Why Siimon Reynolds, one of the world’s leading high performance coaches for CEOs and entrepreneurs, is using virtual teams for many key functions within his highly successful business

Virtual Success Show

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Episode breakdown

In this episode, Siimon Reynolds, mentor to business owners worldwide, shares his own experiences with using virtual teams and how using virtual staff for many vital functions within his business allows him to keep his business running successfully, as a 24/7 operation. This episode is full of insights from Siimon into how to effectively use virtual teams to create business success.

Without systems, processes, and teams, you can’t create the entrepreneurial freedom you’re after or grow an epically large company.

In this episode

Matt and Barbara welcome Siimon Reynolds to the Virtual Success Show. Matt shares how he first met Siimon in 2008 when Siimon had just moved from Australia to Los Angeles. He highlights Siimon’s success in running his coaching business in the US while managing a virtual team in Australia. The episode focuses on exploring Siimon’s experiences with virtual teams, the roles they play, and how they support his business.

Siimon shares that he has worked with a support assistant in Australia for many years who manages scheduling, finances, research, travel planning, and both personal and business tasks. He also has a virtual salesperson in California who handles client calls through his coaching business, and a graphic designer in the Philippines who creates slides, logos, and brochures. Additionally, through another business with Matt, he works with multiple support assistants for design and CRM tasks.

Siimon explains that none of his team members are full-time. His assistant works about 4–5 hours daily on weekdays, his designer in the Philippines works anywhere from zero to around 15 hours per week depending on workload, and his salesperson averages about one day per week while also working for other clients.

Siimon chooses virtual teams mainly for cost savings, access to high-quality talent, and flexibility. He values being able to delegate tasks across time zones, which allows work to be done overnight and shortens turnaround times. Another advantage is not having to hire full-time staff—he can outsource as needed, making virtual teams both efficient and cost-effective.

Siimon notes that time zone differences with his assistant in Australia can be challenging, sometimes leaving gaps in availability. He suggests an ideal setup would be having trusted assistants in different countries ready to cover 24/7 needs without full retainers. All his assistants work from home, which he sees as a benefit since many talented people prefer remote work for lifestyle reasons. He cites IBM’s workforce model—about 60% outsourced—as proof of the growing appeal and success of virtual teams.

Barbara asks Siimon about a common hurdle faced by early-stage entrepreneurs and solopreneurs: the fear that support assistants or virtual teams won’t work for them. She highlights how many end up reverting to doing everything themselves, and seeks his advice on how they can overcome this barrier to grow their businesses.

Siimon explains that entrepreneurs can either hire support assistants directly or through agencies that pre-select and manage them. He recommends the agency route for beginners, as it ensures quality, efficiency, and easier onboarding. He also advises studying the support assistant industry—reading blogs, forums, and resources for a few hours—to build confidence and learn how to manage support assistants effectively.

Barbara highlights that once the HR side of hiring a support assistant is solved, success often depends on having clear processes and systems. Siimon agrees, stressing that support assistants aren’t “set and forget” solutions—like in-office staff, they perform best with defined processes, regular check-ins, and accountability systems. He adds that building such structures not only improves support assistant efficiency but also strengthens the overall business.

Barbara notes that clients succeed with support assistants when they focus on clear processes, build strong relationships, and connect the support assistant to their business vision. Siimon agrees, emphasizing that support assistants should be treated as valued team members and that effective leadership and engagement are just as important virtually as they are in person.

Barbara raises the issue of clients feeling support assistants aren’t proactive enough and asks where the line is between implementer and strategist. Siimon explains it depends on how they’re hired—ad hoc support assistants need clear direction, while those with set hours can show more initiative. He adds that even if business owners must provide extra leadership and planning, the benefits of support assistants far outweigh that effort.

Siimon shares that he meets his support assistant Tanya for lunch whenever he visits Australia, which strengthens their bond though it’s not essential. They email daily and aim for three short phone calls a week to stay connected, since relying only on email can feel isolating. He stresses the importance of scheduling regular calls to maintain smooth communication. Barbara then asks him if it’s possible to grow a company alone.

