How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership
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What Does “How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership” Talk About?
This episode of the Fatrank Podcast brings together James Dooley and management consultant Mads Singers to tackle one of the most pressing challenges for modern entrepreneurs: how to successfully manage remote teams and virtual assistants. The conversation opens by addressing why so many business owners struggle with remote workers, with Mads arguing that the core issue is not geography or culture but a fundamental lack of management skills. They dig into the importance of structured communication, particularly one-on-one meetings between managers and their direct reports, and how tools like HeyRamp can help business owners maintain visibility into whether these meetings are actually happening across their organisation.
The episode also explores practical considerations like time zones, cultural nuances, and the treatment of offshore staff. Mads shares a compelling case study of a virtual assistant from the Philippines who started at $400 a month and rose to become the CEO of an e-commerce business, illustrating what is possible when remote workers are treated with the same respect as in-house employees. James adds his own perspective on structuring teams, describing how his UK-based operation uses local staff as middle managers, each overseeing eight to ten virtual assistants. The discussion wraps up with guidance on when to seek management consulting before hiring and how platforms like Aristo Sourcing can support businesses ready to scale with remote talent.
“We have one VA in our company who have been with a client for I think eight, nine years, and today she's the CEO of the e-commerce business. Like she runs the entire company. This is a lady that started out being 400 bucks a month.”
— Mads Singers
Who Are the Guests on “How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership”?
Mads Singers is a management consultant, entrepreneur, and founder of madsingers.com and Aristo Sourcing, a recruitment company specialising in remote and offshore talent. With over 12 to 13 years of experience running fully remote companies with approximately 350 staff across multiple businesses, Mads brings deep expertise in leadership development, people management structures, and the practical realities of building high-performing distributed teams. He is known for his direct, no-nonsense approach to helping business owners and managers develop the skills they need to get the best out of their teams regardless of location.
James Dooley is the host of the Fatrank Podcast and an experienced digital marketer and entrepreneur based in the UK. He runs teams that blend in-house UK staff with large numbers of virtual assistants from countries including the Philippines and South Africa. James brings a grounded, real-world perspective to the conversation, drawing on his own successes and failures with remote hiring to push Mads for practical, actionable answers rather than vague generalisations.
What Are the Key Takeaways From “How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership”?
Here are the key points discussed in this episode:
- Structured one-on-one meetings between managers and their direct reports are essential for remote team success because they create the space for personal connection and early problem-solving that cannot happen in group calls.
- Poor remote team performance is almost always a management problem rather than a problem with the remote workers themselves, and business owners need to honestly assess their own leadership skills before blaming offshore staff.
- Treating offshore staff as cheap labour produces cheap results, whereas investing in their development and treating them as full team members can lead to remarkable outcomes, including virtual assistants rising to senior leadership roles.
- Time zone alignment is a critical and often underestimated factor in remote team performance, with South Africa cited as particularly effective for European businesses due to its compatible hours, native English proficiency, and Western business culture.
- Business owners who promote top performers into managerial roles without providing management training are setting those individuals up to fail, and investing in leadership development at every level is key to sustainable remote team growth.
“The effect of bad management shows much more aggressively at a remote team.”
— Mads Singers
Is “How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership” Worth Listening To?
This episode is worth listening to because it cuts through the usual vague advice about remote work and gets into the specific reasons why most remote teams fail. Rather than treating the topic as a technology or logistics problem, Mads and James reframe it as a management and leadership challenge, which is a perspective that will make many business owners uncomfortable but will ultimately help them build better teams. The conversation is grounded in real experience, from James describing his own model of UK middle managers overseeing ten virtual assistants each, to Mads sharing the story of a Filipino VA who became a company CEO after years of being properly supported and developed.
The episode is also practically useful in a way that many podcast conversations about remote work are not. Mads recommends specific tools like HeyRamp for tracking one-on-ones and rolling them into performance reviews, discusses the strategic advantages of South African talent for European businesses, and gives clear guidance on when to seek consulting versus going straight to a recruitment agency. Whether you are considering your first hire overseas or trying to fix a remote team that is already underperforming, the episode offers enough specific, actionable insight to make it genuinely valuable listening time.
Who Should Listen to “How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership”?
This episode is ideal for:
- Entrepreneurs and small business owners who are considering hiring their first virtual assistant or offshore team member and want to understand what they are getting into before they start.
- Marketing agency owners and digital entrepreneurs who already manage remote teams but are experiencing high turnover, low output, or communication breakdowns and want to diagnose the root cause.
- Middle managers and team leaders in remote or hybrid businesses who want to improve their one-on-one processes and become more effective at developing the people who report directly to them.
