Are In Person Retreats Necessary for Remote Workers?

In person retreats aren’t magic bullets. But they do give you a chance to see the personal dynamics that play out within and across teams.

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I finally got around to unpacking my suitcase from my last business trip. The presents for the kids came out right away. The rest of the stuff sat in the suitcase for a week while I picked up the pieces of my work/home life and tried to catch up.

I’m convinced that Newton came up with his first law of motion (objects at rest tend to stay at rest) because he was procrastinating about unpacking his suitcase. The inertia on that suitcase was high, let me tell you. However, I managed to break out of it on Saturday after breakfast. In the quiet that comes from the gentle tedium of putting things away, I couldn’t help but wonder if my work retreat was really necessary.

I loved it, I enjoyed it, and as an employee I want to go every year, forever. But was it necessary? At Kaplan, I decide when it makes sense to run a class or cancel it. This isn’t a straightforward task with check boxes. Instead I use a framework to make decisions. Deciding to hold a company retreat is also complicated, and it makes sense to develop a framework for deciding when to hold an in person retreat and when to design a remote retreat. Here are some non financial factors to consider.

Is Your Company New to Remote?

In the Fall of 2010 Kaplan transformed from a company with full time staff working in centers into a company whose staff worked from home. While we were motivated to succeed, most of us lacked prior experience working remotely. We really needed the annual retreat we went to that summer. Over the course of 3 days we built relationships with our colleagues in the way we were used to. Those face to face meetings built goodwill. That goodwill carried us while we learned the skills we needed to succeed in our new working medium.

If your company recently went remote, or employs people new to remote work, consider bringing your people together. Your employees are likely hungry for face to face human interaction with their colleagues. Hosting an in person event is the relationship equivalent of feeding cheese to a starving person. It’s a stimulus rich experience and will leave your employees more satisfied with both the company and their colleagues. Veteran remote workers like retreats too, but just as babies need to eat more often, remote newbies need to meet more often.

Does Work Get Done Efficiently?

You can look at this question in multiple ways. Does information flow freely within and between departments? Are colleagues willing to lend a hand to meet company goals? Are people getting promoted from a variety of departments, or is it always the same half dozen players? How high is your employee churn rate?

It is nearly impossible to build an innovative, disruptive company if teams silo information. It’s hard to stay agile if the next generation of thought leaders feels invisible, because you’ll spend a significant amount of time training their replacements when they leave.

Use Retreats to Resolve Interpersonal Issues

In person retreats aren’t magic bullets. But they do give you a chance to audit the personal dynamics that play out within and across teams. It’s just as important to notice the teams that sit together and ignore everyone else as it is to notice which teams never sit together. If you already know that there’s a problem between certain departments or people, use the event as the first step in an intervention.

Some interpersonal problems can be resolved simply by making people spend time with each other. It’s hard to continue thinking that Joe from sales is an idiot, for example, if you have a conversation about his four step process for overcoming customer resistance.

Realistically, not all interpersonal issues will go away just because you bring colleagues together. You may, in fact, decide that Joe is still an idiot. But if people know they have to talk to each other face to face on a regular basis, it does tend to keep things more civil.

I’ve seen this affect both inside and outside of work. I live in a neighborhood where people attend the same community barques, where children go to the same schools, and where you are very likely to see your neighbor at the community laundromat. We have occasional blowups on the neighborhood Facebook group, but we don’t have internet trolls. It’s hard to behave too badly when you know you’ll have to deal with the person you’re yelling at later.

Use Retreats to Assess Your Future Leaders

If you think your company lacks a deep well of talent to draw from, spend time with your line staff. You may discover that you have plenty of talent–the problem is that your all-stars lack visibility.

There are a couple of ways to use an in-person event to assess your bench. You could hold a couple of round table discussions with people your management team label high-potential. If you can’t meet with everyone, you can also do this more organically by sitting with different groups of people during mealtime, and engaging in conversation.