Barbara asks if it’s possible to grow a large company and achieve entrepreneurial freedom without systems, processes, and teams. Siimon replies it’s essentially impossible unless the business is fully automated. He stresses that growth requires people, strong processes, and fair compensation, noting that true success comes when a leader makes themselves redundant by building a self-sustaining organization.

Barbara and Matt thank Siimon for sharing valuable insights on support teams, noting how beneficial they’ll be for listeners. The episode wraps up with appreciation from all three and an invitation for the audience to keep listening, commenting, and engaging with future Virtual Success Show episodes.


Podcast Transcript:
Why Siimon Reynolds, one of the world’s leading high performance coaches for CEOs and entrepreneurs, is using virtual teams for many key functions within his highly successful business

Intro: Do you find yourself running out of time to accomplish your work? Are you spending time doing things that you’re not that good at? There are effective ways to outsource this task so you can focus on your business.

This is the Virtual Success Show. We bring the inside scoop on outsourcing success for entrepreneurs, by entrepreneurs, and now here are your hosts, Matt Malouf and Barbara Turley.

Matt: Welcome to this episode of the Virtual Success Show. I’m really excited to be sharing and talking with Siimon Reynolds today but before we introduce Siimon, hey Barb, how are you going?

Barbara: I’m great Matt, thank you very much. Delighted and excited about this show to hear Siimon’s great insights into virtual teams.

Matt: Fantastic, and so welcome, Siimon, to today’s show!

Siimon: It’s great to be here!

Matt: Fantastic! Siimon and I, we work closely together at The Fortune Institute and I met Siimon back in 2008 and I think at that time you just moved from Australia to United States, Siimon, is that correct?

Siimon: Yeah absolutely! I’m there now, here in almost always sunny, Los Angeles.

Matt: Fantastic! What amazed me at the time when we met – that time when we met you were coaching me – was that you were running your coaching business, you were living in the US and yet you had a team here in Australia doing a lot of the coordinating and the like for you. So, I guess what we want to share with everybody today was your experiences with virtual teams and using virtual staff for many functions within your businesses and your experiences with that. So if we could start with just sharing who you’ve got on your team, or your virtual team, and what sort of key roles that they play or task that they do for you.

Siimon: Yes sure! Well, look I have a virtual assistant and have had for many years in Australia and she’s responsible for doing a whole lot of stuff, she sets meetings for me, she actually handles a lot of my finances, you know so she pays bills that are needed, all that kind of stuff. I use her also for research, so that could be work research or ‘Can you search for a company that does XY and Z?’, or I even use her for things like holidays, so if I want to go to Italy, I don’t search through for the best hotels in Milan, I say I want a hotel like this within these parameters in Milan, can you present me three good examples of that.’ So that’s incredibly useful and an amazing way to slice off time and I’ll even use her to slice off a minute, numerous times a week, so for instance, if I have or someone wants an appointment with me, I’ll just send it through to her and even though that may only take her one or two or three minutes to actually get in to the diary that’s just one less task I have to do. I use her for super short tasks, I use her for personal and business tasks and I use her for some financial tasks, and in addition to that, I have a sales person in another part of California and through some of my work in America coaching, I have a closer.

So the clients would find about me on the internet and eventually they go through a webinar system and eventually they will get on a call with the sales person and so that’s entirely virtual. I have had one lunch with him at his request, he wanted to actually see if I existed or if I was you know an alien life force. And so we had a physical lunch and since then I haven’t seen him. And then thirdly I have someone in the Philippines who does all my graphic design and my slides for presentations, if I want some kind of brochure done, who would do that, if I need to go logo done, who would do that. So they’re the three people that I’m working with. Now, Matt you and I work together in a whole different company where we use a whole series of virtual assistants for design, for InfusionSoft, the back end CRM systems etc.

Matt: Yep! And with the 3 key people you mentioned there being your assistant, the sales person you’ve got and the designer, are they all full-time? Are they part-time? Or are they on project basis?

Siimon: Yeah, all project basis. None full-time! So my assistant works on average between 4 or 5 hours a day, 5 days a week. My art person in the Philippines could work as little as zero hours to, on the upside, might work on a big week, might work 15 hours for me and then the sales person probably does average of a day a week, so he’s very much doing sales for other people as well.

Matt: Fantastic! And why have you chosen to use virtual teams for these roles Siimon rather than say, having people locally that you can have access to within your office or the like.

