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Transitioning to Remote Work - Tips from Someone Who’s Done It

New to remote work? Find out what to expect and how to make the transition easier.

April 10th 2020

by Michael Karampalas

in Teamwork

First, I know what you’re thinking. Great! - another article about “how to work remotely” or “why remote is great”.

Well, not quite.

This is about my own personal journey transitioning from a traditional office environment to an all remote setting. A situation that unfortunately many folks are finding themselves in today due to Covid-19.

First, some background. I work in software as a product manager. I’ve spent over ten years in various product management and product leadership roles, in large as well as start-up organizations.

I currently work at a large and rather well-known, all remote company. I love it. There are countless benefits - the time I get back from commuting, being able to (actually) get 8 hours of sleep a night, not missing any important family events, the money I save, flexibility etc…

But, it definitely took some getting used to.

Am I cut out for this?

The first day was terrifying. It felt like a test. I was shipped my laptop, and my first task was to get my accounts set up and secured. There was a long checklist of tasks I had to accomplish in my first week. And I didn’t feel like I had anybody to ask for help if I got stuck. Sure, I had a designated “buddy” but I hadn’t yet chatted with them and didn’t want to seem inept by asking for help.

There were multiple “oh shit, what have I done?” moments as well as a mini-panic attack when I thought I completely botched one of my first onboarding tasks.

But I leveraged the extensive documentation and muddled through it, successfully completing my first week. Exhausted. Unsure if I ultimately had what it took to work in this kind of environment.

Settling In

After the first week, I started to get more comfortable. I rearranged the furniture in my sunroom to make room for a designated work area. I’m lucky because, as you might expect, the sunroom is full of windows and natural light while also being separated enough from the rest of the home, allowing for less disruption from my family.

My work generously allowed me to expense a standup desk, office chair, external monitor, keyboard and mouse which arrived my second week.

I was able to recreate the environment I was accustomed to in my old office settings. Mentally, I could get into and out of “work mode” more easily. I had a place where work happened and when I stepped away from the desk, work was over.

No more shifting from couch to table to chair and back. I really started to feel more productive.

Tip 1: Create a designated work environment and try to replicate the desk setup that you found most beneficial while in an office.

Treat Yourself

My next purchase was a coffee machine. I took for granted the free and endless coffee at the old office. For the first week, I was running out multiple times a day to the local coffee spot and I really missed being able to just make a cup when I needed to.

I also began to meal prep. While in the office, lunch was my largest meal of the day. I typically skip breakfast so when lunch comes around, I’m really hungry. What I found was that at home I wasn’t eating nearly enough and it would lead to low energy and irritability.

My go to meal at the office had been a healthy and protein packed salad from one of the local spots. So I bought vegetables, chicken, and all of the toppings I enjoyed and started making it at home. They weren’t exactly Sweetgreen quality but they hit the spot. A good meal can make a big difference. If cooking isn’t your thing, you should figure out a few good lunch spots that are near you.

Don’t feel guilty leaving the house. Even if it’s just for a walk around the block. Fresh air and sunshine go a long way.

Tip 2: Recreate the things that you enjoyed in an office environment - coffee, a good lunch, and a walk can go a long way.


As the days progressed I started meeting more folks and I picked up on different dynamics by attending various team and company meetings. This isn’t too unlike my experiences in traditional offices - observing how team members interact, learning the company buzzwords and TLAs, picking up on the culture. But it’s a little harder in remote meetings because not everyone has their cameras on and even if they do it’s difficult to pick up on body language and more subtle communication.

Meetings were a lot different. They started on time, they ended early, an agenda and notes document existed for every meeting, and participants were expected to come prepared. This meant digesting slide decks ahead of time. Slides were not presented synchronously. Synchronous meetings were for discussions and decisions.

When you have a lot of people working remotely and asynchronous, you need to be really thoughtful about the times you get everyone together for a call. It’s disruptive, and expensive, so it better be worth it.

Tip 3: Exercise discipline when deciding whether or not a meeting is needed. Can you get the answers you need with an email or shared document? If you decide a meeting is necessary, spend time to write out a thoughtful brief and agenda so team members can come prepared to contribute. Lastly, document the decisions and next steps so it’s clear for folks that couldn’t attend what the outcomes are.


Depending on your company and situation, you may be in a synchronous or asynchronous work environment. The majority of companies shifting to remote work due to covid-19 are most likely synchronous, meaning that the majority of team members are expected to work the same schedules.

Other companies, especially ones with geographically dispersed teams, may work asynchronously. This means that each individual is able to work during the hours that they choose. My company is asynchronous.

While asynchronous work has many benefits, one downside is it’s hard to turn it off. Because my teammates are working all around the clock, there is always more for me to do. I can have inbox zero at midnight and when I wake up there will be 20 new issues for me to respond to.

I like to get things done. I’m a doer - it’s my personality. So when there is something to do, regardless of the time, I’m likely to roll up to the computer and get it done. This can be hard on my family and I’m working to create better barriers so that I can be fully present “after work”.

On the flip side, sometimes I am not fully motivated and I feel guilty for not going full speed all the time. This is one of the main benefits of asynchronous work - if you’re not feeling productive, you can stop. Take a break - go for a walk, take a nap even. A fully engaged hour is more productive than a half-hearted afternoon.

When you’re asynchronous you plan your day more thoughtfully. You need to think about your actual goal and what you need to accomplish. It’s about results, not being somewhere from 9am-5pm.

Over time I’ve learned to leverage asynchronous to my advantage. I like to sleep in, so I start my day a little later. I go to the gym in the morning. I take a break when my kids get home. And I work later at night when it’s quiet and I can work more efficiently. I’ve found the schedule that works best for me. I have the freedom to coordinate and align my schedule and I’ve stopped feeling guilty about using it.

Tip 4: Find your ideal working schedule so you can be as productive as possible and leverage the benefits of remote work.

Social Time

Remote work makes socialization hard. To help with this, my company has “coffee chats” which are informal video meetings to just chat and get to know people. They’re great for recreating some of the experiences you’d get hanging around the water cooler or lunch room. Working remotely leads to most interactions being work-related and social calls are a nice way to break out of that cycle and get to know each other better, which ultimately leads to increased trust, empathy, and better teamwork and collaboration.

You can do this one-on-one or as a team. Each week one of the teams that I work with has a 30-minute social call where we get together and chat about our weekends, families, hobbies, side projects, etc… One of the coolest things about working with people across the world is learning more about their countries and cultures.

Tip 5: Find ways to engage socially with your teammates. Have informal 1:1 or group conversations to build team morale and give everyone some social interaction.

Still Working at It

Despite being at this for over six months now, I still struggle at times. I struggle with guilt for days when I don’t feel productive. I struggle with separating myself from work and turning it off. I struggle to give my family the time they deserve. But I’m gradually getting better. It’s a constant challenge and evolution.

I wouldn’t trade it in for the commute or the office again, that’s for sure. I love the freedom, the availability for family, and the flexibility to work how and when I work best.

Final tip: Struggling to adapt to remote work is normal. Keep at it, find what works for you, and you’ll soon find how much better remote work can be.

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