Incidentally, most employees know they should say something intelligent to impress the boss. Not everyone can come up with something witty before the first coffee of the day. If you’re a leader and you choose to sit with people who are lower in the power structure than you, it’s your job to set the tone and put them at ease. You’ll get a more accurate impression of someone if you don’t spook them.

In-person retreats are a great way to get a feel for your remote employees, and to course correct where needed. That’s not to say that in-person retreats are only for companies that need an intervention. High-performing remote teams benefit from getting together. Incidental conversations at dinner can lead to an innovative product down the line. But if you’re on the fence about whether the benefits of a retreat are worth the expense, you might use the state of your interpersonal dynamics to make your decision.

How Much Time Do You Have to Rededicate People to the Company Mission?

Think of company retreats through the metaphor of food. Remote events are like fruits and vegetables. With planning and skill, you can turn them into tasty interludes that feed your employees’ need for human interaction. Like fruits and vegetables, you need a steady stream of them on a regular basis to keep the company juices flowing.

In-person events are like steak and cheese (or peanut butter for my vegan friends)–you need fewer steaks than carrots to hit your calories for the day. Was it a rough year? Are you pivoting? Did you empty the company well of goodwill? An in-person event can fill the well up again very quickly. If the prevailing company culture is competitive and demanding, then in-person retreats can be one way to keep things on the right side of the functional/dysfunctional line.

Does Everyone Need to Go?

I work for a large company. So large, that we stopped holding company-wide gatherings around 2014. Instead, different groups gather together on an as-needed basis. If you can’t swing an all-hands retreat, maybe certain departments should get together. If you’re worried about creating hard feelings, plan a separate remote program for the employees who don’t get to go. In some instances it may make sense to hold an annual meet up and rotate who meets up.

It didn’t take very long to unpack my suitcase from my business trip. I like to travel lightly (with plenty of room for presents for the kids). But I’ll feel the benefits of this work trip for months to come. While I am a veteran employee, I am new to this particular team. Meeting together with my new-to-me colleagues has already made my remote day to day duties easier and more pleasant.

Do remote employees need in person retreats? This one did. Yours may too. Keep this framework in mind as you decide whether the benefits are worth the expense. By thinking through your answers to these questions you can come up with a meeting cadence–in person and remote–that makes sense for your particular situation.

Loneliness and the Remote Worker


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In Buffer’s 2018 survey, 22% of surveyed remote workers said that loneliness was a top struggle, tying for first place alongside communication and collaboration issues. This is worrying on a couple of levels.

In an age where we are less likely to know our neighbors, workplace friendships have an increasingly important place in our social lives. The coworker you chat with today can become your movie buddy tomorrow. According to the folks at Gallup, having a best friend at work can also lead to better business performance, both in terms of profit and fewer safety incidents. Lonely workers, therefore, can miss out on a chance to feel fully engaged and to work at their full potential.

It Doesn’t Have to Be This Way

Working remotely doesn’t have to lead to loneliness. There are many remote workers who make work friends, and enjoy a sense of camaraderie with people whom they never meet in person. They may occasionally feel isolated, but they have a set of steps they follow to bring more human connection into their lives. Those steps vary, depending on work configuration and personality. What works for me may not work for you, and vice versa. If we share what works for us, then that may help someone else to think of a strategy that will work for them. Anything that can help someone to feel less isolated in their office of one is a good thing.

How You Can Help

And this is where you come in. I am conducting research on how remote workers make work friends. Can you spare five minutes to fill out this survey? Once I’ve compiled the data I will write up an article with a toolkit of resources for making friends at work, and share it. Together we can help remote workers feel less isolated.

Is Remote Work Right for You?

Four questions to ask yourself before you take the plunge

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Choosing to work remotely could be the best career decision you make this year. Alternatively, you might make the move to remote work, only to wonder why you thought it was a good idea. The difference between these two paths has less to do with the type of work that you do, and more to do with the type of person that you are. Here are somethings to think about to help you decide if remote work makes sense for you.

Do You Have a Compelling ‘Why’?