Siimon: It’s definitely cheaper, there’s no doubt about it! And it’s really interesting to see the very high quality of people who are virtual assistants. Better and better some of the Asian countries are just improving in leaps and bounds as it becomes a more established career for some to be a virtual assistant. But even in America, you find that there are a number of States, Arizona being one of them, where you can find very inexpensive and good Americans doing virtual assistance, assistant work as well, so clearly price. But too, a huge advantage of virtual assistance is the time. So plenty of times, if I’m up against a deadline, if I was to rely on someone in my own time sphere then I’d probably be paying a fortune for someone to work overnight. But I can just switch to another country and get somebody to start working on something while I sleep and I do that frequently, particularly with the art guy, I’ll wake up in the morning and there will be 7 or 8 hours work done by him, or even with Tania my assistant for my day to day secretarial stuff, she’ll frequently do stuff while I’d be asleep.

So, the advantage is your 24/7 operation and the cycle of getting work done is much shorter. And then finally it’s the fact that they’re not on full time you know. I know that’s often the primary reason that someone chooses a virtual assistant that you can just outsource when you need them but it’s just one of many reasons for using them in my opinion.

Matt: Just on the time zone shift, particularly with Tania your assistant, are there ever any challenges when you’re across, you know, such a wide gap in the time difference?

Siimon: Yeah that’s a good question! Plenty of challenges, half the time I’m in the west coast of America, she’s in Sydney in Australia, so the time difference, in effect, even though its a different day, so it’s technically 17-hours difference, how it manifests is there’s either a 5- or 7-hour difference depending on what country has daylight savings at one point in time. And plenty of times it works, that I’ve stopped work and she’s still working but on the other hand in the mornings, she’s not there so she’s doesn’t come on until about my 2pm typically for most of the year and sometimes she doesn’t come on until 3 or 4 pm.

Once again depending on each country starts its daylight savings or stops daylight savings. When there is a 7-hour difference that’s tough. So for me, unless you just want them to work at night, if you want to liaise with them during the day, you want to keep, you have the difference somewhat relevant. Sometimes it works, sometimes it doesn’t.

If I was really going into virtual assistance in great depth, I’d probably have them, I’d have them standing by but not on retainer so it’s not costing me. I’d have one or two standing by in other countries so, including my own, America where I am now, so if I needed work done at any point in time, I have someone. Now I haven’t organized that yet but I think it’s a potential for me is to have someone that I trust in several different areas, secretarial or admin, in art, possibly in sales but probably not necessary and they’re sitting around the world and 24-hours a day if I need them, they’re ready. That’s the ultimate for me and not having that can be a disadvantage.

Matt: Fantastic! All your assistants work from home?

Siimon: Yeah! Yeah, they do and you know an interesting thing again here is, that you’re getting often a better person because they don’t want to work in an office. Here’s an interesting stat, around 60%, 60% of IBMs staff worldwide are now outsourced. So obviously it’s a giant complex organization doing complex activities and complex products.

So that’s absolutely extraordinary! Now, why are they doing that? Part of the reason is they can attract high caliber people with the promise of working at home and so this is another reason that the virtual workforce is going to grow and grow. A lot of people say, ‘You know what, I’d like to come in at lunch time and cuddle my child!’ I don’t just want to see them for a brief period in the beginning of the day and in the end or even only one of those. And so for the sheer calibre of people it’s a very attractive position as IBM have found out.

Matt: Certainly I think having had people work from home and from a workspace as well, I tend to find both work, like you said, it comes to the person. As long as the person is happy with wherever they’re working and their environment, it works! For some, I’ve had assistants were working from home just doesn’t work for them, they’re not set up properly, their environment doesn’t support it or it’s too noisy or whatever it might be but on the other hand, some of them wouldn’t have it any other way. So I think it’s an interesting point. Barbara, do you have any other questions for Siimon?

Barbara: I do! Actually yes, Siimon I’ve got a very interesting one for you. I would love to know your thoughts on this one. I’m sure you hear this a lot as well.

