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In a recent Make it Work podcast episode with Karen Kirton and Lachy Gray, our Managing Director Richard Phu dropped some serious knowledge bombs on upskilling and training remote teams.

We’re talking Oppenheimer-level.

With remote work becoming the norm, talent agencies are now EVERYWHERE. Your business now has access to remote workers from all corners of the globe.

Yay, you! 🥳

But if you’re reading this, then you know running a successful and scalable company nowadays isn’t just about hiring remote talent; it’s about transforming them into higher-value employees by upskilling and training them.

So in this article, we’ll dive into the 7 following truth bombs:

  • Truth bomb #1: The higher up you go in the business system, the more you’ll be dealing with people.
  • Truth bomb #2: If you really want to improve your remote staff, you have to train them to make decisions on your behalf.
  • Truth bomb #3: Encouraging your team to fail safely helps upskill them into better decision-makers.
  • Truth bomb #4: Things will move MUCH faster in your business if your team isn’t constantly waiting on your approval.
  • Truth bomb #5: Once you’ve started upskilling your team, you won’t be seeing results right away.
  • Truth bomb #6: You have to verbalise that you want tasks X, Y, and Z to be done, and in what way.
  • Truth bomb #7: There’s no foolproof way to know if a candidate is 100% worth your gamble—especially with online training.

Let’s get to it!

Remote Hiring Revolution

The moment emails were invented, your business’ talent pool went global whether you knew it or not. (1971 was when emails were invented according to Google, in case you’re wondering.)

Many business owners think that once their business is up and running, and turning some profit, they’ll have more time to sit back, relax, and watch their business churn out money month after month.

Lesser meetings, less dealing with people…Right?

Here’s truth bomb #1 from Rich: the higher up you go in the business system, the more you’ll actually be dealing with people.

Our Founder & CEO Linh Podetti was aware of this fact way back in 2018. So she set out to hire an operations manager (A.K.A. Rich) to help in upskilling and scaling up Outsourcing Angel.

Founder & CEO Linh Podetti and now Managing Director Richard Phu are both based in Sydney, Australia

The first leadership development directive was to upskill our internal team. There were talks of training, special programs, internal “TedTalks”, and all other fancy to-dos when someone thinks of upskilling and training employees.

👉 Related: Understanding the culture of Filipino virtual assistants

Those initiatives are all great, but at the time, our team wasn’t at the stage to make the most out of those training structures yet. Like many remote businesses out there, our staff was still at the “tell me what to do and I’ll do it” mentality.

What Rich and Linh did was to transition them from that to becoming decision-making powerhouses.

Building Decision-Makers

Our monthly internal meetings are never complete without filters! (Photo taken March 2023)

Here’s truth bomb #2: If you really want to improve your remote staff, you have to train them to make decisions on your behalf.

But how do you do that? 🤔

You can start by delegating small decisions. Let’s say your social media virtual assistant is having a tough time choosing between two pictures for a LinkedIn post. They come to you and ask, “Should I go for Picture A or Picture B?”

As the manager or business owner, one of the most empowering things for leadership development is to ask them, “What do you think? What do you want to do?”

This approach helps them become decision-makers, even on small matters. And If they’re not going in the right direction, that’s when you can say, “Do you want my opinion?”

Hopefully, they say yes and then you can explain your thinking process and rationale behind choosing Picture A (or Picture B.) Letting your remote staff know the factors behind your decision-making will help them carry out the same process every time they face a similar challenge.

👉 Related: Check out our social media virtual assistants ready for hire

The more you adapt this approach, the more empowered they are to make decisions. You’ll have more time on your hands because you’ll be focusing on growth partnerships, how to hire an operations manager, and other crucial tasks instead of helping your staff out with the details of day-to-day work. Plus, this makes it easier to have a scalable company.

It’s a win-win all around!

Uh-oh…Your Staff Made a Mistake?!

That’s bound to happen. But just like what they say, mistakes are stepping stones to success. So here’s truth bomb #3 for you: Failing safely helps upskill your team into better decision-makers. That said, you might want to try fostering a culture that encourages safe failures.

Now what does failing “safely” even mean?

Let’s break it down bit by bit.

The 70-20-10 rule for leadership development suggests that you can learn to become a better contributor in group settings in 3 major ways:

  • 70% through challenging experiences and assignments on the job
  • 20% through developmental relationships (coaching)
  • and 10% through structured training

In other words, the bulk of upskilling is actually achieved on the job. That’s why it was important to start delegating work-related decisions first before diving headfirst into special training programs and whatnot (although those still help.)

Now, how do you encourage your people at work to fail safely?

