How To Lead A Virtual Assistant Team in 2026

Today we're going to cover how to lead a virtual assistant in 2026. Last year in my international recruitment firm, we made 47 placements with our clients. In my e-commerce business, we've done $4.2 million in revenue. And I have my own team based in the Philippines. It helps me run all my operations between the two businesses. Now, leadership is the one. This is going to be the most in-depth one. We covered training, onboarding, vetting, how to find.

This one is the forever game. This is the one that I am constantly playing with my team and it's the one I enjoy the most. It's why like I I enjoy uh hiring in the first place is because I get to be a leader. Now the first part of this is setting the rhythm. So having a regular communication cadence because with my team being fully remote and usually like pretty pretty isolated in their role, I have to be very intentional about this because you don't get like in the office where you might get you know water cooler talk.

I've never worked in an office, but like water cooler talk, you know, I want to create some way of of achieving something similar. And so I have to be overtly intentional about it more than I would um if I had an office. And I do this through regularly scheduled call times. So Monday every week, I'll have one-on- ones with every person from my team, checking on what they're doing, seeing what their confidence level for the week is, what I can help them with.

Um we then we have like as part of that water cooler talk we have a game night every week just like something casual and then on a monthly basis we'll have the KPI meeting to cover metrics and then a recap and goal setting for the upcoming month and these these communication uh events have different purposes but one of my favorite parts about it is I get to project my influence you know when I'm sitting here as this like charismatic nice fun loving guy, you know, they feel like they want to be a part of that.

They feel I mean they are a part of something and but it makes it real that like okay I'm not just numbers on a screen. It's like I'm doing something with other people that I enjoy. And it also means that their motivation stays high because they're like again part of something bigger. With this constant communication cadence problems are not such a big deal when they bring them up. It's like it's not like they have to to go out of their way to do it.

It's like when we're on these meeting, oh by the way, uh this this is an issue. And they also know that I don't like, you know, they see I'm not going to freak out, get mad, react. So problems that I need to be aware of come to me without having to to pry it out of them. Feedback loops, the constant, we're all Pavlovian, we're all dogs at the end of the day.

And so feedback loops, positive and negative, are extremely important for leadership. Now, most people will focus on the negative of like here's what you did wrong and that only creates resentment when you only share the things that they failed on. Instead, I share the positives and the negatives. And in fact, I want to be like have more positives so that the negatives don't really feel like negative. They just feel like criticism.

Like they know that I'm doing it out of us being better, not just because I thought they did something wrong. On the positive side, couple ways to do it. Performance bonuses are a big one. Aligning the incentives so that when the business does well, they see a part of that too. Financially, metric data focus. So whether it be or through KPIs, key performance indicators, metrics, whatever you want to call them, focusing our feedback loops around those as the outcomes of like how can we make this number go up year over year, month over month, public and private recognition.

So, I've noticed that sometimes money is not really what makes the difference. It's the emotions surrounding how they feel about their job. And a part of that is getting recognition. So, public recognition is like in our weekly Slack announcement calling something out that we can be proud of. We put like our KPIs in there actually. And then we have a daily wins channel as well where I can like publicly call it, hey, Cynthia did this really excellent.

Like, keep that up. And then private. So on our one-on-one calls or in our monthly meetings, I guess that would be public, but on our one-on-one calls or in Slack, giving them something to be proud of. It doesn't have to be like a big event, too. It's just like, "Hey, great job on this." Um, and so when I when I say that to them and they feel good about that thing, they're going to do more of that thing.

For the negative side, when I notice that there's drops in output or something that I'm not proud of and it's repeated, I will address that with curiosity. Like, hey, what happened here? What what's going on? Like, if it's repeated, I'll say something like, is there something like this isn't like you? I give them something to live up to. This isn't like you. Like, is there something going on at home with your family?

Um, because sometimes that that does end up being the case and it spills over into their work. Uh but really approaching the negative feedback with a stoic monotone of like what went wrong here? What like how can we how can we fix this? What what can we do to make it better? Now I will bring in emotion if I think it impacts the output because I'm like showing how much I care about the problem.

But that's very situational. Um I usually steer on the side of uh emotionless training their thinking. Now, if you really want to have a virtual assistant team that doesn't need you for every single step of the way, you have to train how they think and train for autonomy, especially in the overseas hiring world, they're very used to step-by-step processes and procedures, which for an entrepreneur business owner mindset, that that doesn't really align well.

And so, I want to share my decision- making process, not just the SOP, but like how I think about things, how I arrived at the outcome. And we do that by defining the outcome and allowing them to work backwards. My team will come to me with questions on like, you know, when they're at a decision point of like, I could do this or I could do this. And a lot of times I know the answer.

I could tell it to them right there and solve their problem. But I don't. I say, "What do you think? What do you think is a better approach?" And then they'll give me reasoning as to why one way is better. And I'm like, "All right, go for it then." Because most of the time that's exactly what I would have said. But if I just tell them the answer, then I reinforce again back to the feedback loops.

I reinforce that like all you have to do is ask me and I will answer. Now of course I make it make known that I'm available for questions, but if I always just train them to to ask me every single inflection point, then they will continue to ask me every single inflection point no matter how many times I tell them that don't do that, but I'm going to help you every single time.

And a part of that is letting them solve problems their own way. Maybe there's something where the answer is not so clear and they say they give a solid argument for why they think this way is better. I'm not going to say yeah no do it this way. I'll let them find out and get the data points as to which if if their way is better, giving them that autonomy of like look you need to you're responsible for the outcome.

So if you think that way is better do it that way. We'll see what happens. Asking for recommendations. So, if I want them to think outside the role of the box that they're in, when I'm faced with different things that need evaluation, I will send it over to them for what they recommend. Whether it be like, oh, if I'm working on a new ad, like, what do you think of this? Or if I'm facing this, and I don't even have to take their advice, but just training them to like think of just training them to thinking of like how to approach this. we get someone that becomes more autonomous in their role.

Not prioritizing busyiness. So again, back to the metrics and the outcomes focus of like I'm not looking at your hours. I'm not trying to we're focused on the the the outcome and the thinking process to get us there. And then from there just playing the long game. So, showing them the ladder early of how they can achieve financial success, how they can achieve growth in their role in the company, providing them the resources to get there, whether it be through YouTube videos that I think are relevant, podcasts, or even so far as if I find a course or a consultant, paying that, investing that into them to see the outcome because that's going to directly impact my bottom line eventually. like because I start start a lot of my team in the lower level roles.

Think of it like working in a Walmart, you know, checkout clerk before you move into the the the general manager, the corporate. And so like they're they're able to slot up move they're able to learn the context of the day-to-day of the ins and outs in order to accomplish that higher role at a more effective level instead of just being like all right having someone come and be like all right you're going to be a senior director of accountability.

Uh I want them to grow into the role and understand the context. And then what I can do is have them build the redundancy training after they master this role so that when they move up, they can just train someone to slot right in. Or we can automate it with AI if that if they get it down to such a process that it's it's repeatable. So this is how you effectively lead in my experience a virtual assistant in 2026.

Last video of the series. Let me know if you want me to cover anything else, but drop a one in the chat if you uh if you're here. Thanks. Oh, and we place uh international talent if you want to click down below and see if uh it's a good fit to work together. Right.