I mean, you deal with entrepreneurs all the time, coaching programs, you’ve privately coached lots of people. What about the hurdle? And I call it a hurdle because it is a big hurdle for people to get over. Early stage entrepreneurs or the solopreneur type person who is currently doing everything themselves, I hear a lot of people say, ‘It doesn’t work for me!’, ‘I can’t get virtual assistance, the whole virtual team thing to work.’ And they just to run back to doing everything themselves. What advice would you give to people who are at that sort of juncture where they can’t really grow unless they get a team but they just have this fear and this thing holding them back that it won’t work for them.

Siimon: Well, there’s 2 types of virtual assistants as far as I can see that you can get. The first is that you deal with them direct and then the second is you use a company that manages them and has pre-selected them. And I would definitely recommend that option for that style of person and in fact for most people who seek a virtual assistant. It may be, not always, but it may be slightly more expensive to have an in-between manager but what happens is you’re very sure of the quality of the person, you’re very sure of the management of the person and the efficiency of the person and it’s an easier process to first step into having a virtual assistant to work with an organization like that. So I’d ask them, I guess I suggest to them, to do a little bit of research, go and check out some of these people who manage and procure on your behalf, high-quality virtual assistants because that makes it easier, so a lot of the problems of ‘how am I going to run it?’ or ‘I don’t know how I can do this’, or ‘I’m not very digitally oriented’, etc. they are all very real problems, most of them are mitigated by using a kind of a middle man to help sort it out and be a lot easier. And then the second thing I’d say is this, like anything on the planet that’s of value, study it. Say, ‘Okay I’m going to spend two or three weeks, I’m going to spend an hour studying the world of virtual assistants and I’m going to look online, we’ll look at the pros and we’ll look at the cons and we’ll look on how to run them.’

All of these are free blogs around the place, free pieces of advice. You know you spend three hours studying the area, it really gives you a lot more confidence. You got to forums etc. online forums it gives you a lot more confidence because you’ll know a) its viable; b) it’s possible for someone who is unskilled in the virtual world to enter this field; and c) give people confidence that there’s a lot of people who are making this work and there’s a good chance it can work for them.

Barbara: And a follow on question from that then would be, because the other problem that I’ve been seeing with a lot of clients of ours would be that’s sort of the first problem and then once we solve for that problem around the management and giving comfort around how the person is manage etc. it comes down to now you have a VA, let’s say for example, and all the HR side of it is managed etc. but then a lot of it boils down to your ability to create your own processes and the systems and how your business operates and what this VA is actually going to be doing for you. So how much weight would you place on people getting very clear around their processes etc. so that they can get success with their VA?

Siimon: Well, I think you know, that’s a really valid point. It’s not just set and forget, it’s not that they’re magical and, you know, you just throw it all over to them. It’s no different from having a real life person in your office. They’re going to run a lot better when they’re given processes. When there’s a system of checking up on them. You know, I was only coaching someone yesterday and they just instituted a system on checking up on their stuff every couple of days as to whether they’ve actually done the stuff they said they were going to do and it’s made a massive difference to their quality. So if that’s the case in real life, it must be even more so in the virtual world when they’re not in front of you and you know it’s a great point because developing these processes is not just going to make them more effective virtual assistant, it’s going to make your business a much better business anyway, instead of you just winging it and being able to get away with it, because the person happens to sit across from you in the office. These kinds of disciplines should be done for real world offices and virtual offices but certainly doing it for virtual offices is a great way in improving the smoothness of operations.

Barbara: Yeah, we see that a lot. The people who do really well, in our experience anyway, are those who really focus on their processes and actually having good relationships, developing that rapport with the VA and actually discussing their business vision, the strategy and how those processes link in and how that VA actually, what part they play I guess in the whole thing.

Siimon: Yeah! You know, again a good point. A lot of people might say, you know, treat these people because they can’t see them as much, that they’re not holistic humans, of course, and that’s you know, ridiculous. Winning them over, winning their hearts over towards your company and towards you is fundamentally the issue and just because someone’s virtual doesn’t mean the fundamentals of leadership don’t apply.

Barbara: I’m sorry Matt, I have just one more question, another follow on point is that sometimes people, what I hear anyway and this is the frustration I guess from clients who are not getting success, sometimes the feedback I would get is, ‘Oh they’re not proactive enough!’ and I sort of feel well, you know, with a virtual assistant, for example, how proactive should we expect them to be or are we… where does the line go between an implementer and a strategist, I’m interested to know your thoughts there!

