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Remote Management Tips

by Ashley
Published: Last Updated on 1 comment 662 views 18 minutes read

We didn’t know how well it would work. There were concerns. There were questions. Backup plans were made. Hands were wrung.

Could I successfully manage my team and work from the Hague for four weeks?


Annoyed husband is annoyed. The real question was not can we work from the Netherlands for four weeks but rather could we work together at the same table for four weeks?

Our company already functions as an entirely remote organization. We do not have an office. Our employees do not all reside in the same town or same timezone. Yet we are able to work together, apart, smoothly and efficiently. We rely on fast internet, messaging apps, our intranet, and, if really in a pinch, the phone. We strive to make and deliver great content, and to always exceed client expectations regardless of where any of us are at any moment.



But a seven hour time difference was a tad intimidating.

Of course, I shouldn’t have worried. The four weeks we spent living and working in the Hague went far more smoothly than any of us could have anticipated because, in reality, it wasn’t much different from living and working in Nashville. Working remotely doesn’t just mean working from coffee shops and airports; it usually means working from your home office, which means it doesn’t matter where you call home.

So don’t be intimidated by remote work or managing a remote team! Here are some things I’ve learned over the years that help me manage my team no matter where any of us are working from.

Over-communicate with one another.

Remote teams can not communicate too much. You might think it’s overkill or annoying or useless to talk about information that was already detailed out in the intranet task list, or going over something that was said in email, but I never get annoyed when my team wants to go over something that was previously communicated. We do not work in the same building and rarely see one another; so even though we communicate effectively through text, it’s always better to verify and confirm something before diving into working on it. You might think you’re being super clear, but your staff might find room for interpretation — which can lead to error!

Provide detailed details on the front-end.

In the same vein as over-communication, you need to provide ALL THE DETAILS at the beginning of a task or project. What might be seen as excessive in an IRL situation is necessary and helpful in a remote situation.

Provide context for the task, the why behind what needs to be done. Be specific about what has to be done and how it should be done. Be detailed about your expectations and those of the client. Don’t assume that your team remembers something you said once three weeks ago; state it again. Reiterate important details that you don’t want them to overlook. Reconfirm file-naming conventions and storage paths, delivery dates and turnaround times, special client requests or last-minute changes.

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You can not provide too much detail. In a remote work environment, where people work in isolation, they need to be able to reference information to complete tasks and projects. If the information is detailed out, they won’t have to bother you sixteen times asking to confirm information.

Check-in weekly with each team member, especially newbies.

I ask that all new team members send me weekly “snippets”, a list of what they worked on the previous week and what they have on their To Do list for the upcoming week. This lets me see their productivity levels (did they do enough? have I assigned too much?) and make sure nothing slips through the cracks for the upcoming week.

New team members have to send me their snippets for their first 90 days, and after that, it’s up to them how to keep me updated. I have one employee who sends me her snippets every week or so, though it’s grown from a simple weekly list to an on-going project list that helps us both keep track of long-term client and development projects. The team members who don’t find the snippets to be a useful exercise keep me updated on their status through regular Skype chats and in comments on tasks in our intranet.

Create team-specific communication channels.

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We use Skype for our real-time in-office communication. I have a saved Skype chat with every single staff-member, as well as every single team. This keeps our communication organized. We can search team-specific conversations for relevant information, and keep team-specific chatter from disrupting other people during work. It also allows all team members to stay in the loop on projects that they might not necessarily be working on; for example, if one of my elearning designers and I are troubleshooting something, we’ll often work it out in the elearning team chat because it’s information that could be useful to the other members, or they might have a suggestion to add to the mix. Having specific group chats also helps foster a sense of team unity and lets you get to know your coworkers in a more specific way.

There are tons of ways to do this, whether it’s a messaging app or within an intranet. (Basecamp, Slack, Tox, Hangouts, Skype, WhatsApp…) Location of the channel doesn’t matter so much as the existence of it.

Use the time difference to your advantage.


If you and your team work across time zones, it’s important to ensure at least a small amount of overlap for real-time communication. But often staggered time zones can mean that you have dedicated hours of uninterrupted work time.