Tip 1: Put your staff in challenging work situations

A proper amount of pressure at work could be a good thing. (Photo of Rich taken May 2023)

We don’t mean chuck them in the deep end, by the way. That’s only going to cause trauma and we don’t want that! 😬

Let’s take an example from Rich. On the Make it Work podcast episode, he shared about how one of our team members asked him how to speak up more. Their problem? They were afraid to voice their opinions because they weren’t an expert on certain topics.

So what does Rich do? He encourages this remote staff member to have more meetings with clients with him present.

And in these meetings, when they stumble upon unfamiliar topics (say a particular automation tool) Rich shows how it’s done. He says, “I’m not an expert on this topic, but let me do a quick search on it.” And the solution starts shaping up from there.

The team member can clearly see how Rich would handle the situation, and the next time they take a meeting, they’d be able to do it as well.

And the more they tag along on client meetings, they’d be more and more comfortable handling the situation and Rich could start slowly removing himself from the equation.

You can think of this growth partnership as going on a wilderness adventure. As a leader, you can’t just go on Bear Grylls mode and take your companion on the most extreme route possible so they can tough it out.

Instead, you walk into the jungle together and teach them how to work a compass and navigate with a map along the way. And as your companion (A.K.A. mentee, employee, remote staff) becomes more and more comfortable in the jungle, you slowly pull yourself out the way you came, while they go further and further by themselves.

Now, here are three things to keep in mind to help with this approach:

#1 Agree on a signal with your staff.

Your staff won’t always get things right, especially in high-level situations like a client call. Agreeing to a signal will help you jump in whenever your remote worker finds themselves out of their depth.

It can be as simple as the following callsign: “Do you have anything to add, Rich?” (This is Rich’s cue to jump in and help steer the discussion to the right path.)

#2 Have a debriefing.

Your remote team can’t always rely on signals. If that’s all you have, you’d be swooping in and saving everyone, day in and day out. And that’s a recipe for managerial burnout. 👀

A debriefing will help to train your staff on how to do better next time. And the key is to NOT go through a million points on your debriefing. No one wants that!

Instead, we suggest focusing on one thing only and explaining the why and how behind it. This will help make your remote staff draw concrete action points from your debriefing and implement them.

#3 Keep your door (or Zoom link) open.

Like what we said in truth bomb #1, you’ll be dealing with more people as a manager or business owner. So always remind your staff that you’re available for catch-ups and one-on-one sessions.

Keeping your door (or Zoom or Calendly link) open will encourage them to approach you with another challenge. And into the wilderness you’ll go again!

👉 Related: Setting up your digital space for virtual assistants

By letting your team have hands-on work experience within your guidance, you’re already covering 90% of your upskilling channels. (We’ll talk about the remaining 10% on structured training in a bit.)

The more experience they have with learning new things and stretching their abilities, the more responsibilities they can take off your plate.

Tip 2: No Naked Questions!

Rich borrowed the “No Naked Questions” leadership development concept from an old business partner and it’s another tip for helping your remote team fail safely.

It simply means that whenever someone in your team approaches you with a question or a challenge, it’s expected that they’ll take the time to research, read or Google for possible answers first BEFORE approaching you.

So let’s say your eCommerce virtual assistant came to you for help. Which interaction would you prefer to have?

👉 Related: Check out our eCommerce virtual assistants ready for hire

Interaction 1 ( ❌ No Naked Question ):

Virtual Assistant: Hey sorry. Still organising orders from Shopify, Amazon, and eBay. It really takes a lot of time.

You (Business Owner): Why what’s the problem?

VA: Lots of orders lately. And I have to collect info from all platforms.

You: How can we speed things up? Any suggestions?

VA: I don’t know.

Yikes. Compare that to this:

Interaction 2 ( ✅ No Naked Question ):

Virtual Assistant: Hey sorry. Still organising orders from Shopify, Amazon, and eBay. It really takes a lot of time but I think I have a solution.

You (Business Owner): What solution?

VA: Found out about this tool called SellBrite. We can track orders from there instead of going into the sites one by one. Basically all-in-one.

You: Cool, I’ll check it out first and see what we can do.

It’s a WORLD of difference.

Implementing the “No Naked Question” principle in your remote team will help them tiptoe out of their comfort zone and learn new things. And if their suggestion doesn’t work out? Then both of you can go look for another solution.

Much better than having interaction 1 over and over again! 💀

👉 Related: How to outsource operations to a VA team

Tip 3: Tell your staff to seek forgiveness, not permission.

