One of my favorite things about hosting a podcast is speaking with people all over the world. My guest in Episode 48, Sandra Lewis, was in France while we were chatting. Gotta love technology!

Episode 48 Sandra Lewis Leader Assistant Podcast

Sandra is Founder and CEO of Boldly, a subscription based remote executive assistant company. We talk about interview questions for assistants, company culture, thoughts on making the transition from in-office assistant to virtual or remote assistant roles, and more.

Remember: If you leave a review and rating on Apple Podcasts, then send me a screenshot of your review to – I’ll send you a sneak peak, digital PDF copy of the first three chapters of my upcoming book for assistants.


And those who urge people to never give up? Charlatans. Sometimes you have to give up. Sometimes knowing when to give up, when to try something else is genius. Giving up doesn’t mean stopping. Don’t ever stop.

– Phil Knight, Founder of Nike

Leader Assistant Sandra Lewis Podcast

Sandra is the founder and CEO of Boldly – a subscription staffing company and hiring model that allows businesses to get Fortune 500 trained, highly qualified, and hand selected remote talent for just the hours they need each month.

Boldly is a remote first, employee focused company allowing its talented team the freedom to build their own schedules, work remotely, and contribute to amazing businesses while developing their own fulfilling careers.

Winners of the Great Place to Work certification and the prestigious When Work Works award, and featured on Entrepreneurs’ 360 list for innovation, Boldly is changing the way talented people and businesses work together for the better.


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Sandra Lewis 0:00
I’m Sandra Lewis. And today’s leadership quote comes from Phil Knight, the founder of Nike. And those who urge people to never give up charlatans. Sometimes you have to give up sometimes knowing when to give up, when to try something else is genius. Giving up doesn’t mean stopping. Don’t ever stop.

Podcast Intro 0:24
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Unknown Speaker 0:36
Hi, it’s episode 48.

Jeremy Burrows 0:39
Hey, friends, thanks for tuning in. I’m excited to share today’s conversation with Sandra Lewis. But before we jump into the interview, I am wrapping up the copy editing with my copy editor for my first book called The leader assistant, four pillars of a confident game changing assistant should come out in July or August of this year 2020. So be on the lookout for that. I’m very excited. It’s been a lot of work. But I am I think about at the 15 yard line, I was going to use a football analogy. So what I wanted to do is I want to share a quick opportunity for you my listeners who have been supporting the show and been with me for now 48 episodes. So I’m going to give away a few chapters of my book, a PDF copy digital PDF version of the first few chapters of my book. So if you would like to read and get a sneak peek at the first few chapters of my book, email me screenshot of your podcast review on Apple podcasts. So I know you hear me talk about this a lot. But it really helps to get reviews and ratings on Apple podcasts for the podcast to get more listens and more exposure to more assistants to help more assistants, which is my ultimate goal is to help more assistants become confident game changing leaders. So if you’d like an advanced digital PDF copy of the first few chapters of my upcoming book, again, before it’s released, then leave me a review and a rating on Apple podcasts for The Leader Assistant Podcast and an email me a screenshot of your review. You can email that to And yeah, I’ll send you three chapters of my upcoming book in digital PDF format. So again, email me your apple podcast review, screenshot to And I’ll share the book. Thanks so much for your support. And let’s get to the interview. Hey, everyone, thanks for tuning in to The Leader Assistant Podcast. Today I’m happy to speak with Sandra Lewis. She’s the founder and CEO of Boldly which is a subscription staffing company that hires virtual assistants to provide top level highly qualified services to business owners and entrepreneurs. So Sandra, thanks for joining me.

Sandra Lewis 3:30
Yeah, thanks so much for having me really happy to be here.

Jeremy Burrows 3:33
So let’s, before we jump into the meat of the interview, let’s talk about your very first job. And maybe what you learned from that job that you still use today.

Sandra Lewis 3:46
Okay, so this was back when I was 18. This was a summer job. And I was a receptionist, in in a hotel in the manager’s office of the hotel. So basically, I was answering calls for the manager and for the assistant manager, taking messages, transferring calls when appropriate. You know, making sure that whoever got to the manager was supposed to get to the manager, basically being kind of that in between. It was it was a fun time, it was actually quite stressful for me because it was to me a big responsibility. It was my first job. I wanted to get the names of the people, right. I wanted to make sure that whoever you know, was calling I was representing the manager properly. One of the things that I learned was how important details are and I’ve carried that forward through my whole professional career. Obviously when you are taking messages, spelling of names, understanding the message being really diligent about who is important sense to make sure you transfer that call and who you shouldn’t transfer the calls to some pay attention to all those details, taking those and being really diligent is something that I, that I learned very early on that really paid off throughout my career.