While working from Holland, I absolutely loved sleeping in, having a cup of coffee and checking my email without interruption. No one Skyping me. No emergencies needing my attention right that very second. I had a calm productive morning every single day because when I started work at 10, it was 3 am for my Nashville team and 4 am for my East Coast coworkers. They were fast asleep while I was buzzing away getting shit done without anyone bugging me. My productivity shot through the roof. And by the time they all signed on, I’d crossed off most of my To Do list, gone out and had lunch, seen a few sights, and was already back at home for happy hour ready to check in with them. We’d work together for a few hours before I’d peace out for the evening, and everything worked very smoothly.

While I wouldn’t want to work 7 hours ahead all of the time, I’d love if I could be two or three hours ahead of my team to give me a few quiet hours at the start of every day. (I suppose I could accomplish this by waking up early, as a few of my coworkers do, but I’ve tried that and it just doesn’t work for me. I prefer working late to early. But it might work for you! Try it! Even if you work in the same time zone as your whole team, you can create the same effect by staggering your work hours.)

Put together monthly status reports.

Screen Shot 2017-04-09 at 1.45.42 PMWe implemented these last spring and it’s one of my favorite monthly tasks. At the end of every month, everyone in the company fills out a survey form, answering specific questions. (I use AirTable, since we use that for a number of things, but you could use any survey or form generator.) The questions circle around projects coming down the pipeline, professional and personal accomplishments, upcoming absences or important dates, announcements that other teams should be aware of, etc. Then I compile all of that data and drop it into a template I created, and distribute a one-page PDF that provides a snapshot of the company’s production and the people who do the work.

Many of the production team members never talk to or work with one another; the sales staff never interacts with the video department; the digital strategy department has no idea what client projects are going on. And because we don’t see one another in person, many of us don’t know what’s going on in each other’s personal lives. So this way, everyone can be kept in the loop about what’s going on within our growing company, celebrate one another’s achievements and successes, and get to know one another better.

Create space for fun.

I think one of the biggest challenges of remote offices is creating a sense of community and getting to know people you work with but never see. We recently hired a project manager, and she’s been tasking my production team for two weeks even though none of them have ever met her in person! Of course, everyone has “met” her through the monthly status report and our company-wide Skype chat.

We call it the Water Cooler, and it is a catch-all for news stories, afternoon chatter, cat pictures, reminders, jokes, memes, complaints, questions, and letting one another know that we’re away from our desks or will be unavailable for a certain period of time.

Often, the Water Cooler goes off on tangents about alien conspiracies, our pets or delicious meals, or 4 pm hits and everyone is antsy, distracted and clearly ready for happy hour. Sometimes a person will have to mute the channel to stop getting the bouncing blooping notifications just in order to finish typing an email or proof-reading a document. But even for all of the distractions and random chatter, the Water Cooler provides us a place “to hang out”, talk about non-work things and get to know one another.

While Justin and I were living in Holland, we’d stumble into the Water Cooler late at night after dinner and drinks, which was only late afternoon for our coworkers. Tyler, another big traveler, often works from California while visiting her husband’s family, and will drop photos of their hikes into the chat. Having a place to let off steam and share funny stories is crucial for team morale!

Encourage time off.

It’s been reported that remote workers are more productive and efficient than in-office employees. (Here and here and here… and here and here and here… and here and here and here.) Remote workers also have a tendency to work longer hours. We get on a roll and don’t want to stop for lunch or to go home — because we already are home. We want to show we’re productive in our pajamas and will work in bed. We know we can get work done on the road so we connect to our hotspot and work from the car.

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My entire team is full of workaholics, putting in late hours even when I don’t ask them to, going above and beyond to produce good, timely work. But taking care of work means they aren’t always taking care of themselves. So I encourage them all to take time off, and sometimes have to force them to take it. (This is obviously easier within companies that don’t have strict time-off policies; we don’t track any sort of vacation or sick days, so our staff can take time whenever they need it, as long as the work gets done.)

