Virtual Assistance

How to Make Remote Work Actually Work?

The last post walked you through the important questions when hiring a virtual staff so that basically goes for employers. This time, let’s work things up for virtual workers – with the help of Hubspot.

One of my favorite things about working remotely — which I do a few times a month — is the freedom to get comfortable. When I work from home, I’m usually find myself in one of three positions: sitting up at the table, laying down with my laptop, or buried in a pillow avalanche on my couch. (Sound familiar to anyone?)

While most offices have a few full-time remote workers — and probably a few that operate like I do — the idea of more remote employees may be one companies need to get used to.

Why is remote work becoming such a big deal? Well, from where I’m sitting (currently “sitting up at the table”), it’s simple: Because good candidates are asking for it, and technology’s making it an easier thing to demand — no matter what the position entails.

For employees, this is great news. They can live where they want, spend less time and money commuting, and wear their bathrobe to meetings. But what do companies get out of it?

According to research by online freelance marketplace Upwork, sourcing and onboarding in-office employees takes an average of 43 days, compared with three days for remote employees. Not to mention, being open to remote team members widens the talent pool.

So to help you sort through the operations and expectations that employers need to consider to make remote work effective, let’s walk through some practices that make it easier for me to communicate and collaborate with my remote teammates.

How to Make Remote Work Work

On Setup & Technology

I have very little in the way of tech savvy, but I do know that a good operational and technical foundation helps remote workforces stay productive. This is where two key teams come into play: Finance & Accounting and IT.

It starts with a commitment — if you’re interested in making it — to investing in your remote team as actual employees that will grow with the company. Not contractors. Not freelancers. That investment means working with Finance & Accounting to understand the administrative costs of paying employees in different states or countries. Are there visa costs you’ll need to consider? Will employees need to travel to the office on a regular basis — and if so, is the company financing it? Do they have the technology they need at home to communicate with you effectively? Again, are you financing it if they don’t?

These questions extend to IT and the infrastructure they’ll need to set up, too. They’ll want to build in security measures for employee devices, and will need to equip your office with the technology your in-office team needs to communicate with remote team members. This includes chat software, remote meeting software, telepresence devices, and potentially some high-tech conference rooms to make coordinating all of that seamless. One of my teammates who works remotely half the week and works with our global offices quite a bit actually takes pains to dial into meetings on video, specifically. She found it difficult at first but says it made her far more productive being visually present in meetings, and is grateful to have the infrastructure to support that.

If you start with all of this built into your budget from the get-go, two things happen: 1) you’re not hit with surprise costs, and you can do a much better job with hiring planning; 2) you end up with streamlined operations for onboarding remote employees so their experience starting with your company is as good as it would be for anyone else.

On Communication

The best IT setup in the world doesn’t help unless we’re all using it toward the right ends. At the risk of being trite, the most successful relationships between in-office employees and their remote team members comes down to good communication from both parties. And figuring out what good communication means is kind of a beast. So bear with me while I try to break it down to its most pertinent parts for our purposes here.

Combat “face time” with over-communication.

One of the challenges remote work presents is the lack of “face time.” Think about all those random one-off conversations you have in the hallway, or at the water cooler, that wouldn’t be possible if you weren’t in-office.

To combat this, you really need to nail the whole “regular and effective communication” thing.

Sam Mallikarjunan, who works from his home down south most of the time, found that a lot of the “random collisions” he used to have in the hallway don’t happen anymore. (Obviously.) When I asked him how he makes up for it, he said “I just over-communicate. I have to proactively find opportunities to work with other people. I make a point of reaching out to people more often to tell them what I’m working on if I think it might be useful to them, and I actively talk to other people about their projects, too. There’s a lot less ‘the ball is in their court’ mentality when I’m remote.”

That proactive approach to communication is something that remote team members may start to pick up on just because they’re experiencing the need for it first-hand, so it’s equally important to have in-office employees reciprocate. Make it a practice in your company to systematize communication — to me, that means in-person decisions and conversations are always formally recapped over email, in your group chat client (provided it’s not in a room with only casual participation and monitoring), or for the big stuff, in a team meeting.

Use your words.

I have this theory that if street signs were properly punctuated we’d all be better writers. My favorite example is the “STOP CHILDREN” sign.