Jeremy Burrows 5:15
Wow. So you essentially sounds like you essentially, were an assistant

as your very first job.

Sandra Lewis 5:22
I guess so I guess so I mean, receptionist slash assistant, it was really mainly taking calls and taking messages. But, you know, every job, I guess, can be made into more than it is. But yes, I can totally relate to that. To that supportive person that’s there, you know, for you, because I’ve been there. I’ve been there. I’ve been that person.

Jeremy Burrows 5:46
So when you were doing that job? Did you ever dream of running your own company? And having a bunch of assistants? And magic matching assistance with clients?

Sandra Lewis 5:59
It’s a good question. I’ve always been very ambitious, perhaps, is the word, I’ve always wanted to do more. And it’s interesting. So you’re talking about, you know, I was a receptionist, and well is wasn’t that like an assistant. So I kind of, you know, always wanted to do more than than just, I guess having, you know, a basic job where I was kind of given direction and followed kind of certain certain paths. So I didn’t dream to do what I’m doing, currently. But I definitely aspire to do more.

Jeremy Burrows 6:38
So tell us a little bit about kind of your career progression and what, when and why you started boldly.

Sandra Lewis 6:48
Yeah, so I mean, after being receptionist, I ventured into the event management in convention centers, and grew into an operations manager for large convention centers. And worked in that field for about 20 years. In New York, and also in the UK. So very busy environment, very stressful environment, working 16 hour, 60 hour, weeks, sometimes 80 hour weeks, on my feet, or they came to a point, about eight, nine years ago, when I realized I needed a break, I really wanted to get away from the rat race, find myself find something that was more flexible, not live in a big city, you know, be in the countryside, be able to walk my dogs do what I wanted. So this was back in 2011. In 2012, I decided to basically venture out into using my skills in a remote way. So being being a consultant online, supporting business owners in different ways, ways that I had learned operationally over over all these years. And it really grew from there, it was very, very organically, you know, you start kind of working with people. I mean, at the time, back in 2012, was the beginning of those online platforms, where you can bid on jobs, and there was a lot of virtual assistants and remote work that was just getting started. And I started finding clients, and then it kind of grew from there where clients started referring other clients, and I realized, my goodness, you know, there, there could be an opportunity here from other for other professionals that are similar to me in a situation where they’ve had a career, they have got a lot of skills, but they don’t want to be tied to that they don’t want the nine to five, they want the flexibility and the freedom to you know, perhaps live in remote locations when there’s where there’s no jobs that are easily accessible. So I started assembling a team and it really grew from there organically.

Jeremy Burrows 9:22
That’s awesome. So what was the what was the hardest part? Or what is the has been the hardest part about running boldly?

Sandra Lewis 9:33
I think one of the hardest part has really been to be very intent on trading very strong company culture. You know, at the beginning, as I said, because we grew organically, I was looking for people who had great skills and who had a lot of professional experience. As the years went by, and actually pretty quickly as a first year went by, I realized that you know, two to three To accompany and the company culture and to, to have values that I could be proud of, I needed to obviously assemble a team that shared those values for us. You know, those values are being kind being service oriented, you know, working with people that are really, really nice that want to go above and beyond. So it was It looks easy, you kind of, you know, you look at companies and say, Oh, my gosh, such a great company culture, well, it’s working on growing a team that that shares your values takes, you know, takes a lot of, of effort. So I think that that was my my biggest challenge. And obviously, we’ve, you know, we’ve grown so much that we have 110 employees, and it’s paid off to, in the early days, really kind of be clear on our values, and then grow from there. So that, you know, we’re a company that has shared values, and it takes a lot of effort, obviously, you know, we have an internal, we have a vault and internal newsletters, and we get to know each other, we do things like, you know, we have because we were 100%, private company, we have a stuffed dog that travels to different location, his name is Pugsy, whoever, whoever is hosting Pugsy talks about themselves in their lives. And there’s a lot of camaraderie that gets established, we’ve got super drills for for, for teams, so people can, you know, win prizes. So worked really, really hard to kind of, you know, have a company that people want to be part of, and whether they want to stay for the long term,

Jeremy Burrows 11:39
what are a couple of the values that you’ll have, you’ve had from the beginning,

Sandra Lewis 11:45
our values are really, to be kind, to be positive service oriented, to work with people who’ve got each other’s back, to be nice and friendly, and to respect to respect one another. So I guess their basic values, but you know, the sometimes I think they’re taken for granted, you see a lot of people who have really, really great skills, but who might not necessarily, you know, have the nice city, nice, nice, nice ways about them, that makes them go above and beyond and say thank you and, and be grateful for for the little things and stay positive in the face of adversity. So those are really important to us. That’s great.