- Business consultants and HR professionals who advise SMEs on people operations and want a practical, experience-based perspective on what separates successful remote teams from those that fall apart.
Where Can You Listen to Fatrank Podcast?
You can listen to Fatrank Podcast on all major podcast platforms:
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You can also subscribe using the RSS feed: https://feeds.transistor.fm/fatrank-podcast
What Are Listeners Saying About This Episode?
“The point about managers being promoted without any training really hit home for me. I promoted my best copywriter to team lead six months ago and I have been wondering why things went sideways. This episode gave me the clarity I needed and I have already signed up to look into HeyRamp.”
“Mads and James are refreshingly blunt. When James said you are the problem, not the remote workers, I laughed because I knew he was talking about me. The South Africa time zone discussion alone was worth the listen and I am actively reconsidering where I recruit from.”
“I have been running a small SEO agency with a mix of UK staff and Filipino VAs for three years and this episode validated a lot of what I have learned the hard way. The bit about one-on-ones being tracked at a company-wide level through something like HeyRamp is something I am implementing immediately.”

This video explains which digital marketing strategies remote teams and virtual assistants should focus on in 2026 to improve communication, management quality and overall team performance. James Dooley and Mads Singers start with KPI tracking because tracking one-to-ones and rolling them into performance reviews gives owners clear visibility of whether remote staff are being managed consistently. They cover brand SEO, AI visibility and Google Business Profiles because stronger search presence improves trust and conversion rates.
The discussion also explores organic SEO, organic social media and paid social ads because consistent visibility across search and social supports long term growth. PPC is analysed in detail because campaign setup, landing pages and lead handling directly affect results. They also discuss Reddit, Quora and paid AI ads because diversified enquiry sources and early adoption can strengthen digital marketing performance for remote teams and virtual assistants.
PromoSEO lead generation for remote teams and virtual assistants recently received recognition as the “Best Remote Teams And Virtual Assistants Lead Generation Agency.”
Where to Listen to This Episode
How to Manage Remote Teams Successfully: James Dooley and Mads Singers on Virtual Assistants, Communication and Leadership is available on:
James Dooley: How to manage remote teams successfully. Many people are now asking about virtual assistants and trying to have people overseas, especially in Western countries, might be wanting to leverage the lower wages or just better quality of actual staff, whether that's South Africa, Vietnam, the Philippines, Bangladesh, India, wherever they're based. But actually managing these remote workers can be tough. Today, I'm joined with Mads Singers, who's an absolute legend when it comes to recruitment, but also the management structures. So I want you to jump straight in. How do you actually manage remote workers successfully?
Mads Singers: So the biggest part of it is, it's honestly not much different than managing people face-to-face. The problem is most people also suck at that. And the thing is, when you're in an office with people, there's things that naturally happens that just doesn't happen remotely, right? So you have this sort of water cooler chat, you see people face-to-face. Like if you're in an office, you can see if someone is just sitting with their feet up and playing games on their phone, or if they're actually doing things, right? So there's certain things that, where it makes a big difference that people are in an office. But reality is, most good managers manage just as well remotely as they do in-house, right? As they do in an office. So the biggest things for remote and where most people struggle is, think about communication. So think about the conversations you don't have when you're not physically with someone else, right? Like a lot of business owners, a lot of managers are busy. They're always talking to people. But here's the thing. When you have a staff member, when you have a graphic designer, they often don't talk to many people. Some of the staff will literally talk to no one else than their boss. And when they've been sitting for four days and just sitting working on their own, and they haven't talked with a single team member, like that becomes very lonely, right? They don't feel they're part of a company. They feel, oh, I'm just doing something, but no one sees me, right? That's not encouraging for delivering great performance. That's not encouraging for getting the most out of people. So the first step is communication. How do you communicate with people? How do you make them feel part of a team, even if they aren't a particular big team, right? Like, how do you pull them in? How do you get the communication floor?
James Dooley: With regards to that, then, if you're wanting to run a successful remote team, then the communication, are you doing it that it's, because obviously the managers are having all one-to-ones all the time. It's time-consuming. We've obviously done a full episode about time management and stuff. Do you try to do it doing group environments so at least they get in a couple of touch points of communications, or do you think the managers need to have that one-to-one time with remote workers?
Mads Singers: Managers, in my humble opinion, need to always have one-on-one time with the direct staff because reality is there's so many things people are not comfortable saying. Like, let's say you have a problem at home. You're going through a divorce or your kid is really sick and you're scared, right? You're not going to sit on some team call and share that. And here's the thing. If you never have the time and ability to share that with your manager, what do you feel like? They don't care, right? So reality is it's so critically important to have one-on-one time with your direct reports. Now, as a business owner, you don't need to talk with everyone in the company, but the people who report directly to you, you want to have consistent one-on-one time on a weekly basis, in my opinion.
