11 things about remote working that I learnt the hard way

I have spent over 15 years working remotely and made many mistakes on the way. Here are 11 mistakes I’ve made and what have I learned from them.

Ten years ago I had no clue about remote working. It never even crossed my mind that one could work from outside of the office. And then I joined Skype family. Compared to my previous work – oh my what a different culture. A culture, a family and the product that I instantly fell in love with.

Often blogs about remote work tend to say how amazing it is to work from anywhere. All the beaches and cool places you get to visit. And whilst that is true, there are challenges as well. Here are few things I have learnt while working remotely for over ten years now.


Quick overview for those in hurry:

  • Consider remote working already when hiring and onboarding new employees. What will be the learning and sharing experience?
  • Enable having face time for the entire team.
  • Make remote work a team thing, not just for a single employee. As a team, practice by doing remote working days.
  • Communicate. A lot.
  • Do not assume – what is common to you is not common to others. Explain what you mean in simple ways to avoid misunderstanding. Visual works well.
  • Build your team culture to support remote working, working across cultures, languages, and locations.
  • Keep working discipline when remote same way you would at the office.
  • Share all information. Don’t keep the important information on your personal drive, personal chat, personal email.
  • Share calendar – it is important to have visibility when each one is available.
  • Choose the right tools. Make sure the tools enable collaboration and sharing needed information. Less tools is often better.
  • Prioritize your communication.
  • Have overlap time.

Let’s dive deeper.

Not thinking about remote working when hiring and onboarding.

There are two different beliefs when it comes to remote work and hiring:

  • Some say you simply hire people and you don’t need to meet.
  • Others find it important to meet in person.

When it comes to onboarding a new employee, same two beliefs are quite common. I think that if you can meet each other when interviewing, then do so. If you cannot, then don’t.

If a new employee can start working first couple weeks together with someone, please do so. If not, then don’t stress about it either. Meeting in person does make a difference in these two processes. You all can get to know each other better and it is important, especially in the beginning.

For those who cannot meet in person while onboarding a new person into the team, here are some tips I’ve found valuable:

For everyone on the team:

  • Give a buddy to a new employee. The bigger your team, the more it takes the time to find out who to ask about what etc. Make sure your new employee has a buddy to ask all those questions from. It could be the manager, but my experience shows that peers are the best buddies.
  • Call often. With video if you can, but audio works too.
  • Explain it simply. A picture says a thousand words, make things easy to understand and remember.
  • Make a list of tools and places new employee needs access to.
  • Use tools that are built for teamwork. Not using tools for collaborating with your team while working remotely is like a flat tire – you can’t get very far until you change.
  • Have regular team events. We do retreats once a quarter and also end up doing something fun together during holidays. What’s an offsite? Offsite is the event when you all get out of the office for couple days to plan and discuss anything important. Fun is important, too. Sometimes place with no internet is even the best.

For the remote worker:

  • When you work remotely, say “Hi” via chats when you come online and start working.
  • Keep in touch with the team. Throughout the day, ask questions and make sure that people know when you are available/away.
  • During meeting calls, make sure that the connection is good. If call drops, make sure team knows that you dropped (for example ask them to repeat and say what was the last thing you heard)

If I’m a remote worker, I never go to the office.

Remote working does not mean that you always must work remotely. Remote work is about the freedom to choose when and where to work from. It could mean working most of the time from office and sometimes from home. But it can also mean working most of the time from outside of the office. No matter of the setup, you still need to connect every now and then face to face.

Simply stated, we, human beings, need to know the people we work with. Office, retreats, team dinners, fun events, company meetings – all are great ways to connect.

It’s okay for just one team member to be a remote employee.

You can work this way in theory, but it’s hard. Really hard. I believe that remote work is a team mindset. When your team works remotely, make it a team effort. If only one person out of ten is working remotely, it will be lonely for that single person. Here’s the trick: if almost everyone works in the office, it is so easy to have a chat in the kitchen over a cup of coffee. It is easy to stand by a whiteboard to discuss things. It is easy to over hear an important conversation. All those things that are easy for people in the office are out of reach for the ones working remotely. Such conversations are not shared with everyone and you cannot return to the discussion thread later. Read more about why this is important below.

