, and you know, we all resist things that are new and unfamiliar. But but that resistance is there. And I think when you're uncomfortable and out of your element, it really does show but I think, you know, for me, now that we've done this podcast a few times, I'm getting more and more comfortable being in front of a camera, looking straight into the lens. I mean, usually I'm behind the camera, and it's a little bit different, but this time, you know, like, being in front of a person and asking more perfect questions. Things that are more relevant and having better dialogue is has really come a long way. And I think it's one of those things, it's like another muscle it's, we have to practice it. So I mean, hopefully that this helps a lot of people in being locked out and getting into this because I think as the world moves into video, and more of a digital environment like this is a really invaluable skill. To have? Tiffany Elsner 19:02 Absolutely. Justin Lam 19:03 So that for you, I know that you have a virtual assistant much like I do as well as like in house staff for me, but like you're because it's completely virtual and you're going to go abroad and we help you in the backend with marketing as well. Can you talk about how that structure works with you in a virtual assistant? Because I think people are often curious about what virtual assistants do and how you can transition that information and you know, get them on board, because I think that's the hardest part of this entire journey, right? Mm hmm. Tiffany Elsner 19:42 I would say that the onboarding process for us was probably simpler than many because I went for a company belay that actually provides VA is all over and so they actually have a system already, where I could come in As their client, and I was walked through it, so there was, first of all was really great was once I was matched is a an interview between me my VA and I would call him like the Engagement Manager. So to basically facilitate that, because that's so important was the fit, right? So it wasn't they just chose a VA for me. I was part of that process. Another big part of the onboarding process was making sure that the skills match. So somebody can be phenomenal as a person, but if their skills don't match what you're looking for, and so there were some resumes that were outstanding, but didn't include what I needed, right. And so like, for example, I have a bookkeeper and accountant. I don't need somebody who's going to excel at that because that's not something I want the VA for. Another one was, this is a big one. For me, it's personality fit, because I don't want somebody who's just attached rabbitt although my VA I, we call him the task Ninja, I was looking for somebody that we can send random gifts towards each other that I care about their life, they care about mine. Because we've been through a lot of ups and downs as individuals and to understand that was also really important that we don't work in a silo because that's not how I want this relationship to be. And as I grow my team, that's not how I want to be structured either. One of the really important things is weekly contact. life gets crazy. And sometimes both one or both of us are like, Oh, I kind of want to cancel our check ins. But our check ins are so important. This allows us to keep grounded as well as to say things that might not necessarily be on our project management system, because there's a lot that happens in between the tasks and going back to the creative realm. That's when we bounce ideas off each other and really grow into what some of these things are. A really big thing is as important as it is to map out the project, we take it step by step, because quite often you'll take a couple steps and stumble and be like, oh, that wasn't quite the right fit. So you pivot. And so it's good to have that overarching but those weekly calls allow us to troubleshoot and become, you know, be more agile to to what we're doing, because as we are helping our clients, we are also growing as a business. Justin Lam 22:30 Yeah, absolutely. And I think, you know, just to recap that for for people, it's really about not only getting a person who is a virtual assistant, but it is about fit, it's, at the end of the day, you're still building a team, you know, it might not be in house or in your office, but you know, they're an extension of you. And if they're not thinking of it on the same page, they have different core values, different belief systems, they conduct their work as such, and I think That's a big part of company culture. And I think that's where a lot of people fail with virtual assistants because they try to look for the cheapest dollar value. And that might not necessarily be the best bang for your buck. I mean, people are going to Fiverr or they're going to Upwork and they're trying to find these people who don't necessarily have that same mindset. They're just scrambling or they're just trying to feed, pay the bills, and they don't really care. And when you're hiring somebody like that, the frustration comes because you want them to perform at this level, but their capacity is only at this level, because you know, they they charging a lower amount for sometimes for an obvious reason. But that skill set differences is really can be really huge. And so in the interview process when you when you went through with your virtual assistant, like how much in depth video did you have to go through Like, what did you prepare for that person to understand or to know that that was going to be the right fit for you? And did you have to go through one or two of them to find the right one for you? Tiffany Elsner 24:12 for this specific placement, because I had somebody else looking at my qualifications, they were already weeding out quite a few of them. But as we met on the interview, he was the first one I interviewed, but it was it was a really good fit right away, but was really nice was that option of like, even he said, and even, you know, the, the engagement manager said, if it's not the right fit, we will find it and there's no hard feelings here. And that's what's really important to know, is like, you know, as humans, we're like, I don't want to offend them, but it's okay if it's not a right fit. And the other part is, is that continued continued communication forever. I look at it as I'm not a boss, and you know, VA, but rather we're working together and our calls and with what would you like to see more of? Or what could I do differently from both of us? Because just because I'm the one paying the VA doesn't mean that I like you know, you know, and it's creating that relationship where communication is open, because, and we laugh about it, but he can, he can provide me honest feedback being like, I need, you know, you to post this more frequently, or I need this. And vice versa. You know, I'm like, I'll need I need this from you. And there's no hard feelings because we know we're coming from a place of growing together. And that's what I think is so important. But if that's not established right off the bat, and that was something that was very clear in the interview process to me, if somebody wasn't willing to say no, or to speak up, that wasn't somebody I wanted to work with. Justin Lam 26:00 That's really good. We had similar, you know, the onboarding process, because our current VA is not the first one, I think she's number three or four over the course of the last few years. But I think one thing that people need to do, especially as you're developing your relationship, is to create a standard operating procedure and keep updating it as, as you evolve, as you find like, ways to be more efficient with your VA. I think a lot