James Dooley: And then what about, I want to talk about the opposite, right? So what do you see people doing wrong? So you've got people that have got successful remote teams. What are people doing wrong majority of the time for remote workers?
Mads Singers: So I have three key points here. Number one is if you do video calls, do video, right? A lot of people it's like, oh, my staff prefer not doing video. And I'm like, right, because they're not comfortable with it because they don't know you and they're not very comfortable with it. Do you know how you get them comfortable with it? By doing it. Now, here's the thing. What about the day they need to get on a video call with a customer and they're not comfortable with it? Right? That's not a good day, right? So again, communication is a skill. You want your team to grow their skill. If they're not comfortable being on video, that's a great indication they should be, right?
James Dooley: And then with regards to the issue there, you talk about the management side and dealing with the remote workers. Is there any tips and tricks for any software or anything that you can be using to maybe track remote workers to being as successful as possible?
Mads Singers: Yeah. So not just remote workers, but generally HeyRamp is for me, the favourite tool that we use to make sure we can manage our staff. So we track our one-to-ones and then what it actually does is it roll all the one-on-ones up into performance reviews. So that way you have all the data, you have everything becomes very easy, right? But that's a great tool. But in general, the key thing I would focus on is making sure that one-to-ones throughout the company get tracked in a way where there's clear visibility. So as a business owner, you want to be able to know at any point, is my staff at any level getting the one-to-ones they need? Because if they aren't, that is a great indication of future failure, right? If a manager stops doing one-on-one, it doesn't mean the week after everything crashes. But when a manager doing one-to-ones for a month or multiple month, at some point you will see things drop off big time. So as a business owner, you really want to have the overview and you really want to make sure that these day-to-day management processes are being carried out on a consistent level.
James Dooley: Is there any rule of thumb that you work to with regards to building a team? I'm on a role-playing mark, a marketing team. Majority of people that are watching this will be an entrepreneur that's in the marketing industry. And I'll tell you what I do. I mean, it'd be interesting to see what you would recommend with how many remote workers you would have versus in-house in the office. So we generally know we've got employee in the UK. So wages are high, national insurance is high, taxes are high. And if I'm being honest with you, from a recruitment standpoint, there's not that many great people that we can get, right? So what we normally do is we normally make the UK our middle management kind of set up. We train them up, we develop them to become middle managers and each UK member of staff can have eight to 10 virtual assistants working underneath them. What would you say? So we've got a lot more now remote workers than we actually have in-house in the office. Is there any rule of thumb that you have for a marketing team of like, what percentage of remote workers should you have versus in-house? Should you only have six? Should you have 10? Like, are you gonna say, I don't want you just going, it depends. It depends.
Mads Singers: I didn't know you were gonna say it depends. No, so I mean, for our companies, right? So I've been running companies the last 12, 13 years. We have about 350 staff across the companies and we're 100% remote. We've been 100% remote for the last, yeah, even way before COVID, right? So for the last 12 years or so. And key thing again, when you have good management, it doesn't matter that much. Now, again, there's certain things that just, the fact you can pull a couple of people, bring them in a room, sit down, go over things, that sometimes makes certain things easier, right? And we definitely try on occasion to get our teams who are remote, get them together, meet up. And I travel a lot, so I get around the world. I see a lot of the core staff we have in different places, right? So generally, there is definitely certain things to seeing people in person, for sure. And I wouldn't neglect that, right? But generally, my experience is from a high level standpoint business-wise, you can have people in-house, you can have them remote, and you can benefit in both ways, right?
James Dooley: I want you to answer this in a passive-aggressive term, and I don't want you to answer it saying, hi, you're a mad singers, right? I want you to ask these certain people that come to me and they say, ah, remote workers don't work. I've tried it, I've tried it a dozen times, they don't work. I've tried Vietnam, I've tried Philippines, I've tried South Africa, VAs just do not work. What would you say to that person?