Here’s truth bomb #4: Things will move MUCH faster in your business if your team isn’t constantly waiting on your approval.

Part of fostering a culture of failing safely is to encourage your staff to be decisive and take action that’s aligned with doing the right thing for clients, the rest of the team, or your entire company.

If you tell them that they don’t need your permission to do X, Y, and Z, then X, Y, and Z will be resolved that much faster instead of piling up on your plate.

And if they make mistakes? That’s the whole point! You’ll be there to assess, debrief, and turn that mistake into an upskilling and leadership development experience.

It’s all about nudging your team in the right direction, letting them make decisions, and then helping them make BETTER decisions whenever they stumble.

👉 Related: How to build a strong remote work culture for VAs and employees

And on the topic of better decisions: please do consider booking a Discovery Call with us—we’d like to help you scale up, hire a capable virtual assistant, or both!

“How long will I see results in my remote team?”

Now hold up, buttercup.

Once you’ve started upskilling your remote team, you won’t be seeing results and become a scalable company overnight. That’s truth bomb #5 for you. If you do see results after one day of upskilling efforts, then that’s awesome—some of your employees might be Superman.

But seriously, your team’s learning curve will most probably take time. And you should take time with your teaching as well.

In Rory Vaden’s book Procrastinate on Purpose, it was suggested that it takes 30 times as long for a person to learn a task that you can do in 5 minutes. So if a certain task takes you 5 minutes, then you should ideally spend 150 minutes teaching your staff how to do it.

This doesn’t mean they’ll get it done in 5 minutes right after you teach them. The 150 minutes is just an ideal teaching duration. Everyone learns at their own pace, we’re sure you know that!

And if you’re thinking about which tasks you should teach to your remote staff, and which ones you should keep doing yourself, just ask yourself: “Do I want to do this task 4 or 5 years down the track?”

If not, then spend an ideal amount of time teaching your staff how to do that task!

Also, if we take Rory Vaden’s 30x principle and apply it to becoming a better decision-maker, then teaching that to your remote team will take way more than just 150 minutes.

So do remember to be patient. If you keep at it, your remote team will get to the level where they willingly learn on their own, share work improvement initiatives, and more. 💯

Setting up training structures

The Outsourcing Angel team at the South West Entrepreneurial Hub (SWEH) Expo 2023 last June.

Once your team is used to making better decisions, then it’s time for you to think about the remaining 10% of their upskilling path: structured training.

This last push will empower them further with specific growth tools and insights to manage their workload independently. So you won’t necessarily have to be available 24/7 in case they need something. (And you can finally take that well-deserved break. 🏖️ )

There are lots of FREE training courses and frameworks available out there, and they offer great stuff that can turn your business system into a fully scalable company.

Here are a couple that we found useful in our internal team:

#1 Alex Hormozi’s $100M Leads Course: This helped our Marketing Team multiply their content production up to three times. 🤯 The course also starts with a great section on lead magnets, which we’re also planning to implement for our upcoming Systemise & Scale Up lead magnet growth tool.

#2 Donald Miller’s StoryBrand Framework: This framework is from the author’s book titled, Building a Brand Story: Clarify Your Message So Customers Will Listen. And it does exactly what it says in the title: it helped our core and management team clarify our messaging since we’re amping up promotion for our scaling up services. The framework helped us craft a new homepage and Systemise & Scale Up page which we will be rolling out slowly.

Aside from that, we’ve also started our version of the TedTalks called Angel Talks (yeah, we’ll get to revising that name. 😆)

Each month, individual staff members from different departments take turns to present a 20-minute talk to the entire team, with room for questions and answers of about 10 minutes. The topic could be about anything they learned: takeaways after overcoming a challenge at work, a new tool they discovered that made their job easier, etc.

Cha, our first Angel Talk presenter, is part of the Systemise & Scale Up team.

And our Managing Director Rich was insistent that the talks should be coming from the internal staff—NOT the management team. That way, everyone else won’t be too afraid to give the talk themselves and will be encouraged to take a similar leap. That’s a sneaky way for leadership development right there!

If you adopt a similar strategy and tweak it to fit your business system, you’ll provide a platform for your team to share what they learned from their individual upskilling journeys. With them helping each other out, there will be no constant, pressuring need for you to be everyone’s go-to problem solver.

Instead, you can focus on higher-level tasks like growth partnerships, networking, strategising, or even learning how to hire an operations manager so they can upskill new team members on your behalf.

And if you wanna kick it up a notch, you can also create highly customised training for your remote workforce.

Specialised training for virtual assistants

Caveat: we’re not complete geniuses at this, since we’re only about to launch our special virtual assistant training while this article is being written.