When communicating without the benefit of body language or tone, clarity with written and verbal communication is more important than ever. In an ideal world, everyone’s already really good at finding the right words to say what they mean. But that’s not reality, so we’re left with a few options here:

1) Try to be better at it. If you’re writing an email, take a beat to reread what you’ve written. See if you’ve really communicated what you’re trying to say clearly and succinctly. Consider whether you’ve included enough context for everyone to understand what’s going on. If you’re having a phone or video conversation, take a moment before responding or posing a question. And if what you said makes no sense, own it and say, “Sorry I don’t know what I’m trying to say, let me start over.”

2) Know that reading comprehension matters. If you’re on the receiving end of a communication that makes you go:

… ask clarifying questions before responding with an equally confusing answer. I try to either copy and paste the exact copy from the email, quote it, and then ask my clarification question — or if it’s a verbal conversation, repeat back what they said before asking my clarifying questions. It’s important to avoid layering confusion on top of confusion.

3) Avoid reading into tone. People’s tones suck sometimes. Especially over email. If a typically bubbly person didn’t include a barrage of emojis or explanation points, they’re probably just running late, or feeling stressed … or something else that has nothing to do with you.

Put some alert metrics in place.

We’ve used the term “pothole” metrics before — the numbers you report on regularly that, if they get out of whack, signify a deeper problem with a part of the business. I like to use that principle here as a way to be sure we’re all catching everything that’s going on if communication ever fails. I also like to expand that principle out to encompass the good stuff as well as the bad stuff.

These could be numbers that indicate someone’s doing well or struggling — for example, setting up traffic waterfalls if a team member’s work is directly tied to hitting a traffic metric. But they can include non-numerical things, too — like hitting project milestones for people that work in roles that are more about discrete deliverables that have changing definitions of success.

Frankly, this is a good exercise to go through for every team member — yourself included — whether in-office or remote. Really, it just means everyone knows what “good” looks like, and you’re all able to break down “good” into its component parts so you know if you’re making reasonable progress.

On Management

If managers are interested in hiring remote team members, they’ll have some specific responsibilities to keep things chugging along nicely. Most of this is just about setting the right precedent for how to think about remote work for your team — I’ve broken it down into the stuff you need to do proactively, and what you need to squash.

Do this:

Over-communicate the work being done by remote team members, and the value of that work. Yes, they should do this on their own. We talked about that earlier. You have to be the champion of your own career, and self-promotion is part of life … and all that jazz. But sometimes people forget. Or they do say it, but it’d sure help if someone else reiterated it.

This becomes particularly important when someone’s work output isn’t very visible. For example, if your job is to write one article a day, it’s pretty easy for people to see that you’re doing your job. You either wrote the article or you didn’t, and everyone can see it. If your role is to build operational efficiencies into backend systems that four people in the company touch … it’s really easy for that work to disappear.

Squash this:

To that end, don’t let resentment or pettiness build toward remote employees — particularly those that are part-time remote. This starts to manifest itself in little comments like: “Oh is this one of the days so-and-so is in? I can’t even remember.”Letting that kind of stuff slide is what makes it seem like in-office employees inherently provide more value than those that are in less often. Worse, it perpetuates the notion that face time is more valuable than work output, which I think we’re all on board with as being total bunk.

Do this:

Encourage other people on your team that are in-office and have roles that allow them to work remotely … to work remotely sometimes. That pettiness I was just talking about? It’s a lot less likely to happen if working from home once in a while doesn’t feel like a special privilege levied on a few special snowflakes.

Squash this:

This is where things can get tricky, too. Remote work only works when it works. Notice how I said you should only encourage remote work when people have roles that allow them to work remotely? We all know not every role makes that possible. But beyond that, not every person is always a good fit for remote work at every point in their career, either. I’ll volunteer myself as an example of someone who, when starting a new role, would struggle to not be around people while I get my footing.

Or if someone is having performance issues, it may not be the right time to green light remote work. That’s another reason giving feedback early, often, and candidly is important. And that rationale extends to remote employees that start having performance issues while they’re already engaged in a remote work agreement with you.

Finally, always remember to do this:

We talked earlier about treating remote employees not like contractors or freelancers, but like actual full-time employees. That means they have career ambitions, and are probably interested in growth and promotion opportunities. Be sure to keep them in mind for new projects, promotions, and additional responsibility. If good people fall out of sight and out of mind, you might lose ’em.

After you’ve got the infrastructure set up, to me, most of this really comes down to good hiring. Get the right person, for the right role. If you’ve got capable people you can trust in a role, you should be able to trust that not only are they doing good work, but that they’ll let you know if and when they need something different from you.

The right person can make even roles that you don’t think will work in a remote scenario, work. (Unless that role is chef. Then you definitely need to be at work.)

How do you make remote work work? Share your thoughts and ideas in the comments section below.



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