To support remote workers, you need to understand each other. And everyone must understand how it feels when you work from other locations. We at Deekit encourage everyone to work remotely every now and then, even if they don’t need to. As a team, we have decided that everyone must spend some time working remotely. Why? Because then we all know how much information reaches you while away and how as a team can we support each other better.

I’m more efficient when remote as I don’t need to talk to others as much.

There is a big difference in working remotely when you work on your own and working well as a remote team. When being remote we often believe that there’s less noise and communication needed, so we are more effective as result. It is true if you rarely pull remote days. But if you work remotely full time, it’s quite the opposite – you and your team need to communicate a lot. And then communicate some more. And to be sure everyone has all information needed, you communicate just a bit more. You get to choose, when do you read chats, when do you have calls and so on. It’s no longer noise or disruption that you must deal with immediately. It’s hard and requires practice. But once you commit to prioritize communication as a team, you will notice that random distractions will turn into a concrete flow of useful information.

Common sense is not so common.

We all have different backgrounds, experience, and cultures. And because of this, we all have different common sense understanding. What might be most elementary and common sense to me, is not so common for You, the person reading this post. So to avoid all those misunderstandings and harsh feelings, let’s all agree to communicate and explain what we mean. I cannot express in how many situations this has helped me.

Working with different cultures, backgrounds, languages, jobs and interests.

We throw many assumptions and comments out there. Rarely do we take the time to get to know our differences, our weaknesses and our straights, our personalities. We talk about same things in a different language. Even if we all speak in English.

Greatest teams I have seen know each other really well. I’m not talking about simply being friends here. You need to know what you are not good at, what are your weaknesses and who on the team can complement you in those areas. You need to know your own strengths and who can you complement. You need to know how as a team you can be best. And you need to do that virtually. Lou Solomon has written a good summary 6 ways to make virtual work more human.

Many agreements need to be made within the team. Two most important agreements are trusting and respecting each other.

Trust that everyone will do their best. Trust that everyone will deliver and do what they committed to deliver. Trust that everyone will tell when there are problems. Trust that team will help you out when you are stuck.

You mutually need to respect that you are different. And the difference is the best thing that can happen to a team. Why? If we all were alike, how could we complement each other? Respect comes in many forms. One important thing is taking the time to understand cultural differences. Things like language differences, values, beliefs, what kind of jokes you make and so on. For example the good old What The British Say vs What The British Mean vs What Foreigners Understand. Take the time to learn and keep an open mind.

You need to find best ways for you as a team to speak the same language. Say and be understood the same way. This is one of the reasons I love visuals and whiteboards so much. I have seen teams fight and argue for days, whilst ten minutes explaining with visual sketches solves the problem.

For example, we used to say in daily standups things like “I’ll try to finish” or “I’ll probably do”. This way of speaking started to bother us at some point because it did not express commitment. It was just one way to say I’m doing something, I’m busy. So we agreed we don’t speak this way as a team. We either do, or we don’t. And if sometimes “I’ll try to do something” slips in the conversation, we correct each other in a nice way.

Continue working the same way, just from different places.

If you don’t adapt the way you work and share information, no-one will be on the same picture. You have to lay everything out in the open. Information must be available for everyone at any time. Information that sits on your computer, one to one chats, inbox or even on a whiteboard in your office is out of reach for people working remotely. Especially if you work across time zones. Ever had to wait for someone to come online just to answer a simple question about what you should be doing or latest status on how things are? We sometimes waste hours of our workday on such things without thinking about it. Yet again time is our most valuable currency, why waste it?

Redbooth team has written a great blog post about this in more detail Top Tips for Fine-Tuning Your Virtual Team

There are many tools out there to support this. Try them out, find the ones that work for you. We will post our favorite tools, when we use them and why they work well for us in the next blog post too, so stay tuned for those.

Share plans and calendars.