There are a great many professional and personal reasons to love remote work. Many successful remote workers enjoy flexible schedules, increased work autonomy, and the opportunity to pursue outside interests. Like any job, however, this set up comes with it’s own stresses. For some, remote work is incredibly isolating. Others fight an ongoing battle to keep friends and family members from interrupting their work day.

In those difficult moments it helps to remind yourself of what you get out of remote work. Does your virtual job allow you to live in a less expensive part of the world? Can you continue to work while caring for a young or ailing family member? Perhaps you are a military spouse who moves every two years. Working remotely may allow you to stay with the same company no matter where you go.

Keeping your ‘why’ in mind will help you in at least three ways. First, it can help you endure whatever is irritating you. Your spouse might have a poor sense of what ‘do not disturb’ means, for example, but at least you get to spend more time with your kids. Your coworkers may forget that you work in a different time zone and try to message you at 6 am, but at least you can train for half marathons. Take a moment to make sure you’re clear about the benefits that remote work brings to your life.

Understanding your ‘why’ also helps you to know when it’s time to cut your losses. Your circumstances may change, and your ‘why’ may no longer apply. If you took a remote job so you could homestead in rural Canada, and discover that you hate homesteading, there may be no overriding reason to stick with remote work.

The quality or urgency of your ‘why’ will also determine how much effort you ought to expend to become an excellent, contented remote worker. The person who has to choose between working remotely or not working at all will be more motivated to excel in this environment than the person who can get a traditional office job at any time. Know where you fall on this spectrum. 

This leads to another question that you should ask yourself.

Are You Willing to Adapt?

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Think back to your first “real job.” For most of us, that job took place in some sort of in-person setting. Even if you didn’t particularly like that job, or the ones that followed, you learned how to navigate your environment. You learned how to look busy and productive, how to make work friends, and how to navigate office politics. You probably learned how to turn work off (even if you still have trouble actually doing so).

Switching to remote work means learning new approaches to these activities. Your boss can’t see you industriously typing away at your computer. It takes effort to figure out that your colleague loves the same movies you do. You CAN make work friends, grow in your career, and learn to turn off your remote job — but you have to be willing to learn. Are you willing to learn? Do you have the bandwidth to try new things, fail, and try again?

It’s important to be honest about your willingness to adapt. Some people really want to work in a traditional office. They may take a remote job for a short time in order to pay the bills, but would not consider such a job a long-term commitment. If this describes your situation, understand that you will still need to learn some remote skills if you wish to keep your remote job until the next in-person job comes along.

Are You Willing to Act?

All of us have a list of things we “should” be doing. I, for example, should have cleaned out and organized my kitchen pantry weeks ago. Fortunately this doesn’t affect anyone but me (and occasionally my spouse when the dried fruit packets avalanche on him, but I digress).

Are you the sort of person who gets your important things done? Your commitment to delivering quality work on time has to be stronger than your commitment to Netflix. No one is watching you. Remote work offers the unparalleled opportunity to dive deep into your task list if you are the sort of person who knows how to focus. If you can’t focus without the threat of a boss walking by or the social pressure of in-person colleagues, this may not be the right work setting for you. If you can self-regulate, then you may never willingly set foot in a traditional office again.

Incidentally, your future remote boss will also want to know the answer to this question. If you haven’t worked remotely before, think about other times when you had a commitment to fulfill with very little oversight. If you are a recent college grad, how disciplined were you in following a study schedule? If you’ve ever stared a side business, or tried to learn a new language or musical instrument, how hard was it to do the things you knew you had to do to succeed? Your answers to these questions can help you figure out how self-directed you are. 

Are You Willing to Play?

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Most people understand that they need to learn to focus on their work during work hours. What comes as a surprise to many remote workers is the need to focus on doing fun things after work. We all need a certain amount of human contact. A successful remote worker not only knows how much contact she needs, she takes steps to hit her weekly quota. That may mean enrolling in dance classes, going to church, or joining your local knitting group. Be the sort of person who can pick something and then actually do it.