of people forget, and then they just leave it up here. And that's not a really good place to be. Because we assume that, you know, in our hearts, we hope that that VA is forever, especially if you find the right one. But the reality is, is people's lives change. And so the the circumstances of which you know, you have to work and so sometimes the VA will have to disappear or be off your radar and then you feel like you have to start all over again. And if you have the proper onboarding process, and you've documented that stuff and you're updating it constantly as you evolve, that makes the transition easier for if you're going to find another person. So, you know, that's something for people to take away. Tiffany Elsner 27:11 That is a great point, Justin. And I would say that that's word of advice for companies period, right? Whether it's a VA or not. And this is actually a lead into what I do as a business. because quite often, when you're a small business, when you onboard, somebody, you're just going by this, you're flying by the seat of your pants, right? It's okay, I'm gonna onboard them. And then the next one joins, and then we're a team of seven and the mate. And you're just kind of doing it as you go along. And maybe you're learning some things. But how are you actually creating a standard operating procedure? Right? Are there things that everybody needs to go through? Because when you get to employee number 10 Oh, I forgot to get them their login credentials. Oh, I didn't order them a uniform or whatever may happen. You and things start to get lost in the shuffle. And when you've spent so long looking for great people who are culture fit talent and you know, have that growth capacity. And then they're like, oh, clearly this business doesn't care about me enough to actually have a nice smooth onboarding process. It's starting the relationship off on the wrong foot. And you as a business owner are sacrificing so much of your investment by not having a really smooth orientation and onboarding to the company. Justin Lam 28:35 Yeah, it's not only the investments, the financial outlay that comes with it, because your onboarding process now longer. And the lead time for that person to get up to speed is, is is way, way more convoluted than it needs to be. And so one of the things that I wanted to see what your opinion was, I personally feel like people should put their onboarding documents into something like Google Documents where it can be changed. It can be indexed and searched quite easily in a shared so people can can search it. I know some people are really big fans of printed documents. But I'm a fan of the virtual one because it's easier to find an index and change and be nimble. Whereas thumbing through stuff means that you have to print it every time that you make a change with it. What are your thoughts on that? Tiffany Elsner 29:29 I would lean towards virtual obviously, because I work with remote and virtual companies. And yeah, something like a simple and free like Google sheets or Google Docs, works wonders. It's amazing how much And again, if you're, if you're a small business, and you're trying to stay low overhead and agile, Google, Google has so many things available. And I would say keep it simple, right, like as you said, a simple word doc takes one second to open up and just start Clicking the other part that depending on what your business structure is, the other part that's beautiful about it is that constant editing, availability from from many different sources and then also to be able to track who's done what in case, you need to go back to back a little bit. Tiffany Elsner 30:19 Yes. My one thing would be is, yes, you can edit the Google Docs, but make sure you save different versions of them as you go along in case you make lots of changes. It is kind of nice to say, oh, what was what did we do five months ago versus what are we doing now in case you want to actually pull some of that information back? But again, very easy to duplicate and archive? Justin Lam 30:43 No, that's a very interesting tip. I think that's a that's something that I can I can learn from. I think that's something that we don't necessarily implemented when we have the Google Docs of onboarding, but it is just ever evolving. And remember, she thought about snapshotting it and As a v1, maybe something to do every quarter or every year to get a different snapshot, but that's a that's an interesting take on it. Cool. And so what what now like in this environment where everything is, is virtual? What What is the outlook for your particular business at this point? Tiffany Elsner 31:26 That's a hard question. Um, I am just as uncertain as many other businesses is, you're familiar. Although I am virtual, a number of my businesses are not entirely virtual. And so they've been cutting staff, a lot of people losing work right now. And so of course, this may seem like a luxury for some. And at the same time, my business because it's virtual and small team is able to pivot and one of the things that we've pivoted to is to help existing businesses who are not necessarily growing but who are moving to remote work. And so, initially, you know, in the last few months, it was really focusing on how do we grow teams that are going virtual bigger. Now it's, well, clearly there's a market need for all of these businesses who were meeting in offices, even small like nonprofits, corporations, or even the ones that work in CO working spaces, just offices have four or five people. How do we move that entirely remote? And for some, it's a massive transition. And for some, it's, you know, especially if they had flex work policies or are smaller, but now it's creating and the structures for these businesses, how do they continue learning and how do we continue developing their cultures that are strong, regardless, and so it's a lesson for general business as well as for my company. It's how do we look at the market and see how best can we serve with our Existing talents and ours, our existing structures. Justin Lam 33:03 Amazing. And for a person who wants to find out more information they can find you at Northwild Leadership.com amazing. So thank you so much. I think this is really amazing. And really excited to share this podcast with people. I think it's really relevant. I think a lot of people are gonna find tremendous value and if they're looking for people to work remotely and or onboard virtual assistants, or to find ways to transition, you know, their existing business into a more virtual space and be able to still onboard a team. I think that that's a lot of the things that people are keeping in their mind right now. So it's bright future ahead and right now laying out that groundwork is going to be tremendous for you. And Tiffany Elsner 33:57 I was going to say that, just keep coming. supporting each other community compassion. That's what we need, not only as businesses but as individuals. So thank you for the opportunity to to share and connect further. Justin Lam 34:09 Yeah, appreciate it. Thank you for your time. All right, everybody, thank you so much. If you guys found value in this, please feel free to like hit that subscribe button because everybody who subscribes really justice just helps the algorithm. My goal is to help 1000 business owners move the needle in any way shape or possible and help you impact the communities that you serve. So I hope you guys found value in this. You can find this on Spotify, if you're watching it on YouTube. And if you're on Spotify, you can go to our YouTube channel And be able to find these videos. Thank you very much, and Tiffany. I look forward to doing another podcast with you in the future. Thanks