Jeremy Burrows 12:34
So let’s kind of talk a little bit about the virtual assistant world in the role of a virtual assistant, what would you tell someone listening, who maybe is an in office assistant that has dreamed about or thought about working from the beach and becoming a remote virtual assistant,

Sandra Lewis 12:58
I would say just do it. Obviously, if you have amazing skills as an executive assistant, those skills are going to translate into the remote world. I mean, you know, we are particularly, you know, boldly, we are a premium subscription staffing company. So we look for executive assistants, remote assistants, who have at least seven or 10, or 15 years of experience in their field of specialty. So, if you’ve got those skills, they can totally be transferable. In a remote environment, I would say that there’s two main differences to be aware of, you know, you will need to learn how to be indispensable at a distance. That’s very daunting, it’s very difficult, it’s a bit more difficult than when you’re in office, you know, it’s the out of sight, out of mind, kind of saying where you have to really learn to over communicate and to be in someone’s face by you know, asking them, what else can I do for you, what else can I do for you, so, you know, the person will not see you and you have to really be a great communicator. And the second thing I would say is you have to really be good and I think most executive assistant are at at structuring your day. Because again, when you’re not at the office, from nine to five, you have to still have the ability to to organize your day in such a way that you’re productive. So yeah, if you’ve got the skills and if you’re a great communicator, and if you’re a great organizer, I think you can totally be very, very successful in a remote environment.

Jeremy Burrows 14:40
So what would you say to the assistants listening thinking? Yeah, that all sounds great. I think I can make the transition no problem. But how am I gonna get clients? Where do I find clients?

Sandra Lewis 14:54
That’s why you join us.

Jeremy Burrows 14:58
You do the hard work.

Sandra Lewis 14:59
Yeah. Well, exactly, no, I mean, I’m serious. In fact, we have a lot of executive assistants, or, as we say, people who are aspiring to become virtual assistants who have tried, and who find it really difficult. And so, you know, they join our team. And, you know, we, in fact, we have a very, very big problem right now, which is we have more clients, and we have assistants on our team. And that’s because we have very, we’re very stringent in our interview process and 90 applications process. And, you know, we’re not quite able to tap into talent as we wish we could. So there’s many, many opportunities. And obviously, we’ve done the hard work of building a company with a great reputation. And, you know, if virtual assistants and if you’re not able to find clients, consider joining, joining a company like ours, obviously, you know, boldly, we hire our team. So, you know, our team are not freelancers, our team are not contractors, we are, you know, everyone is a W two employee with benefits. And that’s the beauty of vet now, you know, like the Oh, in the old world, or perhaps in, you know, still the current world. But what I what I consider, you know, perhaps the old world in in a while, the only way to kind of advance your career, to have an amazing career and with clients has been to be in an office with, you know, more of a rigid schedule. Or the other alternative is to be a freelancer, or part of the gig economy and what we do at boldly as a subscription staffing companies, we hire people to be part of our team, they get to choose the clients that they want to work with, they have a flexible schedule, they can be remote, and it’s a win win. Right? I think it is.

Jeremy Burrows 16:54
Yeah, you know, it’s interesting,

that you mentioned that your team is full time with benefits, because a lot of the virtual staffing companies have contracted, right, since you were nine, not, you know, full time benefits. So what was the kind of just kind of tell us a little bit about that decision? And why you decided to do it that way? And I’m assuming that, you know, just from first hear of this, I would assume that it kind of helps you find higher caliber assistants, because they are they want they liked the full time they like the high level, EA, you know, tasks, but and they can’t afford to lose their benefits or whatever. But yeah, what’s the what’s was kind of the decision point behind that. Yeah,