If you have the authority to do so, build in time off by giving your employees a few long weekends throughout the year. A few extra company holidays throughout the year isn’t going to cost that much money nor cut into productivity. And your employees will appreciate the consideration.

Your employees deserve more than a day or two at Thanksgiving! I'd give them the whole week if we didn't close down production at the end of the year.
Convincing a coworker to take an afternoon off
Our scheduled company holidays

When you, or your staff, do take time off, make sure that it’s OFF. I’m all for a workcation; that’s what allowed us to go to Europe for six weeks in the first place. But we all need opportunities to shut our brains off, reboot and truly vacate. When we went to Mexico last month, that’s precisely what we did and I encourage all of my coworkers to do the same thing.

Sometimes we don’t even need a week or a whole day off. Just a few hours will suffice. Take an afternoon to clear your brain. Sleep in for the heck of it. Pick the kids up from school and go to the zoo. Spend the late morning at the dog park. If it’s a slow day and you got all the big To Dos done, step away from the computer and go for a walk. Make sure you give yourself, and your employees, mental health days — or hours! — because clear-headed, happy employees make for highly productive, creative employees.

Get out of the house now and then.

I mean this in two different ways.

tenor.gifFirst, some people go stir-crazy living and working in the same environment, so if you need a break or a change of scenery, go for it! We don’t do this a lot while working at home in Nashville, but when we work while traveling, we’ll often set up shop at a cafe or bar for a few hours. (Just make sure you use a VPN!! And while we’re at it, make sure you’re a cyber savvy traveler!)

But more importantly, I think, is that the remote team gets out of the house together. This requires planning ahead if you don’t all live in the same city, but it’s important for remote teams to see and interact with one another in both work and non-work situations.

This is how we do it:

  • Quarterly in-person meetings. All production staff and Nashville locals get together for a half-day meeting, providing departmental briefings, development plans for the upcoming quarter, and discussing/brainstorming any development issues.
  • Regular small-group/team meetings. We often conduct meetings on Skype, but more and more we are trying to get our small teams together at least once during the quarter to work out issues, discuss projects and make plans.
  • Regular fun activities. We used to do these in conjunction with the quarterly meetings, but have decided it’s better to offer more, perhaps monthly, fun activities that everyone can pick and choose between, some of which are family friendly or open to significant others. This quarter we’re attending a Nashville Sounds baseball game, doing another Escape Game, and having a company game night at our house.
  • Send team members to conferences. Whether you send them alone or in groups to attend conferences, it’s good for people to get out of the office, to shake up their weekly routine, and go learn things. I took the whole elearning team to Orlando for the Learning Solutions Conference and it was a fantastic experience to get to spend so much time together. We also send non-sales team members to work our booth at industry trade shows because we have such a small sales department. This provides the same routine break and a different type of learning experience, but another great opportunity for employees to get to know one another in person.
  • Company retreats. We don’t usually do these, but I know that many remote companies do an annual retreat of some sort that usually incorporates a meeting or two, team bonding exercises and fun activities. This year, we are having an informal company retreat since our founder (my father) is throwing himself a 65th Birthday Extravaganza at DefCon 25 in Las Vegas this summer, and we’re closing for three days so we can all go.
  • Annual holiday party. The whole staff comes in to town for our end-of-year company meeting and holiday party. This past year we split it up over two days. The meeting on a Friday and the party, open to significant others, on a Saturday. Out-of-town employees stayed with locals, and we all got to spend a weekend together which was an awesome way to end a very productive and successful year.
Company holiday party 2016
Elearning team at Universal
Our founder, Winn Schwartau, and CEO, Bob Todrank, looking very suave at the @RSAConference's SC Awards Banquet!
One of our newest employees thrust into working the booth at a tradeshow only months after joining our team.
We escaped!

So those are some of the most important things I’ve learned over the last 16 years of working remotely and the last 8 years of managing a remote team.

What remote management tips do you have to share? Do you have any remote office success stories to share? If you don’t work remotely, do you think you’d want to? If you do work from home, what’s your favorite productivity hack? What tips do you have for working with coworkers you never see? Hit me up on Twitter!

1 comment

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