Mads Singers: Generally, lack of management skills, right? So I'll flip the script here, and I'll say, we have one VA in our company who have been with a client for I think eight, nine years, and today she's the CEO of the e-commerce business, right? Like she runs the entire company, right? This is a lady that started out being 400 bucks a month. Today, she runs the company. She's making about 10, 11 grand a month or something now, which is pretty good for the Philippines. But like, again, they treated her like a regular employee. The biggest issue I see is business owners and managers treat offshore staff as offshore staff. They treat cheaper labour as cheap labour. And here's the thing, if you treat cheap labour as cheap labour, guess what you're getting, right? Reality is people are resources, right? Like from a business standpoint, people are resources. When I look at my team, every single one is a resource, and I don't care where they're placed. I'm gonna, as a manager of these people, I'm gonna put in the effort to get the most output of these people. And there's people anywhere in the world who are great. Now, is it maybe more difficult if you're in the US or in the UK, is it more difficult to hire someone in the Philippines or in South Africa the first time? Sure, because it's a different culture. There's different aspects, right? But reality is, if you're good at hiring and if you're good at managing, you will get similar output hiring remotely as you will in an office. Now, the big differentiator is, are you good at managing, right? Because the core aspect is that if you're not good at managing, remote becomes a lot harder, right? So learning to become a good manager, learning to become a good leader is very, very critical for succeeding, both with remote staff, but also in-house. But the effect of bad management shows much more aggressively at a remote team.
James Dooley: Yeah, for sure. In a simplistic way, Mads is saying, you're the fucking problem. It's not the remote workers. In a way, though, it is. So many people come to me and I'm just like, you're the issue. I'm not having it that every single virtual assistant is the problem. It's your expectation of what they're gonna do. There's also a few bits with regards to time zones and stuff like that. I quite strongly recommend, like, initially going through a virtual assistant kind of agency, because then they can start to understand that even a few of the things like the holidays in the Philippines and what they expect at Christmas and just little things like that, different nuances that's different to the culture in the UK makes a big difference. And until you start to employ over a dozen, you then start to realize, okay, this new bank holiday is showing up or whatever it is, a Filipino holiday, a Vietnamese holiday and so forth, and their expectation of just giving them like life insurance and stuff like that goes a long way. And all them little bits add up and it makes a big difference between the virtual assistants and running those remote workers successfully.
Mads Singers: I definitely agree. And time zone is a big one for me personally. Like, one of the reasons I absolutely love South Africa is it's native English, but it's also Western mindset, right? So South Africa, it's very Western education. And then the time zone. So time zone is the same as Europe and it's a few hours or six, seven hours different from U.S., right? But compared to the Philippines, for example, if a Filipino have to work U.S. hours, they're working in the middle of the night. And no matter who you are, you never get the best out of people at 4 a.m. in the morning. You don't, right? So my experience has definitely been with South Africa that we're getting significantly better output for those time zones, right? Whereas when we're dealing with client in Australia and New Zealand, we often still utilise the Philippines because again, the time zone there is so much better. And again, I wouldn't wanna try and get South Africans to working in the middle of the night. Can they do it? Yep. Are they willing to do it? Yep. Is it where you get the best work out of them? Nope.
James Dooley: On there, obviously you've got Aristo Sourcing, which is a recruitment company, a lot of remote workers. You've also got madsingers.com. Someone's watching this now and they're saying, I don't employ any remote workers. I need to start jumping on this bandwagon. I need to start leveraging, not saying the cheaper wages, but in a way the cheaper wages, but done to a high quality. What is the best way to reach out to someone like yourself? Should they have a Madsingers consultancy before going to Aristo Sourcing, before they're gonna start hiring these remote workers, or should they go straight into Aristo Sourcing and start hiring the VAs?
Mads Singers: So I would say it depends a little bit on the business. If you're just looking to hire for the first time, then it might be very beneficial to have consulting first. If you already have a team, when you're clear on what you're looking for and what you're hiring for, going straight to Aristo Sourcing or a similar recruitment company makes a lot of sense, right? For me, the core aspect, like what I focus the most on is really the management piece, right? It's really up-leveling the management skill, both of the entrepreneur, but also their management team, right? Because what we see consistently is that business owners are very good at promoting people into managerial roles, and they're also exceptionally good at never giving them any training. And then they wonder how they fail, right? So you have this good old saying that the best sales guy doesn't make the best sales manager. And I actually disagree a lot with that. What happens is just because you're the best sales guy doesn't mean that tomorrow you are the best sales manager. However, if you can learn how to be the best sales guy, you can also learn how to be the best manager, but it's two very different skill sets, right? So every time you have people who excel, that means they've taken the time to figure out how to do something exceptionally well. And if they can learn one skill, they can also learn management, right? So it's more the mindset around it that's important, but most business owners are really losing out because they have leaders and managers who doesn't have appropriate training to do what they're doing.
James Dooley: I know who's watching this episode and you like the how to successfully set up remote workers. You might also like the episode in the description about time management. Try and get some of that time back by being able to outsource to these remote workers. There's also a great episode about levelling up your existing staff in the AI era. Strongly recommend you're watching that. Mads, it's been an absolute pleasure. As always.