But we can guide you through our Managing Director’s helpful insights that made Angel Academy happen.

What is Angel Academy?

Our company beach trip back in 2019 at Davao City, Philippines was super fun!

The Angel Academy is basically a boot camp for virtual assistants within our network who are willing and qualified to be trained to further enhance their skillset.

At Outsourcing Angel, we provide skilled and long-term VAs for clients around the world. Sounds great, right?

👉 Related: Our virtual assistant recruitment process

We do well most of the time, but just like in any other business, there are bumps in the road. For us, those are cancellations from clients.

For many reasons, the matches we create between clients and virtual assistants don’t always work out. For that, we have a Client Happiness Guarantee that gives all our clients free VA replacements at any time, plus a week of complimentary VA service so they can adjust with their new hire.

100% Lifetime Guarantee

If for any reason, you’re not happy with your Virtual Assistant, we’ll find you a replacement at zero additional cost. Plus, you’ll get 1 week of VA service for free! This is to help you get settled with your new VA.

The best part? You’re covered for a lifetime. We extend this Client Happiness Guarantee to all of our clients no matter what stage you’re in – whether you’ve just hired your first VA or you’ve been with us for years.

But to lower our cancellation rates even further, the Angel Academy was set up. The VAs who can finish from the Academy will be given a “certified” status by us whenever they’re presented to our clients. 👌 So that’s how we’re training our virtual assistants to provide amped up service for business owners.

And in the Angel Academy, we do touch on necessary virtual assistant skills for leadership development—but more importantly, we narrow down on the soft skills required to do a smashing job in the industry.

👉 Related: Interesting VA facts you should know as a business owner

We began our focus on communication.

Remote work thrives on clear communication

Once you’ve onboarded your new staff member online, and told them all about the company background, culture, mission and vision, you can’t just expect them to do tasks X, Y, and Z.

Truth bomb #6: You have to verbalise that you want tasks X, Y, and Z to be done, and in what way.

This is especially important for small businesses online, where people’s job descriptions often get thrown out the window because things change so much on the fly. If you hire someone to focus on your lead generation, you may need them to come in and help out on social media from time to time. Or some such scenario.

Setting your expectations early, clearly, and frequently will save you a lot of headaches moving forward.

And yes, communication is a two-way street. Our Angel Academy focuses on enhancing virtual assistants’ communication skills too, so that business owners aren’t left hanging on the status of things they’ve assigned.

Focus on progress over results

In any custom program where you’re spending time, energy, money, and other resources on training remote workers, how do you know if a candidate is worth the gamble for leadership development? 🤔

Truth bomb #7? You don’t. As far as we know, there’s no foolproof way to find out if an individual is 100% ready for a certain position—especially if you’ve never met them in person. That’s why there are interviews and tests before job offers are made after all. 🤷

But with structured training, you can increase your chances of a remote arrangement working out in your favour. And for that, you just need to focus on progress over fast results.

If your candidates are progressing in the right direction, then great! If not, then they probably shouldn’t get to the next stage of training. With progress as a barometer—instead of just a handful of interviews and tests—you’re setting yourself up for a more likely success.

👉 Related: The importance of business systems and processes

In our case, the hope is that business owners will have the deck stacked in their favour whenever they choose an Angel Academy-certified virtual assistant.

Our company beach trip back in 2019 at Davao City, Philippines was super fun!

Fall to the level of your systems

“You do not rise to the level of your goals. You fall to the level of your systems.”
– James Clear, Atomic Habits

When it comes to upskilling and training your remote team, it will all eventually boil down to the business systems and processes you have in place. Your people will need the right attitude, growth tools and technology at their disposal so you can remove yourself as the bottleneck in your own business.

Our team attended James Clear’s Atomic Habits Live on September 2023 and also goes on frequent retreats. (Second photo was taken last June 2023 in Culburra.)

Try to upskill your remote team by prioritising communication, encouraging them to fail safely, embracing a culture of initiative and then investing in training once they’re voluntarily sharing insights and ideas with the rest of the team.

We’re sure that your remote team will be a force to reckon with—if they aren’t already!

Book a free Discovery Call today!

Your team, processes and technology all rely on each other for business success.

If you think systemising those three things will help you scale up, book a FREE Discovery Call with us today and let’s chat!

Arielle Calanas

Arielle is Outsourcing Angel’s resident copywriter. She has over 9 years of writing experience and graduated magna cum laude in Creative Writing from the University of the Philippines Mindanao in 2019. Currently, she crafts high-engagement content that reflects our brand voice, from client case studies to blog articles and more.