Sandra Lewis 17:45
I mean, when we very first started back in 2012, we were a virtual assistant company, and we were a virtual assistant company for the first two to three years. And then we shifted, we evolved to being a subscription staffing company. And our team, we don’t actually call our team virtual assistants, because there’s this, as you say, this connotation of, you know, your virtual assistant, it’s kind of that one mode of uncontracted. And a lot of virtual assistant companies, you know, it’s task based, you don’t get to choose your clients. It’s not, sometimes it’s temporary, you know, you, you get different gigs at different times, we decided that we wanted to be just like any other company, except remote. So, you know, it’s again, in the old model, business owners have to go through a lot of hassle to recruit people, and to hire people to register in a state to pay taxes, I mean, no need to manage a team, etc. So in the new world, you know, businesses subscribe to everything. This is quite to software, you subscribe to cars. But we thought, Well, why can’t you subscribe to stuff, which is where we then pivoted from being a virtual assistant company to being a subscription staffing company where you subscribe to staff, we’re an established company, we hire both the hires the staff, it’s a win win. We, as you said, we get great people that you know, want to continue in their career, but perhaps don’t want the rigidity of the nine to five, perhaps they want to be remote. They want to pick up kids from school 25% of our team, our military spouses, so obviously, they have to move. And it’s a real challenge for them, because every time they move, they have to find a new job. So now they can take their job with them. And it’s been super, super successful, and we’re so happy to be part of part of that movement. So businesses can now you know, tap into that talent and yet the talent is still taken care of which which is how it should be right. We all should be able to work earn a living. And it’s just somewhat, you know, do it on our own terms and do it in a way that, you know, life doesn’t go by and you can still have have a life and have a career and have a life at the same time. So this is this is our concept and we think it’s beneficial to everyone.

Jeremy Burrows 20:20
That’s awesome. So how do you find these high quality assistants? And then kind of walk us through your interview process? Maybe some questions you ask maybe some tests that you have them take, what do you look for on resumes, all that kind of fun stuff.

Sandra Lewis 20:38
Okay. So the first question how we find people it’s really, really hard. I think I talked earlier about how difficult it is to find really great, great people. Obviously, we, we are on major job boards that that are specifically for remote. So you know, flex jobs and remote Dotco and virtual vocations are three, were on Glassdoor. And we use Glassdoor quite a bit to talk about description, staffing and what we do. It’s hard also, because we were different. And to what I said earlier, people are in you know, it’s a new concept. A lot of people don’t want to be freelancers. But you know, that’s not what we’re about. And yet we remote. We, you know, we do a lot of education around what subscription staffing is, and why why would be amazing to, to join to join our company.

Jeremy Burrows 21:29
So tell us about the interview questions and the process that you all use to weed through these 1000s of applicants.

Sandra Lewis 21:41
Right, so we have a three, a three interview process. So there is one interview, which is pre recorded, it’s six questions that you can do in your own time. And then there’s two, in person, I want to say in person remote video interviews with real people. And, you know, as I was saying earlier, we were very big on, on values, and on people, you know, really sharing your values of kindness of service oriented. So we ask questions, such as, if you’re faced with a difficult situation, you know, what would you do? And we look for people who see the positive and see the learnings in those difficult situations, who have the glass half full. We also ask questions, like, tell us about something that you did that was successful, and we look for candidates who are not just speaking about themselves. I was so successful, because I did this, and I did that, and I’m so amazing. But also we attribute the success to to others and to a team that’s really important to us that people you know, able to work as part of a team are able to give each other credit. We work obviously, with senior executives, founders, business owners, your fortune 500, fortune 100, companies, you know, we work with founders at Apple and Facebook and grammerly, we have some very big clients. And we want obviously, your team and, you know, we want executive assistants who will do everything they can to make these people succeed, and who will, you know, again, see, see opportunities when there is a challenge boosts people up uplift people, because we all want to work with someone who’s nice and who’s got your back. So that’s what that’s what we look for,

Jeremy Burrows 23:41
is there something on the resume, particularly that look for or maybe there’s some red flags, even on resumes.

Sandra Lewis 23:50
So it’s interesting with with resumes, one of our criteria to to, to qualify is, you know, to have at least seven years of, of professional experience in the new field and obviously, to work at a senior level, because again, our clients are at a senior level. So that’s kind of what we look for. We look for, for, you know, for the skills for the hard skills. That’s kind of it I mean, obviously, if somebody has made a spelling mistake, that’s a red flag, but the obvious you know, with resumes we just look for, for the hard skills and for somebody who we think has has the experience or an interesting factor, which I want to kind of mention here in case you know, people in the audience are wondering whether they would qualify if they’re in that situation. We don’t mind if you’ve had a gap in your professional career. 90% of our team are mothers, and many of them have had a career, you know, 710 or 15 years and then have stopped for few years to be you know, to Be with your children. And that’s completely fine. So we’re very, very happy for you to reenter the workforce. With us.

Jeremy Burrows 25:11
That’s great. So, what do you personally look for in an assistant?