Make a plan for the week – as a team but also individually. If you work part time, let your team know when you are working and when not. Risto and Andres split their time between Deekit and school. Anyone on the team can have times and moments when they cannot work or need to work at a different time. It is essential for us as a team to know when to expect someone to be available and when not. Shared calendars are awesome for this.

The more tools, the merrier.

Tools are key to support any kind of working, but even more so when you work remotely. Tools are also one of the most difficult questions to deal with because there are just too many tools out there. Simply saying, the more tools we use, the more information is scattered and the more difficult it is to find anything. But we do need tools that support doing our job.

I think choosing a tool always starts with “how are we working and what we need to accomplish” question. Think about:

  • Are you working remotely?
  • Lean? Scrum? Kanban? Something else?
  • What do you need to do?
  • Alone? With team? Everyone in the company?
  • How often?
  • etc

Picking some cool new toys can do more harm than good. Let me give you an example.

We at Deekit use whiteboard a lot. We sketch user experience flows, design architecture, work through problems in the software, we even plan our business on a whiteboard. Our meeting notes are the scribbles on the whiteboard linked with some external info. So this is obviously how we work. We also use a place to track tasks. A calendar. And few other tools. Because they support the way we work and what we need to do.

Traditional tools would say you must document and share documents. Write a lot of texts. So to choose a tool for documentation, we should stop whiteboarding and write texts instead. Or continue whiteboards and post images to whichever tool we use for documentation. Not really effective way to collaborate or get stuff done.

We sketch because it’s easy to explain, understand and remember. We want to add more content from outside not the other way around. Because this way we can do our work faster. So we dogfood our own product (obviously, right?) as it supports how we work and what we need to get done. We have stopped using documentation tools (wikis, confluences etc) because we don’t need them. We don’t send emails because we don’t need them. We don’t need screen sharing and other meeting tools aside of the calling part because we don’t need them.

Think about how you work and what you need to accomplish and work your way to finding right tools from there.

Must. Get. Answer. Now.

We often believe that our question is the most important question. Our problem is the biggest problem. We must get someone’s attention now. In the office, it’s easy to get. You just walk to the other person without putting any thought into it. With remote work, you thankfully cannot do this.

Prioritizing things is equally important for teams who don’t work remotely. But when you are not in the same location, you cannot work around this. So what do you do? You prioritize your question or problem. And then with your team, you agree which priority topics go into which communication channel. Here’s what has worked well for me so far:

  • Emergency. The sky is falling, the world is ending, everything is down, users are impacted etc. It really doesn’t matter what time or day it is. You must wake up, you must deal with this before anything else. This kind of things end up on my mobile.
  • Roadblock. Something is blocking release, the team cannot continue work etc. These are the important things that must be dealt with next, but you don’t need to wake up in the middle of the night. Typically these things come to chat, or if in a real hurry then SMS works well too. At Deekit those are things we also discuss in our daily standups.
  • Important system etc events. This would include monitoring alerts, customers needing response etc. At Deekit we monitor all such events and our monitoring systems would push those messages into appropriate chats. These are chats you don’t discuss or talk. Only the important events go there. And before diving into other chats, you read these first. Always.
  • Team chats. Discussions about releases, problems etc. We hold few meetings with the team at Deekit for this purpose.
  • Fun chats. There must be a place for fun, random links, and jokes, sharing everything unrelated to work.


It doesn’t matter if you work across the oceans or some on your team prefer working during night time – you will probably need some overlap in your working times. It is the time where you sync, get answers, get feedback and simply talk to each other. With no overlap time, there is always everlasting delay. You know the good old story of getting replies the next day? Having overlap time and pprioritizingyour communication helps you around it.

What has been working the best for us so far is for people in Europe work hour or two later and those in US start their day early (usually work from home in the morning at least).

What lesson about remote working would you share? Share your lessons and thoughts in comments! 🙂

Have you checked out these templates?

Scrum Task Board

Scrum weekly planning template

Team Canvas

Team Canvas

Ideal problem solving

IDEAL problem solving template

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