Siimon: Well it depends on the manner in which they’re employed. You know, if someone’s employed on an ad hoc basis versus you would have to of course be completely proactive in briefing them, whereas if someone’s booked for a certain number of hours a week then yes, the virtual person ideally would be a little proactive themselves. But, you know, what do people want for their money? You know, you’ve got someone really keen, you’ve got someone who understands the task, you’ve got them usually incredibly inexpensively versus many other alternatives. If the owner of the business has to do a little more pushing, has to do a little more leadership, has to do a little more planning, well that’s a small price to pay for all the other advantages.

Barbara: Great!

Matt: Siimon I’ve got these two quick questions! Just specifically with regards to Tanya your virtual assistant, like your secretary. How often do you meet face to face with Tanya?

Siimon: Well, each time I fly to Australia. We try, not always, we try to have lunch for an hour and a half and I think that’s good for the relationship. I don’t think by any means it’s necessary. I think it’s good but not necessary, so if we can’t then so be it. I don’t think you have to meet them but you know after you have lunch with someone, you always feel a little closer to them as long as you’ve enjoyed the lunch and I think it’s worth a lot, they feel more loyalty towards you, there’s a better bond, you feel more comfortable talking to them from a great distance, so definitely worth that.

Matt: And then just a follow on from that, how often do you, the both of you communicate week to week?

Siimon: Not enough, I’m pretty bad on that so we’re communicating by email every day and we’ve tried to initiate 10 minute phone calls 3 times a week and often you know we’ll extend to 20, 25 minutes but we started putting short phone calls in the diary to make sure we at least spoke to each other a few times during the week and most of the time I stick with that but it’s something that I’m not being as good as I should and the danger of that if you just constantly emailing people is you begin to be a little disconnected, I mean I’m fine with it but often people and she’s a case in point, she might feel you know a little like she’s sitting on a deserted island. So, yeah I think it’s important to have regular calls and I think it’s important to have them diarized. You can add them, add ad hoc ones to it but definitely have a series, a base series of foundation meetings locked in the diary and that helps, you know, keep the systems smooth.

Matt: Fantastic! Barbara are there any questions that you had for Siimon?

Barbara: I just have one sort of wrap up little question that I’d love to throw out at Siimon and I know what the answers going to be but I think for the listeners it will be good to have this one. Siimon in your view, you know you’ve grown many companies yourself massively, you’ve coached a lot of companies into massive success. Can you grow a company all by yourself?

Siimon: Well, it depends what size!

Barbara: Ok, let me ask the question in a different way. Without you know, once initially in a startup we we’re all after-sales, it’s all about sales and marketing but then when we start to grow you know without systems, processes and teams, can you create the sort of entrepreneurial freedom that everyone is after and grow an epically large company? How difficult is it to do it by yourself?

Siimon: Clearly its… impossible, you will need to have an incredibly automated digital business to be able to do it. Sure you need people and you know, the more you grow, the more you need people to the point where, you know, a guy I used to be in business with used to say to me, he said his main job is to make himself redundant and he was always looking to do that and sure enough you know when we had a company that was worth of over a half a billion dollars, he used to sit in his office and I don’t think he had that much to do. He had truly made himself redundant so that’s the aim but you’re only going to do that through good people, and as you say through good processes and finally through fair remuneration.

Barbara: Great! Thank you so much for the fantastic insights into how you do it. I know the listeners can benefit a lot from some of the insights today.

Matt: Fantastic!

Siimon: Well, thank you! I appreciate being here.

Matt: Fantastic! Thanks Siimon and that’s our show for today. Be sure to continue to listen, add any comments or questions underneath and we’re looking forward to continuing to bring you these amazing interviews and insights into the world of virtual success. Thanks Barb for your time and I look forward to our next episode.

Barbara: Yeah, thanks, Matt. Thanks guys!

Matt: Thanks, Siimon!

Siimon: Thanks!

Outro: Thank you for listening to the Virtual Success Show. If you found this show helpful, take a moment to share it with a friend so that we all grow together. Find out more about the inside scoop in outsourcing success by going to our website, virtualsuccessshow.com. Until next time! Thanks for listening!

 

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