Success as a remote worker won’t come from using the latest team building software, or learning a new skill — though both of those things can enhance your career. To really make it as a remote worker, you need a clear sense of why this lifestyle works for you, a willingness to learn new things, and the ability to have some fun along the way. Armed with these qualities, you can roll with whatever your remote work/life throws at you.

Home for the Holidays

Trying to juggle unexpected childcare can be stressful. Here are some tips to ease the stress.

What to Do When Your Childcare Falls Through

The holidays are nearly upon us, and all across the land, children will soon begin winter break. This presents particular problems for remote working parents whose home office is suddenly overrun by small people.

In our book ‘Secrets of the Remote Workforce,’ my coauthors and I discuss ways to minimize child intrusions and manage work expectations. That discussion assumes you have some form of childcare. But what do you do if your childcare falls through during the holidays? Here are some tips for when you can’t just take a vacation day.

Have a preemptive conversation with your boss. It’s easier to get the flexibility you need if you’ve prepared your manager for the possibility. I usually say something like ‘As a reminder, my children will be home during the day for winter break. I have childcare, but if those plans fall through I’ll need to talk to you about my backup plan to get my work done on time.’

Bank time. Unlike sickness, you know when winter break starts and stops. If you can, preemptively work a little later the week before so you can have an hour or so available to focus on the children.

Work early or late. Or both. Most remote jobs have some flexibility build in to them. Some work tasks can be done at any time of the day or night, while others can be done during someone else’s time zone. Most of my coworkers are on East Coast Time, so I’ll drag my myself out of bed early and work for a few hours before my children wake up. This gives me some flex time during the day when I may need it. And if I don’t need it, I now have an excuse for a long lunchtime run. Woo hoo!

Invite more children over. This may seem counter intuitive, but inviting your child’s friend over for a visit can keep both children occupied and out of your hair. Your house may be trashed afterwards but at least you can work in (relative) peace. Obviously this only works if the children are old enough not to put weird things in their mouth.   

Trying to juggle unexpected childcare can be both tricky and stressful. This is doubly true during the holidays, when backup childcare options are limited. Building in flex hours ahead of time is one way to get ahead of the stress. Do you have other tips that work for you? Let me know in the comments.

How to Set Up Your Remote Office on the Cheap

Besides a computer, the list of must-have office equipment for the new remote worker is smaller than you think.

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Your first remote job is an adventure—complete with the need to gather the right supplies if you don’t want to crash and burn. Admittedly, this is a balancing act. On the one hand you don’t want to over invest until you know that the remote work style works for you. On the other, there are a few key things you absolutely can’t live without. The list is smaller than you think.

Invest in a Great Internet Connection

Wired internet is the gold standard. Many apps take a lot of bandwidth, and you will save yourself some stress if you can plug into a router. That said, if you can’t get a wired connection, get the strongest wifi you can afford. Understand that you may need to find work arounds. Check out the rates for coworking spaces in your area. Some libraries also have wired internet, and private spaces you can reserve.

Buy a Comfortable Chair

This is the one tangible item you should buy as soon as possible. The first time I went remote I worked from my kitchen table. I was a freelance writer in New York City and I was determined to set up my office with money I earned freelancing. I was a hard nosed business woman and that was my hard nosed plan.

Unfortunately my kitchen chair was also hard. A month into my new career I needed a chiropractor. Fixing my bout of sciatica took many chiropractor visits and several hundred dollars, and then I had to invest in a nice chair anyway. My attempt to work on the cheap ended up costing far more than making a simple investment up front.

Clear a Wall

There will be video calls you have to attend. Make sure one wall in your home is work appropriate. A blank wall is perfectly acceptable. You can always add more personality once you understand the work vibe.

And that’s it. There are other things you will add to your remote office eventually, but let yourself settle in first. Some people don’t like working from a desk. Others need their things in a dedicated space. You may not know which category you fit into until you develop your new routine. Give yourself time to figure out what works for you, and you’ll be cruising along on the remote highway in no time.

For those of you who have been working remotely for a while, what things do you absolutely need to be happy and productive? Let me know in the comments.