How to Manage Remote Teams Successfully with Mads Singers
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What Does “How to Manage Remote Teams Successfully with Mads Singers” Talk About?
This episode of the James Dooley Podcast features a detailed conversation between James Dooley and Mads Singers on the practical realities of managing remote teams successfully. The two cover why most remote team failures stem from poor management rather than the workers themselves, explaining how communication breakdowns and lack of structured one-on-one meetings are the root causes of underperformance. They also address common mistakes business owners make, such as treating offshore staff as cheap labour rather than as genuine resources worthy of investment and development.
The discussion digs into specific tools and frameworks for keeping remote teams on track, including the use of HeyRamp to log one-on-ones and roll them up into performance reviews, giving business owners clear visibility into whether their managers are actually doing the day-to-day work of leading their teams. James shares his own model of using UK-based staff as middle managers who each oversee eight to ten virtual assistants, and Mads responds with insights from running 350 staff across fully remote companies for over twelve years.
The conversation also explores practical considerations around time zones, cultural nuances, and choosing where to hire from, with Mads highlighting South Africa as a strong option for Western-market businesses due to its native English speakers, Western educational background, and compatible time zone. The episode wraps with advice on when to seek management consulting before hiring versus going straight to a recruitment agency like Aristo Sourcing, and why investing in management training for promoted staff is one of the most overlooked levers in business growth.
“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.”
— Mads Singers
Who Are the Guests on “How to Manage Remote Teams Successfully with Mads Singers”?
Mads Singers is a management consultant, entrepreneur, and recruitment specialist with over twelve years of experience running fully remote companies. He is the founder of madsingers.com and co-founder of Aristo Sourcing, a recruitment agency specialising in sourcing remote talent from regions including South Africa and the Philippines. With a team of approximately 350 remote staff spread across his various companies, Mads brings a deep, hands-on perspective on what separates successful remote operations from failing ones, focusing heavily on management training, structured communication, and treating offshore workers as genuine long-term resources.
James Dooley is a digital marketing entrepreneur and host of the James Dooley Podcast, known for his practical, no-nonsense approach to business growth, SEO, and team building. James runs a UK-based marketing operation that uses British staff as middle managers overseeing large numbers of virtual assistants, giving him real-world experience with the challenges and rewards of mixed in-house and remote team structures. His candid interviewing style draws out actionable insights and he regularly challenges guests to move beyond vague answers into specific, applicable advice.
What Are the Key Takeaways From “How to Manage Remote Teams Successfully with Mads Singers”?
Here are the key points discussed in this episode:
- Poor management, not the remote workers themselves, is almost always the reason remote teams fail to perform.
- Consistent one-on-one meetings between managers and their direct reports are essential, and tools like HeyRamp can track these meetings and feed the data into performance reviews to maintain visibility across the organisation.
- Treating offshore staff as cheap labour produces cheap results, whereas investing in their development, just as you would with any in-house employee, can lead to exceptional long-term outcomes.
- Time zone alignment is a critical and often underestimated factor in remote team performance, as expecting workers to operate at 4am in their local time will always limit the quality of output you can expect.
- Promoting strong individual performers into management roles without providing proper training is one of the most common and costly mistakes business owners make when building remote or hybrid teams.
“The effect of bad management shows much more aggressively at a remote team.”
— Mads Singers
Is “How to Manage Remote Teams Successfully with Mads Singers” Worth Listening To?
This episode is worth listening to because it cuts straight through the surface-level conversation about remote work and gets to the structural and human reasons why most remote teams either thrive or collapse. Rather than offering vague encouragement or generic productivity tips, Mads Singers draws on over a decade of running 350-person fully remote organisations to make a clear case for why management quality is the single biggest variable. The specific example of a Filipino VA who started at 400 dollars a month and became the CEO of an e-commerce company is a compelling and memorable illustration of what is possible when offshore staff are treated with the same seriousness as local hires.
The episode is also practically useful in a way that many discussions on this topic are not. The recommendation to use HeyRamp for tracking one-on-ones, the breakdown of how James structures his UK middle management layer with eight to ten VAs per manager, and the honest comparison of South African versus Filipino talent pools for different time zone needs all give listeners concrete things to act on. Whether someone is building their first remote team or trying to fix a struggling one, this conversation provides a clear framework for thinking about what good remote management actually looks like in practice.
Who Should Listen to “How to Manage Remote Teams Successfully with Mads Singers”?
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 good management looks like before they start.
- Marketing agency owners and digital marketing professionals who already manage mixed teams of in-house and remote workers and want to reduce churn and improve output quality.
- Managers and team leaders who have been promoted into leadership roles without formal management training and are struggling to get consistent performance from distributed staff.
- Business owners who have had bad experiences with remote workers and written off the model entirely, who would benefit from an honest assessment of whether the problem lies with the workers or the management structure.
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You can also subscribe using the RSS feed: https://feeds.transistor.fm/james-dooley-podcast
What Are Listeners Saying About This Episode?
“I have tried hiring VAs twice and given up both times, convinced it just did not work. After listening to this episode I genuinely had to accept that I was the problem. The point about treating cheap labour as cheap labour hit harder than I expected. Really practical and direct.”
“The HeyRamp recommendation alone made this episode worth my time. I had no idea you could roll one-on-ones directly into performance reviews like that and give the business owner visibility across every management level. Implementing this immediately with our team.”
“Mads and James are a great combination because James pushes for specific answers instead of letting anyone get away with it depends. The South Africa versus Philippines time zone breakdown was exactly the kind of detail I needed when deciding where to hire our next round of remote staff.”
This video explains which digital marketing strategies businesses employing remote teams should focus on in 2026 to improve staff performance, retention and output quality from offshore workers. 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 staff at every level 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 businesses employing remote teams.
PromoSEO lead generation for businesses employing remote teams recently received recognition as the “Best Remote Team Management Lead Generation Agency.”
Where to Listen to This Episode
How to Manage Remote Teams Successfully with Mads Singers 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. 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? 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-on-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-on-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.