Sandra Lewis 25:20
I think everything I’ve said will apply to me, somebody’s somebody who’s got my back, somebody who’s genuinely nice and kind, and somebody who is open hearted and who is positive, you know, all these attributes is really what I think makes for great partnership. And I think so much so much can be achieved when, you know, when, when people are kinda nice, and when somebody you know, I mean, you know, somebody makes a mistake and says, Oh, my gosh, I’m so sorry, I made that mistake, that’s fine. You know, we’re all human. So I look for people who are deeply human perhaps is the, is the is the way to kind of say it. And that’s, you know, even so, so much more important to us as we’re remote and we don’t see each other. And sometimes, you know, there’s so much impersonal in the remote in the remote world. And we want it to be that we’re a company that’s as if you were in the office, as I said earlier, you know, we have many, many different ways to connect and to work together and to collaborate. You know, as an assistant, I think the human is really important. We’re in a supportive role assistants are in a supportive role.

Jeremy Burrows 26:39
So what would you say to an executive who doesn’t have an assistant, but is considering hiring one?

Sandra Lewis 26:48
Oh, I would actually say don’t do it, unless you’re absolutely ready to put the work in the systems in place for it to be successful. And that’s what we say to many of the clients who knock on our door. You know, we our team has been with us for years, our clients have been with us for years, we really, really put a big emphasis on longevity, because it takes as everyone knows, it takes a really long time to get started to get to know someone to understand how they operate, how to best support them. So we always say, you know, if you want to hire an assistant, you’ve got to do some work. First, you have some processes in place that we can succeed, so that your system will be successful and supporting you. It’s not just you know, Can you can you boot this district? Can you schedule this go? Well, you know, what are you preferences? You know, who am I scheduling? It’s always important to you. Some people will think it’s, it’s easy, but it’s, as we all know, it’s our job. Yeah.

Jeremy Burrows 27:56
So what’s something that you maybe a tip for executives that currently have an assistant, but aren’t really empowering them or utilizing them in the way that they should? What’s something that you would share to those executives to help them get more out of their assistant?

Sandra Lewis 28:14
We, we tell our clients to, to over communicate, and to share more than is necessary, and to give their systems, the big picture? Because in that way, we’re able to say, Oh, well, I can do that for you. Oh, well, why don’t I step in and make that call. So, you know, not kind of putting your assistant in a box in terms of, you know, this is all that she or he can do, but sharing, sharing about, you know, your day and what’s happening in the company. So that, you know, slowly but surely, we can help you delegate more.

Jeremy Burrows 29:00
So what about from the assistant side? How, how can an assistant and particularly for for you all remote, full time as executive assistant? How can they become a better leader and kind of lead out in their role while not being in the office? What’s what’s maybe a way that they can step up and kind of pull draw that out of the executive, those extra that extra info so that they can jump in and say, hey, I can help with this. I can help with that. Even though they’re not in the office.

Sandra Lewis 29:37
Yeah, I mean, I’m gonna say over communicate again. To us communication is huge, because again, you know, because you can’t see the person being in their face kind of on Slack or on email, to say, Hey, I’m here. Just to reminder, you know, I’m here from two to four today, if you’ve got anything, you know, let me know One of the things that we we try to work in in terms of becoming better leaders and being more, being better at what we do, I think, whether you’re executive assistant or remote assistant, I think it really kind of starts with knowing yourself better and knowing kind of the patterns and perhaps what holds you back. And finding ways to kind of overcome overcome those. I mean, you know, if you have a tendency to be shy and to be timid, then it’s going to be really difficult to kind of get your boss to delegate more. So finding ways to, to maybe maybe overcoming that and taking an improv class. And I’m just talking out loud, but, you know, kind of knowing, knowing yourself, I think allows allows you to kind of grow and, and, you know, lead better.

Jeremy Burrows 30:59
Yeah. That’s great. Well, Sandra, thanks so much for taking time out of your day. All the way from the other side of the world. You’re in France right now, right?

Sandra Lewis 31:09
Yes, I’m in France, right. Yeah.

Jeremy Burrows 31:11
So thanks so much for joining us and sharing your wisdom and sharing your story. How can we support you? Where would you recommend we check you all out?

Speaker 1 31:24
Yeah, so we’re And anyone who’s interested, obviously, in applying with finding out more about who we are, there’s a careers button right there on the homepage. So feel free to take a look at our jobs page. Awesome.

Jeremy Burrows 31:43
Great. Well, I’ll share that link, and your LinkedIn link and all that fun stuff on the show notes so that people can find you. And check out what you’re up to. And yeah, thanks again for chatting and I hope you have a great one.

Sandra Lewis 31:56
Thank you so much, Jeremy. Thank you.

Jeremy Burrows 31:59
Thanks again, Sandra for a great talk. Hope you can check out her website And again, check out the show notes at Just a friendly reminder if you’d leave a rating and review on Apple podcasts, and then send me a screenshot of your review to I will send you the first three chapters of my upcoming book in digital PDF format so that you can get a sneak peek. All right. We’ll talk to you next week.

Unknown Speaker 32:45
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